CN113376963A - Coloring composition and compound - Google Patents
Coloring composition and compound Download PDFInfo
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- CN113376963A CN113376963A CN202110682591.5A CN202110682591A CN113376963A CN 113376963 A CN113376963 A CN 113376963A CN 202110682591 A CN202110682591 A CN 202110682591A CN 113376963 A CN113376963 A CN 113376963A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 557
- 239000000203 mixture Substances 0.000 title claims abstract description 89
- 238000004040 coloring Methods 0.000 title claims abstract description 55
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 239000011347 resin Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 711
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 568
- 125000001424 substituent group Chemical group 0.000 claims description 449
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 354
- 125000000623 heterocyclic group Chemical group 0.000 claims description 234
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 204
- 229910052736 halogen Inorganic materials 0.000 claims description 156
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
- 229910052783 alkali metal Inorganic materials 0.000 claims description 74
- 150000001340 alkali metals Chemical group 0.000 claims description 69
- 125000004429 atom Chemical group 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 62
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
- 239000004973 liquid crystal related substance Substances 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 239000000040 green colorant Substances 0.000 claims description 2
- 239000001060 yellow colorant Substances 0.000 claims description 2
- -1 heterocyclic radical Chemical class 0.000 description 1490
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 112
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 104
- 125000001309 chloro group Chemical group Cl* 0.000 description 101
- 229910052801 chlorine Inorganic materials 0.000 description 100
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 95
- 239000000126 substance Substances 0.000 description 90
- 150000002367 halogens Chemical class 0.000 description 89
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 description 87
- 229910052757 nitrogen Inorganic materials 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 125000000217 alkyl group Chemical group 0.000 description 62
- 239000003086 colorant Substances 0.000 description 55
- 125000001153 fluoro group Chemical group F* 0.000 description 51
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- 229920006395 saturated elastomer Polymers 0.000 description 33
- 125000003277 amino group Chemical group 0.000 description 32
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 31
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 30
- 125000005843 halogen group Chemical group 0.000 description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 29
- 125000002723 alicyclic group Chemical group 0.000 description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 26
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 24
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 24
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 24
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 23
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 229920006391 phthalonitrile polymer Polymers 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 description 18
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 17
- 229910052708 sodium Inorganic materials 0.000 description 17
- 101000650817 Homo sapiens Semaphorin-4D Proteins 0.000 description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- 102100027744 Semaphorin-4D Human genes 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 16
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 101150056491 BBD1 gene Proteins 0.000 description 14
- 229910052744 lithium Inorganic materials 0.000 description 14
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 14
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 13
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 12
- 125000001841 imino group Chemical group [H]N=* 0.000 description 12
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 11
- 125000004436 sodium atom Chemical group 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 10
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical group C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 10
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 9
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000004423 acyloxy group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 9
- 239000011737 fluorine Substances 0.000 description 9
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000003452 oxalyl group Chemical group *C(=O)C(*)=O 0.000 description 9
- 125000004043 oxo group Chemical group O=* 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 8
- 150000002641 lithium Chemical group 0.000 description 8
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 8
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 7
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 6
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 6
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 239000005456 alcohol based solvent Substances 0.000 description 6
- 125000005236 alkanoylamino group Chemical group 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000003638 chemical reducing agent Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 6
- 239000000470 constituent Substances 0.000 description 6
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 6
- 239000003759 ester based solvent Substances 0.000 description 6
- 239000004210 ether based solvent Substances 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000005453 ketone based solvent Substances 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
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- 235000015165 citric acid Nutrition 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 3
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 3
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000006612 decyloxy group Chemical group 0.000 description 3
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 3
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000000174 gluconic acid Substances 0.000 description 3
- 235000012208 gluconic acid Nutrition 0.000 description 3
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
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- 229940071870 hydroiodic acid Drugs 0.000 description 3
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 3
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 3
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 3
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
- 239000004310 lactic acid Substances 0.000 description 3
- 235000014655 lactic acid Nutrition 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005905 mesyloxy group Chemical group 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 3
- 125000006611 nonyloxy group Chemical group 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005459 perfluorocyclohexyl group Chemical group 0.000 description 3
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- 125000005804 perfluoroheptyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 3
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 3
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 3
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 description 3
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229960000380 propiolactone Drugs 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- 125000005920 sec-butoxy group Chemical group 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 3
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FYGFQAJDFJYPLK-UHFFFAOYSA-N 3-butyloxiran-2-one Chemical compound CCCCC1OC1=O FYGFQAJDFJYPLK-UHFFFAOYSA-N 0.000 description 2
- ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 4,5-dihydroacephenanthrylene Chemical compound C1=CC(CC2)=C3C2=CC2=CC=CC=C2C3=C1 ZBWXZZIIMVVCNZ-UHFFFAOYSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- SSUFDOMYCBCHML-UHFFFAOYSA-N CCCCC[S](=O)=O Chemical group CCCCC[S](=O)=O SSUFDOMYCBCHML-UHFFFAOYSA-N 0.000 description 2
- WASXNYRXXQONPG-UHFFFAOYSA-N Rubia akane RA-VI Natural products C1=CC(OC)=CC=C1CC(N(C)C(=O)C(CO)NC(=O)C(C)NC(=O)C(N(C1=O)C)C2)C(=O)NC(C)C(=O)N(C)C1CC(C=C1)=CC=C1OC1=CC2=CC=C1OC WASXNYRXXQONPG-UHFFFAOYSA-N 0.000 description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 description 2
- 229910006069 SO3H Inorganic materials 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 150000002736 metal compounds Chemical class 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 125000000464 thioxo group Chemical group S=* 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- SQFPKRNUGBRTAR-UHFFFAOYSA-N acephenanthrylene Chemical group C1=CC(C=C2)=C3C2=CC2=CC=CC=C2C3=C1 SQFPKRNUGBRTAR-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- HZSIFDFXFAXICF-UHFFFAOYSA-N acetolactone Chemical compound O=C1CO1 HZSIFDFXFAXICF-UHFFFAOYSA-N 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/004—Mixtures of two or more reactive dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
Abstract
The present invention relates to a coloring composition and a compound. The present invention provides a coloring composition comprising: a compound represented by formula (IZ3), and an alkali-soluble resin.
Description
The present application is a divisional application of an invention application having an application date of 2017, 8/31/2017, an application number of 201710776175.5, and an invention name of "coloring composition and compound".
Technical Field
The present invention relates to a coloring composition and a compound.
Background
The colored curable composition has been used for producing a color filter (color filter) that can be used in a display device such as a liquid crystal display device or an electroluminescence display device. As a colorant contained in this colored curable composition, c.i. pigment yellow 185 is known (japanese patent laid-open No. 2016-66020).
Disclosure of Invention
The present invention includes the following inventions.
[1] A coloring composition comprising:
at least one selected from the group consisting of a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), a compound represented by the formula (IZ3), a compound represented by the formula (IZ4), a compound represented by the formula (IZ5) and a compound represented by the formula (IZ6), and
at least one of a resin and a solvent.
[ formula (IZ1), R O1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Each of which may be bonded to each other to form a ring.
R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[ formula (IZ2), RCO1Z2And RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2。RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Each of which may be bonded to each other to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R O1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[ formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Each of which may be bonded to each other to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[ formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M, optionally substituted carbon atomA hydrocarbon group or a heterocyclic group which may have a substituent, wherein the number of the hydrocarbon groups is 1 to 40.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R 102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z5Represents a hydrogen atom, may haveThe substituent is a hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.
M represents a hydrogen atom or an alkali metal atom.
R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[ in the formula (IZ6), D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10.
b represents an integer of 1 or more. c represents an integer of 2 to 10. d represents an integer of 1 or more. D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6).
The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
[2] A colored curable composition comprising a polymerizable compound and the colored composition according to [1 ].
[3] A color filter comprising the colored composition according to [1] or the colored curable composition according to [2] or [11 ].
[4] A liquid crystal display device comprising the color filter according to [3 ].
[5] A compound represented by the formula (Z1-B).
[ formula (IZ1-B) wherein RO11Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1Each of which may be bonded to each other to form a ring. Wherein R is21Z1、R31Z1、R41Z1And R51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a C1-40 hydrocarbon group which may have a substituent or may have a substituentA heterocyclic radical of a substituent, or, R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[6] A compound represented by the formula (IZ 2-B).
[ formula (IZ2-B) wherein RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2。
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2And R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring, R21Z2、R31Z2、R41Z2And R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[7] A compound represented by the formula (IZ 3-B).
[ formula (IZ3-B) wherein R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another represent hydrogen atomSon, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3Each of which may be bonded to each other to form a ring.
Wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
R101Z3、R102Z3And in the case where there are a plurality of M,they may be the same or different. The wavy line indicates the E-body or the Z-body. ]
[8] A compound represented by the formula (IZ 4).
[ formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[9] A compound represented by the formula (IZ 5).
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R 7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
[10] A compound represented by the formula (IZ 6).
[ formula (IZ6)Wherein D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10.
b represents an integer of 1 or more. c represents an integer of 2 to 10.
d represents an integer of 1 or more. D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6).
The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
[11] The colored curable composition according to [2], further comprising a polymerization initiator.
The invention also includes:
1. a coloring composition comprising:
at least one of a resin and a solvent, and
1 or more selected from the group consisting of a compound represented by formula (IZ1), a compound represented by formula (IZ2), a compound represented by formula (IZ3), a compound represented by formula (IZ4), a compound represented by formula (IZ5), and a compound represented by formula (IZ 6);
in the formula (IZ1), RO1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1and R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1May be bonded to each other to form a ring;
R101Z1represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z1represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z1、R102Z1and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
in the formula (IZ2), RCO1Z2And RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2;RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z2and R3Z2、R3Z2And R4Z2And R4Z2And R5Z2May be bonded to each other to form a ring;
R101Z2represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
RO1Z2and R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
In the formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z3and R3Z3、R3Z3And R4Z3And R4Z3And R5Z3May be bonded to each other to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4and R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z4and R3Z4、R3Z4And R4Z4And R4Z4And R5Z4May be bonded to each other to form a ring;
R101Z4Represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z4represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z4、R102Z4and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
in the formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5and R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring;
R101Z5represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z5、R102Z5and when there are a plurality of M, they may be the same or different; the wavy line represents the E or Z body;
in the formula (IZ6), D represents a structure having an isoindoline skeleton; z represents-SO3 -or-CO2 -;Ac+A metal cation representing a valence of c; a represents an integer of 1 to 10;
b represents an integer of 1 or more; c represents an integer of 2 to 10; d represents an integer of 1 or more; D. z, a or Ac+When there are plural, they may be the same or different; the formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6);
the partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value.
2. The coloring composition as described in the above 1, which comprises: a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), or a compound represented by the formula (IZ3), and a resin.
3. The coloring composition as described in the above 1, which comprises: a compound represented by formula (IZ4), a compound represented by formula (IZ5), or a compound represented by formula (IZ6), and a solvent.
4. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ1) wherein R is1Z1、R6Z1And R7Z1Is a hydrogen atom.
5. The coloring composition according to 1 to 2 or 4, wherein the coloring composition comprises a compound represented by the formula (IZ1) wherein RO1Z1Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
6. The coloring composition according to 1 to 2, 4 or 5, wherein the coloring composition comprises a compound represented by the formula (IZ1) wherein R is2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1At least one group of them is bonded to form a ring.
7. The coloring composition according to any one of the above 1 to 2 or 4 to 6, which comprises a compound represented by the formula (IZ1) wherein R2Z1、R3Z1、R4Z1And R5Z1At least one of which is nitro or tert-butyl.
8. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ2) wherein R isO1Z2、RN1Z2And RN2Z2Independently of each other, a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
9. The coloring composition according to 1 to 2 or 8, wherein the coloring composition comprises a compound represented by the formula (IZ2) wherein R1Z2Is a hydrogen atom.
10. 1 to 2, 8 orThe coloring composition according to 9, which comprises a compound represented by the formula (IZ2) wherein R is2Z2、R3Z2、R4Z2And R5Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2At least one group of them is bonded to form a ring.
11. The coloring composition according to any one of the above 1 to 2 or 8 to 10, which comprises a compound represented by the formula (IZ2) wherein R is2Z2、R3Z2、R4Z2And R5Z2At least one of which is nitro or tert-butyl.
12. The coloring composition according to the above 1 or 2, comprising a compound represented by the formula (IZ3) wherein R is1Z3、R6Z3And R7Z3Is a hydrogen atom.
13. The coloring composition according to 1 to 2 or 12, wherein the coloring composition comprises a compound represented by the formula (IZ3) wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is 2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3At least one group of them is bonded to form a ring.
14. The coloring composition according to 1 to 2, 12 or 13, wherein the coloring composition comprises a compound represented by the formula (IZ3) wherein R is2Z3、R3Z3、R4Z3And R5Z3At least one of which is nitro or tert-butyl.
15. The coloring composition according to any one of the above 1 to 14, which comprises both a resin and a solvent.
16. The coloring composition according to any one of the above 1 to 15, further comprising a yellow coloring agent or a green coloring agent.
17. A colored curable composition comprising a polymerizable compound and the colored composition according to any one of 1 to 16.
18. The colored curable composition according to claim 17, further comprising a polymerization initiator.
19. A color filter comprising the colored composition according to any one of 1 to 16 or the colored curable composition according to 17 or 18.
20. A liquid crystal display device comprising the color filter according to 19.
21. A compound represented by the formula (IZ 1-B);
in the formula (IZ1-B),
RO11Z1represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z1and R31Z1、R31Z1And R41Z1And R41Z1And R51Z1May be bonded to each other to form a ring;
wherein R is21Z1、R31Z1、R41Z1And R51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring;
R101Z1represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z1representing a hydrogen atom which may have a substituentA hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent;
m represents a hydrogen atom or an alkali metal atom;
R101Z1、R102Z1and when there are a plurality of M, they may be the same or different;
the wavy line indicates the E-body or the Z-body.
22. The compound according to claim 21, wherein R1Z1、R61Z1And R71Z1Is a hydrogen atom.
23. The compound according to 21 or 22, wherein RO11Z1Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
24. The compound according to any one of the above 21 to 23, wherein R21Z1、R31Z1、R41Z1And R51Z1At least one of which is nitro or tert-butyl.
25. A compound represented by the formula (IZ 2-B);
in the formula (IZ2-B), RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2;
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2And R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2A halogen atom,Cyano, nitro, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring,
R21Z2、R31Z2、R41Z2and R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring;
R101Z2represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
RO1Z2and R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
26. The compound of claim 25, wherein RO1Z2、RN1Z2And RN2Z2Is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
27. The compound according to claim 25 or 26, wherein R1Z2Is a hydrogen atom.
28. The compound according to any one of the above 25 to 27, wherein R21Z2、R31Z2、R41Z2And R51Z2At least one of which is nitro or tert-butyl.
29. A compound represented by the formula (IZ 3-B);
in the formula (IZ3-B), R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z3and R31Z3、R31Z3And R41Z3And R41Z3And R51Z3May be bonded to each other to form a ring;
wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
M represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
30. The compound of claim 29, wherein R1Z3、R61Z3And R71Z3Is a hydrogen atom.
31. The compound according to claim 29 or 30, wherein R21Z3、R31Z3、R41Z3And R51Z3At least one of which is nitro or tert-butyl.
32. A compound represented by formula (IZ 4);
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4and R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z4and R3Z4、R3Z4And R4Z4And R4Z4And R5Z4May be bonded to each other to form a ring; r101Z4Represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z4represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z4、R102Z4And when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
33. The compound of 32, wherein R1Z4、R6Z4And R7Z4Is a hydrogen atom.
34. The compound according to the above 32 or 33, wherein RN1Z4And RN2Z4Independently of each other, a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent.
35. The compound according to any one of the above 32 to 34, wherein R2Z4、R3Z4、R4Z4And R5Z4At least one of which is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4At least one group of them is bonded to form a ring.
36. The compound according to any one of the above 32 to 35, wherein R2Z4、R3Z4、R4Z4And R5Z4At least one of which is nitro or tert-butyl.
37. A compound represented by formula (IZ 5);
in the formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5and R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is 2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring;
R101Z5represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group; r102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z5、R102Z5and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
38. The compound of claim 37, wherein RN1Z5The hydrocarbon group may have a substituent and has 1 to 10 carbon atoms.
39. The compound according to 37 or 38, wherein R1Z5、R6Z5And R7Z5Is a hydrogen atom.
40. The compound according to any one of claims 37 to 39, wherein R2Z5、R3Z5、R4Z5And R5Z5At least one of which is nitro or tert-butyl.
41. A compound represented by formula (IZ 6);
in the formula (IZ6), D represents a structure having an isoindoline skeleton; z represents-SO 3 -or-CO2 -;Ac+A metal cation representing a valence of c; a represents an integer of 1 to 10;
b represents an integer of 1 or more; c represents an integer of 2 to 10;
d represents an integer of 1 or more; D. z, a or Ac+When there are plural, they may be the same or different; the formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6);
the partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value.
42. The compound according to 41, wherein the compound represented by formula (IZ6) is a compound represented by formula (IZ 6-A);
in the formula (IZ6-A), Ac+B, c and d are as defined above;
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2AZ6and R3AZ6、R3AZ6And R4AZ6、R4AZ6And R5AZ6、RAA1Z6And RAA2Z6And R12AZ6And R13AZ6May be bonded to each other to form a ring;
R101AZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102AZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
the formula (IZ6-A ') and the formula (IZ 6-A') each represent a partial structure of the formula (IZ6-A), Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represents the same meaning as the corresponding symbol in formula (IZ 6-A);
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6、R102AZ6m, c or Ac+When there are plural, they may be the same or different;
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6and R102AZ6Satisfies at least 1 of (ra-i) to (ra-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a);
(ra-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6At least one of which is-SO3 -or-CO2 -;
(ra-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6or-OCON (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(ra-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6and R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group and the heterocyclic group may have-SO3 -or-CO2 -A substituent other than;
a represents the same meaning as the symbol in formula (IZ 6); when a plurality of a exist, they may be the same or different;
The negative valence number of the partial structure represented by the formula (IZ 6-A') is the same as the absolute value of the positive valence number of the partial structure represented by the formula (IZ6-A ");
the wavy line indicates the E-body or the Z-body.
43. The compound according to item 42, wherein the compound represented by formula (IZ6-A) is a compound represented by formula (IZ 6-B);
in the formula (IZ6-B), Ac+B, c, d and the wavy line have the same meanings as described above; l is1represents-CO-or-SO2-;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Independently of one another, represents a hydrogen atom, -CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102BZ6、-NHCO-N(R102AZ6)2、-NHCOOR102BZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2BZ6and R3BZ6、R3BZ6And R4BZ6、R4BZ6And R5BZ6And R12BZ6And R13BZ6May be bonded to each other to form a ring;
R101BZ6independently of each other, the number of carbon atoms which may have a substituent1 to 40 hydrocarbon groups or heterocyclic groups which may have substituents;
R102BZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
the formula (IZ6-B ') and the formula (IZ 6-B') each represent a partial structure of the formula (IZ6-B), Ac+、b、c、d、R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6And L1Represents the same meaning as the corresponding symbol in formula (IZ 6-B);
m represents the same meaning as described above;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6、R102BZ6、L1M, c or Ac+When there are plural, they may be the same or different;
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6and R102BZ6Satisfies at least 1 of (rb-i) to (rb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6having-SO of3 -or-CO2 -The total number of (a);
(rb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6and R13BZ6At least one of which is-SO3 -or-CO2 -;
(rb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102BZ6、-NHCO-N(R102AZ6)2、-NHCOOR102BZ6or-OCON (R)102AZ6)2,
The R is101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6and R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-A); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ6-B ') has the same negative valence as the partial structure represented by the formula (IZ 6-B') has the same positive valence in absolute value.
44. The compound of 43, wherein L1is-CO-.
45. The compound according to 43 or 44, wherein R11BZ6An optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, an optionally substituted phenyl group, an optionally substituted naphthyl group, an optionally substituted tetrahydronaphthyl group A thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
46. The compound according to 43, wherein the compound represented by the formula (IZ6-B) is a compound represented by the formula (IZ 6-C);
in the formula (IZ6-C), Ac+、b、c、d、L1And the wavy line means the same as above;
L2represents-CO-or-SO2-;
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Independently of one another, represents a hydrogen atom, -CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6、-OCON(R102CZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2CZ6and R3CZ6、R3CZ6And R4CZ6And R4CZ6And R5CZ6Respectively can beBonded to each other to form a ring;
R101CZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102CZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents the same meaning as described above;
the formula (IZ6-C ') and the formula (IZ 6-C') each represent a partial structure of the formula (IZ6-C), Ac+、b、c、d、R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、L1And L2Represents the same meaning as the corresponding symbol in formula (IZ 6-C);
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6、R102CZ6、L1、L2m, c or Ac+When there are plural, they may be the same or different;
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Satisfies at least 1 of (rc-i) to (rc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a);
(rc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6and R14CZ6At least one of which is-SO3 -or-CO2 -;
(rc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6and R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-B); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ 6-C') has the same negative valence as the partial structure represented by the formula (IZ6-C ") has the same positive valence in absolute value.
47. The compound of 46, wherein R11CZ6And R14CZ6Are identical radicals, L1And L2Are the same group.
48. The compound of claim 46 or 47, wherein L1And L2is-CO-.
49. Any one of the above 46 to 48A compound of formula (I) wherein R 11CZ6And R14CZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
50. The compound according to 43, wherein the compound represented by the formula (IZ6-B) is a compound represented by the formula (IZ 6-D);
in the formula (IZ6-D), Ac+、b、c、d、L1And the wavy line means the same as above; r20DZ6And R30DZ6Bonded to form a ring Q; the ring Q may have a substituent, and is a ring having 5 to 7 constitutional elements of the ring, and the ring Q may be a hydrocarbon ring or a heterocyclic ring; the following rings may be fused/condensed on ring Q: a monocyclic ring which is selected from hydrocarbon rings and hetero rings and which may have a substituent, wherein the number of constituent elements of the ring is 5 to 7; or a condensed ring in which at least 2 of the monocyclic rings are condensed;
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6Independently of one another, represents a hydrogen atom, -CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6、-OCON(R102DZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R2DZ6and R3DZ6、R3DZ6And R4DZ6And R4DZ6And R5DZ6May be bonded to each other to form a ring;
R101DZ6Independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102DZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents the same meaning as described above;
the formulae (IZ 6-D') and (IZ6-D ") each represent a partial structure of the formula (IZ6-D), Ac+、b、c、d、R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R20DZ6、R30DZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-D);
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6、L1、M、R20DZ6、R30DZ6ring Q, c or Ac+When there are plural, they may be the same or different;
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and ring Q satisfies at least 1 of (rd-i) to (rd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q hasis-SO of3 -or-CO2 -The total number of (a);
(rd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6At least one of which is-SO3 -or-CO2 -;
(rd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)、-NHCOOR102DZ6or-OCON (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(rd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6and R11DZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO 2 -A substituent other than;
(rd-iv) Ring Q has-SO3 -or-CO2 -;
a represents the same meaning as the symbol in the formula (IZ 6-B); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ 6-D') has the same negative valence as the partial structure represented by the formula (IZ6-D ") has the same positive valence in absolute value.
51. A compound as claimed in 50 above, wherein L1is-CO-.
52. The compound according to 50 or 51, wherein R11DZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
53. The compound according to 50, wherein the compound represented by the formula (IZ6-D) is a compound represented by the formula (IZ 6-E);
in the formula (IZ6-E), Ac+、b、c、d、L1And the wavy line means the same as above;
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6Independently of one another, represents a hydrogen atom, -CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6、-OCON(R102EZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -A C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent; r 2EZ6And R3EZ6、R3EZ6And R4EZ6And R4EZ6And R5EZ6May be bonded to each other to form a ring;
R101EZ6independently represent a C1-40 hydrocarbon group which may have a substituent or a heterocyclic group which may have a substituent;
R102EZ6independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group; m represents the same meaning as described above;
the formulae (IZ6-E ') and (IZ 6-E') each represent a partial structure of the formula (IZ6-E), Ac+、b、c、d、R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6And L1Represents the same meaning as the corresponding symbol in formula (IZ 6-E);
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6、R102EZ6、L1m, c or Ac+When there are plural, they may be the same or different;
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6and R102EZ6Satisfies at least 1 of (re-i) to (re-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a);
(re-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6At least one of which is-SO3 -or-CO2 -;
(re-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6or-OCON (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -A substituent other than;
(re-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6and R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -A heterocyclic group of (a); wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -A substituent other than;
a represents the same meaning as the symbol in the formula (IZ 6-D); when a plurality of a exist, they may be the same or different;
the partial structure represented by the formula (IZ6-E ') has the same negative valence as the partial structure represented by the formula (IZ 6-E') has the same positive valence in absolute value.
54. A compound as described in 53 above, wherein L1is-CO-.
55. The compound according to 53 or 54 above, wherein R11EZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
Detailed Description
The coloring composition of the present invention comprises: at least one of a resin (hereinafter, sometimes referred to as a resin (B)) and a solvent (hereinafter, sometimes referred to as a solvent (E)), and at least one selected from the group consisting of a compound represented by formula (IZ1) (hereinafter, sometimes referred to as a compound IZ 1)), a compound represented by formula (IZ2) (hereinafter, sometimes referred to as a compound IZ 2)), a compound represented by formula (IZ3) (hereinafter, sometimes referred to as a compound IZ3), a compound represented by formula (IZ4) (hereinafter, sometimes referred to as a compound IZ4), a compound represented by formula (IZ5) (hereinafter, sometimes referred to as a compound IZ5), and a compound represented by formula (IZ6) (hereinafter, sometimes referred to as a compound IZ6) (hereinafter, sometimes referred to as a compound Z).
The compound IZ1, the compound IZ2, the compound IZ3, the compound IZ4, the compound IZ5 and the compound IZ6 include tautomers thereof and salts thereof, respectively.
The above compounds can be used as colorants, respectively.
The coloring composition of the present invention may contain 1 or 2 or more compounds IZ1, may contain 1 or 2 or more compounds IZ2, may contain 1 or 2 or more compounds IZ3, may contain 1 or 2 or more compounds IZ4, may contain 1 or 2 or more compounds IZ5, and may contain 1 or 2 or more compounds IZ 6.
When the coloring composition of the present invention contains 1 or more selected from the group consisting of the compound IZ1, the compound IZ2, and the compound IZ3, it is preferable that the coloring composition contains the resin (B) as an essential component.
When the coloring composition of the present invention contains 1 or more selected from the group consisting of the compound IZ4, the compound IZ5, and the compound IZ6, it is preferable that the coloring composition contains the solvent (E) as an essential component.
When the coloring composition of the present invention contains a solvent, the compound IZ1, the compound IZ2, the compound IZ3, the compound IZ4, the compound IZ5, and the compound IZ6 are preferably dispersed in the solvent (E).
When the coloring composition of the present invention contains the compound IZ1, the coloring composition may further contain a colorant other than the compound IZ1 (hereinafter, sometimes referred to as the colorant a1z1. also, hereinafter, sometimes the compound IZ1 and the colorant A1Z1 are collectively referred to as the "colorant AZ 1"). The colorant A1Z1 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ2, the coloring composition may further contain a colorant other than the compound IZ2 (hereinafter, sometimes referred to as a colorant a1z2. also, hereinafter, sometimes the compound IZ2 and the colorant A1Z2 are collectively referred to as a "colorant AZ 2"). The colorant A1Z2 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ3, the coloring composition may further contain a colorant other than the compound IZ3 (hereinafter, sometimes referred to as a colorant a1z3. also, hereinafter, sometimes the compound IZ3 and the colorant A1Z3 are collectively referred to as a "colorant AZ 3"). The colorant A1Z3 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ4, the coloring composition may further contain a colorant other than the compound IZ4 (hereinafter, sometimes referred to as a colorant a1z4. also, hereinafter, sometimes the compound IZ4 and the colorant A1Z4 are collectively referred to as a "colorant AZ 4"). The colorant A1Z4 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ5, the coloring composition may further contain a colorant other than the compound IZ5 (hereinafter, sometimes referred to as a colorant a1z5. furthermore, hereinafter, sometimes the compound IZ5 and the colorant A1Z5 are collectively referred to as a "colorant AZ 5"). The colorant A1Z5 may contain 1 or 2 or more colorants.
When the coloring composition of the present invention contains the compound IZ6, the coloring composition may further contain a colorant other than the compound IZ6 (hereinafter, sometimes referred to as a colorant a1z6. furthermore, the compound IZ6 and the colorant A1Z6 are sometimes collectively referred to as a "colorant AZ 6"). The colorant A1Z6 may contain 1 or 2 or more colorants.
Hereinafter, 1 or more selected from the group consisting of the colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 are collectively referred to as the colorant ZZ. The colorant ZZ preferably comprises a yellow colorant or a green colorant.
Hereinafter, 1 or more selected from the colorant AZ1, the colorant AZ2, the colorant AZ3, the colorant AZ4, the colorant AZ5, and the colorant AZ6 will be collectively referred to as a colorant ZZZ.
The coloring composition of the present invention preferably contains both the resin (B) and the solvent (E).
Further, the colored curable composition of the present invention comprises:
at least one selected from the group consisting of a compound represented by the formula (IZ1), a compound represented by the formula (IZ2), a compound represented by the formula (IZ3), a compound represented by the formula (IZ4), a compound represented by the formula (IZ5) and a compound represented by the formula (IZ6), and
at least one of resin (B) and solvent (E), and
A polymerizable compound (C).
In other words, the colored curable composition of the present invention comprises a colored composition and a polymerizable compound (C).
The colored curable composition of the invention may contain a polymerization initiator (D).
The colored curable composition of the invention may contain a polymerization initiation aid (D1).
The coloring composition of the present invention may further comprise a leveling agent (F) and an antioxidant.
< Compound IZ1 >)
Compound IZ1 is a compound represented by formula (IZ 1).
[ formula (IZ1), RO1Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Each of which may be bonded to each other to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R 101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10。
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and 1-methylcyclohexyl2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1, 2-dimethylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 1, 4-dimethylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 2, 5-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 2-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, cyclooctyl group, 2,4, 6-trimethylcyclohexyl group, 2,6, 6-tetramethylcyclohexyl group, 3,5, 5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 3, 4-octylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 2,3, 5-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 2,3, 2, 4-dimethylcyclohexyl group, 2,3, 4-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 3, 2,3, 2,3, 4-dimethylcyclohexyl group, 2,6, 2,3, 2,6, 2,3, 6, 3, 2,6, and the like, Cycloalkyl groups such as 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1、R101Z1And R102Z1The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl (mesityl group), a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 4-pentylphenyl group, a, Aromatic hydrocarbon groups such as 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group; a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3a thio group bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)Carbonyl (thiocarbonyl), -CO-S-C 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo (oxo) group, a thioxo (thioxo) group, an imino group, and a group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms)And imino groups substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof; a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; oxo radical。
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom;
-CO2m (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbyl group having 1 to 40 carbon atoms which is a substituent represented by the formula (I) includes those having 1 to 40 carbon atoms which are substituents having a valence of 1 or 2The hydrocarbon group is preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, or a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which is a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine;
five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine;
Condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone-based heterocycles such as α -acetolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone;
five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole (benzodioxole), chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include a five-membered ring system saturated heterocyclic ring such as dithiolane; saturated heterocycles with six-membered ring systems, such as thiacyclohexane (thiane), 1, 3-dithiane, 2-methyl-1, 3-dithiane; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene;
Fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone;
a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole); fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1Z1~R5Z12 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z1~R5Z1The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group represented may have a substituent. As the substituent, there may be mentionedAre mentioned with RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The preferable examples of the substituents which the hydrocarbon group may have are the same. As RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1Of (a) is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z1Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z1 to 7Z1 and 10Z1 to 13Z1 correspond to — CO — R.102Z1Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-CO-R 102Z1And the like.
as-COO-R101Z1Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-COO-R.101Z1Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-COO-R101Z1And the like.
as-OCO-R102Z1Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (carbon number 2 to 41 in the case where the carbonyloxy group is an acyloxy group), carbonyloxy group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as the group represented by the above chemical formula, and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-OCO- R 102Z1Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms in the case where the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 corresponds to-OCO-R102Z1And the like.
as-COCO-R102Z1Examples thereof include a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof bonded (for example, via a carboxyl group, a sulfo group, a nitro group, a carboxyl group, a sulfo group, a carboxyl group, a nitro group, a carboxyl group, a sulfo group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, an eicosyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a tolyl group, a p-tolyl group and the likeOxalyl groups derived from a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like), and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, wherein the oxalyl groups correspond to-COCO-R 102Z1And the like.
as-O-R102Z1There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or the like, and a group represented by the above chemical formulae), and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to — O — R. 102Z1Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-O-R102Z1And the like.
as-SO2-R101Z1Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, and heptylsulfonylSulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a alkylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, and the like, and a group represented by the above chemical formulae (i) and (ii) are bonded, and (ii) compounds corresponding to-SO in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 are listed2-R101Z1Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO 2-R101Z1And the like.
as-SO2N(R102Z1)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl substituted with a raw group (e.g., a group derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), etc.), and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO2NH(R102Z1X)(R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), and sulfamoyl groups shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 Corresponding to-SO in the compound 2N(R102Z1X)2(wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1, which correspond to-SO2N(R102Z1)2And the like.
as-CON (R)102Z1)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoylCarbamoyl groups such as carbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, and carbamoyl groups represented by the above chemical formulae which are substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like), and also, in tables 1Z1 to 7Z1 and 10Z1 to the compounds shown in Table 13Z1 correspond to-CONH (R) 102Z1X) (wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, Nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), and the like) and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-CON (R)102Z1X)2(wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z1 to 7Z1 and 10Z1 to 13Z1 which corresponds to-CON (R)102Z1)2And the like.
as-N (R)102Z1)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z1 to 7Z1 and 10Z1 to 13Z1, wherein the compound corresponds to-NH (R 102Z1X) (wherein, R102Z1XIs not a hydrogen atom, other than, and R102Z1The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di (1-ethylpropyl) amino group, N-di (tert-butylamino group, N-dibutylamino group, N-dipentylamino group, N-di (1-ethylpropyl) amino group, N-di (i-butylamino group, N-butylamino group, N-butylamino group, N-butylamino group, N-butylamino, N, or the like, N, or the like, N,an amino group substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like, and a compound shown in tables 1Z1 to 7Z1 and tables 10Z 35 1 to 13Z1, such as a compound shown in tables 1Z 8932 and tables 10Z 353925 Is equivalent to-N (R) 102Z1X)2And the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-N (R)102Z1)2And the like.
as-NHCO-R102Z1Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (carbon number 1 to 40 in the case of carbonylamino being an acylamino group, carbon number 1 to 40 in the case of carbonylamino), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 in the case of carbonylamino being a carbonylamino group) or a derivative thereof (for example, a derivative thereof such as a hydrocarbon group having 1 to 10 carbon atoms (preferably a C1 to 10 alkylsulfamoyl group) is bonded such as a group represented by the above formula, and compounds represented by tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 correspond to-NHCO- R 102Z1And the like,
preferably, the carbonyl amino group (in which the carbonyl amino group is an alkanoylamino group) to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bondedIn the case where the number of carbon atoms is more preferably 1 to 10), and the compounds shown in Table 1Z1 to Table 7Z1 and Table 10Z1 to Table 13Z1 correspond to-NHCO-R102Z1And the like.
as-NHCON (R)102Z1)2Examples thereof include the groups listed above and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1 which correspond to-NHCON (R)102Z1)2And the like.
as-NHCOOR102Z1Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1102Z1And the like.
as-OCON (R)102Z1)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z1 to 7Z1 and tables 10Z1 to 13Z1102Z1)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z1、-COO-R102Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R102Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCON(R102Z)2、-NHCOOR102Z1、-OCON(R102Z1)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 1). As R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene (biphenylene), indacene (indacene), acenaphthylene, fluorene, phenalene (phenalene), phenanthrene, anthracene, fluoranthene, acephenanthrylene (aceanthrylene), aceanthrylene (aceanthrylene), and benzo [9,10 ] benzo]Phenanthrene (triphenylene), pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide, and tetracene, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, and the like); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1In the case of forming a ring, the ring may have a substituent. Examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1、R7Z1、R101Z1And R102Z1The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z1And R4Z1When forming a ring, as R2Z1And R5Z1Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z1And R3Z1When a ring is formed, R is preferably4Z1And R5Z1Does not form a ring, more preferably R4Z1And R5Z1Is a hydrogen atom.
In addition, R4Z1And R5Z1When a ring is formed, R is preferably2Z1And R3Z1Does not form a ring, more preferably R2Z1And R3Z1Is a hydrogen atom.
In the present invention, R1Z1、R6Z1And R7Z1Preferably a hydrogen atom.
In the present invention, RO1Z1The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、A hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent,
more preferably a C1-40 hydrocarbon group which may have a substituent, a halogen atom, or-N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z1And R3Z1、R3Z1And R4Z1Or R4Z1And R5Z1Form a ring.
Compound IZ1 is preferably the following compound: r2Z1、R3Z1、R4Z1And R5Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R2Z1And R3Z1、R3Z1And R4Z1And R4Z1And R5Z1At least one group of the compounds (hereinafter, this compound may be referred to as "compound IZ 1-B") is bonded to form a ring. When the compound IZ1 is the compound IZ1-B, the retardation value of the color filter produced from the colored composition becomes small.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z1、R3Z1、R4Z1And R5Z1At least one of the above (B) is a C1-4 carbon atom which may have a substituent0 hydrocarbyl group, halogen atom, -N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R3Z1Is nitro or tert-butyl, R2Z1、R4Z1And R5Z1Is a hydrogen atom; or, R2Z1、R3Z1And R5Z1Is a hydrogen atom, R4Z1Is nitro or tert-butyl.
When the above compound IZ1-B is defined by a chemical formula, it is as follows.
[ formula (IZ1-B) wherein RO11Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. R1Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Independently of one another, represents a hydrogen atom, -CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1Can be bonded to each other to form a ring。
Wherein R is21Z1、R31Z1、R41Z1And R 51Z1At least one of which is-CO-R102Z1、-COO-R101Z1、-OCO-R102Z1、-COCO-R102Z1、-O-R102Z1、-SO2-R101Z1、-SO2N(R102Z1)2、-CON(R102Z1)2、-N(R102Z1)2、-NHCO-R102Z1、-NHCO-N(R102Z1)2、-NHCOOR102Z1、-OCON(R102Z1)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z1And R31Z1、R31Z1And R41Z1And R41Z1And R51Z1At least one group of them is bonded to form a ring. R101Z1The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z1Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z1、R102Z1And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
With respect to R in the formula (IZ1-B)O11Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Respectively, R in the formula (IZ1)O1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1The same example.
With respect to the preferred R in the formula (IZ1-B)O11Z1、R21Z1、R31Z1、R41Z1、R51Z1、R61Z1And R71Z1Respectively, R in the formula (IZ1)O1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1Is superior toThe same example was chosen.
In the formula (IZI-B), (mode 1) R1Z1、R61Z1And R71Z1Is preferably a hydrogen atom. In addition, (mode 2) RO11Z1It is also preferable that the hydrocarbon group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent. Further, (mode 3) R21Z1、R31Z1、R41Z1And R51Z1It is also preferred that at least one of them is nitro or tert-butyl. The above-mentioned modes 1 to 3 can be adopted individually, or they can be combined appropriately.
Specific examples of the compound IZ1 include compounds IZ1-1 to IZ1-529 and alkali metal salts thereof having a substituent shown in table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1 and table 13Z1 in formula (IZ 1-aa).
Ba1Z1Ba2Z1The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. As Ba1Z1Ba2Z1Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Each symbol in table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1, and table 13Z1 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group,
"TBu" means t-butyl, "Hex" means hexyl, "Oct" means octyl,
"2 EH" represents 2-ethylhexyl, "CHM" represents cyclohexylmethyl, "CH" represents cyclohexyl, "PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl,
"IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5,
"NOT" means-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond.
Ba1Z1And Ba2Z1Each represents a chemical bond, Ba1Z1Is as follows B1When a chemical bond of (A) is present, Ba2Z1B is as follows2The chemical bond of (a); b isa1Z1Is as follows B2When a chemical bond of (A) is present, Ba2Z1B is as follows1The chemical bond of (1).
[ Table 1Z1]
TABLE 1Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-1 | H | BB1 | H | H | H |
IZ1-2 | Me | BB1 | H | H | H |
IZ1-3 | Et | BB1 | H | H | H |
IZ1-4 | Bu | BB1 | H | H | H |
IZ1-5 | TBu | BB1 | H | H | H |
IZ1-6 | Hex | BB1 | H | H | H |
IZ1-7 | Oct | BB1 | H | H | H |
IZ1-8 | 2EH | BB1 | H | H | H |
IZ1-9 | CHM | BB1 | H | H | H |
IZ1-10 | CH | BB1 | H | H | H |
IZ1-11 | PH | BB1 | H | H | H |
IZ1-12 | BZ | BB1 | H | H | H |
IZ1-13 | NPR | BB1 | H | H | H |
IZ1-14 | IPR | BB1 | H | H | H |
IZ1-15 | IBu | BB1 | H | H | H |
IZ1-16 | EOE | BB1 | H | H | H |
IZ1-17 | ALL | BB1 | H | H | H |
IZ1-18 | HYE | BB1 | H | H | H |
IZ1-19 | H | BB6 | H | H | H |
IZ1-20 | Me | BB6 | H | H | H |
IZ1-21 | Et | BB6 | H | H | H |
IZ1-22 | Bu | BB6 | H | H | H |
IZ1-23 | TBu | BB6 | H | H | H |
IZ1-24 | Hex | BB6 | H | H | H |
IZ1-25 | Oct | BB6 | H | H | H |
IZ1-26 | 2EH | BB6 | H | H | H |
IZ1-27 | CHM | BB6 | H | H | H |
IZ1-28 | CH | BB6 | H | H | H |
IZ1-29 | PH | BB6 | H | H | H |
IZ1-30 | BZ | BB6 | H | H | H |
IZ1-31 | NPR | BB6 | H | H | H |
IZ1-32 | IPR | BB6 | H | H | H |
IZ1-33 | IBu | BB6 | H | H | H |
IZ1-34 | EOE | BB6 | H | H | H |
IZ1-35 | ALL | BB6 | H | H | H |
IZ1-36 | HYE | BB6 | H | H | H |
IZ1-37 | H | BB19 | H | H | H |
IZ1-38 | Me | BB19 | H | H | H |
IZ1-39 | Et | BB19 | H | H | H |
IZ1-40 | Bu | BB19 | H | H | H |
[ Table 2Z1]
TABLE 2Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-41 | TBu | BB19 | H | H | H |
IZ1-42 | Hex | BB19 | H | H | H |
IZ1-43 | Oct | BB19 | H | H | H |
IZ1-44 | 2EH | BB19 | H | H | H |
IZ1-45 | CHM | BB19 | H | H | H |
IZ1-46 | CH | BB19 | H | H | H |
IZ1-47 | PH | BB19 | H | H | H |
IZ1-48 | BZ | BB19 | H | H | H |
IZ1-49 | NPR | BB19 | H | H | H |
IZ1-50 | IPR | BB19 | H | H | H |
IZ1-51 | IBu | BB19 | H | H | H |
IZ1-52 | EOE | BB19 | H | H | H |
IZ1-53 | ALL | BB19 | H | H | H |
IZ1-54 | HYE | BB19 | H | H | H |
IZ1-55 | H | BB2 | H | H | H |
IZ1-56 | Me | BB3 | H | H | H |
IZ1-57 | Et | BB4 | H | H | H |
IZ1-58 | Bu | BB5 | H | H | H |
IZ1-59 | TBu | BB7 | H | H | H |
IZ1-60 | Hex | BB8 | H | H | H |
IZ1-61 | Oct | BB9 | H | H | H |
IZ1-62 | 2EH | BB10 | H | H | H |
IZ1-63 | CHM | BB11 | H | H | H |
IZ1-64 | CH | BB12 | H | H | H |
IZ1-65 | PH | BB13 | H | H | H |
IZ1-66 | BZ | BB14 | H | H | H |
IZ1-67 | NPR | BB15 | H | H | H |
IZ1-68 | IPR | BB16 | H | H | H |
IZ1-69 | IBu | BB17 | H | H | H |
IZ1-70 | EOE | BB18 | H | H | H |
IZ1-71 | ALL | BB20 | H | H | H |
IZ1-72 | HYE | BB21 | H | H | H |
IZ1-73 | H | BB22 | H | H | H |
IZ1-74 | Me | BB23 | H | H | H |
IZ1-75 | Et | BB24 | H | H | H |
IZ1-76 | Bu | BB25 | H | H | H |
IZ1-77 | TBu | BB26 | H | H | H |
IZ1-78 | Hex | BB27 | H | H | H |
IZ1-79 | Oct | BB28 | H | H | H |
IZ1-80 | 2EH | BB29 | H | H | H |
[ Table 3Z1]
TABLE 3Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-81 | CHM | BB30 | H | H | H |
IZ1-82 | CH | BB31 | H | H | H |
IZ1-83 | PH | BB32 | H | H | H |
IZ1-84 | BZ | BB33 | H | H | H |
IZ1-85 | NPR | BB34 | H | H | H |
IZ1-86 | IPR | BB35 | H | H | H |
IZ1-87 | IBu | BB36 | H | H | H |
IZ1-88 | EOE | BB37 | H | H | H |
IZ1-89 | ALL | BB38 | H | H | H |
IZ1-90 | HYE | BB39 | H | H | H |
IZ1-91 | H | BB40 | H | H | H |
IZ1-92 | Me | BB41 | H | H | H |
IZ1-93 | Et | BB42 | H | H | H |
IZ1-94 | Bu | BB43 | H | H | H |
IZ1-95 | TBu | BB44 | H | H | H |
IZ1-96 | Hex | BB45 | H | H | H |
IZ1-97 | Oct | BB46 | H | H | H |
IZ1-98 | 2EH | BB47 | H | H | H |
IZ1-99 | CHM | BB48 | H | H | H |
IZ1-100 | CH | BB49 | H | H | H |
IZ1-101 | PH | BB50 | H | H | H |
IZ1-102 | BZ | BB51 | H | H | H |
IZ1-103 | NPR | BB52 | H | H | H |
IZ1-104 | IPR | BB53 | H | H | H |
IZ1-105 | IBu | BB54 | H | H | H |
IZ1-106 | EOE | BB55 | H | H | H |
IZ1-107 | ALL | BB56 | H | H | H |
IZ1-108 | HYE | BB57 | H | H | H |
IZ1-109 | H | BB58 | H | H | H |
IZ1-110 | Me | BB59 | H | H | H |
IZ1-111 | Et | BB60 | H | H | H |
IZ1-112 | Et | BB1 | H | Me | Me |
IZ1-113 | Bu | BB2 | H | CH | CH |
IZ1-114 | TBu | BB3 | H | BZ | H |
IZ1-115 | Hex | BB4 | Me | Me | Me |
IZ1-116 | H | BB5 | Et | CH | CH |
IZ1-117 | Me | BB6 | H | Et | Et |
IZ1-118 | Et | BB7 | H | Bu | Bu |
IZ1-119 | Bu | BB8 | H | TBu | TBu |
IZ1-120 | TBu | BB9 | H | Hex | Hex |
[ Table 4Z1]
TABLE 4Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-121 | Hex | BB10 | H | Oct | Oct |
IZ1-122 | Oct | BB11 | H | 2EH | 2EH |
IZ1-123 | 2EH | BB12 | H | CHM | CHM |
IZ1-124 | CHM | BB13 | H | PH | PH |
IZ1-125 | CH | BB14 | H | BZ | BZ |
IZ1-126 | PH | BB15 | H | NPR | NPR |
IZ1-127 | BZ | BB16 | H | IPR | IPR |
IZ1-128 | NPR | BB17 | H | IBu | IBu |
IZ1-129 | IPR | BB18 | H | EOE | EOE |
IZ1-130 | IBu | BB19 | H | ALL | ALL |
IZ1-131 | EOE | BB20 | H | NH2 | NH2 |
IZ1-132 | ALL | BB21 | H | CBM | CBM |
IZ1-133 | HYE | BB22 | H | COM | COM |
IZ1-134 | H | BB23 | H | COE | COE |
IZ1-135 | Me | BB24 | H | CBA | CBA |
IZ1-136 | Et | BB25 | H | HYE | HYE |
IZ1-137 | Bu | BB26 | H | Me | Me |
IZ1-138 | TBu | BB27 | H | CH | CH |
IZ1-139 | Hex | BB28 | H | BZ | H |
IZ1-140 | Oct | BB29 | Me | Me | Me |
IZ1-141 | 2EH | BB30 | Et | CH | CH |
IZ1-142 | CHM | BB31 | H | Et | Et |
IZ1-143 | CH | BB32 | H | Bu | Bu |
IZ1-144 | PH | BB33 | H | TBu | TBu |
IZ1-145 | BZ | BB34 | H | Hex | Hex |
IZ1-146 | NPR | BB35 | H | Oct | Oct |
IZ1-147 | IPR | BB36 | H | 2EH | 2EH |
IZ1-148 | IBu | BB37 | H | CHM | CHM |
IZ1-149 | EOE | BB38 | H | PH | PH |
IZ1-150 | ALL | BB39 | H | BZ | BZ |
IZ1-151 | HYE | BB40 | H | NPR | NPR |
IZ1-152 | H | BB41 | H | IPR | IPR |
IZ1-153 | Me | BB42 | H | IBu | IBu |
IZ1-154 | Et | BB43 | H | EOE | EOE |
IZ1-155 | Bu | BB44 | H | ALL | ALL |
IZ1-156 | TBu | BB45 | H | NH2 | NH2 |
IZ1-157 | Hex | BB46 | H | CBM | CBM |
IZ1-158 | Oct | BB47 | H | COM | COM |
IZ1-159 | 2EH | BB48 | H | COE | COE |
IZ1-160 | CHM | BB49 | H | CBA | CBA |
[ Table 5Z1]
TABLE 5Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-161 | CH | BB50 | H | HYE | HYE |
IZ1-162 | PH | BB51 | H | Me | Me |
IZ1-163 | BZ | BB52 | H | CH | CH |
IZ1-164 | NPR | BB53 | H | BZ | H |
IZ1-165 | IPR | BB54 | Me | Me | Me |
IZ1-166 | IBu | BB55 | Et | CH | CH |
IZ1-167 | EOE | BB56 | H | Et | Et |
IZ1-168 | ALL | BB57 | H | Bu | Bu |
IZ1-169 | HYE | BB58 | H | TBu | TBu |
IZ1-170 | H | BB59 | H | Hex | Hex |
IZ1-171 | Me | BB60 | H | Oct | Oct |
IZ1-172 | CHM | BB1 | Me | H | H |
IZ1-173 | CH | BB2 | COM | H | H |
IZ1-174 | PH | BB3 | COE | H | H |
IZ1-175 | BZ | BB4 | Et | H | H |
IZ1-176 | NPR | BB5 | OCM | H | H |
IZ1-177 | IPR | BB6 | OME | H | H |
IZ1-178 | IBu | BB7 | Bu | H | H |
IZ1-179 | EOE | BB8 | SOT | H | H |
IZ1-180 | ALL | BB9 | SNH | H | H |
IZ1-181 | HYE | BB10 | TBu | H | H |
IZ1-182 | H | BB11 | SN2 | H | H |
IZ1-183 | Me | BB12 | CNM | H | H |
IZ1-184 | Et | BB13 | Hex | H | H |
IZ1-185 | Bu | BB14 | CN2 | H | H |
IZ1-186 | TBu | BB15 | NPH | H | H |
IZ1-187 | Hex | BB16 | Oct | H | H |
IZ1-188 | Oct | BB17 | NOT | H | H |
IZ1-189 | 2EH | BB18 | NCO | H | H |
IZ1-190 | CHM | BB19 | 2EH | H | H |
IZ1-191 | CH | BB20 | F | H | H |
IZ1-192 | PH | BB21 | Cl | H | H |
IZ1-193 | BZ | BB22 | CHM | H | H |
IZ1-194 | NPR | BB23 | Br | H | H |
IZ1-195 | IPR | BB24 | CN | H | H |
IZ1-196 | IBu | BB25 | CH | H | H |
IZ1-197 | EOE | BB26 | NO2 | H | H |
IZ1-198 | ALL | BB27 | SUA | H | H |
IZ1-199 | HYE | BB28 | PH | H | H |
IZ1-200 | H | BB29 | CBA | H | H |
[ Table 6Z1]
TABLE 6Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-201 | Me | BB30 | CHO | H | H |
IZ1-202 | Et | BB31 | BZ | H | H |
IZ1-203 | Bu | BB32 | OCH | H | H |
IZ1-204 | TBu | BB33 | NPR | H | H |
IZ1-205 | Hex | BB34 | OH | H | H |
IZ1-206 | Oct | BB35 | IPR | H | H |
IZ1-207 | 2EH | BB36 | SFM | H | H |
IZ1-208 | CHM | BB37 | IBu | H | H |
IZ1-209 | CH | BB38 | CBM | H | H |
IZ1-210 | PH | BB39 | EOE | H | H |
IZ1-211 | BZ | BB40 | NH2 | H | H |
IZ1-212 | NPR | BB41 | ALL | H | H |
IZ1-213 | IPR | BB42 | NCH | H | H |
IZ1-214 | IBu | BB43 | HYE | H | H |
IZ1-215 | EOE | BB44 | H | Me | H |
IZ1-216 | ALL | BB45 | H | H | COM |
IZ1-217 | HYE | BB46 | H | COE | H |
IZ1-218 | H | BB47 | H | H | Et |
IZ1-219 | Me | BB48 | H | OCM | H |
IZ1-220 | Et | BB49 | H | H | OME |
IZ1-221 | Bu | BB50 | H | Bu | H |
IZ1-222 | TBu | BB51 | H | H | SOT |
IZ1-223 | Hex | BB52 | H | SNH | H |
IZ1-224 | Oct | BB53 | H | H | TBu |
IZ1-225 | 2EH | BB54 | H | SN2 | H |
IZ1-226 | CHM | BB55 | H | H | CNM |
IZ1-227 | CH | BB56 | H | Hex | H |
IZ1-228 | PH | BB57 | H | H | CN2 |
IZ1-229 | BZ | BB58 | H | NPH | H |
IZ1-230 | NPR | BB59 | H | H | Oct |
IZ1-231 | IPR | BB60 | H | NOT | H |
IZ1-232 | IBu | BB1 | H | H | NCO |
IZ1-233 | EOE | BB2 | H | 2EH | H |
IZ1-234 | ALL | BB3 | H | H | F |
IZ1-235 | HYE | BB4 | H | Cl | H |
IZ1-236 | H | BB5 | H | H | CHM |
IZ1-237 | Me | BB6 | H | Br | H |
IZ1-238 | Et | BB7 | H | H | CN |
IZ1-239 | Bu | BB8 | H | CH | H |
IZ1-240 | TBu | BB9 | H | H | NO2 |
[ Table 7Z1]
TABLE 7Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-241 | Hex | BB10 | H | SUA | H |
IZ1-242 | Oct | BB11 | H | H | PH |
IZ1-243 | 2EH | BB12 | H | CBA | H |
IZ1-244 | CHM | BB13 | H | H | CHO |
IZ1-245 | CH | BB14 | H | BZ | BZ |
IZ1-246 | PH | BB15 | H | H | OCH |
IZ1-247 | BZ | BB16 | H | NPR | H |
IZ1-248 | NPR | BB17 | H | H | OH |
IZ1-249 | IPR | BB18 | H | IPR | H |
IZ1-250 | IBu | BB19 | H | H | SFM |
IZ1-251 | EOE | BB20 | H | IBu | H |
IZ1-252 | ALL | BB21 | H | H | CBM |
IZ1-253 | HYE | BB22 | H | EOE | H |
IZ1-254 | H | BB23 | H | H | NH2 |
IZ1-255 | Me | BB24 | H | ALL | H |
IZ1-256 | Et | BB25 | H | H | NCH |
IZ1-257 | Bu | BB26 | H | HYE | H |
IZ1-258 | Me | BB8 | H | H | H |
[ Table 10Z1]
TABLE 10Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | ||
IZ1-259 | NA1 | BB1 | H | H | H | IZ1-299 | H | BB11 | H | H | H |
IZ1-260 | HHk8 | BB1 | H | H | H | IZ1-300 | Me | BB11 | H | H | H |
IZ1-261 | NA2 | BB1 | H | H | H | IZ1-301 | Et | BB11 | H | H | H |
IZ1-262 | HHk7 | BB1 | H | H | H | IZ1-302 | Bu | BB11 | H | H | H |
IZ1-263 | HH37 | BB1 | H | H | H | IZ1-303 | TBu | BB11 | H | H | H |
IZ1-264 | HHk6 | BB1 | H | H | H | IZ1-304 | Hex | BB11 | H | H | H |
IZ1-265 | NA3 | BB1 | H | H | H | IZ1-305 | Oct | BB11 | H | H | H |
IZ1-266 | HHJ2 | BB1 | H | H | H | IZ1-306 | 2EH | BB11 | H | H | H |
IZ1-267 | HHk11 | BB1 | H | H | H | IZ1-307 | CH | BB11 | H | H | H |
IZ1-268 | NA1 | BB6 | H | H | H | IZ1-308 | PH | BB11 | H | H | H |
IZ1-269 | HHk8 | BB6 | H | H | H | IZ1-309 | BZ | BB11 | H | H | H |
IZ1-270 | NA2 | BB6 | H | H | H | IZ1-310 | EOE | BB11 | H | H | H |
IZ1-271 | HHk7 | BB6 | H | H | H | IZ1-311 | ALL | BB11 | H | H | H |
IZ1-272 | HH37 | BB6 | H | H | H | IZ1-312 | HYE | BB11 | H | H | H |
IZ1-273 | HHk6 | BB6 | H | H | H | IZ1-313 | NA1 | BB11 | H | H | H |
IZ1-274 | NA3 | BB6 | H | H | H | IZ1-314 | HHk8 | BB11 | H | H | H |
IZ1-275 | HHJ2 | BB6 | H | H | H | IZ1-315 | NA2 | BB11 | H | H | H |
IZ1-276 | HHk11 | BB6 | H | H | H | IZ1-316 | HHk7 | BB11 | H | H | H |
IZ1-277 | H | BB8 | H | H | H | IZ1-317 | HH37 | BB11 | H | H | H |
IZ1-278 | Et | BB8 | H | H | H | IZ1-318 | HHk6 | BB11 | H | H | H |
IZ1-279 | Bu | BB8 | H | H | H | IZ1-319 | NA3 | BB11 | H | H | H |
IZ1-280 | TBu | BB8 | H | H | H | IZ1-320 | HHJ2 | BB11 | H | H | H |
IZ1-281 | Oct | BB8 | H | H | H | IZ1-321 | HHk11 | BB11 | H | H | H |
IZ1-282 | 2EH | BB8 | H | H | H | IZ1-322 | H | BB14 | H | H | H |
IZ1-283 | CHM | BB8 | H | H | H | IZ1-323 | Me | BB14 | H | H | H |
IZ1-284 | CH | BB8 | H | H | H | IZ1-324 | Et | BB14 | H | H | H |
IZ1-285 | PH | BB8 | H | H | H | IZ1-325 | Bu | BB14 | H | H | H |
IZ1-286 | BZ | BB8 | H | H | H | IZ1-326 | TBu | BB14 | H | H | H |
IZ1-287 | EOE | BB8 | H | H | H | IZ1-327 | Hex | BB14 | H | H | H |
IZ1-288 | ALL | BB8 | H | H | H | IZ1-328 | Oct | BB14 | H | H | H |
IZ1-289 | HYE | BB8 | H | H | H | IZ1-329 | 2EH | BB14 | H | H | H |
IZ1-290 | NA1 | BB8 | H | H | H | IZ1-330 | CHM | BB14 | H | H | H |
IZ1-291 | HHk8 | BB8 | H | H | H | IZ1-331 | CH | BB14 | H | H | H |
IZ1-292 | NA2 | BB8 | H | H | H | IZ1-332 | PH | BB14 | H | H | H |
IZ1-293 | HHk7 | BB8 | H | H | H | IZ1-333 | EOE | BB14 | H | H | H |
IZ1-294 | HH37 | BB8 | H | H | H | IZ1-334 | ALL | BB14 | H | H | H |
IZ1-295 | HHk6 | BB8 | H | H | H | IZ1-335 | HYE | BB14 | H | H | H |
IZ1-296 | NA3 | BB8 | H | H | H | IZ1-336 | NA1 | BB14 | H | H | H |
IZ1-297 | HHJ2 | BB8 | H | H | H | IZ1-337 | HHk8 | BB14 | H | H | H |
IZ1-298 | HHk11 | BB8 | H | H | H | IZ1-338 | NA2 | BB14 | H | H | H |
[ Table 11Z1]
TABLE 11Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | ||
IZ1-339 | HHk7 | BB14 | H | H | H | IZ1-379 | Bu | BB58 | H | H | H |
IZ1-340 | HH37 | BB14 | H | H | H | IZ1-380 | TBu | BB58 | H | H | H |
IZ1-341 | HHk6 | BB14 | H | H | H | IZ1-381 | Hex | BB58 | H | H | H |
IZ1-342 | NA3 | BB14 | H | H | H | IZ1-382 | Oct | BB58 | H | H | H |
IZ1-343 | HHJ2 | BB14 | H | H | H | IZ1-383 | 2EH | BB58 | H | H | H |
IZ1-344 | HHk11 | BB14 | H | H | H | IZ1-384 | CHM | BB58 | H | H | H |
IZ1-345 | NA1 | BB19 | H | H | H | IZ1-385 | CH | BB58 | H | H | H |
IZ1-346 | HHk8 | BB19 | H | H | H | IZ1-386 | PH | BB58 | H | H | H |
IZ1-347 | NA2 | BB19 | H | H | H | IZ1-387 | BZ | BB58 | H | H | H |
IZ1-348 | HHk7 | BB19 | H | H | H | IZ1-388 | EOE | BB58 | H | H | H |
IZ1-349 | HH37 | BB19 | H | H | H | IZ1-389 | ALL | BB58 | H | H | H |
IZ1-350 | HHk6 | BB19 | H | H | H | IZ1-390 | HYE | BB58 | H | H | H |
IZ1-351 | NA3 | BB19 | H | H | H | IZ1-391 | NA1 | BB58 | H | H | H |
IZ1-352 | HHJ2 | BB19 | H | H | H | IZ1-392 | HHk8 | BB58 | H | H | H |
IZ1-353 | HHk11 | BB19 | H | H | H | IZ1-393 | NA2 | BB58 | H | H | H |
IZ1-354 | H | BB37 | H | H | H | IZ1-394 | HHk7 | BB58 | H | H | H |
IZ1-355 | Me | BB37 | H | H | H | IZ1-395 | HH37 | BB58 | H | H | H |
IZ1-356 | Et | BB37 | H | H | H | IZ1-396 | HHk6 | BB58 | H | H | H |
IZ1-357 | Bu | BB37 | H | H | H | IZ1-397 | NA3 | BB58 | H | H | H |
IZ1-358 | TBu | BB37 | H | H | H | IZ1-398 | HHJ2 | BB58 | H | H | H |
IZ1-359 | Hex | BB37 | H | H | H | IZ1-399 | HHk11 | BB58 | H | H | H |
IZ1-360 | Oct | BB37 | H | H | H | IZ1-400 | H | BBJ2 | H | H | H |
IZ1-361 | 2EH | BB37 | H | H | H | IZ1-401 | Me | BBJ2 | H | H | H |
IZ1-362 | CHM | BB37 | H | H | H | IZ1-402 | Et | BBJ2 | H | H | H |
IZ1-363 | CH | BB37 | H | H | H | IZ1-403 | Bu | BBJ2 | H | H | H |
IZ1-364 | PH | BB37 | H | H | H | IZ1-404 | TBu | BBJ2 | H | H | H |
IZ1-365 | BZ | BB37 | H | H | H | IZ1-405 | Hex | BBJ2 | H | H | H |
IZ1-366 | ALL | BB37 | H | H | H | IZ1-406 | Oct | BBJ2 | H | H | H |
IZ1-367 | HYE | BB37 | H | H | H | IZ1-407 | 2EH | BBJ2 | H | H | H |
IZ1-368 | NA1 | BB37 | H | H | H | IZ1-408 | CHM | BBJ2 | H | H | H |
IZ1-369 | HHk8 | BB37 | H | H | H | IZ1-409 | CH | BBJ2 | H | H | H |
IZ1-370 | NA2 | BB37 | H | H | H | IZ1-410 | PH | BBJ2 | H | H | H |
IZ1-371 | HHk7 | BB37 | H | H | H | IZ1-411 | BZ | BBJ2 | H | H | H |
IZ1-372 | HH37 | BB37 | H | H | H | IZ1-412 | EOE | BBJ2 | H | H | H |
IZ1-373 | HHk6 | BB37 | H | H | H | IZ1-413 | ALL | BBJ2 | H | H | H |
IZ1-374 | NA3 | BB37 | H | H | H | IZ1-414 | HYE | BBJ2 | H | H | H |
IZ1-375 | HHJ2 | BB37 | H | H | H | IZ1-415 | NA1 | BBJ2 | H | H | H |
IZ1-376 | HHk11 | BB37 | H | H | H | IZ1-416 | HHk8 | BBJ2 | H | H | H |
IZ1-377 | Me | BB58 | H | H | H | IZ1-417 | NA2 | BBJ2 | H | H | H |
IZ1-378 | Et | BB58 | H | H | H | IZ1-418 | HHk7 | BBJ2 | H | H | H |
[ Table 12Z1]
TABLE 12Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | ||
IZ1-419 | HH37 | BBJ2 | H | H | H | IZ1-459 | BZ | BBO10 | H | H | H |
IZ1-420 | HHk6 | BBJ2 | H | H | H | IZ1-460 | EOE | BBO10 | H | H | H |
IZ1-421 | NA3 | BBJ2 | H | H | H | IZ1-461 | ALL | BBO10 | H | H | H |
IZ1-422 | HHJ2 | BBJ2 | H | H | H | IZ1-462 | HYE | BBO10 | H | H | H |
IZ1-423 | HHk11 | BBJ2 | H | H | H | IZ1-463 | NA1 | BBO10 | H | H | H |
IZ1-424 | H | BBO8 | H | H | H | IZ1-464 | HHk8 | BBO10 | H | H | H |
IZ1-425 | Me | BBO8 | H | H | H | IZ1-465 | NA2 | BBO10 | H | H | H |
IZ1-426 | Et | BBO8 | H | H | H | IZ1-466 | HHk7 | BBO10 | H | H | H |
IZ1-427 | Bu | BBO8 | H | H | H | IZ1-467 | HH37 | BBO10 | H | H | H |
IZ1-428 | TBu | BBO8 | H | H | H | IZ1-468 | HHk6 | BBO10 | H | H | H |
IZ1-429 | Hex | BBO8 | H | H | H | IZ1-469 | NA3 | BBO10 | H | H | H |
IZ1-430 | Oct | BBO8 | H | H | H | IZ1-470 | HHJ2 | BBO10 | H | H | H |
IZ1-431 | 2EH | BBO8 | H | H | H | IZ1-471 | HHk11 | BBO10 | H | H | H |
IZ1-432 | CHM | BBO8 | H | H | H | IZ1-472 | HH9 | BB2 | H | H | H |
IZ1-433 | CH | BBO8 | H | H | H | IZ1-473 | HHk7 | BB3 | H | H | H |
IZ1-434 | PH | BBO8 | H | H | H | IZ1-474 | HHk8 | BB4 | H | H | H |
IZ1-435 | BZ | BBO8 | H | H | H | IZ1-475 | HHe4 | BB5 | H | H | H |
IZ1-436 | EOE | BBO8 | H | H | H | IZ1-476 | HHa2 | BB7 | H | H | H |
IZ1-437 | ALL | BBO8 | H | H | H | IZ1-477 | HHj10 | BB9 | H | H | H |
IZ1-438 | HYE | BBO8 | H | H | H | IZ1-478 | HH46 | BB10 | H | H | H |
IZ1-439 | NA1 | BBO8 | H | H | H | IZ1-479 | HHh8 | BB12 | H | H | H |
IZ1-440 | HHk8 | BBO8 | H | H | H | IZ1-480 | HHf5 | BB13 | H | H | H |
IZ1-441 | NA2 | BBO8 | H | H | H | IZ1-481 | HH81 | BB15 | H | H | H |
IZ1-442 | HHk7 | BBO8 | H | H | H | IZ1-482 | HHJ2 | BB16 | H | H | H |
IZ1-443 | HH37 | BBO8 | H | H | H | IZ1-483 | HHk5 | BB17 | H | H | H |
IZ1-444 | HHk6 | BBO8 | H | H | H | IZ1-484 | HH76 | BB18 | H | H | H |
IZ1-445 | NA3 | BBO8 | H | H | H | IZ1-485 | HHJ10 | BB20 | H | H | H |
IZ1-446 | HHJ2 | BBO8 | H | H | H | IZ1-486 | HH13 | BB21 | H | H | H |
IZ1-447 | HHk11 | BBO8 | H | H | H | IZ1-487 | HHJ3 | BB22 | H | H | H |
IZ1-448 | H | BBO10 | H | H | H | IZ1-488 | HHj19 | BB23 | H | H | H |
IZ1-449 | Me | BBO10 | H | H | H | IZ1-489 | NA1 | BB24 | H | H | H |
IZ1-450 | Et | BBO10 | H | H | H | IZ1-490 | HH36 | BB25 | H | H | H |
IZ1-451 | Bu | BBO10 | H | H | H | IZ1-491 | HH49 | BB26 | H | H | H |
IZ1-452 | TBu | BBO10 | H | H | H | IZ1-492 | HH40 | BB27 | H | H | H |
IZ1-453 | Hex | BBO10 | H | H | H | IZ1-493 | NA5 | BB28 | H | H | H |
IZ1-454 | Oct | BBO10 | H | H | H | IZ1-494 | HH37 | BB29 | H | H | H |
IZ1-455 | 2EH | BBO10 | H | H | H | IZ1-495 | HH65 | BB30 | H | H | H |
IZ1-456 | CHM | BBO10 | H | H | H | IZ1-496 | HHj17 | BB31 | H | H | H |
IZ1-457 | CH | BBO10 | H | H | H | IZ1-497 | HH35 | BB32 | H | H | H |
IZ1-458 | PH | BBO10 | H | H | H | IZ1-498 | HH43 | BB33 | H | H | H |
[ Table 13Z1]
TABLE 13Z1
RO1Z1 | Ba1Z1Ba2Z1 | R1Z1 | R6Z1 | R7Z1 | |
IZ1-499 | HHg2 | BB34 | H | H | H |
IZ1-500 | HHJ4 | BB35 | H | H | H |
IZ1-501 | NA4 | BB36 | H | H | H |
IZ1-502 | HHc1 | BB38 | H | H | H |
IZ1-503 | HHk4 | BB39 | H | H | H |
IZ1-504 | HHk1 | BB40 | H | H | H |
IZ1-505 | HHk3 | BB41 | H | H | H |
IZ1-506 | HHf14 | BB42 | H | H | H |
IZ1-507 | HH34 | BB43 | H | H | H |
IZ1-508 | HHi11 | BB44 | H | H | H |
IZ1-509 | HHh1 | BB45 | H | H | H |
IZ1-510 | HH83 | BB46 | H | H | H |
IZ1-511 | HH78 | BB47 | H | H | H |
IZ1-512 | NA2 | BB48 | H | H | H |
IZ1-513 | HHd6 | BB49 | H | H | H |
IZ1-514 | HH61 | BB50 | H | H | H |
IZ1-515 | HH80 | BB51 | H | H | H |
IZ1-516 | HH28 | BB52 | H | H | H |
IZ1-517 | NA3 | BB53 | H | H | H |
IZ1-518 | HHf11 | BB54 | H | H | H |
IZ1-519 | HH55 | BB55 | H | H | H |
IZ1-520 | HH69 | BB56 | H | H | H |
IZ1-521 | HHk11 | BB57 | H | H | H |
IZ1-522 | HHh4 | BB59 | H | H | H |
IZ1-523 | HHk6 | BB60 | H | H | H |
IZ1-524 | HHb3 | BBI1 | H | H | H |
IZ1-525 | HH58 | BBD1 | H | H | H |
IZ1-526 | HHf1 | BBK2 | H | H | H |
IZ1-527 | HH22 | BBK3 | H | H | H |
IZ1-528 | HHg1 | BBK4 | H | H | H |
IZ1-529 | HHg5 | BBK14 | H | H | H |
For example, the compound IZ1-1 is a compound represented by the formula (IZ 1-1).
As a compound of formula (I) Z1,
preferably a compound IZ1-1 to a compound IZ1-171, a compound IZ1-258 to a compound IZ1-529, more preferably a compound IZ1-1 to a compound IZ1-171, a compound IZ1-258 to a compound IZ1-471,
the compound IZ1-1 to the compound IZ1-171 are more preferable, the compound IZ1-1 to the compound IZ1-111 are still more preferable, the compound IZ1-1 to the compound IZ1-54 are particularly preferable, and the compound IZ1-2 to the compound IZ1-3, the compound IZ1-20 to the compound IZ1-21 and the compound IZ1-38 to the compound IZ1-39 are particularly preferable.
Specific examples of the compound IZ1 include compounds represented by table 1Z1, table 2Z1, table 3Z1, table 4Z1, table 5Z1, table 6Z1, table 7Z1, table 10Z1, table 11Z1, table 12Z1, and table 13Z1 in which 1 to 3 hydrogen atoms contained in the compound are replaced by — SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ1-1 of Table 1Z1 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ1-1 of Table 1Z1 is substituted.
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-171, the compound IZ1-258 to the compound IZ1-5293M or-CO2More preferably, the compound of M is a compound in which 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-171, the compound IZ1-258 to the compound IZ1-4313M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-1713M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-1113M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ1-1 to the compound IZ1-543M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ1-2 to the compound IZ1-3, the compound IZ1-20 to the compound IZ1-21, and the compound IZ1-38 to the compound IZ1-393M or-CO2M, or a salt thereof.
As the compound (IZ1), the following compounds are preferable: in the formula (IZ1), RO1Z1Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z1Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO 3M or-CO2M,R2Z1~R5Z1Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z1)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,
R102Z1Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RO1Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z1is a hydrogen atom, and is a hydrogen atom,
R2Z1~R5Z1each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z1)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z1、-O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1Are the same radicals, are hydrogenAtoms, or may have radicals selected from-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R102Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO 3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RO1Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z1is a hydrogen atom, and is a hydrogen atom,
R2Z1~R5Z1each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z1)2Nitro, trifluoromethyl, -O-R102Z1、-SO3M or-CO2M,
R6Z1And R7Z1The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z1is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
m is a hydrogen atom or an alkali metal atom.
For compound IZ1, R1Z1In the case of a hydrogen atom, the compound represented by the formula (pt1Z1) (hereinafter, may be referred to as phthalonitrile (phthalonitrile) compound) may be reacted with the compound represented by the formula (pt2Z1) (hereinafter, may be referred to as alkoxide (alkoxide) compound), and then, the compound represented by the formula (pt3Z1) and the compound represented by the formula (pt4Z1) may be further reacted in the presence of an acid. In addition, R1Z1When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z1) to produce a compound IZ 1.
In [ formula (pt1Z1), formula (pt2Z1), formula (pt3Z1), formula (pt4Z1), formula (pt5Z1) and formula (IZ1), RO1Z1、R1Z1、R2Z1、R3Z1、R4Z1、R5Z1、R6Z1And R7Z1The same meanings as described above are indicated. R14Z1Represents an alkyl group having 1 to 20 carbon atoms. M1Z1Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z1Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z1Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z1 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z1, and the compound pt4Z1 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z1 used, relative to R1Z1The amount of the compound IZ11 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
In addition, when the compound pt5Z1 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z1The amount of the compound IZ11 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
In addition, the reaction of the compound pt5Z1 can be generally carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z1The amount of the compound IZ 11 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z1 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ1 having no sulfo group or-SO3M22In the case of (3), the compound IZ1 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M2。
M22Represents an alkali metal atom.
As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 11 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 11 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 11 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ1 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 1. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ2 >)
Compound IZ2 is a compound represented by formula (IZ 2).
[ in the formula (IZ2),
RCO1Z2and RCO2Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2。
RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Each of which may be bonded to each other to form a ring. R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The number of carbon atoms of the optionally substituted hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, particularly preferably 1 to 10, and particularly preferably 1 to 5.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentylBranched alkyl groups such as a tert-pentyl group, a (1-methyl) pentyl group, a (2-methyl) pentyl group, a (1-ethyl) pentyl group, a (3-ethyl) pentyl group, an isohexyl group, a (5-methyl) hexyl group, a (2-ethyl) hexyl group, and a (3-ethyl) heptyl group; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl group, and the like are particularly preferable, Cyclohexyl, cycloheptyl, cyclooctyl.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2As the group represented, a group obtained by combining the above-mentioned hydrocarbon groups (for example, a chain hydrocarbon group and an alicyclic hydrocarbon group) may be mentionedExamples of the alkyl group include an alkyl group to which 1 or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, and a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formulae;
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, and N, N-phenylmethylsulfamoyl);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3Or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereofA group derived from a percarboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereofA group derived from a percarboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom;
-CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof;
a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a hydroxyl group; fluorine atom, chlorine atom, bromine atom;
-CO2m (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group;
a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like. The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a group obtained by combining the hydrocarbon groups listed above, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1Z2~R5Z22 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z2~R5Z2The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group represented may have a substituent. Examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The preferable examples of the substituents which the hydrocarbon group may have are the same. As RO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2Of (a) is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z2Examples thereof include a formyl group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, or a halogen group (preferably 1 to 20 carbon atoms) is bonded to a group represented by the above formula or the like (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, or a halogen group is bonded to a group represented by the above formula)Chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like) and a carbonyl group (having 2 to 41 carbon atoms when the carbonyl group is an acyl group) corresponding to-CO-R in the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2102Z2Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2 correspond to-CO-R 102Z2And the like.
as-COO-R101Z2Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-COO-R.101Z2Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 which correspond to-COO-R101Z2And the like.
as-OCO-R102Z2Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy A carbonyloxy group (having 2 to 41 carbon atoms when the carbonyloxy group is an acyloxy group) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded to a group represented by the above chemical formula, or the like, and a compound represented by table 1Z2 to table 22Z2 and table 27Z2 to table 37Z2 corresponds to-OCO-R102Z2Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 corresponds to-OCO-R102Z2And the like.
as-COCO-R102Z2Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, an oxalyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded, such as decyl oxalyl group, undecyloxalyl group, dodecyl oxalyl group, eicosyl oxalyl group, cyclopentyl oxalyl group, cyclohexyl oxalyl group, phenyl oxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to — COCO — R. 102Z2And the like.
as-O-R102Z2Examples of the group include a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxyA group, an eicosyloxy group, a 1-phenylethoxy group, a 1-methyl-1-phenylethoxy group, a phenyloxy group, a 2, 3-dimethylphenyloxy group, a 2, 4-dimethylphenyloxy group, a 2, 5-dimethylphenyloxy group, a 2, 6-dimethylphenyloxy group, a 3, 4-dimethylphenyloxy group, a 3, 5-dimethylphenyloxy group, a 2, 2-dicyanophenyloxy group, a 2, 3-dicyanophenyloxy group, a 2, 4-dicyanophenyloxy group, a 2, 5-dicyanophenyloxy group, a 2, 6-dicyanophenyloxy group, a 3, 4-dicyanophenyloxy group, a 3, 5-dicyanophenyloxy group, a 4-methoxyphenyloxy group, a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a, An oxy group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula, and compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-O-R 102Z2Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, which correspond to-O-R102Z2And the like.
as-SO2-R101Z2Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl group, decyl sulfonyl group, undecyl sulfonyl group, dodecyl sulfonyl group, eicosyl sulfonyl group, phenyl sulfonyl group, p-tolyl sulfonyl group, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (a derivative thereof such as carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octyl sulfamoyl group) is bonded, such as the group represented by the above chemical formula), and-SO corresponds to the compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z 2.2-R101Z2Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO 2-R101Z2And the like.
as-SO2N(R102Z2)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl substituted with a raw group (e.g., a group derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), etc.), and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO2NH(R102Z2X)(R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.; n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl Sulfamoyl groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl groups, sulfo groups, nitro groups, hydroxyl groups, halogens (preferably chlorine atoms), alkylsulfamoyl groups having 1 to 10 carbon atoms (preferably octylsulfamoyl groups), and the like, such as a group represented by the above chemical formula, N-undecylmethylsulfamoyl group, N-dodecylmethylsulfamoyl group, N-eicosylmethylsulfamoyl group, N-phenylmethylsulfamoyl group, N-diphenylsulfamoyl group, and the like, and the sulfamoyl groups corresponding to-SO-in the compounds represented by tables 1Z2 to 22Z2 and 27Z2 to 37Z2, and the like2N(R102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-SO2N(R102Z2)2And the like.
as-CON (R)102Z2)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, Carbamoyl groups substituted with a 1-40 (preferably 1-20) carbon hydrocarbon group or a derivative thereof (e.g., a derivative derived from a carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), 1-10 carbon alkylsulfamoyl group (preferably octylsulfamoyl group)), such as the group represented by the above formula, and The compounds shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-CONH (R)102Z2X) (wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and a compound represented by any one of tables 1Z2 to 22Z2, 27Z2 to 37Z2, wherein-CON (R) is the equivalent of 102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z2 to 22Z2 and 27Z2 to 37Z2 which corresponds to-CON (R)102Z2)2And the like.
as-N (R)102Z2)2Examples thereof include:
an amino group;
a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, wherein the compound corresponds to-NH (R 102Z2X) (wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, amino groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), such as N-dinonylamino, N-decylmethylamino, N-undecylmethylamino, N-dodecylmethylamino, N-eicosylmethylamino, N-phenylmethylamino, N-diphenylamino and the like, and groups represented by the above chemical formulae, and amino groups represented by the above formulae, and tables 1Z2 to 22Z2 and 27Z 2 2 to the compounds shown in Table 37Z2 corresponding to-N (R)102Z2X)2(wherein, R102Z2XIs not a hydrogen atom, other than, and R102Z2The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2, which correspond to-N (R)102Z2)2And the like.
as-NHCO-R102Z2Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (for example, in the case where the carbonylamino is an acylamino group, the carbon number is 1 to 40), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as a group represented by the above formula) and carbonylamino groups having 1 to 40 carbon atoms among the compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2 correspond to-NHCO- R 102Z2And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2, which correspond to-NHCO-R102Z2And the like.
as-NHCON (R)102Z2)2Examples thereof include the groups listed above and the compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2 which correspond to-NHCON (R)102Z2)2And the like.
as-NHCOOR102Z2Examples thereof include the groups listed above and those shown in tables 1Z2 to 22Z2 and tables 27Z2 to 37Z2Corresponding to-NHCOOR in the compound102Z2And the like.
as-OCON (R)102Z2)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z2 to 22Z2 and 27Z2 to 37Z2102Z2)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z2、-COO-R102Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R102Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCON(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 2). As R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z2And R3Z2、R3Z2And R4Z2And R4Z2And R5Z2In the case of forming a ring, the ring may have a substituent. Examples of the substituent include O1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeO1Z2、RN1Z2、RN2Z2、R1Z2、R2Z2、R3Z2、R4Z2、R5Z2、R101Z2And R102Z2The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z2And R4Z2When forming a ring, as R2Z2And R5Z2Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z2And R3Z2When a ring is formed, R is preferably4Z2And R5Z2Does not form a ring, more preferably R4Z2And R5Z2Is a hydrogen atom.
R4Z2And R5Z2When a ring is formed, R is preferably2Z2And R3Z2Does not form a ring, more preferably R2Z2And R3Z2Is a hydrogen atom. R1Z2Preferably a hydrogen atom. RO1Z2The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
RN1Z2And RN2Z2Preferably a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2、-N(R102Z2)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group. In addition, R N1Z2And RN2Z2The groups may be the same or different, but preferably the same.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z2、R3Z2、R4Z2、R5Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z2And R3Z2、R3Z2And R4Z2Or R4Z2And R5Z2Form a ring.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z2、R3Z2、R4Z2、R5Z2At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z2、-O-R102Z2、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and further preferably a nitro group or a tert-butyl group. Among them, R is more preferable3Z2Is nitro or tert-butyl, R2Z2、R4Z2And R5Z2Is a hydrogen atom; or, R2Z2、R3Z2And R5Z2Is a hydrogen atom, R4Z2Is nitro or tert-butyl.
The compound IZ2 is preferably a compound represented by the formula (IZ2-B) (hereinafter, may be referred to as a compound IZ 2-B.). When the compound IZ2 is the compound IZ2-B, the phase difference value of the color filter formed from the colored composition containing the compound IZ2-B becomes smaller.
[ formula (IZ2-B) wherein RCO11Z2And RCO21Z2Independently of one another represent-O-RO1Z2or-NRN1Z2RN2Z2,RCO11Z2And RCO21Z2At least one of which is-NRN1Z2RN2Z2。
RN1Z2、RN2Z2、R1Z2、R21Z2、R31Z2、R41Z2、R51Z2Independently of one another, represents a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2Each of which may be bonded to each other to form a ring, R21Z2、R31Z2、R41Z2And R51Z2At least one of which is-CO-R102Z2、-COO-R101Z2、-OCO-R102Z2、-COCO-R102Z2、-O-R102Z2、-SO2-R101Z2、-SO2N(R102Z2)2、-CON(R102Z2)2、-N(R102Z2)2、-NHCO-R102Z2、-NHCO-N(R102Z2)2、-NHCOOR102Z2、-OCON(R102Z2)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z2And R31Z2、R31Z2And R41Z2And R41Z2And R51Z2At least one group of them is bonded to form a ring.
R101Z2The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. RO1Z2And R102Z2Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
RO1Z2、RN1Z2、RN2Z2、R101Z2、R102Z2And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
As R in the formula (IZ2-B)CO11Z2、RCO21Z2、R21Z2、R31Z2、R41Z2And R51Z2Examples thereof include the compounds represented by the formula (IZ2) and RCO1Z2、RCO2Z2、R2Z2、R3Z2、R4Z2And R5Z2The same example.
As preferred R in the formula (IZ2-B)CO11Z2、RCO21Z2、R21Z2、R31Z2、R41Z2And R51Z2Examples thereof include the compounds represented by the formula (IZ2) and RCO1Z2、RCO2Z2、R2Z2、R3Z2、R4Z2And R5Z2The same preferred examples as those of (1).
In the formula (IZ2-B), R is1Z2Preferably a hydrogen atom.
In the formula (IZ2-B), RO1Z2The hydrocarbon group is preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, and particularly preferably a hydrogen atom, a methyl group or an ethyl group.
RN1Z2And RN2Z2Preferably a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2、-N(R102Z2)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more particularly preferably a hydrogen atom, a methyl group, an ethyl group or a phenyl group, and most preferably a hydrogen atom, a methyl group or an ethyl group. In addition, RN1Z2And RN2Z2The groups may be the same or different, but preferably the same.
In the formula (IZ2-B), R is preferably R from the viewpoint of reducing the retardation value of the color filter formed of the colored composition21Z2、R31Z2、R41Z2And R51Z2At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z2、-O-R102Z2、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Among them, R is more preferable31Z2Is nitro or tert-butyl, R21Z2、R41Z2And R51Z2Is a hydrogen atom; or, R21Z2、R31Z2And R51Z2Is a hydrogen atom, R41Z2Is nitro or tert-butyl.
Specific examples of the compound IZ2 include, for example,
examples of the compound of formula (IaZ2) include compounds IaZ2-1 to IaZ2-494 and alkali metal salts thereof each having a substituent shown in table 1Z2, table 2Z2, table 3Z2, table 4Z2, table 5Z2, table 6Z2, table 27Z2, table 28Z2, table 29Z2 and table 30Z 2;
in formula (IbZ2), examples of compounds IbZ2-1 to IbZ2-840 or alkali metal salts thereof having a substituent shown in table 7Z2, table 8Z2, table 9Z2, table 10Z2, table 11Z2, table 12Z2, table 13Z2, table 14Z2, table 31Z2, table 32Z2, table 33Z2, table 34Z2, table 35Z2, table 36Z2, and table 37Z 2;
in formula (IcZ2), compounds IcZ2-1 to IcZ2-296 having a substituent shown in table 15Z2, table 16Z2, table 17Z2, table 18Z2, table 19Z2, table 20Z2, table 21Z2, and table 22Z2, or an alkali metal salt thereof are mentioned.
Ba1Z2Ba2Z2The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB1) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa) a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z2And Ba2Z2Each represents a chemical bond, Ba1Z2B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z2To be B2The chemical bond of (a); b isa1Z2B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)2When a chemical bond of (A) is present, Ba2Z2To be B1The chemical bond of (1).
As Ba1Z2Ba2Z2Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Each symbol in table 1Z2, table 2Z2, table 3Z2, table 4Z2, table 5Z2, table 6Z2, table 7Z2, table 8Z2, table 9Z2, table 10Z2, table 11Z2, table 12Z2, table 13Z2, table 14Z2, table 15Z2, table 16Z2, table 17Z2, table 18Z2, table 19Z2, table 20Z2, table 21Z2, table 22Z2, table 27Z2, table 28Z2, table 29Z2, table 30Z2, table 31Z2, table 32Z2, table 33Z2, table 34Z2, table 35Z2, table 36Z2, and table 37Z2 represents a partial structure below. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, and "EOE" represents a-CH group 2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3"CBA" means-CO2H, "CBM" denotes-CONH2"NH 2" means-NH2Denotes a bond.
In the table, a partial structure represented by the following formula is represented by a symbol.
[ Table 1Z2]
TABLE 1Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-1 | H | H | BB1 | H |
IaZ2-2 | Me | Me | BB1 | H |
IaZ2-3 | Et | Et | BB1 | H |
IaZ2-4 | Bu | Bu | BB1 | H |
IaZ2-5 | TBu | TBu | BB1 | H |
IaZ2-6 | Hex | Hex | BB1 | H |
IaZ2-7 | Oct | Oct | BB1 | H |
IaZ2-8 | 2EH | 2EH | BB1 | H |
IaZ2-9 | CHM | CHM | BB1 | H |
IaZ2-10 | CH | CH | BB1 | H |
IaZ2-11 | PH | PH | BB1 | H |
IaZ2-12 | BZ | BZ | BB1 | H |
IaZ2-13 | NPR | NPR | BB1 | H |
IaZ2-14 | IPR | IPR | BB1 | H |
IaZ2-15 | IBu | IBu | BB1 | H |
IaZ2-16 | EOE | EOE | BB1 | H |
IaZ2-17 | ALL | ALL | BB1 | H |
IaZ2-18 | HYE | HYE | BB1 | H |
IaZ2-19 | H | H | BB6 | H |
IaZ2-20 | Me | Me | BB6 | H |
IaZ2-21 | Et | Et | BB6 | H |
IaZ2-22 | Bu | Bu | BB6 | H |
IaZ2-23 | TBu | TBu | BB6 | H |
IaZ2-24 | Hex | Hex | BB6 | H |
IaZ2-25 | Oct | Oct | BB6 | H |
IaZ2-26 | 2EH | 2EH | BB6 | H |
IaZ2-27 | CHM | CHM | BB6 | H |
IaZ2-28 | CH | CH | BB6 | H |
IaZ2-29 | PH | PH | BB6 | H |
IaZ2-30 | BZ | BZ | BB6 | H |
IaZ2-31 | NPR | NPR | BB6 | H |
IaZ2-32 | IPR | IPR | BB6 | H |
IaZ2-33 | IBu | IBu | BB6 | H |
IaZ2-34 | EOE | EOE | BB6 | H |
IaZ2-35 | ALL | ALL | BB6 | H |
IaZ2-36 | HYE | HYE | BB6 | H |
IaZ2-37 | H | H | BB19 | H |
IaZ2-38 | Me | Me | BB19 | H |
IaZ2-39 | Et | Et | BB19 | H |
IaZ2-40 | Bu | Bu | BB19 | H |
[ Table 2Z2]
TABLE 2Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-41 | TBu | TBu | BB19 | H |
IaZ2-42 | Hex | Hex | BB19 | H |
IaZ2-43 | Oct | Oct | BB19 | H |
IaZ2-44 | 2EH | 2EH | BB19 | H |
IaZ2-45 | CHM | CHM | BB19 | H |
IaZ2-46 | CH | CH | BB19 | H |
IaZ2-47 | PH | PH | BB19 | H |
IaZ2-48 | BZ | BZ | BB19 | H |
IaZ2-49 | NPR | NPR | BB19 | H |
IaZ2-50 | IPR | IPR | BB19 | H |
IaZ2-51 | IBu | IBu | BB19 | H |
IaZ2-52 | EOE | EOE | BB19 | H |
IaZ2-53 | ALL | ALL | BB19 | H |
IaZ2-54 | HYE | HYE | BB19 | H |
IaZ2-55 | H | H | BB2 | H |
IaZ2-56 | Me | Me | BB3 | H |
IaZ2-57 | Et | Et | BB4 | H |
IaZ2-58 | Bu | Bu | BB5 | H |
IaZ2-59 | TBu | TBu | BB7 | H |
IaZ2-60 | Hex | Hex | BB8 | H |
IaZ2-61 | Oct | Oct | BB9 | H |
IaZ2-62 | 2EH | 2EH | BB10 | H |
IaZ2-63 | CHM | CHM | BB11 | H |
IaZ2-64 | CH | CH | BB12 | H |
IaZ2-65 | PH | PH | BB13 | H |
IaZ2-66 | BZ | BZ | BB14 | H |
IaZ2-67 | NPR | NPR | BB15 | H |
IaZ2-68 | IPR | IPR | BB16 | H |
IaZ2-69 | IBu | IBu | BB17 | H |
IaZ2-70 | EOE | EOE | BB18 | H |
IaZ2-71 | ALL | ALL | BB20 | H |
IaZ2-72 | HYE | HYE | BB21 | H |
IaZ2-73 | H | H | BB22 | H |
IaZ2-74 | Me | Me | BB23 | H |
IaZ2-75 | Et | Et | BB24 | H |
IaZ2-76 | Bu | Bu | BB25 | H |
IaZ2-77 | TBu | TBu | BB26 | H |
IaZ2-78 | Hex | Hex | BB27 | H |
IaZ2-79 | Oct | Oct | BB28 | H |
IaZ2-80 | 2EH | 2EH | BB29 | H |
[ Table 3Z2]
TABLE 3Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-81 | CHM | CHM | BB30 | H |
IaZ2-82 | CH | CH | BB31 | H |
IaZ2-83 | PH | PH | BB32 | H |
IaZ2-84 | BZ | BZ | BB33 | H |
IaZ2-85 | NPR | NPR | BB34 | H |
IaZ2-86 | IPR | IPR | BB35 | H |
IaZ2-87 | IBu | IBu | BB36 | H |
IaZ2-88 | EOE | EOE | BB37 | H |
IaZ2-89 | ALL | ALL | BB38 | H |
IaZ2-90 | HYE | HYE | BB39 | H |
IaZ2-91 | H | H | BB40 | H |
IaZ2-92 | Me | Me | BB41 | H |
IaZ2-93 | Et | Et | BB42 | H |
IaZ2-94 | Bu | Bu | BB43 | H |
IaZ2-95 | TBu | TBu | BB44 | H |
IaZ2-96 | Hex | Hex | BB45 | H |
IaZ2-97 | Oct | Oct | BB46 | H |
IaZ2-98 | 2EH | 2EH | BB47 | H |
IaZ2-99 | CHM | CHM | BB48 | H |
IaZ2-100 | CH | CH | BB49 | H |
IaZ2-101 | PH | PH | BB50 | H |
IaZ2-102 | BZ | BZ | BB51 | H |
IaZ2-103 | NPR | NPR | BB52 | H |
IaZ2-104 | IPR | IPR | BB53 | H |
IaZ2-105 | IBu | IBu | BB54 | H |
IaZ2-106 | EOE | EOE | BB55 | H |
IaZ2-107 | ALL | ALL | BB56 | H |
IaZ2-108 | HYE | HYE | BB57 | H |
IaZ2-109 | H | H | BB58 | H |
IaZ2-110 | Me | Me | BB59 | H |
IaZ2-111 | Et | Et | BB60 | H |
IaZ2-112 | H | HYE | BB1 | H |
IaZ2-113 | Me | H | BB1 | H |
IaZ2-114 | Et | Me | BB1 | H |
IaZ2-115 | Bu | Et | BB1 | H |
IaZ2-116 | TBu | Bu | BB1 | H |
IaZ2-117 | Hex | TBu | BB1 | H |
IaZ2-118 | Oct | Hex | BB1 | H |
IaZ2-119 | 2EH | Oct | BB1 | H |
IaZ2-120 | CHM | 2EH | BB1 | H |
[ Table 4Z2]
TABLE 4Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-121 | CH | CHM | BB1 | H |
IaZ2-122 | PH | CH | BB1 | H |
IaZ2-123 | BZ | PH | BB1 | H |
IaZ2-124 | NPR | BZ | BB1 | H |
IaZ2-125 | IPR | NPR | BB1 | H |
IaZ2-126 | IBu | IPR | BB1 | H |
IaZ2-127 | EOE | IBu | BB1 | H |
IaZ2-128 | ALL | EOE | BB1 | H |
IaZ2-129 | HYE | ALL | BB1 | H |
IaZ2-130 | H | BZ | BB6 | H |
IaZ2-131 | Me | NPR | BB6 | H |
IaZ2-132 | Et | Me | BB6 | H |
IaZ2-133 | Bu | IBu | BB6 | H |
IaZ2-134 | TBu | EOE | BB6 | H |
IaZ2-135 | Hex | ALL | BB6 | H |
IaZ2-136 | Oct | HYE | BB6 | H |
IaZ2-137 | 2EH | H | BB6 | H |
IaZ2-138 | CHM | IPR | BB6 | H |
IaZ2-139 | CH | Et | BB6 | H |
IaZ2-140 | PH | Bu | BB6 | H |
IaZ2-141 | BZ | TBu | BB6 | H |
IaZ2-142 | NPR | Hex | BB6 | H |
IaZ2-143 | IPR | Oct | BB6 | H |
IaZ2-144 | IBu | 2EH | BB6 | H |
IaZ2-145 | EOE | CHM | BB6 | H |
IaZ2-146 | ALL | CH | BB6 | H |
IaZ2-147 | HYE | PH | BB6 | H |
IaZ2-148 | H | Oct | BB19 | H |
IaZ2-149 | Me | Et | BB19 | H |
IaZ2-150 | Et | CHM | BB19 | H |
IaZ2-151 | Bu | CH | BB19 | H |
IaZ2-152 | TBu | PH | BB19 | H |
IaZ2-153 | Hex | BZ | BB19 | H |
IaZ2-154 | Oct | 2EH | BB19 | H |
IaZ2-155 | 2EH | IPR | BB19 | H |
IaZ2-156 | CHM | IBu | BB19 | H |
IaZ2-157 | CH | EOE | BB19 | H |
IaZ2-158 | PH | ALL | BB19 | H |
IaZ2-159 | BZ | HYE | BB19 | H |
IaZ2-160 | NPR | H | BB19 | H |
[ Table 5Z2]
TABLE 5Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-161 | IPR | Me | BB19 | H |
IaZ2-162 | IBu | NPR | BB19 | H |
IaZ2-163 | EOE | Bu | BB19 | H |
IaZ2-164 | ALL | TBu | BB19 | H |
IaZ2-165 | HYE | Hex | BB19 | H |
IaZ2-166 | H | EOE | BB2 | H |
IaZ2-167 | Me | ALL | BB3 | H |
IaZ2-168 | Et | HYE | BB4 | H |
IaZ2-169 | Bu | H | BB5 | H |
IaZ2-170 | TBu | Me | BB7 | H |
IaZ2-171 | Hex | Et | BB8 | H |
IaZ2-172 | Oct | Bu | BB9 | H |
IaZ2-173 | 2EH | TBu | BB10 | H |
IaZ2-174 | CHM | Hex | BB11 | H |
IaZ2-175 | CH | Oct | BB12 | H |
IaZ2-176 | PH | 2EH | BB13 | H |
IaZ2-177 | BZ | CHM | BB14 | H |
IaZ2-178 | NPR | CH | BB15 | H |
IaZ2-179 | IPR | PH | BB16 | H |
IaZ2-180 | IBu | BZ | BB17 | H |
IaZ2-181 | EOE | NPR | BB18 | H |
IaZ2-182 | ALL | IPR | BB20 | H |
IaZ2-183 | HYE | IBu | BB21 | H |
IaZ2-184 | H | TBu | BB22 | H |
IaZ2-185 | Me | Hex | BB23 | H |
IaZ2-186 | Et | Oct | BB24 | H |
IaZ2-187 | Bu | 2EH | BB25 | H |
IaZ2-188 | TBu | CHM | BB26 | H |
IaZ2-189 | Hex | CH | BB27 | H |
IaZ2-190 | Oct | PH | BB28 | H |
IaZ2-191 | 2EH | BZ | BB29 | H |
IaZ2-192 | CHM | NPR | BB30 | H |
IaZ2-193 | CH | IPR | BB31 | H |
IaZ2-194 | PH | IBu | BB32 | H |
IaZ2-195 | BZ | EOE | BB33 | H |
IaZ2-196 | NPR | ALL | BB34 | H |
IaZ2-197 | IPR | HYE | BB35 | H |
IaZ2-198 | IBu | H | BB36 | H |
IaZ2-199 | EOE | Me | BB37 | H |
IaZ2-200 | ALL | Et | BB38 | H |
[ Table 6Z2]
TABLE 6Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-201 | HYE | Bu | BB39 | H |
IaZ2-202 | H | CHM | BB40 | H |
IaZ2-203 | Me | CH | BB41 | H |
IaZ2-204 | Et | PH | BB42 | H |
IaZ2-205 | Bu | BZ | BB43 | H |
IaZ2-206 | TBu | NPR | BB44 | H |
IaZ2-207 | Hex | IPR | BB45 | H |
IaZ2-208 | Oct | IBu | BB46 | H |
IaZ2-209 | 2EH | EOE | BB47 | H |
IaZ2-210 | CHM | ALL | BB48 | H |
IaZ2-211 | CH | HYE | BB49 | H |
IaZ2-212 | PH | H | BB50 | H |
IaZ2-213 | BZ | Me | BB51 | H |
IaZ2-214 | NPR | Et | BB52 | H |
IaZ2-215 | IPR | Bu | BB53 | H |
IaZ2-216 | IBu | TBu | BB54 | H |
IaZ2-217 | EOE | Hex | BB55 | H |
IaZ2-218 | ALL | Oct | BB56 | H |
IaZ2-219 | HYE | 2EH | BB57 | H |
IaZ2-220 | H | Me | BB58 | H |
IaZ2-221 | Me | Et | BB59 | H |
IaZ2-222 | Et | Bu | BB60 | H |
IaZ2-223 | Me | Me | BB14 | H |
[ Table 7Z2]
TABLE 7Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-1 | H | H | H | H | BB1 | H |
IbZ2-2 | Me | H | Me | H | BB1 | H |
IbZ2-3 | Et | H | Et | H | BB1 | H |
IbZ2-4 | PH | H | PH | H | BB1 | H |
IbZ2-5 | Bu | H | Bu | H | BB1 | H |
IbZ2-6 | TBu | H | TBu | H | BB1 | H |
IbZ2-7 | Hex | H | Hex | H | BB1 | H |
IbZ2-8 | Oct | H | Oct | H | BB1 | H |
IbZ2-9 | 2EH | H | 2EH | H | BB1 | H |
IbZ2-10 | CHM | H | CHM | H | BB1 | H |
IbZ2-11 | CH | H | CH | H | BB1 | H |
IbZ2-12 | BZ | H | BZ | H | BB1 | H |
IbZ2-13 | NPR | H | NPR | H | BB1 | H |
IbZ2-14 | IPR | H | IPR | H | BB1 | H |
IbZ2-15 | IBu | H | IBu | H | BB1 | H |
IbZ2-16 | EOE | H | EOE | H | BB1 | H |
IbZ2-17 | ALL | H | ALL | H | BB1 | H |
IbZ2-18 | NH2 | H | NH2 | H | BB1 | H |
IbZ2-19 | CBM | H | CBM | H | BB1 | H |
IbZ2-20 | COM | H | COM | H | BB1 | H |
IbZ2-21 | COE | H | COE | H | BB1 | H |
IbZ2-22 | CBA | H | CBA | H | BB1 | H |
IbZ2-23 | HYE | H | HYE | H | BB1 | H |
IbZ2-24 | Me | Me | Me | Me | BB1 | H |
IbZ2-25 | Et | Et | Et | Et | BB1 | H |
IbZ2-26 | PH | PH | PH | PH | BB1 | H |
IbZ2-27 | Bu | Me | Bu | Me | BB1 | H |
IbZ2-28 | TBu | Et | TBu | Et | BB1 | H |
IbZ2-29 | Hex | NPR | Hex | NPR | BB1 | H |
IbZ2-30 | Oct | IPR | Oct | IPR | BB1 | H |
IbZ2-31 | 2EH | HYE | 2EH | HYE | BB1 | H |
IbZ2-32 | CHM | ALL | CHM | ALL | BB1 | H |
IbZ2-33 | CH | COM | CH | COM | BB1 | H |
IbZ2-34 | BZ | Me | BZ | Me | BB1 | H |
IbZ2-35 | NPR | Et | NPR | Et | BB1 | H |
IbZ2-36 | IPR | NPR | IPR | NPR | BB1 | H |
IbZ2-37 | IBu | IPR | IBu | IPR | BB1 | H |
IbZ2-38 | EOE | HYE | EOE | HYE | BB1 | H |
IbZ2-39 | ALL | ALL | ALL | ALL | BB1 | H |
IbZ2-40 | NH2 | COM | NH2 | COM | BB1 | H |
[ Table 8Z2]
TABLE 8Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-41 | CBM | Me | CBM | Me | BB1 | H |
IbZ2-42 | COM | Et | COM | Et | BB1 | H |
IbZ2-43 | COE | NPR | COE | NPR | BB1 | H |
IbZ2-44 | CBA | IPR | CBA | IPR | BB1 | H |
IbZ2-45 | HYE | HYE | HYE | HYE | BB1 | H |
IbZ2-46 | Bu | Bu | Bu | Bu | BB1 | H |
IbZ2-47 | TBu | TBu | TBu | TBu | BB1 | H |
IbZ2-48 | Hex | Hex | Hex | Hex | BB1 | H |
IbZ2-49 | Oct | Oct | Oct | Oct | BB1 | H |
IbZ2-50 | 2EH | 2EH | 2EH | 2EH | BB1 | H |
IbZ2-51 | CHM | CHM | CHM | CHM | BB1 | H |
IbZ2-52 | CH | CH | CH | CH | BB1 | H |
IbZ2-53 | BZ | BZ | BZ | BZ | BB1 | H |
IbZ2-54 | NPR | NPR | NPR | NPR | BB1 | H |
IbZ2-55 | IPR | IPR | IPR | IPR | BB1 | H |
IbZ2-56 | IBu | IBu | IBu | IBu | BB1 | H |
IbZ2-57 | EOE | EOE | EOE | EOE | BB1 | H |
IbZ2-58 | NH2 | NH2 | NH2 | NH2 | BB1 | H |
IbZ2-59 | CBM | CBM | CBM | CBM | BB1 | H |
IbZ2-60 | COM | COM | COM | COM | BB1 | H |
IbZ2-61 | COE | COE | COE | COE | BB1 | H |
IbZ2-62 | CBA | CBA | CBA | CBA | BB1 | H |
IbZ2-63 | H | H | H | H | BB6 | H |
IbZ2-64 | Me | H | Me | H | BB6 | H |
IbZ2-65 | Et | H | Et | H | BB6 | H |
IbZ2-66 | PH | H | PH | H | BB6 | H |
IbZ2-67 | Bu | H | Bu | H | BB6 | H |
IbZ2-68 | TBu | H | TBu | H | BB6 | H |
IbZ2-69 | Hex | H | Hex | H | BB6 | H |
IbZ2-70 | Oct | H | Oct | H | BB6 | H |
IbZ2-71 | 2EH | H | 2EH | H | BB6 | H |
IbZ2-72 | CHM | H | CHM | H | BB6 | H |
IbZ2-73 | CH | H | CH | H | BB6 | H |
IbZ2-74 | BZ | H | BZ | H | BB6 | H |
IbZ2-75 | NPR | H | NPR | H | BB6 | H |
IbZ2-76 | IPR | H | IPR | H | BB6 | H |
IbZ2-77 | IBu | H | IBu | H | BB6 | H |
IbZ2-78 | EOE | H | EOE | H | BB6 | H |
IbZ2-79 | ALL | H | ALL | H | BB6 | H |
IbZ2-80 | NH2 | H | NH2 | H | BB6 | H |
[ Table 9Z2]
TABLE 9Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-81 | CBM | H | CBM | H | BB6 | H |
IbZ2-82 | COM | H | COM | H | BB6 | H |
IbZ2-83 | COE | H | COE | H | BB6 | H |
IbZ2-84 | CBA | H | CBA | H | BB6 | H |
IbZ2-85 | HYE | H | HYE | H | BB6 | H |
IbZ2-86 | Me | Me | Me | Me | BB6 | H |
IbZ2-87 | Et | Et | Et | Et | BB6 | H |
IbZ2-88 | PH | PH | PH | PH | BB6 | H |
IbZ2-89 | Bu | Me | Bu | Me | BB6 | H |
IbZ2-90 | TBu | Et | TBu | Et | BB6 | H |
IbZ2-91 | Hex | NPR | Hex | NPR | BB6 | H |
IbZ2-92 | Oct | IPR | Oct | IPR | BB6 | H |
IbZ2-93 | 2EH | HYE | 2EH | HYE | BB6 | H |
IbZ2-94 | CHM | ALL | CHM | ALL | BB6 | H |
IbZ2-95 | CH | COM | CH | COM | BB6 | H |
IbZ2-96 | BZ | Me | BZ | Me | BB6 | H |
IbZ2-97 | NPR | Et | NPR | Et | BB6 | H |
IbZ2-98 | IPR | NPR | IPR | NPR | BB6 | H |
IbZ2-99 | IBu | IPR | IBu | IPR | BB6 | H |
IbZ2-100 | EOE | HYE | EOE | HYE | BB6 | H |
IbZ2-101 | ALL | ALL | ALL | ALL | BB6 | H |
IbZ2-102 | NH2 | COM | NH2 | COM | BB6 | H |
IbZ2-103 | CBM | Me | CBM | Me | BB6 | H |
IbZ2-104 | COM | Et | COM | Et | BB6 | H |
IbZ2-105 | COE | NPR | COE | NPR | BB6 | H |
IbZ2-106 | CBA | IPR | CBA | IPR | BB6 | H |
IbZ2-107 | HYE | HYE | HYE | HYE | BB6 | H |
IbZ2-108 | Bu | Bu | Bu | Bu | BB6 | H |
IbZ2-109 | TBu | TBu | TBu | TBu | BB6 | H |
IbZ2-110 | Hex | Hex | Hex | Hex | BB6 | H |
IbZ2-111 | Oct | Oct | Oct | Oct | BB6 | H |
IbZ2-112 | 2EH | 2EH | 2EH | 2EH | BB6 | H |
IbZ2-113 | CHM | CHM | CHM | CHM | BB6 | H |
IbZ2-114 | CH | CH | CH | CH | BB6 | H |
IbZ2-115 | BZ | BZ | BZ | BZ | BB6 | H |
IbZ2-116 | NPR | NPR | NPR | NPR | BB6 | H |
IbZ2-117 | IPR | IPR | IPR | IPR | BB6 | H |
IbZ2-118 | IBu | IBu | IBu | IBu | BB6 | H |
IbZ2-119 | EOE | EOE | EOE | EOE | BB6 | H |
IbZ2-120 | NH2 | NH2 | NH2 | NH2 | BB6 | H |
[ Table 10Z2]
TABLE 10Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-121 | CBM | CBM | CBM | CBM | BB6 | H |
IbZ2-122 | COM | COM | COM | COM | BB6 | H |
IbZ2-123 | COE | COE | COE | COE | BB6 | H |
IbZ2-124 | CBA | CBA | CBA | CBA | BB6 | H |
IbZ2-125 | H | H | H | H | BB19 | H |
IbZ2-126 | Me | H | Me | H | BB19 | H |
IbZ2-127 | Et | H | Et | H | BB19 | H |
IbZ2-128 | PH | H | PH | H | BB19 | H |
IbZ2-129 | Bu | H | Bu | H | BB19 | H |
IbZ2-130 | TBu | H | TBu | H | BB19 | H |
IbZ2-131 | Hex | H | Hex | H | BB19 | H |
IbZ2-132 | Oct | H | Oct | H | BB19 | H |
IbZ2-133 | 2EH | H | 2EH | H | BB19 | H |
IbZ2-134 | CHM | H | CHM | H | BB19 | H |
IbZ2-135 | CH | H | CH | H | BB19 | H |
IbZ2-136 | BZ | H | BZ | H | BB19 | H |
IbZ2-137 | NPR | H | NPR | H | BB19 | H |
IbZ2-138 | IPR | H | IPR | H | BB19 | H |
IbZ2-139 | IBu | H | IBu | H | BB19 | H |
IbZ2-140 | EOE | H | EOE | H | BB19 | H |
IbZ2-141 | ALL | H | ALL | H | BB19 | H |
IbZ2-142 | NH2 | H | NH2 | H | BB19 | H |
IbZ2-143 | CBM | H | CBM | H | BB19 | H |
IbZ2-144 | COM | H | COM | H | BB19 | H |
IbZ2-145 | COE | H | COE | H | BB19 | H |
IbZ2-146 | CBA | H | CBA | H | BB19 | H |
IbZ2-147 | HYE | H | HYE | H | BB19 | H |
IbZ2-148 | Me | Me | Me | Me | BB19 | H |
IbZ2-149 | Et | Et | Et | Et | BB19 | H |
IbZ2-150 | PH | PH | PH | PH | BB19 | H |
IbZ2-151 | Bu | Me | Bu | Me | BB19 | H |
IbZ2-152 | TBu | Et | TBu | Et | BB19 | H |
IbZ2-153 | Hex | NPR | Hex | NPR | BB19 | H |
IbZ2-154 | Oct | IPR | Oct | IPR | BB19 | H |
IbZ2-155 | 2EH | HYE | 2EH | HYE | BB19 | H |
IbZ2-156 | CHM | ALL | CHM | ALL | BB19 | H |
IbZ2-157 | CH | COM | CH | COM | BB19 | H |
IbZ2-158 | BZ | Me | BZ | Me | BB19 | H |
IbZ2-159 | NPR | Et | NPR | Et | BB19 | H |
IbZ2-160 | IPR | NPR | IPR | NPR | BB19 | H |
[ Table 11Z2]
TABLE 11Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-161 | IBu | IPR | IBu | IPR | BB19 | H |
IbZ2-162 | EOE | HYE | EOE | HYE | BB19 | H |
IbZ2-163 | ALL | ALL | ALL | ALL | BB19 | H |
IbZ2-164 | NH2 | COM | NH2 | COM | BB19 | H |
IbZ2-165 | CBM | Me | CBM | Me | BB19 | H |
IbZ2-166 | COM | Et | COM | Et | BB19 | H |
IbZ2-167 | COE | NPR | COE | NPR | BB19 | H |
IbZ2-168 | CBA | IPR | CBA | IPR | BB19 | H |
IbZ2-169 | HYE | HYE | HYE | HYE | BB19 | H |
IbZ2-170 | Bu | Bu | Bu | Bu | BB19 | H |
IbZ2-171 | TBu | TBu | TBu | TBu | BB19 | H |
IbZ2-172 | Hex | Hex | Hex | Hex | BB19 | H |
IbZ2-173 | Oct | Oct | Oct | Oct | BB19 | H |
IbZ2-174 | 2EH | 2EH | 2EH | 2EH | BB19 | H |
IbZ2-175 | CHM | CHM | CHM | CHM | BB19 | H |
IbZ2-176 | CH | CH | CH | CH | BB19 | H |
IbZ2-177 | BZ | BZ | BZ | BZ | BB19 | H |
IbZ2-178 | NPR | NPR | NPR | NPR | BB19 | H |
IbZ2-179 | IPR | IPR | IPR | IPR | BB19 | H |
IbZ2-180 | IBu | IBu | IBu | IBu | BB19 | H |
IbZ2-181 | EOE | EOE | EOE | EOE | BB19 | H |
IbZ2-182 | NH2 | NH2 | NH2 | NH2 | BB19 | H |
IbZ2-183 | CBM | CBM | CBM | CBM | BB19 | H |
IbZ2-184 | COM | COM | COM | COM | BB19 | H |
IbZ2-185 | COE | COE | COE | COE | BB19 | H |
IbZ2-186 | CBA | CBA | CBA | CBA | BB19 | H |
IbZ2-187 | H | H | H | H | BB2 | H |
IbZ2-188 | HYE | HYE | HYE | HYE | BB3 | H |
IbZ2-189 | BZ | BZ | BZ | BZ | BB4 | H |
IbZ2-190 | Me | H | Me | H | BB5 | H |
IbZ2-191 | CBA | IPR | CBA | IPR | BB7 | H |
IbZ2-192 | NPR | NPR | NPR | NPR | BB8 | H |
IbZ2-193 | Et | H | Et | H | BB9 | H |
IbZ2-194 | COE | NPR | COE | NPR | BB10 | H |
IbZ2-195 | CH | CH | CH | CH | BB11 | H |
IbZ2-196 | PH | H | PH | H | BB12 | H |
IbZ2-197 | COM | Et | COM | Et | BB13 | H |
IbZ2-198 | IPR | IPR | IPR | IPR | BB14 | H |
IbZ2-199 | Bu | H | Bu | H | BB15 | H |
IbZ2-200 | CBM | Me | CBM | Me | BB16 | H |
[ Table 12Z2]
TABLE 12Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-201 | IBu | IBu | IBu | IBu | BB17 | H |
IbZ2-202 | TBu | H | TBu | H | BB18 | H |
IbZ2-203 | NH2 | COM | NH2 | COM | BB20 | H |
IbZ2-204 | CHM | CHM | CHM | CHM | BB21 | H |
IbZ2-205 | Hex | H | Hex | H | BB22 | H |
IbZ2-206 | ALL | ALL | ALL | ALL | BB23 | H |
IbZ2-207 | EOE | EOE | EOE | EOE | BB24 | H |
IbZ2-208 | Oct | H | Oct | H | BB25 | H |
IbZ2-209 | EOE | HYE | EOE | HYE | BB26 | H |
IbZ2-210 | 2EH | 2EH | 2EH | 2EH | BB27 | H |
IbZ2-211 | 2EH | H | 2EH | H | BB28 | H |
IbZ2-212 | IBu | IPR | IBu | IPR | BB29 | H |
IbZ2-213 | NH2 | NH2 | NH2 | NH2 | BB30 | H |
IbZ2-214 | CHM | H | CHM | H | BB31 | H |
IbZ2-215 | IPR | NPR | IPR | NPR | BB32 | H |
IbZ2-216 | Oct | Oct | Oct | Oct | BB33 | H |
IbZ2-217 | CH | H | CH | H | BB34 | H |
IbZ2-218 | NPR | Et | NPR | Et | BB35 | H |
IbZ2-219 | CBM | CBM | CBM | CBM | BB36 | H |
IbZ2-220 | BZ | H | BZ | H | BB37 | H |
IbZ2-221 | BZ | Me | BZ | Me | BB38 | H |
IbZ2-222 | Hex | Hex | Hex | Hex | BB39 | H |
IbZ2-223 | HYE | H | HYE | H | BB40 | H |
IbZ2-224 | CH | COM | CH | COM | BB41 | H |
IbZ2-225 | COM | COM | COM | COM | BB42 | H |
IbZ2-226 | NPR | H | NPR | H | BB43 | H |
IbZ2-227 | 2EH | HYE | 2EH | HYE | BB44 | H |
IbZ2-228 | IPR | H | IPR | H | BB45 | H |
IbZ2-229 | CHM | ALL | CHM | ALL | BB46 | H |
IbZ2-230 | COE | COE | COE | COE | BB47 | H |
IbZ2-231 | IBu | H | IBu | H | BB48 | H |
IbZ2-232 | Hex | NPR | Hex | NPR | BB49 | H |
IbZ2-233 | EOE | H | EOE | H | BB50 | H |
IbZ2-234 | Oct | IPR | Oct | IPR | BB51 | H |
IbZ2-235 | TBu | TBu | TBu | TBu | BB52 | H |
IbZ2-236 | ALL | H | ALL | H | BB53 | H |
IbZ2-237 | TBu | Et | TBu | Et | BB54 | H |
IbZ2-238 | NH2 | H | NH2 | H | BB55 | H |
IbZ2-239 | Bu | Bu | Bu | Bu | BB56 | H |
IbZ2-240 | CBM | H | CBM | H | BB57 | H |
[ Table 13Z2]
TABLE 13Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-241 | PH | PH | PH | PH | BB58 | H |
IbZ2-242 | COM | H | COM | H | BB59 | H |
IbZ2-243 | Bu | Me | Bu | Me | BB60 | H |
IbZ2-244 | CBA | CBA | CBA | CBA | BB2 | H |
IbZ2-245 | COE | H | COE | H | BB3 | H |
IbZ2-246 | Me | Me | Me | Me | BB4 | H |
IbZ2-247 | CBA | H | CBA | H | BB5 | H |
IbZ2-248 | Et | Et | Et | Et | BB7 | H |
IbZ2-249 | H | H | NPR | Et | BB1 | H |
IbZ2-250 | HYE | HYE | CBM | CBM | BB2 | H |
IbZ2-251 | BZ | BZ | BZ | H | BB3 | H |
IbZ2-252 | Me | H | BZ | Me | BB4 | H |
IbZ2-253 | CBA | IPR | Hex | Hex | BB5 | H |
IbZ2-254 | NPR | NPR | HYE | H | BB6 | H |
IbZ2-255 | Et | H | CH | COM | BB7 | H |
IbZ2-256 | COE | NPR | COM | COM | BB8 | H |
IbZ2-257 | CH | CH | NPR | H | BB9 | H |
IbZ2-258 | PH | H | 2EH | HYE | BB10 | H |
IbZ2-259 | COM | Et | IPR | H | BB11 | H |
IbZ2-260 | IPR | IPR | CHM | ALL | BB12 | H |
IbZ2-261 | Bu | H | COE | COE | BB13 | H |
IbZ2-262 | CBM | Me | IBu | H | BB14 | H |
IbZ2-263 | IBu | IBu | Hex | NPR | BB15 | H |
IbZ2-264 | TBu | H | EOE | H | BB16 | H |
IbZ2-265 | NH2 | COM | Oct | IPR | BB17 | H |
IbZ2-266 | CHM | CHM | TBu | TBu | BB18 | H |
IbZ2-267 | Hex | H | ALL | H | BB19 | H |
IbZ2-268 | ALL | ALL | TBu | Et | BB20 | H |
IbZ2-269 | EOE | EOE | NH2 | H | BB21 | H |
IbZ2-270 | Oct | H | Bu | Bu | BB22 | H |
IbZ2-271 | EOE | HYE | CBM | H | BB23 | H |
IbZ2-272 | 2EH | 2EH | PH | PH | BB24 | H |
IbZ2-273 | 2EH | H | COM | H | BB25 | H |
IbZ2-274 | IBu | IPR | Bu | Me | BB26 | H |
IbZ2-275 | NH2 | NH2 | CBA | CBA | BB27 | H |
IbZ2-276 | CHM | H | COE | H | BB28 | H |
IbZ2-277 | IPR | NPR | Me | Me | BB29 | H |
IbZ2-278 | Oct | Oct | CBA | H | BB30 | H |
IbZ2-279 | CH | H | Et | Et | BB31 | H |
IbZ2-280 | NPR | Et | H | H | BB32 | H |
[ Table 14Z2]
TABLE 14Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IbZ2-281 | CBM | CBM | HYE | HYE | BB33 | H |
IbZ2-282 | BZ | H | BZ | BZ | BB34 | H |
IbZ2-283 | BZ | Me | Me | H | BB35 | H |
IbZ2-284 | Hex | Hex | CBA | IPR | BB36 | H |
IbZ2-285 | HYE | H | NPR | NPR | BB37 | H |
IbZ2-286 | CH | COM | Et | H | BB38 | H |
IbZ2-287 | COM | COM | COE | NPR | BB39 | H |
IbZ2-288 | NPR | H | CH | CH | BB40 | H |
IbZ2-289 | 2EH | HYE | PH | H | BB41 | H |
IbZ2-290 | IPR | H | COM | Et | BB42 | H |
IbZ2-291 | CHM | ALL | IPR | IPR | BB43 | H |
IbZ2-292 | COE | COE | Bu | H | BB44 | H |
IbZ2-293 | IBu | H | CBM | Me | BB45 | H |
IbZ2-294 | Hex | NPR | IBu | IBu | BB46 | H |
IbZ2-295 | EOE | H | TBu | H | BB47 | H |
IbZ2-296 | Oct | IPR | NH2 | COM | BB48 | H |
IbZ2-297 | TBu | TBu | CHM | CHM | BB49 | H |
IbZ2-298 | ALL | H | Hex | H | BB50 | H |
IbZ2-299 | TBu | Et | ALL | ALL | BB51 | H |
IbZ2-300 | NH2 | H | EOE | EOE | BB52 | H |
IbZ2-301 | Bu | Bu | Oct | H | BB53 | H |
IbZ2-302 | CBM | H | EOE | HYE | BB54 | H |
IbZ2-303 | PH | PH | 2EH | 2EH | BB55 | H |
IbZ2-304 | COM | H | 2EH | H | BB56 | H |
IbZ2-305 | Bu | Me | IBu | IPR | BB57 | H |
IbZ2-306 | CBA | CBA | NH2 | NH2 | BB58 | H |
IbZ2-307 | COE | H | CHM | H | BB59 | H |
IbZ2-308 | Me | Me | IPR | NPR | BB60 | H |
IbZ2-309 | CBA | H | Oct | Oct | BB1 | H |
IbZ2-310 | Et | Et | CH | H | BB19 | H |
IbZ2-311 | NA1 | H | NA1 | H | BB1 | H |
IbZ2-312 | NA1 | H | NA1 | H | BB19 | H |
IbZ2-313 | NA2 | H | NA2 | H | BB1 | H |
IbZ2-314 | NA2 | H | NA2 | H | BB19 | H |
IbZ2-315 | NA1 | H | NA1 | H | BBO8 | H |
IbZ2-316 | NA1 | H | NA1 | H | BB8 | H |
[ Table 15Z2]
TABLE 15Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-1 | H | H | H | BB1 | H |
IcZ2-2 | H | Me | H | BB1 | H |
IcZ2-3 | H | Et | H | BB1 | H |
IcZ2-4 | H | PH | H | BB1 | H |
IcZ2-5 | H | NPR | H | BB1 | H |
IcZ2-6 | H | NH2 | H | BB1 | H |
IcZ2-7 | H | CBM | H | BB1 | H |
IcZ2-8 | H | COM | H | BB1 | H |
IcZ2-9 | H | HYE | H | BB1 | H |
IcZ2-10 | H | Me | Me | BB1 | H |
IcZ2-11 | H | Et | Et | BB1 | H |
IcZ2-12 | H | PH | PH | BB1 | H |
IcZ2-13 | H | HYE | HYE | BB1 | H |
IcZ2-14 | Me | H | H | BB1 | H |
IcZ2-15 | Me | Me | H | BB1 | H |
IcZ2-16 | Me | Et | H | BB1 | H |
IcZ2-17 | Me | PH | H | BB1 | H |
IcZ2-18 | Me | NPR | H | BB1 | H |
IcZ2-19 | Me | NH2 | H | BB1 | H |
IcZ2-20 | Me | CBM | H | BB1 | H |
IcZ2-21 | Me | COM | H | BB1 | H |
IcZ2-22 | Me | HYE | H | BB1 | H |
IcZ2-23 | Me | Me | Me | BB1 | H |
IcZ2-24 | Me | Et | Et | BB1 | H |
IcZ2-25 | Me | PH | PH | BB1 | H |
IcZ2-26 | Me | HYE | HYE | BB1 | H |
IcZ2-27 | Et | H | H | BB1 | H |
IcZ2-28 | Et | Me | H | BB1 | H |
IcZ2-29 | Et | Et | H | BB1 | H |
IcZ2-30 | Et | PH | H | BB1 | H |
IcZ2-31 | Et | NPR | H | BB1 | H |
IcZ2-32 | Et | NH2 | H | BB1 | H |
IcZ2-33 | Et | CBM | H | BB1 | H |
IcZ2-34 | Et | COM | H | BB1 | H |
IcZ2-35 | Et | HYE | H | BB1 | H |
IcZ2-36 | Et | Me | Me | BB1 | H |
IcZ2-37 | Et | Et | Et | BB1 | H |
IcZ2-38 | Et | PH | PH | BB1 | H |
IcZ2-39 | Et | HYE | HYE | BB1 | H |
IcZ2-40 | PH | H | H | BB1 | H |
[ Table 16Z2]
TABLE 16Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-41 | PH | Me | H | BB1 | H |
IcZ2-42 | PH | Et | H | BB1 | H |
IcZ2-43 | PH | PH | H | BB1 | H |
IcZ2-44 | PH | NPR | H | BB1 | H |
IcZ2-45 | PH | NH2 | H | BB1 | H |
IcZ2-46 | PH | CBM | H | BB1 | H |
IcZ2-47 | PH | COM | H | BB1 | H |
IcZ2-48 | PH | HYE | H | BB1 | H |
IcZ2-49 | PH | Me | Me | BB1 | H |
IcZ2-50 | PH | Et | Et | BB1 | H |
IcZ2-51 | PH | PH | PH | BB1 | H |
IcZ2-52 | PH | HYE | HYE | BB1 | H |
IcZ2-53 | NPR | H | H | BB1 | H |
IcZ2-54 | NPR | Me | H | BB1 | H |
IcZ2-55 | NPR | Et | H | BB1 | H |
IcZ2-56 | NPR | PH | H | BB1 | H |
IcZ2-57 | NPR | NPR | H | BB1 | H |
IcZ2-58 | NPR | NH2 | H | BB1 | H |
IcZ2-59 | NPR | CBM | H | BB1 | H |
IcZ2-60 | NPR | COM | H | BB1 | H |
IcZ2-61 | NPR | HYE | H | BB1 | H |
IcZ2-62 | NPR | Me | Me | BB1 | H |
IcZ2-63 | NPR | Et | Et | BB1 | H |
IcZ2-64 | NPR | PH | PH | BB1 | H |
IcZ2-65 | NPR | HYE | HYE | BB1 | H |
IcZ2-66 | HYE | H | H | BB1 | H |
IcZ2-67 | HYE | Me | H | BB1 | H |
IcZ2-68 | HYE | Et | H | BB1 | H |
IcZ2-69 | HYE | PH | H | BB1 | H |
IcZ2-70 | HYE | NPR | H | BB1 | H |
IcZ2-71 | HYE | NH2 | H | BB1 | H |
IcZ2-72 | HYE | CBM | H | BB1 | H |
IcZ2-73 | HYE | COM | H | BB1 | H |
IcZ2-74 | HYE | HYE | H | BB1 | H |
IcZ2-75 | HYE | Me | Me | BB1 | H |
IcZ2-76 | HYE | Et | Et | BB1 | H |
IcZ2-77 | HYE | PH | PH | BB1 | H |
IcZ2-78 | HYE | HYE | HYE | BB1 | H |
IcZ2-79 | H | H | H | BB6 | H |
IcZ2-80 | H | Me | H | BB6 | H |
[ Table 17Z2]
TABLE 17Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-81 | H | Et | H | BB6 | H |
IcZ2-82 | H | PH | H | BB6 | H |
IcZ2-83 | H | NPR | H | BB6 | H |
IcZ2-84 | H | NH2 | H | BB6 | H |
IcZ2-85 | H | CBM | H | BB6 | H |
IcZ2-86 | H | COM | H | BB6 | H |
IcZ2-87 | H | HYE | H | BB6 | H |
IcZ2-88 | H | Me | Me | BB6 | H |
IcZ2-89 | H | Et | Et | BB6 | H |
IcZ2-90 | H | PH | PH | BB6 | H |
IcZ2-91 | H | HYE | HYE | BB6 | H |
IcZ2-92 | Me | H | H | BB6 | H |
IcZ2-93 | Me | Me | H | BB6 | H |
IcZ2-94 | Me | Et | H | BB6 | H |
IcZ2-95 | Me | PH | H | BB6 | H |
IcZ2-96 | Me | NPR | H | BB6 | H |
IcZ2-97 | Me | NH2 | H | BB6 | H |
IcZ2-98 | Me | CBM | H | BB6 | H |
IcZ2-99 | Me | COM | H | BB6 | H |
IcZ2-100 | Me | HYE | H | BB6 | H |
IcZ2-101 | Me | Me | Me | BB6 | H |
IcZ2-102 | Me | Et | Et | BB6 | H |
IcZ2-103 | Me | PH | PH | BB6 | H |
IcZ2-104 | Me | HYE | HYE | BB6 | H |
IcZ2-105 | Et | H | H | BB6 | H |
IcZ2-106 | Et | Me | H | BB6 | H |
IcZ2-107 | Et | Et | H | BB6 | H |
IcZ2-108 | Et | PH | H | BB6 | H |
IcZ2-109 | Et | NPR | H | BB6 | H |
IcZ2-110 | Et | NH2 | H | BB6 | H |
IcZ2-111 | Et | CBM | H | BB6 | H |
IcZ2-112 | Et | COM | H | BB6 | H |
IcZ2-113 | Et | HYE | H | BB6 | H |
IcZ2-114 | Et | Me | Me | BB6 | H |
IcZ2-115 | Et | Et | Et | BB6 | H |
IcZ2-116 | Et | PH | PH | BB6 | H |
IcZ2-117 | Et | HYE | HYE | BB6 | H |
IcZ2-118 | PH | H | H | BB6 | H |
IcZ2-119 | PH | Me | H | BB6 | H |
IcZ2-120 | PH | Et | H | BB6 | H |
[ Table 18Z2]
TABLE 18Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-121 | PH | PH | H | BB6 | H |
IcZ2-122 | PH | NPR | H | BB6 | H |
IcZ2-123 | PH | NH2 | H | BB6 | H |
IcZ2-124 | PH | CBM | H | BB6 | H |
IcZ2-125 | PH | COM | H | BB6 | H |
IcZ2-126 | PH | HYE | H | BB6 | H |
IcZ2-127 | PH | Me | Me | BB6 | H |
IcZ2-128 | PH | Et | Et | BB6 | H |
IcZ2-129 | PH | PH | PH | BB6 | H |
IcZ2-130 | PH | HYE | HYE | BB6 | H |
IcZ2-131 | NPR | H | H | BB6 | H |
IcZ2-132 | NPR | Me | H | BB6 | H |
IcZ2-133 | NPR | Et | H | BB6 | H |
IcZ2-134 | NPR | PH | H | BB6 | H |
IcZ2-135 | NPR | NPR | H | BB6 | H |
IcZ2-136 | NPR | NH2 | H | BB6 | H |
IcZ2-137 | NPR | CBM | H | BB6 | H |
IcZ2-138 | NPR | COM | H | BB6 | H |
IcZ2-139 | NPR | HYE | H | BB6 | H |
IcZ2-140 | NPR | Me | Me | BB6 | H |
IcZ2-141 | NPR | Et | Et | BB6 | H |
IcZ2-142 | NPR | PH | PH | BB6 | H |
IcZ2-143 | NPR | HYE | HYE | BB6 | H |
IcZ2-144 | HYE | H | H | BB6 | H |
IcZ2-145 | HYE | Me | H | BB6 | H |
IcZ2-146 | HYE | Et | H | BB6 | H |
IcZ2-147 | HYE | PH | H | BB6 | H |
IcZ2-148 | HYE | NPR | H | BB6 | H |
IcZ2-149 | HYE | NH2 | H | BB6 | H |
IcZ2-150 | HYE | CBM | H | BB6 | H |
IcZ2-151 | HYE | COM | H | BB6 | H |
IcZ2-152 | HYE | HYE | H | BB6 | H |
IcZ2-153 | HYE | Me | Me | BB6 | H |
IcZ2-154 | HYE | Et | Et | BB6 | H |
IcZ2-155 | HYE | PH | PH | BB6 | H |
IcZ2-156 | HYE | HYE | HYE | BB6 | H |
IcZ2-157 | H | H | H | BB19 | H |
IcZ2-158 | H | Me | H | BB19 | H |
IcZ2-159 | H | Et | H | BB19 | H |
IcZ2-160 | H | PH | H | BB19 | H |
[ Table 19Z2]
TABLE 19Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-161 | H | NPR | H | BB19 | H |
IcZ2-162 | H | NH2 | H | BB19 | H |
IcZ2-163 | H | CBM | H | BB19 | H |
IcZ2-164 | H | COM | H | BB19 | H |
IcZ2-165 | H | HYE | H | BB19 | H |
IcZ2-166 | H | Me | Me | BB19 | H |
IcZ2-167 | H | Et | Et | BB19 | H |
IcZ2-168 | H | PH | PH | BB19 | H |
IcZ2-169 | H | HYE | HYE | BB19 | H |
IcZ2-170 | Me | H | H | BB19 | H |
IcZ2-171 | Me | Me | H | BB19 | H |
IcZ2-172 | Me | Et | H | BB19 | H |
IcZ2-173 | Me | PH | H | BB19 | H |
IcZ2-174 | Me | NPR | H | BB19 | H |
IcZ2-175 | Me | NH2 | H | BB19 | H |
IcZ2-176 | Me | CBM | H | BB19 | H |
IcZ2-177 | Me | COM | H | BB19 | H |
IcZ2-178 | Me | HYE | H | BB19 | H |
IcZ2-179 | Me | Me | Me | BB19 | H |
IcZ2-180 | Me | Et | Et | BB19 | H |
IcZ2-181 | Me | PH | PH | BB19 | H |
IcZ2-182 | Me | HYE | HYE | BB19 | H |
IcZ2-183 | Et | H | H | BB19 | H |
IcZ2-184 | Et | Me | H | BB19 | H |
IcZ2-185 | Et | Et | H | BB19 | H |
IcZ2-186 | Et | PH | H | BB19 | H |
IcZ2-187 | Et | NPR | H | BB19 | H |
IcZ2-188 | Et | NH2 | H | BB19 | H |
IcZ2-189 | Et | CBM | H | BB19 | H |
IcZ2-190 | Et | COM | H | BB19 | H |
IcZ2-191 | Et | HYE | H | BB19 | H |
IcZ2-192 | Et | Me | Me | BB19 | H |
IcZ2-193 | Et | Et | Et | BB19 | H |
IcZ2-194 | Et | PH | PH | BB19 | H |
IcZ2-195 | Et | HYE | HYE | BB19 | H |
IcZ2-196 | PH | H | H | BB19 | H |
IcZ2-197 | PH | Me | H | BB19 | H |
IcZ2-198 | PH | Et | H | BB19 | H |
IcZ2-199 | PH | PH | H | BB19 | H |
IcZ2-200 | PH | NPR | H | BB19 | H |
[ Table 20Z2]
TABLE 20Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-201 | PH | NH2 | H | BB19 | H |
IcZ2-202 | PH | CBM | H | BB19 | H |
IcZ2-203 | PH | COM | H | BB19 | H |
IcZ2-204 | PH | HYE | H | BB19 | H |
IcZ2-205 | PH | Me | Me | BB19 | H |
IcZ2-206 | PH | Et | Et | BB19 | H |
IcZ2-207 | PH | PH | PH | BB19 | H |
IcZ2-208 | PH | HYE | HYE | BB19 | H |
IcZ2-209 | NPR | H | H | BB19 | H |
IcZ2-210 | NPR | Me | H | BB19 | H |
IcZ2-211 | NPR | Et | H | BB19 | H |
IcZ2-212 | NPR | PH | H | BB19 | H |
IcZ2-213 | NPR | NPR | H | BB19 | H |
IcZ2-214 | NPR | NH2 | H | BB19 | H |
IcZ2-215 | NPR | CBM | H | BB19 | H |
IcZ2-216 | NPR | COM | H | BB19 | H |
IcZ2-217 | NPR | HYE | H | BB19 | H |
IcZ2-218 | NPR | Me | Me | BB19 | H |
IcZ2-219 | NPR | Et | Et | BB19 | H |
IcZ2-220 | NPR | PH | PH | BB19 | H |
IcZ2-221 | NPR | HYE | HYE | BB19 | H |
IcZ2-222 | HYE | H | H | BB19 | H |
IcZ2-223 | HYE | Me | H | BB19 | H |
IcZ2-224 | HYE | Et | H | BB19 | H |
IcZ2-225 | HYE | PH | H | BB19 | H |
IcZ2-226 | HYE | NPR | H | BB19 | H |
IcZ2-227 | HYE | NH2 | H | BB19 | H |
IcZ2-228 | HYE | CBM | H | BB19 | H |
IcZ2-229 | HYE | COM | H | BB19 | H |
IcZ2-230 | HYE | HYE | H | BB19 | H |
IcZ2-231 | HYE | Me | Me | BB19 | H |
IcZ2-232 | HYE | Et | Et | BB19 | H |
IcZ2-233 | HYE | PH | PH | BB19 | H |
IcZ2-234 | HYE | HYE | HYE | BB19 | H |
IcZ2-235 | H | Hex | H | BB1 | H |
IcZ2-236 | Me | ALL | ALL | BB2 | H |
IcZ2-237 | Et | EOE | EOE | BB3 | H |
IcZ2-238 | PH | Oct | H | BB4 | H |
IcZ2-239 | NPR | EOE | HYE | BB5 | H |
IcZ2-240 | HYE | 2EH | 2EH | BB6 | H |
[ Table 21Z2]
TABLE 21Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-241 | Me | 2EH | H | BB7 | H |
IcZ2-242 | Et | IBu | IPR | BB8 | H |
IcZ2-243 | H | NH2 | NH2 | BB9 | H |
IcZ2-244 | Me | CHM | H | BB10 | H |
IcZ2-245 | Et | IPR | NPR | BB11 | H |
IcZ2-246 | Bu | Oct | Oct | BB12 | H |
IcZ2-247 | TBu | CH | H | BB13 | H |
IcZ2-248 | Hex | NPR | Et | BB14 | H |
IcZ2-249 | Oct | CBM | CBM | BB15 | H |
IcZ2-250 | 2EH | BZ | H | BB16 | H |
IcZ2-251 | CHM | BZ | Me | BB17 | H |
IcZ2-252 | CH | Hex | Hex | BB18 | H |
IcZ2-253 | PH | HYE | H | BB19 | H |
IcZ2-254 | BZ | CH | COM | BB20 | H |
IcZ2-255 | NPR | COM | COM | BB21 | H |
IcZ2-256 | IPR | NPR | H | BB22 | H |
IcZ2-257 | IBu | 2EH | HYE | BB23 | H |
IcZ2-258 | EOE | IPR | H | BB24 | H |
IcZ2-259 | ALL | CHM | ALL | BB25 | H |
IcZ2-260 | HYE | COE | COE | BB26 | H |
IcZ2-261 | H | IBu | H | BB27 | H |
IcZ2-262 | Me | Hex | NPR | BB28 | H |
IcZ2-263 | Et | EOE | H | BB29 | H |
IcZ2-264 | Bu | Oct | IPR | BB30 | H |
IcZ2-265 | TBu | TBu | TBu | BB31 | H |
IcZ2-266 | Hex | ALL | H | BB32 | H |
IcZ2-267 | Oct | TBu | Et | BB33 | H |
IcZ2-268 | 2EH | NH2 | H | BB34 | H |
IcZ2-269 | CHM | Bu | Bu | BB35 | H |
IcZ2-270 | CH | CBM | H | BB36 | H |
IcZ2-271 | PH | PH | PH | BB37 | H |
IcZ2-272 | BZ | COM | H | BB38 | H |
IcZ2-273 | NPR | Bu | Me | BB39 | H |
IcZ2-274 | IPR | CBA | CBA | BB40 | H |
IcZ2-275 | IBu | COE | H | BB41 | H |
IcZ2-276 | EOE | Me | Me | BB42 | H |
IcZ2-277 | ALL | CBA | H | BB43 | H |
IcZ2-278 | HYE | Et | Et | BB44 | H |
IcZ2-279 | H | H | H | BB45 | H |
IcZ2-280 | Me | HYE | HYE | BB46 | H |
[ Table 22Z2]
TABLE 22Z2
RO13Z2 | RN13Z2 | RN23Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IcZ2-281 | Et | BZ | BZ | BB47 | H |
IcZ2-282 | Bu | Me | H | BB48 | H |
IcZ2-283 | TBu | CBA | IPR | BB49 | H |
IcZ2-284 | Hex | NPR | NPR | BB50 | H |
IcZ2-285 | Oct | Et | H | BB51 | H |
IcZ2-286 | 2EH | COE | NPR | BB52 | H |
IcZ2-287 | CHM | CH | CH | BB53 | H |
IcZ2-288 | CH | PH | H | BB54 | H |
IcZ2-289 | PH | COM | Et | BB55 | H |
IcZ2-290 | BZ | IPR | IPR | BB56 | H |
IcZ2-291 | NPR | Bu | H | BB57 | H |
IcZ2-292 | IPR | CBM | Me | BB58 | H |
IcZ2-293 | IBu | IBu | IBu | BB59 | H |
IcZ2-294 | EOE | TBu | H | BB60 | H |
IcZ2-295 | ALL | NH2 | COM | BB1 | H |
IcZ2-296 | HYE | CHM | CHM | BB19 | H |
[ Table 27Z2]
TABLE 27Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IaZ2-224 | NA1 | NA1 | BB1 | H | IaZ2-264 | HHk11 | HHk11 | BB8 | H |
IaZ2-225 | HHk8 | HHk8 | BB1 | H | IaZ2-265 | H | H | BB11 | H |
IaZ2-226 | NA2 | NA2 | BB1 | H | IaZ2-266 | Me | Me | BB11 | H |
IaZ2-227 | HHk7 | HHk7 | BB1 | H | IaZ2-267 | Et | Et | BB11 | H |
IaZ2-228 | HH37 | HH37 | BB1 | H | IaZ2-268 | Bu | Bu | BB11 | H |
IaZ2-229 | HHk6 | HHk6 | BB1 | H | IaZ2-269 | TBu | TBu | BB11 | H |
IaZ2-230 | NA3 | NA3 | BB1 | H | IaZ2-270 | Hex | Hex | BB11 | H |
IaZ2-231 | HHJ2 | HHJ2 | BB1 | H | IaZ2-271 | Oct | Oct | BB11 | H |
IaZ2-232 | HHk11 | HHk11 | BB1 | H | IaZ2-272 | 2EH | 2EH | BB11 | H |
IaZ2-233 | NA1 | NA1 | BB6 | H | IaZ2-273 | CH | CH | BB11 | H |
IaZ2-234 | HHk8 | HHk8 | BB6 | H | IaZ2-274 | PH | PH | BB11 | H |
IaZ2-235 | NA2 | NA2 | BB6 | H | IaZ2-275 | BZ | BZ | BB11 | H |
IaZ2-236 | HHk7 | HHk7 | BB6 | H | IaZ2-276 | EOE | EOE | BB11 | H |
IaZ2-237 | HH37 | HH37 | BB6 | H | IaZ2-277 | ALL | ALL | BB11 | H |
IaZ2-238 | HHk6 | HHk6 | BB6 | H | IaZ2-278 | HYE | HYE | BB11 | H |
IaZ2-239 | NA3 | NA3 | BB6 | H | IaZ2-279 | NA1 | NA1 | BB11 | H |
IaZ2-240 | HHJ2 | HHJ2 | BB6 | H | IaZ2-280 | HHk8 | HHk8 | BB11 | H |
IaZ2-241 | HHk11 | HHk11 | BB6 | H | IaZ2-281 | NA2 | NA2 | BB11 | H |
IaZ2-242 | H | H | BB8 | H | IaZ2-282 | HHk7 | HHk7 | BB11 | H |
IaZ2-243 | Me | Me | BB8 | H | IaZ2-283 | HH37 | HH37 | BB11 | H |
IaZ2-244 | Et | Et | BB8 | H | IaZ2-284 | HHk6 | HHk6 | BB11 | H |
IaZ2-245 | Bu | Bu | BB8 | H | IaZ2-285 | NA3 | NA3 | BB11 | H |
IaZ2-246 | TBu | TBu | BB8 | H | IaZ2-286 | HHJ2 | HHJ2 | BB11 | H |
IaZ2-247 | Oct | Oct | BB8 | H | IaZ2-287 | HHk11 | HHk11 | BB11 | H |
IaZ2-248 | 2EH | 2EH | BB8 | H | IaZ2-288 | H | H | BB14 | H |
IaZ2-249 | CHM | CHM | BB8 | H | IaZ2-289 | Et | Et | BB14 | H |
IaZ2-250 | CH | CH | BB8 | H | IaZ2-290 | Bu | Bu | BB14 | H |
IaZ2-251 | PH | PH | BB8 | H | IaZ2-291 | TBu | TBu | BB14 | H |
IaZ2-252 | BZ | BZ | BB8 | H | IaZ2-292 | Hex | Hex | BB14 | H |
IaZ2-253 | EOE | EOE | BB8 | H | IaZ2-293 | Oct | Oct | BB14 | H |
IaZ2-254 | ALL | ALL | BB8 | H | IaZ2-294 | 2EH | 2EH | BB14 | H |
IaZ2-255 | HYE | HYE | BB8 | H | IaZ2-295 | CHM | CHM | BB14 | H |
IaZ2-256 | NA1 | NA1 | BB8 | H | IaZ2-296 | CH | CH | BB14 | H |
IaZ2-257 | HHk8 | HHk8 | BB8 | H | IaZ2-297 | PH | PH | BB14 | H |
IaZ2-258 | NA2 | NA2 | BB8 | H | IaZ2-298 | EOE | EOE | BB14 | H |
IaZ2-259 | HHk7 | HHk7 | BB8 | H | IaZ2-299 | ALL | ALL | BB14 | H |
IaZ2-260 | HH37 | HH37 | BB8 | H | IaZ2-300 | HYE | HYE | BB14 | H |
IaZ2-261 | HHk6 | HHk6 | BB8 | H | IaZ2-301 | NA1 | NA1 | BB14 | H |
IaZ2-262 | NA3 | NA3 | BB8 | H | IaZ2-302 | HHk8 | HHk8 | BB14 | H |
IaZ2-263 | HHJ2 | HHJ2 | BB8 | H | IaZ2-303 | NA2 | NA2 | BB14 | H |
[ Table 28Z2]
TABLE 28Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IaZ2-304 | HHk7 | HHk7 | BB14 | H | IaZ2-344 | Bu | Bu | BB58 | H |
IaZ2-305 | HH37 | HH37 | BB14 | H | IaZ2-345 | TBu | TBu | BB58 | H |
IaZ2-306 | HHk6 | HHk6 | BB14 | H | IaZ2-346 | Hex | Hex | BB58 | H |
IaZ2-307 | NA3 | NA3 | BB14 | H | IaZ2-347 | Oct | Oct | BB58 | H |
IaZ2-308 | HHJ2 | HHJ2 | BB14 | H | IaZ2-348 | 2EH | 2EH | BB58 | H |
IaZ2-309 | HHk11 | HHk11 | BB14 | H | IaZ2-349 | CHM | CHM | BB58 | H |
IaZ2-310 | NA1 | NA1 | BB19 | H | IaZ2-350 | CH | CH | BB58 | H |
IaZ2-311 | HHk8 | HHk8 | BB19 | H | IaZ2-351 | PH | PH | BB58 | H |
IaZ2-312 | NA2 | NA2 | BB19 | H | IaZ2-352 | BZ | BZ | BB58 | H |
IaZ2-313 | HHk7 | HHk7 | BB19 | H | IaZ2-353 | EOE | EOE | BB58 | H |
IaZ2-314 | HH37 | HH37 | BB19 | H | IaZ2-354 | ALL | ALL | BB58 | H |
IaZ2-315 | HHk6 | HHk6 | BB19 | H | IaZ2-355 | HYE | HYE | BB58 | H |
IaZ2-316 | NA3 | NA3 | BB19 | H | IaZ2-356 | NA1 | NA1 | BB58 | H |
IaZ2-317 | HHJ2 | HHJ2 | BB19 | H | IaZ2-357 | HHk8 | HHk8 | BB58 | H |
IaZ2-318 | HHk11 | HHk11 | BB19 | H | IaZ2-358 | NA2 | NA2 | BB58 | H |
IaZ2-319 | H | H | BB37 | H | IaZ2-359 | HHk7 | HHk7 | BB58 | H |
IaZ2-320 | Me | Me | BB37 | H | IaZ2-360 | HH37 | HH37 | BB58 | H |
IaZ2-321 | Et | Et | BB37 | H | IaZ2-361 | HHk6 | HHk6 | BB58 | H |
IaZ2-322 | Bu | Bu | BB37 | H | IaZ2-362 | NA3 | NA3 | BB58 | H |
IaZ2-323 | TBu | TBu | BB37 | H | IaZ2-363 | HHJ2 | HHJ2 | BB58 | H |
IaZ2-324 | Hex | Hex | BB37 | H | IaZ2-364 | HHk11 | HHk11 | BB58 | H |
IaZ2-325 | Oct | Oct | BB37 | H | IaZ2-365 | H | H | BBJ2 | H |
IaZ2-326 | 2EH | 2EH | BB37 | H | IaZ2-366 | Me | Me | BBJ2 | H |
IaZ2-327 | CHM | CHM | BB37 | H | IaZ2-367 | Et | Et | BBJ2 | H |
IaZ2-328 | CH | CH | BB37 | H | IaZ2-368 | Bu | Bu | BBJ2 | H |
IaZ2-329 | PH | PH | BB37 | H | IaZ2-369 | TBu | TBu | BBJ2 | H |
IaZ2-330 | BZ | BZ | BB37 | H | IaZ2-370 | Hex | Hex | BBJ2 | H |
IaZ2-331 | ALL | ALL | BB37 | H | IaZ2-371 | Oct | Oct | BBJ2 | H |
IaZ2-332 | HYE | HYE | BB37 | H | IaZ2-372 | 2EH | 2EH | BBJ2 | H |
IaZ2-333 | NA1 | NA1 | BB37 | H | IaZ2-373 | CHM | CHM | BBJ2 | H |
IaZ2-334 | HHk8 | HHk8 | BB37 | H | IaZ2-374 | CH | CH | BBJ2 | H |
IaZ2-335 | NA2 | NA2 | BB37 | H | IaZ2-375 | PH | PH | BBJ2 | H |
IaZ2-336 | HHk7 | HHk7 | BB37 | H | IaZ2-376 | BZ | BZ | BBJ2 | H |
IaZ2-337 | HH37 | HH37 | BB37 | H | IaZ2-377 | EOE | EOE | BBJ2 | H |
IaZ2-338 | HHk6 | HHk6 | BB37 | H | IaZ2-378 | ALL | ALL | BBJ2 | H |
IaZ2-339 | NA3 | NA3 | BB37 | H | IaZ2-379 | HYE | HYE | BBJ2 | H |
IaZ2-340 | HHJ2 | HHJ2 | BB37 | H | IaZ2-380 | NA1 | NA1 | BBJ2 | H |
IaZ2-341 | HHk11 | HHk11 | BB37 | H | IaZ2-381 | HHk8 | HHk8 | BBJ2 | H |
IaZ2-342 | Me | Me | BB58 | H | IaZ2-382 | NA2 | NA2 | BBJ2 | H |
IaZ2-343 | Et | Et | BB58 | H | IaZ2-383 | HHk7 | HHk7 | BBJ2 | H |
[ Table 29Z2]
TABLE 29Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IaZ2-384 | HH37 | HH37 | BBJ2 | H | IaZ2-424 | BZ | BZ | BBO10 | H |
IaZ2-385 | HHk6 | HHk6 | BBJ2 | H | IaZ2-425 | EOE | EOE | BBO10 | H |
IaZ2-386 | NA3 | NA3 | BBJ2 | H | IaZ2-426 | ALL | ALL | BBO10 | H |
IaZ2-387 | HHJ2 | HHJ2 | BBJ2 | H | IaZ2-427 | HYE | HYE | BBO10 | H |
IaZ2-388 | HHk11 | HHk11 | BBJ2 | H | IaZ2-428 | NA1 | NA1 | BBO10 | H |
IaZ2-389 | H | H | BBO8 | H | IaZ2-429 | HHk8 | HHk8 | BBO10 | H |
IaZ2-390 | Me | Me | BBO8 | H | IaZ2-430 | NA2 | NA2 | BBO10 | H |
IaZ2-391 | Et | Et | BBO8 | H | IaZ2-431 | HHk7 | HHk7 | BBO10 | H |
IaZ2-392 | Bu | Bu | BBO8 | H | IaZ2-432 | HH37 | HH37 | BBO10 | H |
IaZ2-393 | TBu | TBu | BBO8 | H | IaZ2-433 | HHk6 | HHk6 | BBO10 | H |
IaZ2-394 | Hex | Hex | BBO8 | H | IaZ2-434 | NA3 | NA3 | BBO10 | H |
IaZ2-395 | Oct | Oct | BBO8 | H | IaZ2-435 | HHJ2 | HHJ2 | BBO10 | H |
IaZ2-396 | 2EH | 2EH | BBO8 | H | IaZ2-436 | HHk11 | HHk11 | BBO10 | H |
IaZ2-397 | CHM | CHM | BBO8 | H | IaZ2-437 | HHf1 | HHf1 | BB2 | H |
IaZ2-398 | CH | CH | BBO8 | H | IaZ2-438 | HH55 | HH55 | BB3 | H |
IaZ2-399 | PH | PH | BBO8 | H | IaZ2-439 | HHh8 | HHh8 | BB4 | H |
IaZ2-400 | BZ | BZ | BBO8 | H | IaZ2-440 | HHf5 | HHf5 | BB5 | H |
IaZ2-401 | EOE | EOE | BBO8 | H | IaZ2-441 | HH83 | HH83 | BB7 | H |
IaZ2-402 | ALL | ALL | BBO8 | H | IaZ2-442 | HH58 | HH58 | BB9 | H |
IaZ2-403 | HYE | HYE | BBO8 | H | IaZ2-443 | HHf11 | HHf11 | BB10 | H |
IaZ2-404 | NA1 | NA1 | BBO8 | H | IaZ2-444 | HH34 | HH34 | BB12 | H |
IaZ2-405 | HHk8 | HHk8 | BBO8 | H | IaZ2-445 | HH80 | HH80 | BB13 | H |
IaZ2-406 | NA2 | NA2 | BBO8 | H | IaZ2-446 | HHb3 | HHb3 | BB15 | H |
IaZ2-407 | HHk7 | HHk7 | BBO8 | H | IaZ2-447 | HH13 | HH13 | BB16 | H |
IaZ2-408 | HH37 | HH37 | BBO8 | H | IaZ2-448 | HH81 | HH81 | BB17 | H |
IaZ2-409 | HHk6 | HHk6 | BBO8 | H | IaZ2-449 | HH49 | HH49 | BB18 | H |
IaZ2-410 | NA3 | NA3 | BBO8 | H | IaZ2-450 | HHk6 | HHk6 | BB20 | H |
IaZ2-411 | HHJ2 | HHJ2 | BBO8 | H | IaZ2-451 | HHk7 | HHk7 | BB21 | H |
IaZ2-412 | HHk11 | HHk11 | BBO8 | H | IaZ2-452 | HHJ2 | HHJ2 | BB22 | H |
IaZ2-413 | H | H | BBO10 | H | IaZ2-453 | HH28 | HH28 | BB23 | H |
IaZ2-414 | Me | Me | BBO10 | H | IaZ2-454 | HHd6 | HHd6 | BB24 | H |
IaZ2-415 | Et | Et | BBO10 | H | IaZ2-455 | HH37 | HH37 | BB25 | H |
IaZ2-416 | Bu | Bu | BBO10 | H | IaZ2-456 | HH43 | HH43 | BB26 | H |
IaZ2-417 | TBu | TBu | BBO10 | H | IaZ2-457 | NA4 | NA4 | BB27 | H |
IaZ2-418 | Hex | Hex | BBO10 | H | IaZ2-458 | HH40 | HH40 | BB28 | H |
IaZ2-419 | Oct | Oct | BBO10 | H | IaZ2-459 | HHg5 | HHg5 | BB29 | H |
IaZ2-420 | 2EH | 2EH | BBO10 | H | IaZ2-460 | HHk3 | HHk3 | BB30 | H |
IaZ2-421 | CHM | CHM | BBO10 | H | IaZ2-461 | HHk5 | HHk5 | BB31 | H |
IaZ2-422 | CH | CH | BBO10 | H | IaZ2-462 | HH76 | HH76 | BB32 | H |
IaZ2-423 | PH | PH | BBO10 | H | IaZ2-463 | HH78 | HH78 | BB33 | H |
[ Table 30Z2]
TABLE 30Z2
RO11Z2 | RO12Z2 | Ba1Z2Ba2Z2 | R1Z2 | |
IaZ2-464 | HHJ10 | HHJ10 | BB34 | H |
IaZ2-465 | HHJ3 | HHJ3 | BB35 | H |
IaZ2-466 | HHk4 | HHk4 | BB36 | H |
IaZ2-467 | HHc1 | HHc1 | BB38 | H |
IaZ2-468 | HH61 | HH61 | BB39 | H |
IaZ2-469 | HH65 | HH65 | BB40 | H |
IaZ2-470 | HHg2 | HHg2 | BB41 | H |
IaZ2-471 | HH69 | HH69 | BB42 | H |
IaZ2-472 | HHJ4 | HHJ4 | BB43 | H |
IaZ2-473 | HHi11 | HHi11 | BB44 | H |
IaZ2-474 | NA2 | NA2 | BB45 | H |
IaZ2-475 | HHk8 | HHk8 | BB46 | H |
IaZ2-476 | NA3 | NA3 | BB47 | H |
IaZ2-477 | HHe4 | HHe4 | BB48 | H |
IaZ2-478 | HHk1 | HHk1 | BB49 | H |
IaZ2-479 | HHh1 | HHh1 | BB50 | H |
IaZ2-480 | HHj19 | HHj19 | BB51 | H |
IaZ2-481 | HHk11 | HHk11 | BB52 | H |
IaZ2-482 | HHh4 | HHh4 | BB53 | H |
IaZ2-483 | HH22 | HH22 | BB54 | H |
IaZ2-484 | HHj10 | HHj10 | BB55 | H |
IaZ2-485 | HH36 | HH36 | BB56 | H |
IaZ2-486 | NA5 | NA5 | BB57 | H |
IaZ2-487 | NA1 | NA1 | BB59 | H |
IaZ2-488 | HHf14 | HHf14 | BB60 | H |
IaZ2-489 | HH35 | HH35 | BBI1 | H |
IaZ2-490 | HHg1 | HHg1 | BBD1 | H |
IaZ2-491 | HH9 | HH9 | BBK2 | H |
IaZ2-492 | HHa2 | HHa2 | BBK3 | H |
IaZ2-493 | HHj17 | HHj17 | BBK4 | H |
IaZ2-494 | HH46 | HH46 | BBK14 | H |
[ Table 31Z2]
TABLE 31Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-317 | HHk8 | H | HHk8 | H | BB1 | H | IbZ2-357 | NA3 | NA3 | NA3 | NA3 | BB6 | H |
IbZ2-318 | HHk7 | H | HHk7 | H | BB1 | H | IbZ2-358 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB6 | H |
IbZ2-319 | HH37 | H | HH37 | H | BB1 | H | IbZ2-359 | HHk11 | HHk11 | HHk11 | HHk11 | BB6 | H |
IbZ2-320 | HHk6 | H | HHk6 | H | BB1 | H | IbZ2-360 | NA1 | Me | NA1 | Me | BB6 | H |
IbZ2-321 | NA3 | H | NA3 | H | BB1 | H | IbZ2-361 | HHk8 | Me | HHk8 | Me | BB6 | H |
IbZ2-322 | HHJ2 | H | HHJ2 | H | BB1 | H | IbZ2-362 | NA2 | Me | NA2 | Me | BB6 | H |
IbZ2-323 | HHk11 | H | HHk11 | H | BB1 | H | IbZ2-363 | HHk7 | Me | HHk7 | Me | BB6 | H |
IbZ2-324 | NA1 | NA1 | NA1 | NA1 | BB1 | H | IbZ2-364 | HH37 | Me | HH37 | Me | BB6 | H |
IbZ2-325 | HHk8 | HHk8 | HHk8 | HHk8 | BB1 | H | IbZ2-365 | HHk6 | Me | HHk6 | Me | BB6 | H |
IbZ2-326 | NA2 | NA2 | NA2 | NA2 | BB1 | H | IbZ2-366 | NA3 | Me | NA3 | Me | BB6 | H |
IbZ2-327 | HHk7 | HHk7 | HHk7 | HHk7 | BB1 | H | IbZ2-367 | HHJ2 | Me | HHJ2 | Me | BB6 | H |
IbZ2-328 | HH37 | HH37 | HH37 | HH37 | BB1 | H | IbZ2-368 | HHk11 | Me | HHk11 | Me | BB6 | H |
IbZ2-329 | HHk6 | HHk6 | HHk6 | HHk6 | BB1 | H | IbZ2-369 | H | H | H | H | BB8 | H |
IbZ2-330 | NA3 | NA3 | NA3 | NA3 | BB1 | H | IbZ2-370 | Me | H | Me | H | BB8 | H |
IbZ2-331 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB1 | H | IbZ2-371 | Et | H | Et | H | BB8 | H |
IbZ2-332 | HHk11 | HHk11 | HHk11 | HHk11 | BB1 | H | IbZ2-372 | PH | H | PH | H | BB8 | H |
IbZ2-333 | NA1 | Me | NA1 | Me | BB1 | H | IbZ2-373 | Bu | H | Bu | H | BB8 | H |
IbZ2-334 | HHk8 | Me | HHk8 | Me | BB1 | H | IbZ2-374 | TBu | H | TBu | H | BB8 | H |
IbZ2-335 | NA2 | Me | NA2 | Me | BB1 | H | IbZ2-375 | Hex | H | Hex | H | BB8 | H |
IbZ2-336 | HHk7 | Me | HHk7 | Me | BB1 | H | IbZ2-376 | Oct | H | Oct | H | BB8 | H |
IbZ2-337 | HH37 | Me | HH37 | Me | BB1 | H | IbZ2-377 | 2EH | H | 2EH | H | BB8 | H |
IbZ2-338 | HHk6 | Me | HHk6 | Me | BB1 | H | IbZ2-378 | CHM | H | CHM | H | BB8 | H |
IbZ2-339 | NA3 | Me | NA3 | Me | BB1 | H | IbZ2-379 | CH | H | CH | H | BB8 | H |
IbZ2-340 | HHJ2 | Me | HHJ2 | Me | BB1 | H | IbZ2-380 | BZ | H | BZ | H | BB8 | H |
IbZ2-341 | HHk11 | Me | HHk11 | Me | BB1 | H | IbZ2-381 | EOE | H | EOE | H | BB8 | H |
IbZ2-342 | NA1 | H | NA1 | H | BB6 | H | IbZ2-382 | ALL | H | ALL | H | BB8 | H |
IbZ2-343 | HHk8 | H | HHk8 | H | BB6 | H | IbZ2-383 | NH2 | H | NH2 | H | BB8 | H |
IbZ2-344 | NA2 | H | NA2 | H | BB6 | H | IbZ2-384 | CBM | H | CBM | H | BB8 | H |
IbZ2-345 | HHk7 | H | HHk7 | H | BB6 | H | IbZ2-385 | COM | H | COM | H | BB8 | H |
IbZ2-346 | HH37 | H | HH37 | H | BB6 | H | IbZ2-386 | COE | H | COE | H | BB8 | H |
IbZ2-347 | HHk6 | H | HHk6 | H | BB6 | H | IbZ2-387 | CBA | H | CBA | H | BB8 | H |
IbZ2-348 | NA3 | H | NA3 | H | BB6 | H | IbZ2-388 | HYE | H | HYE | H | BB8 | H |
IbZ2-349 | HHJ2 | H | HHJ2 | H | BB6 | H | IbZ2-389 | HHk8 | H | HHk8 | H | BB8 | H |
IbZ2-350 | HHk11 | H | HHk11 | H | BB6 | H | IbZ2-390 | NA2 | H | NA2 | H | BB8 | H |
IbZ2-351 | NA1 | NA1 | NA1 | NA1 | BB6 | H | IbZ2-391 | HHk7 | H | HHk7 | H | BB8 | H |
IbZ2-352 | HHk8 | HHk8 | HHk8 | HHk8 | BB6 | H | IbZ2-392 | HH37 | H | HH37 | H | BB8 | H |
IbZ2-353 | NA2 | NA2 | NA2 | NA2 | BB6 | H | IbZ2-393 | HHk6 | H | HHk6 | H | BB8 | H |
IbZ2-354 | HHk7 | HHk7 | HHk7 | HHk7 | BB6 | H | IbZ2-394 | NA3 | H | NA3 | H | BB8 | H |
IbZ2-355 | HH37 | HH37 | HH37 | HH37 | BB6 | H | IbZ2-395 | HHJ2 | H | HHJ2 | H | BB8 | H |
IbZ2-356 | HHk6 | HHk6 | HHk6 | HHk6 | BB6 | H | IbZ2-396 | HHk11 | H | HHk11 | H | BB8 | H |
[ Table 32Z2]
TABLE 32Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-397 | Me | Me | Me | Me | BB8 | H | IbZ2-437 | NA1 | H | NA1 | H | BB11 | H |
IbZ2-398 | PH | PH | PH | PH | BB8 | H | IbZ2-438 | HHk8 | H | HHk8 | H | BB11 | H |
IbZ2-399 | NA1 | NA1 | NA1 | NA1 | BB8 | H | IbZ2-439 | NA2 | H | NA2 | H | BB11 | H |
IbZ2-400 | HHk8 | HHk8 | HHk8 | HHk8 | BB8 | H | IbZ2-440 | HHk7 | H | HHk7 | H | BB11 | H |
IbZ2-401 | NA2 | NA2 | NA2 | NA2 | BB8 | H | IbZ2-441 | HH37 | H | HH37 | H | BB11 | H |
IbZ2-402 | HHk7 | HHk7 | HHk7 | HHk7 | BB8 | H | IbZ2-442 | HHk6 | H | HHk6 | H | BB11 | H |
IbZ2-403 | HH37 | HH37 | HH37 | HH37 | BB8 | H | IbZ2-443 | NA3 | H | NA3 | H | BB11 | H |
IbZ2-404 | HHk6 | HHk6 | HHk6 | HHk6 | BB8 | H | IbZ2-444 | HHJ2 | H | HHJ2 | H | BB11 | H |
IbZ2-405 | NA3 | NA3 | NA3 | NA3 | BB8 | H | IbZ2-445 | HHk11 | H | HHk11 | H | BB11 | H |
IbZ2-406 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB8 | H | IbZ2-446 | Me | Me | Me | Me | BB11 | H |
IbZ2-407 | HHk11 | HHk11 | HHk11 | HHk11 | BB8 | H | IbZ2-447 | PH | PH | PH | PH | BB11 | H |
IbZ2-408 | NA1 | Me | NA1 | Me | BB8 | H | IbZ2-448 | NA1 | NA1 | NA1 | NA1 | BB11 | H |
IbZ2-409 | HHk8 | Me | HHk8 | Me | BB8 | H | IbZ2-449 | HHk8 | HHk8 | HHk8 | HHk8 | BB11 | H |
IbZ2-410 | NA2 | Me | NA2 | Me | BB8 | H | IbZ2-450 | NA2 | NA2 | NA2 | NA2 | BB11 | H |
IbZ2-411 | HHk7 | Me | HHk7 | Me | BB8 | H | IbZ2-451 | HHk7 | HHk7 | HHk7 | HHk7 | BB11 | H |
IbZ2-412 | HH37 | Me | HH37 | Me | BB8 | H | IbZ2-452 | HH37 | HH37 | HH37 | HH37 | BB11 | H |
IbZ2-413 | HHk6 | Me | HHk6 | Me | BB8 | H | IbZ2-453 | HHk6 | HHk6 | HHk6 | HHk6 | BB11 | H |
IbZ2-414 | NA3 | Me | NA3 | Me | BB8 | H | IbZ2-454 | NA3 | NA3 | NA3 | NA3 | BB11 | H |
IbZ2-415 | HHJ2 | Me | HHJ2 | Me | BB8 | H | IbZ2-455 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB11 | H |
IbZ2-416 | HHk11 | Me | HHk11 | Me | BB8 | H | IbZ2-456 | HHk11 | HHk11 | HHk11 | HHk11 | BB11 | H |
IbZ2-417 | H | H | H | H | BB11 | H | IbZ2-457 | NA1 | Me | NA1 | Me | BB11 | H |
IbZ2-418 | Me | H | Me | H | BB11 | H | IbZ2-458 | HHk8 | Me | HHk8 | Me | BB11 | H |
IbZ2-419 | Et | H | Et | H | BB11 | H | IbZ2-459 | NA2 | Me | NA2 | Me | BB11 | H |
IbZ2-420 | PH | H | PH | H | BB11 | H | IbZ2-460 | HHk7 | Me | HHk7 | Me | BB11 | H |
IbZ2-421 | Bu | H | Bu | H | BB11 | H | IbZ2-461 | HH37 | Me | HH37 | Me | BB11 | H |
IbZ2-422 | TBu | H | TBu | H | BB11 | H | IbZ2-462 | HHk6 | Me | HHk6 | Me | BB11 | H |
IbZ2-423 | Hex | H | Hex | H | BB11 | H | IbZ2-463 | NA3 | Me | NA3 | Me | BB11 | H |
IbZ2-424 | Oct | H | Oct | H | BB11 | H | IbZ2-464 | HHJ2 | Me | HHJ2 | Me | BB11 | H |
IbZ2-425 | 2EH | H | 2EH | H | BB11 | H | IbZ2-465 | HHk11 | Me | HHk11 | Me | BB11 | H |
IbZ2-426 | CHM | H | CHM | H | BB11 | H | IbZ2-466 | H | H | H | H | BB14 | H |
IbZ2-427 | CH | H | CH | H | BB11 | H | IbZ2-467 | Me | H | Me | H | BB14 | H |
IbZ2-428 | BZ | H | BZ | H | BB11 | H | IbZ2-468 | Et | H | Et | H | BB14 | H |
IbZ2-429 | EOE | H | EOE | H | BB11 | H | IbZ2-469 | PH | H | PH | H | BB14 | H |
IbZ2-430 | ALL | H | ALL | H | BB11 | H | IbZ2-470 | Bu | H | Bu | H | BB14 | H |
IbZ2-431 | NH2 | H | NH2 | H | BB11 | H | IbZ2-471 | TBu | H | TBu | H | BB14 | H |
IbZ2-432 | CBM | H | CBM | H | BB11 | H | IbZ2-472 | Hex | H | Hex | H | BB14 | H |
IbZ2-433 | COM | H | COM | H | BB11 | H | IbZ2-473 | Oct | H | Oct | H | BB14 | H |
IbZ2-434 | COE | H | COE | H | BB11 | H | IbZ2-474 | 2EH | H | 2EH | H | BB14 | H |
IbZ2-435 | CBA | H | CBA | H | BB11 | H | IbZ2-475 | CHM | H | CHM | H | BB14 | H |
IbZ2-436 | HYE | H | HYE | H | BB11 | H | IbZ2-476 | CH | H | CH | H | BB14 | H |
[ Table 33Z2]
TABLE 33Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-477 | BZ | H | BZ | H | BB14 | H | IbZ2-517 | HH37 | H | HH37 | H | BB19 | H |
IbZ2-478 | EOE | H | EOE | H | BB14 | H | IbZ2-518 | HHk6 | H | HHk6 | H | BB19 | H |
IbZ2-479 | ALL | H | ALL | H | BB14 | H | IbZ2-519 | NA3 | H | NA3 | H | BB19 | H |
IbZ2-480 | NH2 | H | NH2 | H | BB14 | H | IbZ2-520 | HHJ2 | H | HHJ2 | H | BB19 | H |
IbZ2-481 | CBM | H | CBM | H | BB14 | H | IbZ2-521 | HHk11 | H | HHk11 | H | BB19 | H |
IbZ2-482 | COM | H | COM | H | BB14 | H | IbZ2-522 | NA1 | NA1 | NA1 | NA1 | BB19 | H |
IbZ2-483 | COE | H | COE | H | BB14 | H | IbZ2-523 | HHk8 | HHk8 | HHk8 | HHk8 | BB19 | H |
IbZ2-484 | CBA | H | CBA | H | BB14 | H | IbZ2-524 | NA2 | NA2 | NA2 | NA2 | BB19 | H |
IbZ2-485 | HYE | H | HYE | H | BB14 | H | IbZ2-525 | HHk7 | HHk7 | HHk7 | HHk7 | BB19 | H |
IbZ2-486 | NA1 | H | NA1 | H | BB14 | H | IbZ2-526 | HH37 | HH37 | HH37 | HH37 | BB19 | H |
IbZ2-487 | HHk8 | H | HHk8 | H | BB14 | H | IbZ2-527 | HHk6 | HHk6 | HHk6 | HHk6 | BB19 | H |
IbZ2-488 | NA2 | H | NA2 | H | BB14 | H | IbZ2-528 | NA3 | NA3 | NA3 | NA3 | BB19 | H |
IbZ2-489 | HHk7 | H | HHk7 | H | BB14 | H | IbZ2-529 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB19 | H |
IbZ2-490 | HH37 | H | HH37 | H | BB14 | H | IbZ2-530 | HHk11 | HHk11 | HHk11 | HHk11 | BB19 | H |
IbZ2-491 | HHk6 | H | HHk6 | H | BB14 | H | IbZ2-531 | NA1 | Me | NA1 | Me | BB19 | H |
IbZ2-492 | NA3 | H | NA3 | H | BB14 | H | IbZ2-532 | HHk8 | Me | HHk8 | Me | BB19 | H |
IbZ2-493 | HHJ2 | H | HHJ2 | H | BB14 | H | IbZ2-533 | NA2 | Me | NA2 | Me | BB19 | H |
IbZ2-494 | HHk11 | H | HHk11 | H | BB14 | H | IbZ2-534 | HHk7 | Me | HHk7 | Me | BB19 | H |
IbZ2-495 | Me | Me | Me | Me | BB14 | H | IbZ2-535 | HH37 | Me | HH37 | Me | BB19 | H |
IbZ2-496 | PH | PH | PH | PH | BB14 | H | IbZ2-536 | HHk6 | Me | HHk6 | Me | BB19 | H |
IbZ2-497 | NA1 | NA1 | NA1 | NA1 | BB14 | H | IbZ2-537 | NA3 | Me | NA3 | Me | BB19 | H |
IbZ2-498 | HHk8 | HHk8 | HHk8 | HHk8 | BB14 | H | IbZ2-538 | HHJ2 | Me | HHJ2 | Me | BB19 | H |
IbZ2-499 | NA2 | NA2 | NA2 | NA2 | BB14 | H | IbZ2-539 | HHk11 | Me | HHk11 | Me | BB19 | H |
IbZ2-500 | HHk7 | HHk7 | HHk7 | HHk7 | BB14 | H | IbZ2-540 | H | H | H | H | BB37 | H |
IbZ2-501 | HH37 | HH37 | HH37 | HH37 | BB14 | H | IbZ2-541 | Me | H | Me | H | BB37 | H |
IbZ2-502 | HHk6 | HHk6 | HHk6 | HHk6 | BB14 | H | IbZ2-542 | Et | H | Et | H | BB37 | H |
IbZ2-503 | NA3 | NA3 | NA3 | NA3 | BB14 | H | IbZ2-543 | PH | H | PH | H | BB37 | H |
IbZ2-504 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB14 | H | IbZ2-544 | Bu | H | Bu | H | BB37 | H |
IbZ2-505 | HHk11 | HHk11 | HHk11 | HHk11 | BB14 | H | IbZ2-545 | TBu | H | TBu | H | BB37 | H |
IbZ2-506 | NA1 | Me | NA1 | Me | BB14 | H | IbZ2-546 | Hex | H | Hex | H | BB37 | H |
IbZ2-507 | HHk8 | Me | HHk8 | Me | BB14 | H | IbZ2-547 | Oct | H | Oct | H | BB37 | H |
IbZ2-508 | NA2 | Me | NA2 | Me | BB14 | H | IbZ2-548 | 2EH | H | 2EH | H | BB37 | H |
IbZ2-509 | HHk7 | Me | HHk7 | Me | BB14 | H | IbZ2-549 | CHM | H | CHM | H | BB37 | H |
IbZ2-510 | HH37 | Me | HH37 | Me | BB14 | H | IbZ2-550 | CH | H | CH | H | BB37 | H |
IbZ2-511 | HHk6 | Me | HHk6 | Me | BB14 | H | IbZ2-551 | EOE | H | EOE | H | BB37 | H |
IbZ2-512 | NA3 | Me | NA3 | Me | BB14 | H | IbZ2-552 | ALL | H | ALL | H | BB37 | H |
IbZ2-513 | HHJ2 | Me | HHJ2 | Me | BB14 | H | IbZ2-553 | NH2 | H | NH2 | H | BB37 | H |
IbZ2-514 | HHk11 | Me | HHk11 | Me | BB14 | H | IbZ2-554 | CBM | H | CBM | H | BB37 | H |
IbZ2-515 | HHk8 | H | HHk8 | H | BB19 | H | IbZ2-555 | COM | H | COM | H | BB37 | H |
IbZ2-516 | HHk7 | H | HHk7 | H | BB19 | H | IbZ2-556 | COE | H | COE | H | BB37 | H |
[ Table 34Z2]
TABLE 34Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-557 | CBA | H | CBA | H | BB37 | H | IbZ2-597 | CHM | H | CHM | H | BB58 | H |
IbZ2-558 | HYE | H | HYE | H | BB37 | H | IbZ2-598 | CH | H | CH | H | BB58 | H |
IbZ2-559 | NA1 | H | NA1 | H | BB37 | H | IbZ2-599 | BZ | H | BZ | H | BB58 | H |
IbZ2-560 | HHk8 | H | HHk8 | H | BB37 | H | IbZ2-600 | EOE | H | EOE | H | BB58 | H |
IbZ2-561 | NA2 | H | NA2 | H | BB37 | H | IbZ2-601 | ALL | H | ALL | H | BB58 | H |
IbZ2-562 | HHk7 | H | HHk7 | H | BB37 | H | IbZ2-602 | NH2 | H | NH2 | H | BB58 | H |
IbZ2-563 | HH37 | H | HH37 | H | BB37 | H | IbZ2-603 | CBM | H | CBM | H | BB58 | H |
IbZ2-564 | HHk6 | H | HHk6 | H | BB37 | H | IbZ2-604 | COM | H | COM | H | BB58 | H |
IbZ2-565 | NA3 | H | NA3 | H | BB37 | H | IbZ2-605 | COE | H | COE | H | BB58 | H |
IbZ2-566 | HHJ2 | H | HHJ2 | H | BB37 | H | IbZ2-606 | CBA | H | CBA | H | BB58 | H |
IbZ2-567 | HHk11 | H | HHk11 | H | BB37 | H | IbZ2-607 | HYE | H | HYE | H | BB58 | H |
IbZ2-568 | Me | Me | Me | Me | BB37 | H | IbZ2-608 | NA1 | H | NA1 | H | BB58 | H |
IbZ2-569 | PH | PH | PH | PH | BB37 | H | IbZ2-609 | HHk8 | H | HHk8 | H | BB58 | H |
IbZ2-570 | NA1 | NA1 | NA1 | NA1 | BB37 | H | IbZ2-610 | NA2 | H | NA2 | H | BB58 | H |
IbZ2-571 | HHk8 | HHk8 | HHk8 | HHk8 | BB37 | H | IbZ2-611 | HHk7 | H | HHk7 | H | BB58 | H |
IbZ2-572 | NA2 | NA2 | NA2 | NA2 | BB37 | H | IbZ2-612 | HH37 | H | HH37 | H | BB58 | H |
IbZ2-573 | HHk7 | HHk7 | HHk7 | HHk7 | BB37 | H | IbZ2-613 | HHk6 | H | HHk6 | H | BB58 | H |
IbZ2-574 | HH37 | HH37 | HH37 | HH37 | BB37 | H | IbZ2-614 | NA3 | H | NA3 | H | BB58 | H |
IbZ2-575 | HHk6 | HHk6 | HHk6 | HHk6 | BB37 | H | IbZ2-615 | HHJ2 | H | HHJ2 | H | BB58 | H |
IbZ2-576 | NA3 | NA3 | NA3 | NA3 | BB37 | H | IbZ2-616 | HHk11 | H | HHk11 | H | BB58 | H |
IbZ2-577 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB37 | H | IbZ2-617 | Me | Me | Me | Me | BB58 | H |
IbZ2-578 | HHk11 | HHk11 | HHk11 | HHk11 | BB37 | H | IbZ2-618 | PH | PH | PH | PH | BB58 | H |
IbZ2-579 | NA1 | Me | NA1 | Me | BB37 | H | IbZ2-619 | NA1 | NA1 | NA1 | NA1 | BB58 | H |
IbZ2-580 | HHk8 | Me | HHk8 | Me | BB37 | H | IbZ2-620 | HHk8 | HHk8 | HHk8 | HHk8 | BB58 | H |
IbZ2-581 | NA2 | Me | NA2 | Me | BB37 | H | IbZ2-621 | NA2 | NA2 | NA2 | NA2 | BB58 | H |
IbZ2-582 | HHk7 | Me | HHk7 | Me | BB37 | H | IbZ2-622 | HHk7 | HHk7 | HHk7 | HHk7 | BB58 | H |
IbZ2-583 | HH37 | Me | HH37 | Me | BB37 | H | IbZ2-623 | HH37 | HH37 | HH37 | HH37 | BB58 | H |
IbZ2-584 | HHk6 | Me | HHk6 | Me | BB37 | H | IbZ2-624 | HHk6 | HHk6 | HHk6 | HHk6 | BB58 | H |
IbZ2-585 | NA3 | Me | NA3 | Me | BB37 | H | IbZ2-625 | NA3 | NA3 | NA3 | NA3 | BB58 | H |
IbZ2-586 | HHJ2 | Me | HHJ2 | Me | BB37 | H | IbZ2-626 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BB58 | H |
IbZ2-587 | HHk11 | Me | HHk11 | Me | BB37 | H | IbZ2-627 | HHk11 | HHk11 | HHk11 | HHk11 | BB58 | H |
IbZ2-588 | H | H | H | H | BB58 | H | IbZ2-628 | NA1 | Me | NA1 | Me | BB58 | H |
IbZ2-589 | Me | H | Me | H | BB58 | H | IbZ2-629 | HHk8 | Me | HHk8 | Me | BB58 | H |
IbZ2-590 | Et | H | Et | H | BB58 | H | IbZ2-630 | NA2 | Me | NA2 | Me | BB58 | H |
IbZ2-591 | PH | H | PH | H | BB58 | H | IbZ2-631 | HHk7 | Me | HHk7 | Me | BB58 | H |
IbZ2-592 | Bu | H | Bu | H | BB58 | H | IbZ2-632 | HH37 | Me | HH37 | Me | BB58 | H |
IbZ2-593 | TBu | H | TBu | H | BB58 | H | IbZ2-633 | HHk6 | Me | HHk6 | Me | BB58 | H |
IbZ2-594 | Hex | H | Hex | H | BB58 | H | IbZ2-634 | NA3 | Me | NA3 | Me | BB58 | H |
IbZ2-595 | Oct | H | Oct | H | BB58 | H | IbZ2-635 | HHJ2 | Me | HHJ2 | Me | BB58 | H |
IbZ2-596 | 2EH | H | 2EH | H | BB58 | H | IbZ2-636 | HHk11 | Me | HHk11 | Me | BB58 | H |
[ Table 35Z2]
TABLE 35Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-637 | H | H | H | H | BBJ2 | H | IbZ2-677 | NA1 | Me | NA1 | Me | BBJ2 | H |
IbZ2-638 | Me | H | Me | H | BBJ2 | H | IbZ2-678 | HHk8 | Me | HHk8 | Me | BBJ2 | H |
IbZ2-639 | Et | H | Et | H | BBJ2 | H | IbZ2-679 | NA2 | Me | NA2 | Me | BBJ2 | H |
IbZ2-640 | PH | H | PH | H | BBJ2 | H | IbZ2-680 | HHk7 | Me | HHk7 | Me | BBJ2 | H |
IbZ2-641 | Bu | H | Bu | H | BBJ2 | H | IbZ2-681 | HH37 | Me | HH37 | Me | BBJ2 | H |
IbZ2-642 | TBu | H | TBu | H | BBJ2 | H | IbZ2-682 | HHk6 | Me | HHk6 | Me | BBJ2 | H |
IbZ2-643 | Hex | H | Hex | H | BBJ2 | H | IbZ2-683 | NA3 | Me | NA3 | Me | BBJ2 | H |
IbZ2-644 | Oct | H | Oct | H | BBJ2 | H | IbZ2-684 | HHJ2 | Me | HHJ2 | Me | BBJ2 | H |
IbZ2-645 | 2EH | H | 2EH | H | BBJ2 | H | IbZ2-685 | HHk11 | Me | HHk11 | Me | BBJ2 | H |
IbZ2-646 | CHM | H | CHM | H | BBJ2 | H | IbZ2-686 | H | H | H | H | BBO8 | H |
IbZ2-647 | CH | H | CH | H | BBJ2 | H | IbZ2-687 | Me | H | Me | H | BBO8 | H |
IbZ2-648 | BZ | H | BZ | H | BBJ2 | H | IbZ2-688 | Et | H | Et | H | BBO8 | H |
IbZ2-649 | EOE | H | EOE | H | BBJ2 | H | IbZ2-689 | PH | H | PH | H | BBO8 | H |
IbZ2-650 | ALL | H | ALL | H | BBJ2 | H | IbZ2-690 | Bu | H | Bu | H | BBO8 | H |
IbZ2-651 | NH2 | H | NH2 | H | BBJ2 | H | IbZ2-691 | TBu | H | TBu | H | BBO8 | H |
IbZ2-652 | CBM | H | CBM | H | BBJ2 | H | IbZ2-692 | Hex | H | Hex | H | BBO8 | H |
IbZ2-653 | COM | H | COM | H | BBJ2 | H | IbZ2-693 | Oct | H | Oct | H | BBO8 | H |
IbZ2-654 | COE | H | COE | H | BBJ2 | H | IbZ2-694 | 2EH | H | 2EH | H | BBO8 | H |
IbZ2-655 | CBA | H | CBA | H | BBJ2 | H | IbZ2-695 | CHM | H | CHM | H | BBO8 | H |
IbZ2-656 | HYE | H | HYE | H | BBJ2 | H | IbZ2-696 | CH | H | CH | H | BBO8 | H |
IbZ2-657 | NA1 | H | NA1 | H | BBJ2 | H | IbZ2-697 | BZ | H | BZ | H | BBO8 | H |
IbZ2-658 | HHk8 | H | HHk8 | H | BBJ2 | H | IbZ2-698 | EOE | H | EOE | H | BBO8 | H |
IbZ2-659 | NA2 | H | NA2 | H | BBJ2 | H | IbZ2-699 | ALL | H | ALL | H | BBO8 | H |
IbZ2-660 | HHk7 | H | HHk7 | H | BBJ2 | H | IbZ2-700 | NH2 | H | NH2 | H | BBO8 | H |
IbZ2-661 | HH37 | H | HH37 | H | BBJ2 | H | IbZ2-701 | CBM | H | CBM | H | BBO8 | H |
IbZ2-662 | HHk6 | H | HHk6 | H | BBJ2 | H | IbZ2-702 | COM | H | COM | H | BBO8 | H |
IbZ2-663 | NA3 | H | NA3 | H | BBJ2 | H | IbZ2-703 | COE | H | COE | H | BBO8 | H |
IbZ2-664 | HHJ2 | H | HHJ2 | H | BBJ2 | H | IbZ2-704 | CBA | H | CBA | H | BBO8 | H |
IbZ2-665 | HHk11 | H | HHk11 | H | BBJ2 | H | IbZ2-705 | HYE | H | HYE | H | BBO8 | H |
IbZ2-666 | Me | Me | Me | Me | BBJ2 | H | IbZ2-706 | HHk8 | H | HHk8 | H | BBO8 | H |
IbZ2-667 | PH | PH | PH | PH | BBJ2 | H | IbZ2-707 | NA2 | H | NA2 | H | BBO8 | H |
IbZ2-668 | NA1 | NA1 | NA1 | NA1 | BBJ2 | H | IbZ2-708 | HHk7 | H | HHk7 | H | BBO8 | H |
IbZ2-669 | HHk8 | HHk8 | HHk8 | HHk8 | BBJ2 | H | IbZ2-709 | HH37 | H | HH37 | H | BBO8 | H |
IbZ2-670 | NA2 | NA2 | NA2 | NA2 | BBJ2 | H | IbZ2-710 | HHk6 | H | HHk6 | H | BBO8 | H |
IbZ2-671 | HHk7 | HHk7 | HHk7 | HHk7 | BBJ2 | H | IbZ2-711 | NA3 | H | NA3 | H | BBO8 | H |
IbZ2-672 | HH37 | HH37 | HH37 | HH37 | BBJ2 | H | IbZ2-712 | HHJ2 | H | HHJ2 | H | BBO8 | H |
IbZ2-673 | HHk6 | HHk6 | HHk6 | HHk6 | BBJ2 | H | IbZ2-713 | HHk11 | H | HHk11 | H | BBO8 | H |
IbZ2-674 | NA3 | NA3 | NA3 | NA3 | BBJ2 | H | IbZ2-714 | Me | Me | Me | Me | BBO8 | H |
IbZ2-675 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BBJ2 | H | IbZ2-715 | PH | PH | PH | PH | BBO8 | H |
IbZ2-676 | HHk11 | HHk11 | HHk11 | HHk11 | BBJ2 | H | IbZ2-716 | NA1 | NA1 | NA1 | NA1 | BBO8 | H |
[ Table 36Z2]
TABLE 36Z2
RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | RN11Z2 | RN21Z2 | RN12Z2 | RN22Z2 | Ba1Z2Ba2Z2 | R1Z2 | ||
IbZ2-717 | HHk8 | HHk8 | HHk8 | HHk8 | BBO8 | H | IbZ2-757 | HHk7 | H | HHk7 | H | BBO10 | H |
IbZ2-718 | NA2 | NA2 | NA2 | NA2 | BBO8 | H | IbZ2-758 | HH37 | H | HH37 | H | BBO10 | H |
IbZ2-719 | HHk7 | HHk7 | HHk7 | HHk7 | BBO8 | H | IbZ2-759 | HHk6 | H | HHk6 | H | BBO10 | H |
IbZ2-720 | HH37 | HH37 | HH37 | HH37 | BBO8 | H | IbZ2-760 | NA3 | H | NA3 | H | BBO10 | H |
IbZ2-721 | HHk6 | HHk6 | HHk6 | HHk6 | BBO8 | H | IbZ2-761 | HHJ2 | H | HHJ2 | H | BBO10 | H |
IbZ2-722 | NA3 | NA3 | NA3 | NA3 | BBO8 | H | IbZ2-762 | HHk11 | H | HHk11 | H | BBO10 | H |
IbZ2-723 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BBO8 | H | IbZ2-763 | Me | Me | Me | Me | BBO10 | H |
IbZ2-724 | HHk11 | HHk11 | HHk11 | HHk11 | BBO8 | H | IbZ2-764 | PH | PH | PH | PH | BBO10 | H |
IbZ2-725 | NA1 | Me | NA1 | Me | BBO8 | H | IbZ2-765 | NA1 | NA1 | NA1 | NA1 | BBO10 | H |
IbZ2-726 | HHk8 | Me | HHk8 | Me | BBO8 | H | IbZ2-766 | HHk8 | HHk8 | HHk8 | HHk8 | BBO10 | H |
IbZ2-727 | NA2 | Me | NA2 | Me | BBO8 | H | IbZ2-767 | NA2 | NA2 | NA2 | NA2 | BBO10 | H |
IbZ2-728 | HHk7 | Me | HHk7 | Me | BBO8 | H | IbZ2-768 | HHk7 | HHk7 | HHk7 | HHk7 | BBO10 | H |
IbZ2-729 | HH37 | Me | HH37 | Me | BBO8 | H | IbZ2-769 | HH37 | HH37 | HH37 | HH37 | BBO10 | H |
IbZ2-730 | HHk6 | Me | HHk6 | Me | BBO8 | H | IbZ2-770 | HHk6 | HHk6 | HHk6 | HHk6 | BBO10 | H |
IbZ2-731 | NA3 | Me | NA3 | Me | BBO8 | H | IbZ2-771 | NA3 | NA3 | NA3 | NA3 | BBO10 | H |
IbZ2-732 | HHJ2 | Me | HHJ2 | Me | BBO8 | H | IbZ2-772 | HHJ2 | HHJ2 | HHJ2 | HHJ2 | BBO10 | H |
IbZ2-733 | HHk11 | Me | HHk11 | Me | BBO8 | H | IbZ2-773 | HHk11 | HHk11 | HHk11 | HHk11 | BBO10 | H |
IbZ2-734 | H | H | H | H | BBO10 | H | IbZ2-774 | NA1 | Me | NA1 | Me | BBO10 | H |
IbZ2-735 | Me | H | Me | H | BBO10 | H | IbZ2-775 | HHk8 | Me | HHk8 | Me | BBO10 | H |
IbZ2-736 | Et | H | Et | H | BBO10 | H | IbZ2-776 | NA2 | Me | NA2 | Me | BBO10 | H |
IbZ2-737 | PH | H | PH | H | BBO10 | H | IbZ2-777 | HHk7 | Me | HHk7 | Me | BBO10 | H |
IbZ2-738 | Bu | H | Bu | H | BBO10 | H | IbZ2-778 | HH37 | Me | HH37 | Me | BBO10 | H |
IbZ2-739 | TBu | H | TBu | H | BBO10 | H | IbZ2-779 | HHk6 | Me | HHk6 | Me | BBO10 | H |
IbZ2-740 | Hex | H | Hex | H | BBO10 | H | IbZ2-780 | NA3 | Me | NA3 | Me | BBO10 | H |
IbZ2-741 | Oct | H | Oct | H | BBO10 | H | IbZ2-781 | HHJ2 | Me | HHJ2 | Me | BBO10 | H |
IbZ2-742 | 2EH | H | 2EH | H | BBO10 | H | IbZ2-782 | HHk11 | Me | HHk11 | Me | BBO10 | H |
IbZ2-743 | CHM | H | CHM | H | BBO10 | H | IbZ2-783 | HHj10 | H | HHj10 | H | BB2 | H |
IbZ2-744 | CH | H | CH | H | BBO10 | H | IbZ2-784 | HHk1 | H | HHk1 | H | BB3 | H |
IbZ2-745 | BZ | H | BZ | H | BBO10 | H | IbZ2-785 | HH61 | H | HH61 | H | BB4 | H |
IbZ2-746 | EOE | H | EOE | H | BBO10 | H | IbZ2-786 | HH65 | H | HH65 | H | BB5 | H |
IbZ2-747 | ALL | H | ALL | H | BBO10 | H | IbZ2-787 | HHk5 | H | HHk5 | H | BB7 | H |
IbZ2-748 | NH2 | H | NH2 | H | BBO10 | H | IbZ2-788 | HHf14 | H | HHf14 | H | BB9 | H |
IbZ2-749 | CBM | H | CBM | H | BBO10 | H | IbZ2-789 | HHk6 | H | HHk6 | H | BB10 | H |
IbZ2-750 | COM | H | COM | H | BBO10 | H | IbZ2-790 | HH37 | H | HH37 | H | BB12 | H |
IbZ2-751 | COE | H | COE | H | BBO10 | H | IbZ2-791 | HH46 | H | HH46 | H | BB13 | H |
IbZ2-752 | CBA | H | CBA | H | BBO10 | H | IbZ2-792 | HHk3 | H | HHk3 | H | BB15 | H |
IbZ2-753 | HYE | H | HYE | H | BBO10 | H | IbZ2-793 | HH22 | H | HH22 | H | BB16 | H |
IbZ2-754 | NA1 | H | NA1 | H | BBO10 | H | IbZ2-794 | HHc1 | H | HHc1 | H | BB17 | H |
IbZ2-755 | HHk8 | H | HHk8 | H | BBO10 | H | IbZ2-795 | NA4 | H | NA4 | H | BB18 | H |
IbZ2-756 | NA2 | H | NA2 | H | BBO10 | H | IbZ2-796 | HH40 | H | HH40 | H | BB20 | H |
[ Table 37Z2]
TABLE 37Z2
For example, compound IaZ2-1 is a compound represented by formula (IaZ 2-1).
Preferably IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-494, compound IbZ2-1 to IbZ2-248, compound IbZ2-311 to IbZ2-840, compound IcZ2-1 to IcZ2-234, more preferably IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-436, compound IbZ2-1 to IbZ2-248, compound IbZ2-311 to IbZ2-782, compound IcZ2-1 to IcZ2-234,
More preferred are compound IaZ2-1 to compound IaZ2-165, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234, still more preferred are compound IaZ2-1 to compound IaZ2-111, compound IbZ2-1 to compound IbZ2-248, and compound IcZ2-1 to compound IcZ2-234, and particularly preferred are compound IaZ2-1 to compound IaZ2-54, and compound IbZ2-1 to compound IbZ 2-186.
Specific examples of the compound IZ2 include: tables 1Z2, 2Z2, 3Z2, 4Z2, 5Z2, 6Z2, 7Z2, 8Z2, 9Z2, 10Z2, 11Z2, 12Z2, 13Z2, 14Z2, 15Z2, 16Z2, 17Z2, 18Z2, 19Z2, 20Z2, 21Z2, 22Z2, 27Z2, 28Z2, 29Z2, 30Z2, 31Z2, 32Z2, 33Z2, 34Z2, 35Z2, 36Z2, and 37Z2 show that 1 to 3 hydrogen atoms contained in the compound are replaced with — SO3M or-CO2M is substituted. For example, a compound having 1 to 3 sulfo groups bonded to compound IaZ2-1 of table 1Z2 is represented by the following structure. Wherein, in the formula, - (SO)3H) Represents a compound IaZ2-1 in which any hydrogen atom in table 1Z2 is substituted.
Preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-165, the compound IaZ2-223 to the compound IaZ2-494, the compound IbZ2-1 to the compound IbZ2-248, the compound IbZ2-311 to the compound IbZ2-840, and the compound IcZ2-1 to the compound IcZ2-234 3M or-CO2A compound formed by the reaction of M,
more preferably, the compound is one selected from the group consisting of compounds IaZ2-1 to IaZ2-165, IaZ2-223 to IaZ2-436, and IbZ2-1 to IbZ2-248Compounds IbZ 2-311-IbZ 2-782, compounds IcZ 2-1-IcZ 2-234, to which 1-3-SO groups are bonded3M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-165, the compound IbZ2-1 to the compound IbZ2-248, and the compound IcZ2-1 to the compound IcZ2-2343M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-111, the compound IbZ2-1 to the compound IbZ2-248, and the compound IcZ2-1 to the compound IcZ2-2343M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IaZ2-1 to the compound IaZ2-54 and the compound IbZ2-1 to the compound IbZ2-1863M or-CO2M, or a salt thereof.
As a bond with-CO2Examples of the compound of M include compounds wherein 2-CO-CO groups are bonded to compound IbZ2-2, compound IbZ2-3, compound IbZ2-4, compound IbZ2-12, compound IbZ2-126, compound IbZ2-127, compound IbZ2-687, compound IbZ2-370, and the like2Among the compounds of H, particularly, compounds IbZ2 to 317, compounds IbZ2 to 318, compounds IbZ2 to 319, compounds IbZ2 to 320, compounds IbZ2 to 515, compounds IbZ2 to 516, compounds IbZ2 to 706, compounds IbZ2 to 389 and the like are particularly preferable.
As the compound (IZ2), the following compounds are preferable: in the formula (IZ2), RCO1Z2And RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-COO-R101Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2M in the groupA substituent group of a hydrocarbon group having 1 to 20 carbon atoms, R1Z2Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
R101Z2may have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RCO1Z2and RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO 3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z2Is a hydrogen atom, R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z2)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z2、-O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z2To be provided withIs selected from-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RCO1Z2and RCO1Z2Are identical radicals, RO1Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, RN1Z2And RN2Z2Independently of one another, a hydrogen atom, -CO-R102Z2、-CON(R102Z2)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R 1Z2Is a hydrogen atom, R2Z2~R5Z2Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z2)2Nitro, trifluoromethyl, -O-R102Z2、-SO3M or-CO2M,R102Z2Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z2May have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ2, R1Z2In the case of a hydrogen atom, the compound represented by the formula (pt1Z2) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z2) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z2) and the compound represented by the formula (pt4Z2) in the presence of an acid. In addition, R1Z2When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z2) to produce a compound IZ 2.
In [ formula (pt1Z2), formula (pt2Z2), formula (pt3Z2), formula (pt4Z2), formula (pt5Z2) and formula (IZ2), RCO1Z2、RCO2Z2、R1Z2、R2Z2、R3Z2、R4Z2And R5Z2The same meanings as described above are indicated. R14Z2Represents an alkyl group having 1 to 20 carbon atoms. M1Z2Represents an alkali metal atom.
LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group. ]
As R14Z2Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z2Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z2 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z2 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z2, and the compound pt4Z2 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z2 used, relative to R1Z2The amount of the compound IZ21 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z2 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z2The amount of the compound IZ21 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z2 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z2The amount of the compound IZ 21 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z2 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ2 having no sulfo group or-SO3M22In the case of (3), the compound IZ2 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M2。
M22Represents an alkali metal atom.
As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 21 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 21 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 21 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ2 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 2. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ3 >)
Compound IZ3 is a compound represented by formula (IZ 3).
[ formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Each of which may be bonded to each other to form a ring. R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z3Represents a hydrogen atom or an optionally substituted carbonA hydrocarbon group having 1 to 40 atoms or a heterocyclic group which may have a substituent. M represents a hydrogen atom or an alkali metal atom. R 101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Wherein A linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, or a tert-butyl group is particularly preferable.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, and a homo-tert-butylphenyl groupAromatic hydrocarbon groups such as a trimethylphenyl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 5,6,7, 8-tetrahydro-1-naphthyl group, a 5,6,7, 8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, and a pyrenyl group; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbyl group represented may haveAnd (4) a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group; a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms; a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octyl group) Sulfamoyl) and the like, and the R groups may be the same or different from each other and may be bonded to each other to form a ring);
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR 3(wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above)) Or a derivative thereof (e.g., a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably hydrogenAn atom. ) (ii) a A nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof;
a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
A hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine;
an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
A carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
Particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group may be a monocyclic or monocyclic ringAnd polycyclic, preferably heterocyclic, containing a heteroatom as a ring member. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
A fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane; saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1Z3~R5Z32 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z3~R5Z3The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group represented may have a substituent. Examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The preferable examples of the substituents which the hydrocarbon group may have are the same. As R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. As for the above-mentioned first substituent, another substituent (second substituent) may be bonded to the hydrocarbon group contained in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Of (a) is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z3Examples thereof include a formyl group; a carbonyl group (e.g., a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (e.g., a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, a benzoyl group, and a group represented by the above chemical formula, and the like, and the carbonyl group corresponding to-CO-R-in the compounds represented by tables 1Z3 to 6Z3 102Z3Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a group corresponding to-CO-R in the compounds shown in tables 1Z3 to 6Z3102Z3And the like.
as-COO-R101Z3Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, icosyl-L-butyloxycarbonylAn alkoxycarbonyl group having a C1-40 (preferably C1-20) hydrocarbon group or a derivative thereof (e.g., a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group (preferably an octylsulfamoyl group) having C1-10) bonded thereto such as an alkyloxycarbonyl group or the like, and a group represented by the above chemical formula, and a compound corresponding to-COO-R in tables 1Z3 to 6Z3 102Z3Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and compounds represented by tables 1Z3 to 6Z3 corresponding to-COO-R102Z3And the like.
as-OCO-R102Z3Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And the compounds shown in tables 1Z3 to 6Z3 correspond to-OCO-R102Z3Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z3 to 6Z3 corresponding to-OCO-R 102Z3And the like.
as-COCO-R102Z3Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalylOxalyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as oxalyl group, decyloxyl group, undecyloxalyl group, dodecyloxalyl group, eicosanyl group, cyclopentyloxalyl group, cyclohexyloxalyl group, phenyloxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds represented by tables 1Z3 to 6Z3 corresponding to-COCO-R102Z3And the like.
as-O-R102Z3There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula), and compounds shown in tables 1Z3 to 6Z3, which correspond to — O — R. 102Z3Preferable examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and groups shown in tables 1Z3 to 6Z3In the compounds shown, the corresponding-O-R102Z3And the like.
as-SO2-R101Z3Examples thereof include sulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof by a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.) is bonded, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, (2-ethyl) hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, eicosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group, etc., and groups represented by the above chemical formulae, and sulfonyl groups corresponding to-SO-in the compounds represented by tables 1Z3 to 6Z32-R102Z3Preferable examples of the group (b) include a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and a group corresponding to-SO in the compounds represented by tables 1Z3 to 6Z3 2-R102Z3And the like.
as-SO2N(R102Z3)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and the like, and the amino groups shown in tables 1Z3 to 6Z3Corresponding to-SO in the compound (A) of2NH(R102Z3X) (wherein, R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like, and the compounds represented by tables 1Z3 to 6Z3 correspond to those of the compounds represented by tables 1Z3 to 6Z3 -SO 2N(R102Z3X)2(wherein, R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z3 to 6Z3, which correspond to-SO2N(R102Z3)2And the like.
as-CON (R)102Z3)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, an N-pentylcarbamoyl group, an N- (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N- (2-ethyl) hexylcarbamoyl group, an N-heptylcarbamoyl group, an N-octylcarbamoyl group, an N-nonylcarbamoyl group, an N-decylcarbamoyl group, an N-undecylcarbamoyl group, an N-dodecylcarbamoyl group, an N-eicosylcarbamoyl group, an N-phenylcarbamoyl group and the like, and a group represented by the above chemical formula, A carbamoyl group substituted with a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and a compound represented by any of tables 1Z3 to 6Z3, wherein the carbamoyl group corresponds to-CONH (R is R 102Z3X)(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, n, N-dihexylcarbamoyl group, N-di (2-ethyl) hexylcarbamoyl group, N-diheptylcarbamoyl group, N-octylmethylcarbamoyl group, N-dioctylcarbamoyl group, N-dinonylcarbamoyl group, N-decylmethylcarbamoyl group, N-undecylmethylcarbamoyl group, N-dodecylmethylcarbamoyl group, N-eicosylmethylcarbamoyl group, N-phenylmethylcarbamoyl group, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, etc., each having 2 carbon atoms Carbamoyl groups substituted with a hydrocarbyl group having 1 to 40 (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl (preferably octylsulfamoyl) having 1 to 10 carbon atoms) and compounds shown in tables 1Z3 to 6Z3 corresponding to-CON (R102Z3X)2(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z3 to 6Z3 corresponding to-CON (R)102Z3)2And the like.
as-N (R)102Z3)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like) and a compound shown in tables 1Z3 to 6Z3 corresponding to-NH (R 102Z3X)(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-A group derived from a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like, such as a dipentylamino group, an N, N-di (1-ethylpropyl) amino group, an N, N-dihexylamino group, an N, N-di (2-ethyl) hexylamino group, an N, N-diheptylamino group, an N, N-dioctylamino group, an N, N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, or the like, and a group represented by the above chemical formula ) The substituted amino group and the compounds shown in tables 1Z3 to 6Z3 correspond to-N (R) 102Z3X)2(R102Z3XIs not a hydrogen atom, other than, and R102Z3The same as defined above), and the like, and preferably include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and groups corresponding to-N (R) in the compounds shown in tables 1Z3 to 6Z3102Z3)2And the like.
as-NHCO-R102Z3Examples thereof include formylamino; a carbonylamino group (in the case where the carbonylamino group is an acylamino group, the number of carbon atoms is 1 to 40) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as an acetylamino group, a propionylamino group, a butyrylamino group, a 2, 2-dimethylpropionylamino group, a valerylamino group, a hexanoylamino group, (2-ethyl) hexanoylamino group, a heptanoylamino group, an octanoylamino group, a nonanoylamino group, a decanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group, and the like, and a group represented by the above-mentioned chemical formula, and-NHCO-R is equivalent to in the compounds shown in tables 1Z3 to 6Z3 102Z3And the like,
preferably, the carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded(in the case where the carbonylamino group is an alkanoylamino group, the number of carbon atoms is more preferably 1 to 10) and the compounds represented by tables 1Z3 to 6Z3 correspond to-NHCO-R102Z3And the like.
as-NHCON (R)102Z3)2Examples thereof include the groups listed above and the compounds shown in tables 1Z3 to 6Z3 which correspond to-NHCON (R)102Z3)2And the like.
as-NHCOOR102Z3Examples thereof include the groups listed above and the groups corresponding to-NHCOOR among the compounds shown in tables 1Z3 to 6Z3102Z3And the like.
as-OCON (R)102Z3)2Examples thereof include those corresponding to-OCON (R) in the above-mentioned groups and the compounds shown in tables 1Z3 to 6Z3102Z3)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z3、-COO-R102Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R102Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCON(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 3). As R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3In the case of forming a ring, the ring may have a substituent. Examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3、R7Z3、R101Z3And R102Z3The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z3And R4Z3When forming a ring, as R2Z3And R5Z3Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z3And R3Z3When a ring is formed, R is preferably4Z3And R5Z3Does not form a ring, more preferably R4Z3And R5Z3Is a hydrogen atom.
R4Z3And R5Z3When a ring is formed, R is preferably2Z3And R3Z3Does not form a ring, more preferably R2Z3And R3Z3Is a hydrogen atom.
In the present invention, R1Z3、R6Z3And R7Z3Preferably a hydrogen atom.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z3And R3Z3、R3Z3And R4Z3Or R4Z3And R5Z3Form a ring.
Compound IZ3 is preferably the following compound: r 2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z3And R3Z3、R3Z3And R4Z3And R4Z3And R5Z3At least one group of the compounds (hereinafter, this compound may be referred to as "compound IZ 3-B") is bonded to form a ring. When the compound IZ3 is the compound IZ3-B, the retardation value of the color filter produced from the colored composition becomes small.
When the above compound IZ3-B is defined by a chemical formula, it is as follows.
[ formula (IZ3-B) wherein R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3Each of which may be bonded to each other to form a ring.
Wherein R is21Z3、R31Z3、R41Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring.
R101Z3The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z3Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z3、R102Z3And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
In the formula (IZ3-B), with respect to R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Respectively, R in the formula (IZ3)2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3The same example.
In the formula (IZ3-B), with respect to preferred R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Respectively, R in the formula (IZ3)2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3The same preferred examples as those of (1).
In the formula (IZ3-B), (mode 1) R1Z3、R61Z3And R71Z3Is preferably a hydrogen atom. In addition, (mode 2) R21Z3、R31Z3、R41Z3And R51Z3It is also preferred that at least one of them is nitro or tert-butyl. Either or both of the modes 1 and 2 may be employed.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z3、R3Z3、R4Z3And R5Z3At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R 3Z3Is nitro or tert-butyl, R2Z3、R4Z3And R5Z3Is a hydrogen atom; or, R2Z3、R3Z3And R5Z3Is a hydrogen atom, R4Z3Is nitro or tert-butyl.
Specific examples of the compound IZ3 include compounds IZ3-1 to IZ3-212 having a substituent shown in table 1Z3, table 2Z3, table 3Z3, table 4Z3, table 5Z3, and table 6Z3 in formula (IZ3-aa), and alkali metal salts thereof.
Ba1Z3Ba2Z3The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. Formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8),Formula (BBO10), formula (BBD1) and formula (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z3And Ba2Z3Each represents a chemical bond, Ba1Z3B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z3To be B2The chemical bond of (a); b isa1Z3B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 2When a chemical bond of (A) is present, Ba2Z3To be B1The chemical bond of (1). As Ba1Z3Ba2Z3Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Each symbol in table 1Z3, table 2Z3, table 3Z3, table 4Z3, table 5Z3, and table 6Z3 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group,
"PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl, "IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3,“SOT"represents a tosyl group," SNH "represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH) 3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-NHCOH.
[ Table 1Z3]
TABLE 1Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-1 | BB1 | H | H | H |
IZ3-2 | BB2 | H | H | H |
IZ3-3 | BB3 | H | H | H |
IZ3-4 | BB4 | H | H | H |
IZ3-5 | BB5 | H | H | H |
IZ3-6 | BB6 | H | H | H |
IZ3-7 | BB7 | H | H | H |
IZ3-8 | BB8 | H | H | H |
IZ3-9 | BB9 | H | H | H |
IZ3-10 | BB10 | H | H | H |
IZ3-11 | BB11 | H | H | H |
IZ3-12 | BB12 | H | H | H |
IZ3-13 | BB13 | H | H | H |
IZ3-14 | BB14 | H | H | H |
IZ3-15 | BB15 | H | H | H |
IZ3-16 | BB16 | H | H | H |
IZ3-17 | BB17 | H | H | H |
IZ3-18 | BB18 | H | H | H |
IZ3-19 | BB19 | H | H | H |
IZ3-20 | BB20 | H | H | H |
IZ3-21 | BB21 | H | H | H |
IZ3-22 | BB22 | H | H | H |
IZ3-23 | BB23 | H | H | H |
IZ3-24 | BB24 | H | H | H |
IZ3-25 | BB25 | H | H | H |
IZ3-26 | BB26 | H | H | H |
IZ3-27 | BB27 | H | H | H |
IZ3-28 | BB28 | H | H | H |
IZ3-29 | BB29 | H | H | H |
IZ3-30 | BB30 | H | H | H |
IZ3-31 | BB31 | H | H | H |
IZ3-32 | BB32 | H | H | H |
IZ3-33 | BB33 | H | H | H |
IZ3-34 | BB34 | H | H | H |
IZ3-35 | BB35 | H | H | H |
IZ3-36 | BB36 | H | H | H |
IZ3-37 | BB37 | H | H | H |
IZ3-38 | BB38 | H | H | H |
IZ3-39 | BB39 | H | H | H |
IZ3-40 | BB40 | H | H | H |
[ Table 2Z3]
TABLE 2Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-41 | BB41 | H | H | H |
IZ3-42 | BB42 | H | H | H |
IZ3-43 | BB43 | H | H | H |
IZ3-44 | BB44 | H | H | H |
IZ3-45 | BB45 | H | H | H |
IZ3-46 | BB46 | H | H | H |
IZ3-47 | BB47 | H | H | H |
IZ3-48 | BB48 | H | H | H |
IZ3-49 | BB49 | H | H | H |
IZ3-50 | BB50 | H | H | H |
IZ3-51 | BB51 | H | H | H |
IZ3-52 | BB52 | H | H | H |
IZ3-53 | BB53 | H | H | H |
IZ3-54 | BB54 | H | H | H |
IZ3-55 | BB55 | H | H | H |
IZ3-56 | BB56 | H | H | H |
IZ3-57 | BB57 | H | H | H |
IZ3-58 | BB58 | H | H | H |
IZ3-59 | BB59 | H | H | H |
IZ3-60 | BB60 | H | H | H |
IZ3-61 | BB1 | H | EOE | EOE |
IZ3-62 | BB2 | H | ALL | ALL |
IZ3-63 | BB3 | H | NH2 | NH2 |
IZ3-64 | BB4 | H | CBM | CBM |
IZ3-65 | BB5 | H | COM | COM |
IZ3-66 | BB6 | H | COE | COE |
IZ3-67 | BB7 | H | CBA | CBA |
IZ3-68 | BB8 | H | HYE | HYE |
IZ3-69 | BB9 | H | Me | Me |
IZ3-70 | BB10 | H | CH | CH |
IZ3-71 | BB11 | H | BZ | H |
IZ3-72 | BB12 | Me | Me | Me |
IZ3-73 | BB13 | Et | CH | CH |
IZ3-74 | BB14 | H | Et | Et |
IZ3-75 | BB15 | H | Bu | Bu |
IZ3-76 | BB16 | H | TBu | TBu |
IZ3-77 | BB17 | H | Hex | Hex |
IZ3-78 | BB18 | H | Oct | Oct |
IZ3-79 | BB19 | H | Me | Me |
IZ3-80 | BB20 | H | CH | CH |
[ Table 3Z3]
TABLE 3Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-81 | BB21 | H | BZ | H |
IZ3-82 | BB22 | Me | Me | Me |
IZ3-83 | BB23 | Et | CH | CH |
IZ3-84 | BB24 | H | Et | Et |
IZ3-85 | BB25 | H | Bu | Bu |
IZ3-86 | BB26 | H | TBu | TBu |
IZ3-87 | BB27 | H | Hex | Hex |
IZ3-88 | BB28 | H | Oct | Oct |
IZ3-89 | BB29 | H | 2EH | 2EH |
IZ3-90 | BB30 | H | CHM | CHM |
IZ3-91 | BB31 | H | PH | PH |
IZ3-92 | BB32 | H | BZ | BZ |
IZ3-93 | BB33 | H | NPR | NPR |
IZ3-94 | BB34 | H | IPR | IPR |
IZ3-95 | BB35 | H | IBu | IBu |
IZ3-96 | BB36 | H | EOE | EOE |
IZ3-97 | BB37 | H | ALL | ALL |
IZ3-98 | BB38 | H | NH2 | NH2 |
IZ3-99 | BB39 | H | CBM | CBM |
IZ3-100 | BB40 | H | COM | COM |
IZ3-101 | BB41 | H | COE | COE |
IZ3-102 | BB42 | H | CBA | CBA |
IZ3-103 | BB43 | H | HYE | HYE |
IZ3-104 | BB44 | H | Me | Me |
IZ3-105 | BB45 | H | CH | CH |
IZ3-106 | BB46 | H | BZ | H |
IZ3-107 | BB47 | Me | Me | Me |
IZ3-108 | BB48 | Et | CH | CH |
IZ3-109 | BB49 | H | Et | Et |
IZ3-110 | BB50 | H | Bu | Bu |
IZ3-111 | BB51 | H | TBu | TBu |
IZ3-112 | BB52 | H | Hex | Hex |
IZ3-113 | BB53 | H | Oct | Oct |
IZ3-114 | BB54 | H | 2EH | 2EH |
IZ3-115 | BB55 | H | CHM | CHM |
IZ3-116 | BB56 | H | PH | PH |
IZ3-117 | BB57 | H | BZ | BZ |
IZ3-118 | BB58 | H | NPR | NPR |
IZ3-119 | BB59 | H | IPR | IPR |
IZ3-120 | BB60 | H | IBu | IBu |
[ Table 4Z3]
TABLE 4Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-121 | BB1 | H | Me | H |
IZ3-122 | BB2 | H | H | COM |
IZ3-123 | BB3 | H | COE | H |
IZ3-124 | BB4 | H | H | Et |
IZ3-125 | BB5 | H | OCM | H |
IZ3-126 | BB6 | H | H | OME |
IZ3-127 | BB7 | H | Bu | H |
IZ3-128 | BB8 | H | H | SOT |
IZ3-129 | BB9 | H | SNH | H |
IZ3-130 | BB10 | H | H | TBu |
IZ3-131 | BB11 | H | SN2 | H |
IZ3-132 | BB12 | H | H | CNM |
IZ3-133 | BB13 | H | Hex | H |
IZ3-134 | BB14 | H | H | CN2 |
IZ3-135 | BB15 | H | NPH | H |
IZ3-136 | BB16 | H | H | Oct |
IZ3-137 | BB17 | H | NOT | H |
IZ3-138 | BB18 | H | H | NCO |
IZ3-139 | BB19 | H | 2EH | H |
IZ3-140 | BB20 | H | H | F |
IZ3-141 | BB21 | H | Cl | H |
IZ3-142 | BB22 | H | H | CHM |
IZ3-143 | BB23 | H | Br | H |
IZ3-144 | BB24 | H | H | CN |
IZ3-145 | BB25 | H | CH | H |
IZ3-146 | BB26 | H | H | NO2 |
IZ3-147 | BB27 | H | SUA | H |
IZ3-148 | BB28 | H | H | PH |
IZ3-149 | BB29 | H | CBA | H |
IZ3-150 | BB30 | H | H | CHO |
IZ3-151 | BB31 | H | BZ | BZ |
IZ3-152 | BB32 | H | H | OCH |
IZ3-153 | BB33 | H | NPR | H |
IZ3-154 | BB34 | H | H | OH |
IZ3-155 | BB35 | H | IPR | H |
IZ3-156 | BB36 | H | H | SFM |
IZ3-157 | BB37 | H | IBu | H |
IZ3-158 | BB38 | H | H | CBM |
IZ3-159 | BB39 | H | EOE | H |
IZ3-160 | BB40 | H | H | NH2 |
[ Table 5Z3]
TABLE 5Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-161 | BB41 | H | ALL | H |
IZ3-162 | BB42 | H | H | NCH |
IZ3-163 | BB43 | H | HYE | H |
IZ3-164 | BB44 | Me | H | H |
IZ3-165 | BB45 | COM | H | H |
IZ3-166 | BB46 | COE | H | H |
IZ3-167 | BB47 | Et | H | H |
IZ3-168 | BB48 | OCM | H | H |
IZ3-169 | BB49 | OME | H | H |
IZ3-170 | BB50 | Bu | H | H |
IZ3-171 | BB51 | SOT | H | H |
IZ3-172 | BB52 | SNH | H | H |
IZ3-173 | BB53 | TBu | H | H |
IZ3-174 | BB54 | SN2 | H | H |
IZ3-175 | BB55 | CNM | H | H |
IZ3-176 | BB56 | Hex | H | H |
IZ3-177 | BB57 | CN2 | H | H |
IZ3-178 | BB58 | NPH | H | H |
IZ3-179 | BB59 | Oct | H | H |
IZ3-180 | BB60 | NOT | H | H |
IZ3-181 | BB1 | NCO | H | H |
IZ3-182 | BB2 | 2EH | H | H |
IZ3-183 | BB3 | F | H | H |
IZ3-184 | BB4 | Cl | H | H |
IZ3-185 | BB5 | CHM | H | H |
IZ3-186 | BB6 | Br | H | H |
IZ3-187 | BB7 | CN | H | H |
IZ3-188 | BB8 | CH | H | H |
IZ3-189 | BB9 | NO2 | H | H |
IZ3-190 | BB10 | SUA | H | H |
IZ3-191 | BB11 | PH | H | H |
IZ3-192 | BB12 | CBA | H | H |
IZ3-193 | BB13 | CHO | H | H |
IZ3-194 | BB14 | BZ | H | H |
IZ3-195 | BB15 | OCH | H | H |
IZ3-196 | BB16 | NPR | H | H |
IZ3-197 | BB17 | OH | H | H |
IZ3-198 | BB18 | IPR | H | H |
IZ3-199 | BB19 | SFM | H | H |
IZ3-200 | BB20 | IBu | H | H |
[ Table 6Z3]
TABLE 6Z3
Ba1Z3Ba2Z3 | R1Z3 | R6Z3 | R7Z3 | |
IZ3-201 | BB21 | CBM | H | H |
IZ3-202 | BB22 | EOE | H | H |
IZ3-203 | BB23 | NH2 | H | H |
IZ3-204 | BB24 | ALL | H | H |
IZ3-205 | BB25 | NCH | H | H |
IZ3-206 | BB26 | HYE | H | H |
IZ3-207 | BBI1 | H | H | H |
IZ3-208 | BBD1 | H | H | H |
IZ3-209 | BBK2 | H | H | H |
IZ3-210 | BBK3 | H | H | H |
IZ3-211 | BBK4 | H | H | H |
IZ3-212 | BBK14 | H | H | H |
For example, the compound IZ3-1 is a compound represented by the formula (IZ 3-1).
The compound IZ3 is preferably a compound IZ3-1 to a compound IZ3-120 and a compound IZ3-207 to a compound IZ3-212, more preferably a compound IZ3-1 to a compound IZ3-120, further preferably a compound IZ3-1 to a compound IZ3-60, further more preferably a compound IZ3-1 to a compound IZ3-36, a compound IZ3-37 and a compound IZ3-58,
particularly preferred are the compounds IZ3-1 to IZ3-36, particularly more preferred are the compounds IZ3-1, IZ3-6, IZ3-8, IZ3-11, IZ3-14 and IZ3-19, and particularly preferred are the compounds IZ3-1, IZ3-6 and IZ 3-19.
Specific examples of the compound IZ3 include those shown in tables 1Z3 to 6Z31 to 3 hydrogen atoms contained in the compound are replaced by-SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ3-1 of Table 1Z3 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ3-1 of Table 1Z3 is substituted.
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-120 and the compound IZ3-207 to the compound IZ3-2123M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-1203M or-CO2M, more preferably 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-603M or-CO2More preferably, the compound of M is one in which 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-36, the compound IZ3-37 or the compound IZ3-583M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1 to the compound IZ3-363M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1, the compound IZ3-6, the compound IZ3-8, the compound IZ3-11, the compound IZ3-14 and the compound IZ3-19 3M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ3-1, the compound IZ3-6 or the compound IZ3-193M or-CO2M, or a salt thereof.
As the compound (IZ3), the following compounds are preferable:
in the formula (IZ3), R1Z3Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2The number of carbon atoms of the substituent in the group consisting of M is1 to 20 hydrocarbyl groups, -SO3M or-CO2M,
R2Z3~R5Z3Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z3、-O-R102Z3、-SO3M or-CO2M,
R6Z3And R7Z3Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R102Z3Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
R1Z3is a hydrogen atom, and is a hydrogen atom,
R2Z3~R5Z3each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z3)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z3、-O-R102Z3、-SO3M or-CO2M,R6Z3And R7Z3Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R102Z3Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
a compound in which M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
R1Z3is a hydrogen atom, R2Z3~R5Z3Each independently a hydrogen atom, a C1-10 hydrocarbon group, a halogenAtom, -N (R)102Z3)2Nitro, trifluoromethyl, -O-R102Z3、-SO3M or-CO2M,R6Z3And R7Z3The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z3is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
m is a hydrogen atom or an alkali metal atom.
For compound IZ3, R1Z3In the case of a hydrogen atom, the compound represented by the formula (pt1Z3) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z3) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z3) and the compound represented by the formula (pt4Z3) in the presence of an acid. In addition, R 1Z3When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z3) to produce a compound IZ 3.
In [ formula (pt1Z3), formula (pt2Z3), formula (pt3Z3), formula (pt4Z3), formula (pt5Z3) and formula (IZ3), R1Z3~R7Z3The same meanings as described above are indicated. R14Z3Represents an alkyl group having 1 to 20 carbon atoms. M1Z3Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z3Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z3Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z3 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z3 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z3, and the compound pt4Z3 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z3 used, relative to R1Z3The amount of the compound IZ31 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z3 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z3The amount of the compound IZ31 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z3 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z3The amount of the compound IZ 31 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z3 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ3 having no sulfo group or-SO3M2In the case of (3), the compound IZ3 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22。
M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 31 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 31 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 31 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ3 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 3. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ4 >)
Compound IZ4 is a compound represented by formula (IZ 4).
[ in the formula (IZ4),RN1Z4and RN2Z4Independently of one another represent-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4Independently of one another, represents a hydrogen atom, -CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent. R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Each of which may be bonded to each other to form a ring. R 101Z4The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent. R102Z4Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents a hydrogen atom or an alkali metal atom.
R101Z4、R102Z4And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10. RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, and a 2, 6-bis (2-propyl) benzeneAn aromatic hydrocarbon group such as a phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a 5,6,7, 8-tetrahydro-1-naphthyl group, a 5,6,7, 8-tetrahydro-2-naphthyl group, a fluorenyl group, a phenanthryl group, an anthracyl group, or a pyrenyl group; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl; a formyl group; a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, or a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3、-CO-S-CH2-CH2-CH2-CH3or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorogen) A derivative of an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), wherein R's may be the same or different and may be bonded to each other to form a ring);
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms) (for exampleA hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (you)Sulfo group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom. ) (ii) a A nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
A hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine;
an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; fluorine A hydrocarbon group having 1 to 10 carbon atoms in which all hydrogen atoms are substituted with atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
Particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4Hetero ofThe cyclic group may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
A fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine;
condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane;
bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane;
lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone;
five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman;
fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1Z4~R5Z42 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z4~R5Z4The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocyclic ring is a portion where any hydrogen atom contained in each ring is removed.
RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The heterocyclic group represented may have a substituent. Examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may have the same substituent as the substituent. In the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The preferable examples of the substituents which the hydrocarbon group may have are the same.
As RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The heterocyclic group having a substituent(s) represented by (a) may be a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably Preferred examples thereof include heterocyclic groups having a substituent of group s 2. The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4Of (a) is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z4Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 correspond to — CO — R. 102Z4The group (b) preferably includes a carbonyl group (in which the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bondedIn the case, the number of carbon atoms is more preferably 2 to 12) and the compounds shown in Table 1Z4 to Table 8Z4 and Table 11Z4 to Table 16Z4 correspond to-CO-R102Z4And the like.
as-COO-R101Z4Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl and heptyloxycarbonyl, an oxycarbonyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, an eicosyloxycarbonyl group and the like, and the groups represented by the above chemical formulae, and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-COO-R. 102Z4Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 which correspond to-COO-R102Z4And the like.
as-OCO-R102Z4Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyloxy group, the carbon number is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, and a benzoyloxy group, and tables 1Z4 to 8Z4 and 11Z4 to 16Z 4.Corresponding to-OCO-R in the compound102Z4Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 corresponds to-OCO-R 102Z4And the like.
as-COCO-R102Z4Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, an oxalyl group in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded, such as decyl oxalyl group, undecyloxalyl group, dodecyl oxalyl group, eicosyl oxalyl group, cyclopentyl oxalyl group, cyclohexyl oxalyl group, phenyl oxalyl group, p-tolyloxalyl group, and the group represented by the above chemical formula), and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to — COCO — R.102Z4And the like.
as-O-R102Z4There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy, 2, 6-dicyanophenyloxy, 3, 4-dicyanophenyloxy, 3, 5-dicyanophenyloxy, 4-methoxyphenyloxy An oxy group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as a phenylphenoxy group, a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula, and a group corresponding to-O-R-4 and the compounds represented by tables 1Z4 to 8Z4 and 11Z4 to 16Z4102Z4Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-O-R102Z4And the like.
as-SO2-R101Z4Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl, decyl sulfonyl, undecyl sulfonyl, dodecyl sulfonyl, eicosyl sulfonyl, phenyl sulfonyl, p-tolyl sulfonyl, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like is bonded, such as the group represented by the above chemical formula, and-SO corresponds to the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z 4. 2-R102Z4Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO2-R102Z4And the like.
as-SO2N(R102Z4)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N-butylsulfamoyl group, an N-sec-butylsulfamoyl group, an N-tert-butylsulfamoyl group, an N-pentylsulfamoyl group, an N- (1-ethylpropyl) sulfamoyl group, an N-hexylsulfamoyl group, an N- (2-ethyl) hexylsulfamoyl group, an N-heptylsulfamoyl group, an N-octylsulfamoyl group, an N-nonylsulfamoyl group, an N-decylsulfamoyl group, an N-undecylsulfamoyl group, an N-dodecylsulfamoyl group, an N-eicosylsulfamoyl group, an N-phenylsulfamoyl group and the like, and a group represented by the above formula, A derivative of nitro group, hydroxy group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), or the like), and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO 2NH(R102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.;
n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, A hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon atom, or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a carbon atom), and the like, such as an N, N-diheptylsulfamoyl group, an N, N-dioctylsulfamoyl group, an N, N-dinonylsulfamoyl group, an N, N-decylmethylsulfamoyl group, an N, N-undecylmethylsulfamoyl group, an N, N-dodecylmethylsulfamoyl group, an N, N-eicosylmethylsulfamoyl group, an N, N-phenylmethanesulfonyl group, an N, and an N, N-diphenylsulfamoyl group, and the like, and a group represented by the above chemical formula Groups derived from 1 to 10 alkylsulfamoyl groups (preferably octylsulfamoyl groups) and compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-SO2N(R102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-SO2N(R102Z4)2And the like.
as-CON (R)102Z4)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl and N-nonylcarbamoyl, N-decylcarbamoyl, N-undecylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, Carbamoyl groups substituted with a 1-40 (preferably 1-20) carbon hydrocarbon group or derivative thereof (e.g., a derivative derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), 1-10 carbon alkylsulfamoyl group (preferably octylsulfamoyl group)) such as the group represented by the above formula, and compounds shown in tables 1Z 4-8Z 4 and tables 11Z 4-16Z 4 corresponding to-CONH (R) 102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.;
n, N-dimethylcarbamoyl, N-ethylmethylcarbamoyl, N-diethylcarbamoyl, N-propylmethylcarbamoyl, N-dipropylcarbamoylN, N-isopropylmethylcarbamoyl, N-diisopropylcarbamoyl, N-tert-butylmethylcarbamoyl, N-diisobutylcarbamoyl, N-di-sec-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butyloctylcarbamoyl, N-dipentylcarbamoyl, N-bis (1-ethylpropyl) carbamoyl, N-dihexylcarbamoyl, N-bis (2-ethyl) hexylcarbamoyl, N-diheptylcarbamoyl, N-octylmethylcarbamoyl, N-dioctylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-dibutylcarbamoyl, N-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butylmethylcarbamoyl, N-butylt-butyl, N, N-dinonylcarbamoyl, N-decylmethylcarbamoyl, N-undecylmethylcarbamoyl, N-dodecylmethylcarbamoyl, N-eicosylmethyl-carbamoyl, N-phenylmethylcarbamoyl, N, n-diphenylcarbamoyl and carbamoyl groups such as those represented by the above chemical formula which are substituted with 2 hydrocarbon groups having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group), and the like), and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 correspond to-CON (R). 102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which corresponds to-CON (R)102Z4)2And the like.
as-N (R)102Z4)2There may be mentioned amino groups; n-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N-pentylamino, N-hexylamino, N- (2-ethyl) hexylamino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-isobutylamino, N-sec-butylamino, N-pentylamino, N-hexylamino, N- (2-ethyl) hexylamino, N-heptylamino, N-octylamino, N-nonylamino, N-decylamino, N-undecylamino, N-dodecylamino, N-eicosylamino, N-dodecylamino, N-2-d-y-d-y-d-y-d,An amino group such as an N-phenylamino group, which is substituted with a 1-C1-40 (preferably C1-20) hydrocarbon group or a derivative thereof (e.g., a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a C1-10 alkylsulfamoyl group (preferably octylsulfamoyl group), etc.), or a group represented by the above formula, or an equivalent of-NH (R) in the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4 102Z4X) (wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above), etc.; n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, an amino group substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc., such as an N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, etc., and a group represented by the above chemical formula, and an amino group corresponding to-N (R) in the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, respectively 102Z4X)2(wherein, R102Z4XIs not a hydrogen atom, other than, and R102Z4The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which correspond to-N (R)102Z4)2And the like.
as-NHCO-R102Z4Can do toTo produce formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like, carbonylamino (for example, in the case where the carbonylamino is an acylamino group, the carbon number is 1 to 40), carbonylamino to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as a group represented by the above-mentioned chemical formula) and carbonylamino (in the case where the carbonylamino group is an acylamino group, the carbon number is 1 to 40) corresponding to-NHCO- R 102Z4And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4, which correspond to-NHCO-R102Z4And the like.
as-NHCON (R)102Z4)2Examples thereof include the groups listed above and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4 which correspond to-NHCON (R)102Z4)2A group of (a); and so on.
as-NHCOOR102Z4Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z4 to 8Z4 and tables 11Z4 to 16Z4102Z4And the like.
as-OCON (R)102Z4)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z4 to 8Z4 and 11Z4 to 16Z4102Z4)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M of M is hydrogen atomA seed; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z4、-COO-R102Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R102Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCON(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 4). As R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Pyridine, phenanthroline and thiopheneNitrogen-containing fused heterocycles such as oxazines and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z4And R3Z4、R3Z4And R4Z4And R4Z4And R5Z4In the case of forming a ring, the ring may have a substituent. Examples of the substituent include N1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4、R7Z4、R101Z4And R102Z4The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z4And R4Z4When forming a ring, as R2Z4And R5Z4Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z4And R3Z4When a ring is formed, R is preferably4Z4And R5Z4Does not form a ring, more preferably R4Z4And R5Z4Is a hydrogen atom.
In addition, R4Z4And R5Z4When a ring is formed, R is preferably2Z4And R3Z4Does not form a ring, more preferably R2Z4And R3Z4Is a hydrogen atom.
In the present invention, R1Z4、R6Z4And R7Z4Preferably a hydrogen atom.
In the present invention, RN1Z4And RN2Z4Independently of one another, are preferably-CO-R102Z4、-COO-R101Z4、-CON(R102Z4)2、-N(R102Z4)2、-CO2M or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferablyThe hydrocarbon group having 1 to 20 carbon atoms which may have a substituent is selected, the hydrocarbon group having 1 to 15 carbon atoms which may have a substituent is particularly preferable, the hydrocarbon group having 1 to 10 carbon atoms which may have a substituent is particularly preferable, the hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or the hydrocarbon group having 1 to 5 carbon atoms which may have a substituent is particularly preferable, the methyl group, the ethyl group or the phenyl group is further particularly preferable, and the methyl group or the ethyl group is most preferable. In addition, R N1Z4And RN2Z4The groups may be the same or different, but preferably the same.
From the viewpoint of reducing the retardation value of a color filter made of the colored composition, R is preferably2Z4、R3Z4、R4Z4And R5Z4At least one of which is-CO-R102Z4、-COO-R101Z4、-OCO-R102Z4、-COCO-R102Z4、-O-R102Z4、-SO2-R101Z4、-SO2N(R102Z4)2、-CON(R102Z4)2、-N(R102Z4)2、-NHCO-R102Z4、-NHCO-N(R102Z4)2、-NHCOOR102Z4、-OCON(R102Z4)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent,
more preferably a C1-40 hydrocarbon group which may have a substituent, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z4、-O-R102Z4、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z4And R3Z4、R3Z4And R4Z4Or R4Z4And R5Z4Form a ring.
From coloringFrom the viewpoint of reducing the retardation value of the color filter produced from the composition, R is preferably2Z4、R3Z4、R4Z4And R5Z4At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z4、-O-R102Z4、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. It is especially preferred that R3Z4Is nitro or tert-butyl, R2Z4、R4Z4And R5Z4Is a hydrogen atom; or, R2Z4、R3Z4And R5Z4Is a hydrogen atom, R4Z4Is nitro or tert-butyl.
Specific examples of the compound IZ4 include compounds IZ4-1 to IZ4-769 having a substituent shown in table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and table 11Z4 to table 16Z4 in formula (IZ4-aa), and alkali metal salts thereof.
Ba1Z4Ba2Z4The partial structure represented by any one of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB1) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z4And Ba2Z4Each represents a chemical bond, Ba1Z4B of formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 1When a chemical bond of (A) is present, Ba2Z4To be B2The chemical bond of (a); b isa1Z4Are represented by the formulae (BB1) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK 14)) B of the formulae (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2)2When a chemical bond of (A) is present, Ba2Z4To be B1The chemical bond of (1).
As Ba1Z4Ba2Z4Formula (BB1), formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB1), formula (BB6), and formula (BB19) are more preferable.
Each symbol in table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and tables 11Z4 to 16Z4 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group,
"Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group,
"CH" represents cyclohexyl, "PH" represents phenyl, "BZ" represents benzyl, "NPR" represents propyl,
"IPR" represents isopropyl, "IBu" represents isobutyl, and "EOE" represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH 3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2,“NCO "represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond.
In the table, a part of the structure shown in the following formula is represented by a symbol denoted by the structure.
[ Table 1Z4]
TABLE 1Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-1 | Me | Me | BB1 | H | H | H |
IZ4-2 | Et | Et | BB1 | H | H | H |
IZ4-3 | PH | PH | BB1 | H | H | H |
IZ4-4 | Bu | Me | BB1 | H | H | H |
IZ4-5 | TBu | Et | BB1 | H | H | H |
IZ4-6 | Hex | NPR | BB1 | H | H | H |
IZ4-7 | Oct | IPR | BB1 | H | H | H |
IZ4-8 | 2EH | HYE | BB1 | H | H | H |
IZ4-9 | CHM | ALL | BB1 | H | H | H |
IZ4-10 | CH | COM | BB1 | H | H | H |
IZ4-11 | BZ | Me | BB1 | H | H | H |
IZ4-12 | NPR | Et | BB1 | H | H | H |
IZ4-13 | IPR | NPR | BB1 | H | H | H |
IZ4-14 | IBu | IPR | BB1 | H | H | H |
IZ4-15 | EOE | HYE | BB1 | H | H | H |
IZ4-16 | ALL | ALL | BB1 | H | H | H |
IZ4-17 | NH2 | COM | BB1 | H | H | H |
IZ4-18 | CBM | Me | BB1 | H | H | H |
IZ4-19 | COM | Et | BB1 | H | H | H |
IZ4-20 | COE | NPR | BB1 | H | H | H |
IZ4-21 | CBA | IPR | BB1 | H | H | H |
IZ4-22 | HYE | HYE | BB1 | H | H | H |
IZ4-23 | Bu | Bu | BB1 | H | H | H |
IZ4-24 | TBu | TBu | BB1 | H | H | H |
IZ4-25 | Hex | Hex | BB1 | H | H | H |
IZ4-26 | Oct | Oct | BB1 | H | H | H |
IZ4-27 | 2EH | 2EH | BB1 | H | H | H |
IZ4-28 | CHM | CHM | BB1 | H | H | H |
IZ4-29 | CH | CH | BB1 | H | H | H |
IZ4-30 | BZ | BZ | BB1 | H | H | H |
IZ4-31 | NPR | NPR | BB1 | H | H | H |
IZ4-32 | IPR | IPR | BB1 | H | H | H |
IZ4-33 | IBu | IBu | BB1 | H | H | H |
IZ4-34 | EOE | EOE | BB1 | H | H | H |
IZ4-35 | NH2 | NH2 | BB1 | H | H | H |
IZ4-36 | CBM | CBM | BB1 | H | H | H |
IZ4-37 | COM | COM | BB1 | H | H | H |
IZ4-38 | COE | COE | BB1 | H | H | H |
IZ4-39 | CBA | CBA | BB1 | H | H | H |
IZ4-40 | Me | Me | BB6 | H | H | H |
[ Table 2Z4]
TABLE 2Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-41 | Et | Et | BB6 | H | H | H |
IZ4-42 | PH | PH | BB6 | H | H | H |
IZ4-43 | Bu | Me | BB6 | H | H | H |
IZ4-44 | TBu | Et | BB6 | H | H | H |
IZ4-45 | Hex | NPR | BB6 | H | H | H |
IZ4-46 | Oct | IPR | BB6 | H | H | H |
IZ4-47 | 2EH | HYE | BB6 | H | H | H |
IZ4-48 | CHM | ALL | BB6 | H | H | H |
IZ4-49 | CH | COM | BB6 | H | H | H |
IZ4-50 | BZ | Me | BB6 | H | H | H |
IZ4-51 | NPR | Et | BB6 | H | H | H |
IZ4-52 | IPR | NPR | BB6 | H | H | H |
IZ4-53 | IBu | IPR | BB6 | H | H | H |
IZ4-54 | EOE | HYE | BB6 | H | H | H |
IZ4-55 | ALL | ALL | BB6 | H | H | H |
IZ4-56 | NH2 | COM | BB6 | H | H | H |
IZ4-57 | CBM | Me | BB6 | H | H | H |
IZ4-58 | COM | Et | BB6 | H | H | H |
IZ4-59 | COE | NPR | BB6 | H | H | H |
IZ4-60 | CBA | IPR | BB6 | H | H | H |
IZ4-61 | HYE | HYE | BB6 | H | H | H |
IZ4-62 | Bu | Bu | BB6 | H | H | H |
IZ4-63 | TBu | TBu | BB6 | H | H | H |
IZ4-64 | Hex | Hex | BB6 | H | H | H |
IZ4-65 | Oct | Oct | BB6 | H | H | H |
IZ4-66 | 2EH | 2EH | BB6 | H | H | H |
IZ4-67 | CHM | CHM | BB6 | H | H | H |
IZ4-68 | CH | CH | BB6 | H | H | H |
IZ4-69 | BZ | BZ | BB6 | H | H | H |
IZ4-70 | NPR | NPR | BB6 | H | H | H |
IZ4-71 | IPR | IPR | BB6 | H | H | H |
IZ4-72 | IBu | IBu | BB6 | H | H | H |
IZ4-73 | EOE | EOE | BB6 | H | H | H |
IZ4-74 | NH2 | NH2 | BB6 | H | H | H |
IZ4-75 | CBM | CBM | BB6 | H | H | H |
IZ4-76 | COM | COM | BB6 | H | H | H |
IZ4-77 | COE | COE | BB6 | H | H | H |
IZ4-78 | CBA | CBA | BB6 | H | H | H |
IZ4-79 | Me | Me | BB19 | H | H | H |
IZ4-80 | Et | Et | BB19 | H | H | H |
[ Table 3Z4]
TABLE 3Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-81 | PH | PH | BB19 | H | H | H |
IZ4-82 | Bu | Me | BB19 | H | H | H |
IZ4-83 | TBu | Et | BB19 | H | H | H |
IZ4-84 | Hex | NPR | BB19 | H | H | H |
IZ4-85 | Oct | IPR | BB19 | H | H | H |
IZ4-86 | 2EH | HYE | BB19 | H | H | H |
IZ4-87 | CHM | ALL | BB19 | H | H | H |
IZ4-88 | CH | COM | BB19 | H | H | H |
IZ4-89 | BZ | Me | BB19 | H | H | H |
IZ4-90 | NPR | Et | BB19 | H | H | H |
IZ4-91 | IPR | NPR | BB19 | H | H | H |
IZ4-92 | IBu | IPR | BB19 | H | H | H |
IZ4-93 | EOE | HYE | BB19 | H | H | H |
IZ4-94 | ALL | ALL | BB19 | H | H | H |
IZ4-95 | NH2 | COM | BB19 | H | H | H |
IZ4-96 | CBM | Me | BB19 | H | H | H |
IZ4-97 | COM | Et | BB19 | H | H | H |
IZ4-98 | COE | NPR | BB19 | H | H | H |
IZ4-99 | CBA | IPR | BB19 | H | H | H |
IZ4-100 | HYE | HYE | BB19 | H | H | H |
IZ4-101 | Bu | Bu | BB19 | H | H | H |
IZ4-102 | TBu | TBu | BB19 | H | H | H |
IZ4-103 | Hex | Hex | BB19 | H | H | H |
IZ4-104 | Oct | Oct | BB19 | H | H | H |
IZ4-105 | 2EH | 2EH | BB19 | H | H | H |
IZ4-106 | CHM | CHM | BB19 | H | H | H |
IZ4-107 | CH | CH | BB19 | H | H | H |
IZ4-108 | BZ | BZ | BB19 | H | H | H |
IZ4-109 | NPR | NPR | BB19 | H | H | H |
IZ4-110 | IPR | IPR | BB19 | H | H | H |
IZ4-111 | IBu | IBu | BB19 | H | H | H |
IZ4-112 | EOE | EOE | BB19 | H | H | H |
IZ4-113 | NH2 | NH2 | BB19 | H | H | H |
IZ4-114 | CBM | CBM | BB19 | H | H | H |
IZ4-115 | COM | COM | BB19 | H | H | H |
IZ4-116 | COE | COE | BB19 | H | H | H |
IZ4-117 | CBA | CBA | BB19 | H | H | H |
IZ4-118 | Me | Me | BB2 | H | H | H |
IZ4-119 | Et | Et | BB3 | H | H | H |
IZ4-120 | PH | PH | BB4 | H | H | H |
[ Table 4Z4]
TABLE 4Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-121 | Bu | Me | BB5 | H | H | H |
IZ4-122 | TBu | Et | BB7 | H | H | H |
IZ4-123 | Hex | NPR | BB8 | H | H | H |
IZ4-124 | Oct | IPR | BB9 | H | H | H |
IZ4-125 | 2EH | HYE | BB10 | H | H | H |
IZ4-126 | CHM | ALL | BB11 | H | H | H |
IZ4-127 | CH | COM | BB12 | H | H | H |
IZ4-128 | BZ | Me | BB13 | H | H | H |
IZ4-129 | NPR | Et | BB14 | H | H | H |
IZ4-130 | IPR | NPR | BB15 | H | H | H |
IZ4-131 | IBu | IPR | BB16 | H | H | H |
IZ4-132 | EOE | HYE | BB17 | H | H | H |
IZ4-133 | ALL | ALL | BB18 | H | H | H |
IZ4-134 | NH2 | COM | BB20 | H | H | H |
IZ4-135 | CBM | Me | BB21 | H | H | H |
IZ4-136 | COM | Et | BB22 | H | H | H |
IZ4-137 | COE | NPR | BB23 | H | H | H |
IZ4-138 | CBA | IPR | BB24 | H | H | H |
IZ4-139 | HYE | HYE | BB25 | H | H | H |
IZ4-140 | Bu | Bu | BB26 | H | H | H |
IZ4-141 | TBu | TBu | BB27 | H | H | H |
IZ4-142 | Hex | Hex | BB28 | H | H | H |
IZ4-143 | Oct | Oct | BB29 | H | H | H |
IZ4-144 | 2EH | 2EH | BB30 | H | H | H |
IZ4-145 | CHM | CHM | BB31 | H | H | H |
IZ4-146 | CH | CH | BB32 | H | H | H |
IZ4-147 | BZ | BZ | BB33 | H | H | H |
IZ4-148 | NPR | NPR | BB34 | H | H | H |
IZ4-149 | IPR | IPR | BB35 | H | H | H |
IZ4-150 | IBu | IBu | BB36 | H | H | H |
IZ4-151 | EOE | EOE | BB37 | H | H | H |
IZ4-152 | NH2 | NH2 | BB38 | H | H | H |
IZ4-153 | CBM | CBM | BB39 | H | H | H |
IZ4-154 | COM | COM | BB40 | H | H | H |
IZ4-155 | COE | COE | BB41 | H | H | H |
IZ4-156 | CBA | CBA | BB42 | H | H | H |
IZ4-157 | Me | Me | BB43 | H | H | H |
IZ4-158 | Et | Et | BB44 | H | H | H |
IZ4-159 | PH | PH | BB45 | H | H | H |
IZ4-160 | Bu | Me | BB46 | H | H | H |
[ Table 5Z4]
TABLE 5Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-161 | TBu | Et | BB47 | H | H | H |
IZ4-162 | Hex | NPR | BB48 | H | H | H |
IZ4-163 | Oct | IPR | BB49 | H | H | H |
IZ4-164 | 2EH | HYE | BB50 | H | H | H |
IZ4-165 | CHM | ALL | BB51 | H | H | H |
IZ4-166 | CH | COM | BB52 | H | H | H |
IZ4-167 | BZ | Me | BB53 | H | H | H |
IZ4-168 | NPR | Et | BB54 | H | H | H |
IZ4-169 | IPR | NPR | BB55 | H | H | H |
IZ4-170 | IBu | IPR | BB56 | H | H | H |
IZ4-171 | EOE | HYE | BB57 | H | H | H |
IZ4-172 | ALL | ALL | BB58 | H | H | H |
IZ4-173 | NH2 | COM | BB59 | H | H | H |
IZ4-174 | CBM | Me | BB60 | H | H | H |
IZ4-175 | Bu | Me | BB1 | H | Et | Et |
IZ4-176 | TBu | Et | BB2 | H | PH | PH |
IZ4-177 | Hex | NPR | BB3 | H | NPR | NPR |
IZ4-178 | Oct | IPR | BB4 | H | IPR | IPR |
IZ4-179 | 2EH | HYE | BB5 | H | ALL | ALL |
IZ4-180 | CHM | ALL | BB6 | H | Me | Me |
IZ4-181 | CH | COM | BB7 | H | CH | CH |
IZ4-182 | BZ | Me | BB8 | H | BZ | H |
IZ4-183 | NPR | Et | BB9 | Me | Me | Me |
IZ4-184 | IPR | NPR | BB10 | Et | CH | CH |
IZ4-185 | IBu | IPR | BB11 | H | Et | Et |
IZ4-186 | EOE | HYE | BB12 | H | Bu | Bu |
IZ4-187 | ALL | ALL | BB13 | H | TBu | TBu |
IZ4-188 | NH2 | COM | BB14 | H | Hex | Hex |
IZ4-189 | CBM | Me | BB15 | H | Oct | Oct |
IZ4-190 | COM | Et | BB16 | H | 2EH | 2EH |
IZ4-191 | COE | NPR | BB17 | H | CHM | CHM |
IZ4-192 | CBA | IPR | BB18 | H | PH | PH |
IZ4-193 | Me | Me | BB19 | H | BZ | BZ |
IZ4-194 | Et | Et | BB20 | H | NPR | NPR |
IZ4-195 | PH | PH | BB21 | H | IPR | IPR |
IZ4-196 | Bu | Me | BB22 | H | IBu | IBu |
IZ4-197 | TBu | Et | BB23 | H | EOE | EOE |
IZ4-198 | Hex | NPR | BB24 | H | ALL | ALL |
IZ4-199 | Oct | IPR | BB25 | H | NH2 | NH2 |
IZ4-200 | 2EH | HYE | BB26 | H | CBM | CBM |
[ Table 6Z4]
TABLE 6Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-201 | CHM | ALL | BB27 | H | COM | COM |
IZ4-202 | CH | COM | BB28 | H | COE | COE |
IZ4-203 | BZ | Me | BB29 | H | CBA | CBA |
IZ4-204 | NPR | Et | BB30 | H | HYE | HYE |
IZ4-205 | IPR | NPR | BB31 | H | Me | Me |
IZ4-206 | IBu | IPR | BB32 | H | CH | CH |
IZ4-207 | EOE | HYE | BB33 | H | BZ | H |
IZ4-208 | ALL | ALL | BB34 | Me | Me | Me |
IZ4-209 | NH2 | COM | BB35 | Et | CH | CH |
IZ4-210 | CBM | Me | BB36 | H | Et | Et |
IZ4-211 | COM | Et | BB37 | H | Bu | Bu |
IZ4-212 | COE | NPR | BB38 | H | TBu | TBu |
IZ4-213 | CBA | IPR | BB39 | H | Hex | Hex |
IZ4-214 | HYE | HYE | BB40 | H | Oct | Oct |
IZ4-215 | Bu | Bu | BB41 | H | 2EH | 2EH |
IZ4-216 | TBu | TBu | BB42 | H | CHM | CHM |
IZ4-217 | Hex | Hex | BB43 | H | PH | PH |
IZ4-218 | Oct | Oct | BB44 | H | BZ | BZ |
IZ4-219 | 2EH | 2EH | BB45 | H | NPR | NPR |
IZ4-220 | CHM | CHM | BB46 | H | IPR | IPR |
IZ4-221 | CH | CH | BB47 | H | IBu | IBu |
IZ4-222 | BZ | BZ | BB48 | H | EOE | EOE |
IZ4-223 | NPR | NPR | BB49 | H | ALL | ALL |
IZ4-224 | IPR | IPR | BB50 | H | NH2 | NH2 |
IZ4-225 | IBu | IBu | BB51 | H | CBM | CBM |
IZ4-226 | EOE | EOE | BB52 | H | COM | COM |
IZ4-227 | NH2 | NH2 | BB53 | H | COE | COE |
IZ4-228 | CBM | CBM | BB54 | H | CBA | CBA |
IZ4-229 | COM | COM | BB55 | H | HYE | HYE |
IZ4-230 | COE | COE | BB56 | H | Me | Me |
IZ4-231 | CBA | CBA | BB57 | H | CH | CH |
IZ4-232 | Me | Me | BB58 | H | BZ | H |
IZ4-233 | Et | Et | BB59 | Me | Me | Me |
IZ4-234 | PH | PH | BB60 | Et | CH | CH |
IZ4-235 | Bu | Me | BB1 | H | H | NO2 |
IZ4-236 | TBu | Et | BB2 | H | SUA | H |
IZ4-237 | Hex | NPR | BB3 | H | H | PH |
IZ4-238 | Oct | IPR | BB4 | H | CBA | H |
IZ4-239 | 2EH | HYE | BB5 | H | H | CHO |
IZ4-240 | Me | Me | BB6 | H | BZ | BZ |
[ Table 7Z4]
TABLE 7Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-241 | Et | Et | BB7 | H | H | OCH |
IZ4-242 | PH | PH | BB8 | H | NPR | H |
IZ4-243 | Bu | Me | BB9 | H | H | OH |
IZ4-244 | TBu | Et | BB10 | H | IPR | H |
IZ4-245 | Hex | NPR | BB11 | H | H | SFM |
IZ4-246 | Oct | IPR | BB12 | H | IBu | H |
IZ4-247 | 2EH | HYE | BB13 | H | H | CBM |
IZ4-248 | CHM | ALL | BB14 | H | EOE | H |
IZ4-249 | CH | COM | BB15 | H | H | NH2 |
IZ4-250 | BZ | Me | BB16 | H | ALL | H |
IZ4-251 | NPR | Et | BB17 | H | H | NCH |
IZ4-252 | IPR | NPR | BB18 | H | HYE | H |
IZ4-253 | IBu | IPR | BB19 | Me | H | H |
IZ4-254 | EOE | HYE | BB20 | COM | H | H |
IZ4-255 | ALL | ALL | BB21 | COE | H | H |
IZ4-256 | NH2 | COM | BB22 | Et | H | H |
IZ4-257 | CBM | Me | BB23 | OCM | H | H |
IZ4-258 | COM | Et | BB24 | OME | H | H |
IZ4-259 | COE | NPR | BB25 | Bu | H | H |
IZ4-260 | CBA | IPR | BB26 | SOT | H | H |
IZ4-261 | HYE | HYE | BB27 | SNH | H | H |
IZ4-262 | Bu | Bu | BB28 | TBu | H | H |
IZ4-263 | TBu | TBu | BB29 | SN2 | H | H |
IZ4-264 | Hex | Hex | BB30 | CNM | H | H |
IZ4-265 | Oct | Oct | BB31 | Hex | H | H |
IZ4-266 | 2EH | 2EH | BB32 | CN2 | H | H |
IZ4-267 | CHM | CHM | BB33 | NPH | H | H |
IZ4-268 | CH | CH | BB34 | Oct | H | H |
IZ4-269 | BZ | BZ | BB35 | NOT | H | H |
IZ4-270 | NPR | NPR | BB36 | NCO | H | H |
IZ4-271 | IPR | IPR | BB37 | H | Me | H |
IZ4-272 | IBu | IBu | BB38 | H | H | COM |
IZ4-273 | EOE | EOE | BB39 | H | COE | H |
IZ4-274 | NH2 | NH2 | BB40 | H | H | Et |
IZ4-275 | CBM | CBM | BB41 | H | OCM | H |
IZ4-276 | COM | COM | BB42 | H | H | OME |
IZ4-277 | COE | COE | BB43 | H | Bu | H |
IZ4-278 | CBA | CBA | BB44 | H | H | SOT |
IZ4-279 | Me | Me | BB45 | H | SNH | H |
IZ4-280 | Et | Et | BB46 | H | H | TBu |
[ Table 8Z4]
TABLE 8Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | |
IZ4-281 | PH | PH | BB47 | H | SN2 | H |
IZ4-282 | Bu | Me | BB48 | H | H | CNM |
IZ4-283 | TBu | Et | BB49 | H | Hex | H |
IZ4-284 | Hex | NPR | BB50 | H | H | CN2 |
IZ4-285 | Oct | IPR | BB51 | H | NPH | H |
IZ4-286 | 2EH | HYE | BB52 | H | H | Oct |
IZ4-287 | CHM | ALL | BB53 | H | NOT | H |
IZ4-288 | CH | COM | BB54 | H | H | NCO |
IZ4-289 | BZ | Me | BB55 | H | 2EH | H |
IZ4-290 | NPR | Et | BB56 | H | H | F |
IZ4-291 | IPR | NPR | BB57 | H | Cl | H |
IZ4-292 | IBu | IPR | BB58 | H | H | CHM |
IZ4-293 | EOE | HYE | BB59 | H | Br | H |
IZ4-294 | ALL | ALL | BB60 | H | H | CN |
IZ4-295 | NH2 | COM | BB1 | H | CH | H |
IZ4-296 | CBM | Me | BB2 | 2EH | H | H |
IZ4-297 | COM | Et | BB3 | F | H | H |
IZ4-298 | COE | NPR | BB4 | Cl | H | H |
IZ4-299 | CBA | IPR | BB5 | CHM | H | H |
IZ4-300 | HYE | HYE | BB6 | Br | H | H |
IZ4-301 | Bu | Bu | BB7 | CN | H | H |
IZ4-302 | TBu | TBu | BB8 | CH | H | H |
IZ4-303 | Hex | Hex | BB9 | NO2 | H | H |
IZ4-304 | Oct | Oct | BB10 | SUA | H | H |
IZ4-305 | 2EH | 2EH | BB11 | PH | H | H |
IZ4-306 | CHM | CHM | BB12 | CBA | H | H |
IZ4-307 | CH | CH | BB13 | CHO | H | H |
IZ4-308 | BZ | BZ | BB14 | BZ | H | H |
IZ4-309 | NPR | NPR | BB15 | OCH | H | H |
IZ4-310 | IPR | IPR | BB16 | NPR | H | H |
IZ4-311 | IBu | IBu | BB17 | OH | H | H |
IZ4-312 | EOE | EOE | BB18 | IPR | H | H |
IZ4-313 | NH2 | NH2 | BB19 | SFM | H | H |
IZ4-314 | CBM | CBM | BB20 | IBu | H | H |
IZ4-315 | COM | COM | BB21 | CBM | H | H |
IZ4-316 | COE | COE | BB22 | EOE | H | H |
IZ4-317 | CBA | CBA | BB23 | NH2 | H | H |
IZ4-318 | Me | Me | BB24 | ALL | H | H |
IZ4-319 | Et | Et | BB25 | NCH | H | H |
IZ4-320 | PH | PH | BB26 | HYE | H | H |
IZ4-321 | Me | Me | BB8 | H | H | H |
[ Table 11Z4]
TABLE 11Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | ||
IZ4-322 | NA1 | NA1 | BB1 | H | H | H | IZ4-362 | CH | Me | BB6 | H | H | H |
IZ4-323 | HHk8 | HHk8 | BB1 | H | H | H | IZ4-363 | EOE | Me | BB6 | H | H | H |
IZ4-324 | NA2 | NA2 | BB1 | H | H | H | IZ4-364 | ALL | Me | BB6 | H | H | H |
IZ4-325 | HHk7 | HHk7 | BB1 | H | H | H | IZ4-365 | CBA | Me | BB6 | H | H | H |
IZ4-326 | HH37 | HH37 | BB1 | H | H | H | IZ4-366 | HYE | Me | BB6 | H | H | H |
IZ4-327 | HHk6 | HHk6 | BB1 | H | H | H | IZ4-367 | NA1 | Me | BB6 | H | H | H |
IZ4-328 | NA3 | NA3 | BB1 | H | H | H | IZ4-368 | HHk8 | Me | BB6 | H | H | H |
IZ4-329 | HHJ2 | HHJ2 | BB1 | H | H | H | IZ4-369 | NA2 | Me | BB6 | H | H | H |
IZ4-330 | HHk11 | HHk11 | BB1 | H | H | H | IZ4-370 | HHk7 | Me | BB6 | H | H | H |
IZ4-331 | Et | Me | BB1 | H | H | H | IZ4-371 | HH37 | Me | BB6 | H | H | H |
IZ4-332 | PH | Me | BB1 | H | H | H | IZ4-372 | HHk6 | Me | BB6 | H | H | H |
IZ4-333 | Oct | Me | BB1 | H | H | H | IZ4-373 | NA3 | Me | BB6 | H | H | H |
IZ4-334 | CHM | Me | BB1 | H | H | H | IZ4-374 | HHJ2 | Me | BB6 | H | H | H |
IZ4-335 | CH | Me | BB1 | H | H | H | IZ4-375 | HHk11 | Me | BB6 | H | H | H |
IZ4-336 | EOE | Me | BB1 | H | H | H | IZ4-376 | Et | Et | BB8 | H | H | H |
IZ4-337 | ALL | Me | BB1 | H | H | H | IZ4-377 | PH | PH | BB8 | H | H | H |
IZ4-338 | CBA | Me | BB1 | H | H | H | IZ4-378 | Oct | Oct | BB8 | H | H | H |
IZ4-339 | HYE | Me | BB1 | H | H | H | IZ4-379 | CHM | CHM | BB8 | H | H | H |
IZ4-340 | NA1 | Me | BB1 | H | H | H | IZ4-380 | CH | CH | BB8 | H | H | H |
IZ4-341 | HHk8 | Me | BB1 | H | H | H | IZ4-381 | BZ | BZ | BB8 | H | H | H |
IZ4-342 | NA2 | Me | BB1 | H | H | H | IZ4-382 | EOE | EOE | BB8 | H | H | H |
IZ4-343 | HHk7 | Me | BB1 | H | H | H | IZ4-383 | ALL | ALL | BB8 | H | H | H |
IZ4-344 | HH37 | Me | BB1 | H | H | H | IZ4-384 | CBA | CBA | BB8 | H | H | H |
IZ4-345 | HHk6 | Me | BB1 | H | H | H | IZ4-385 | HYE | HYE | BB8 | H | H | H |
IZ4-346 | NA3 | Me | BB1 | H | H | H | IZ4-386 | NA1 | NA1 | BB8 | H | H | H |
IZ4-347 | HHJ2 | Me | BB1 | H | H | H | IZ4-387 | HHk8 | HHk8 | BB8 | H | H | H |
IZ4-348 | HHk11 | Me | BB1 | H | H | H | IZ4-388 | NA2 | NA2 | BB8 | H | H | H |
IZ4-349 | NA1 | NA1 | BB6 | H | H | H | IZ4-389 | HHk7 | HHk7 | BB8 | H | H | H |
IZ4-350 | HHk8 | HHk8 | BB6 | H | H | H | IZ4-390 | HH37 | HH37 | BB8 | H | H | H |
IZ4-351 | NA2 | NA2 | BB6 | H | H | H | IZ4-391 | HHk6 | HHk6 | BB8 | H | H | H |
IZ4-352 | HHk7 | HHk7 | BB6 | H | H | H | IZ4-392 | NA3 | NA3 | BB8 | H | H | H |
IZ4-353 | HH37 | HH37 | BB6 | H | H | H | IZ4-393 | HHJ2 | HHJ2 | BB8 | H | H | H |
IZ4-354 | HHk6 | HHk6 | BB6 | H | H | H | IZ4-394 | HHk11 | HHk11 | BB8 | H | H | H |
IZ4-355 | NA3 | NA3 | BB6 | H | H | H | IZ4-395 | Et | Me | BB8 | H | H | H |
IZ4-356 | HHJ2 | HHJ2 | BB6 | H | H | H | IZ4-396 | PH | Me | BB8 | H | H | H |
IZ4-357 | HHk11 | HHk11 | BB6 | H | H | H | IZ4-397 | Oct | Me | BB8 | H | H | H |
IZ4-358 | Et | Me | BB6 | H | H | H | IZ4-398 | CHM | Me | BB8 | H | H | H |
IZ4-359 | PH | Me | BB6 | H | H | H | IZ4-399 | CH | Me | BB8 | H | H | H |
IZ4-360 | Oct | Me | BB6 | H | H | H | IZ4-400 | BZ | Me | BB8 | H | H | H |
IZ4-361 | CHM | Me | BB6 | H | H | H | IZ4-401 | EOE | Me | BB8 | H | H | H |
[ Table 12Z4]
TABLE 12Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | ||
IZ4-402 | ALL | Me | BB8 | H | H | H | IZ4-442 | CBA | Me | BB11 | H | H | H |
IZ4-403 | CBA | Me | BB8 | H | H | H | IZ4-443 | HYE | Me | BB11 | H | H | H |
IZ4-404 | HYE | Me | BB8 | H | H | H | IZ4-444 | NA1 | Me | BB11 | H | H | H |
IZ4-405 | NA1 | Me | BB8 | H | H | H | IZ4-445 | HHk8 | Me | BB11 | H | H | H |
IZ4-406 | HHk8 | Me | BB8 | H | H | H | IZ4-446 | NA2 | Me | BB11 | H | H | H |
IZ4-407 | NA2 | Me | BB8 | H | H | H | IZ4-447 | HHk7 | Me | BB11 | H | H | H |
IZ4-408 | HHk7 | Me | BB8 | H | H | H | IZ4-448 | HH37 | Me | BB11 | H | H | H |
IZ4-409 | HH37 | Me | BB8 | H | H | H | IZ4-449 | HHk6 | Me | BB11 | H | H | H |
IZ4-410 | HHk6 | Me | BB8 | H | H | H | IZ4-450 | NA3 | Me | BB11 | H | H | H |
IZ4-411 | NA3 | Me | BB8 | H | H | H | IZ4-451 | HHJ2 | Me | BB11 | H | H | H |
IZ4-412 | HHJ2 | Me | BB8 | H | H | H | IZ4-452 | HHk11 | Me | BB11 | H | H | H |
IZ4-413 | HHk11 | Me | BB8 | H | H | H | IZ4-453 | Me | Me | BB14 | H | H | H |
IZ4-414 | Me | Me | BB11 | H | H | H | IZ4-454 | Et | Et | BB14 | H | H | H |
IZ4-415 | Et | Et | BB11 | H | H | H | IZ4-455 | PH | PH | BB14 | H | H | H |
IZ4-416 | PH | PH | BB11 | H | H | H | IZ4-456 | Oct | Oct | BB14 | H | H | H |
IZ4-417 | Oct | Oct | BB11 | H | H | H | IZ4-457 | CHM | CHM | BB14 | H | H | H |
IZ4-418 | CHM | CHM | BB11 | H | H | H | IZ4-458 | CH | CH | BB14 | H | H | H |
IZ4-419 | CH | CH | BB11 | H | H | H | IZ4-459 | BZ | BZ | BB14 | H | H | H |
IZ4-420 | BZ | BZ | BB11 | H | H | H | IZ4-460 | EOE | EOE | BB14 | H | H | H |
IZ4-421 | EOE | EOE | BB11 | H | H | H | IZ4-461 | ALL | ALL | BB14 | H | H | H |
IZ4-422 | ALL | ALL | BB11 | H | H | H | IZ4-462 | CBA | CBA | BB14 | H | H | H |
IZ4-423 | CBA | CBA | BB11 | H | H | H | IZ4-463 | HYE | HYE | BB14 | H | H | H |
IZ4-424 | HYE | HYE | BB11 | H | H | H | IZ4-464 | NA1 | NA1 | BB14 | H | H | H |
IZ4-425 | NA1 | NA1 | BB11 | H | H | H | IZ4-465 | HHk8 | HHk8 | BB14 | H | H | H |
IZ4-426 | HHk8 | HHk8 | BB11 | H | H | H | IZ4-466 | NA2 | NA2 | BB14 | H | H | H |
IZ4-427 | NA2 | NA2 | BB11 | H | H | H | IZ4-467 | HHk7 | HHk7 | BB14 | H | H | H |
IZ4-428 | HHk7 | HHk7 | BB11 | H | H | H | IZ4-468 | HH37 | HH37 | BB14 | H | H | H |
IZ4-429 | HH37 | HH37 | BB11 | H | H | H | IZ4-469 | HHk6 | HHk6 | BB14 | H | H | H |
IZ4-430 | HHk6 | HHk6 | BB11 | H | H | H | IZ4-470 | NA3 | NA3 | BB14 | H | H | H |
IZ4-431 | NA3 | NA3 | BB11 | H | H | H | IZ4-471 | HHJ2 | HHJ2 | BB14 | H | H | H |
IZ4-432 | HHJ2 | HHJ2 | BB11 | H | H | H | IZ4-472 | HHk11 | HHk11 | BB14 | H | H | H |
IZ4-433 | HHk11 | HHk11 | BB11 | H | H | H | IZ4-473 | Et | Me | BB14 | H | H | H |
IZ4-434 | Et | Me | BB11 | H | H | H | IZ4-474 | PH | Me | BB14 | H | H | H |
IZ4-435 | PH | Me | BB11 | H | H | H | IZ4-475 | Oct | Me | BB14 | H | H | H |
IZ4-436 | Oct | Me | BB11 | H | H | H | IZ4-476 | CHM | Me | BB14 | H | H | H |
IZ4-437 | CHM | Me | BB11 | H | H | H | IZ4-477 | CH | Me | BB14 | H | H | H |
IZ4-438 | CH | Me | BB11 | H | H | H | IZ4-478 | BZ | Me | BB14 | H | H | H |
IZ4-439 | BZ | Me | BB11 | H | H | H | IZ4-479 | EOE | Me | BB14 | H | H | H |
IZ4-440 | EOE | Me | BB11 | H | H | H | IZ4-480 | ALL | Me | BB14 | H | H | H |
IZ4-441 | ALL | Me | BB11 | H | H | H | IZ4-481 | CBA | Me | BB14 | H | H | H |
[ Table 13Z4]
TABLE 13Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | ||
IZ4-482 | HYE | Me | BB14 | H | H | H | IZ4-522 | Oct | Oct | BB37 | H | H | H |
IZ4-483 | NA1 | Me | BB14 | H | H | H | IZ4-523 | CHM | CHM | BB37 | H | H | H |
IZ4-484 | HHk8 | Me | BB14 | H | H | H | IZ4-524 | CH | CH | BB37 | H | H | H |
IZ4-485 | NA2 | Me | BB14 | H | H | H | IZ4-525 | BZ | BZ | BB37 | H | H | H |
IZ4-486 | HHk7 | Me | BB14 | H | H | H | IZ4-526 | ALL | ALL | BB37 | H | H | H |
IZ4-487 | HH37 | Me | BB14 | H | H | H | IZ4-527 | CBA | CBA | BB37 | H | H | H |
IZ4-488 | HHk6 | Me | BB14 | H | H | H | IZ4-528 | HYE | HYE | BB37 | H | H | H |
IZ4-489 | NA3 | Me | BB14 | H | H | H | IZ4-529 | NA1 | NA1 | BB37 | H | H | H |
IZ4-490 | HHJ2 | Me | BB14 | H | H | H | IZ4-530 | HHk8 | HHk8 | BB37 | H | H | H |
IZ4-491 | HHk11 | Me | BB14 | H | H | H | IZ4-531 | NA2 | NA2 | BB37 | H | H | H |
IZ4-492 | NA1 | NA1 | BB19 | H | H | H | IZ4-532 | HHk7 | HHk7 | BB37 | H | H | H |
IZ4-493 | HHk8 | HHk8 | BB19 | H | H | H | IZ4-533 | HH37 | HH37 | BB37 | H | H | H |
IZ4-494 | NA2 | NA2 | BB19 | H | H | H | IZ4-534 | HHk6 | HHk6 | BB37 | H | H | H |
IZ4-495 | HHk7 | HHk7 | BB19 | H | H | H | IZ4-535 | NA3 | NA3 | BB37 | H | H | H |
IZ4-496 | HH37 | HH37 | BB19 | H | H | H | IZ4-536 | HHJ2 | HHJ2 | BB37 | H | H | H |
IZ4-497 | HHk6 | HHk6 | BB19 | H | H | H | IZ4-537 | HHk11 | HHk11 | BB37 | H | H | H |
IZ4-498 | NA3 | NA3 | BB19 | H | H | H | IZ4-538 | Et | Me | BB37 | H | H | H |
IZ4-499 | HHJ2 | HHJ2 | BB19 | H | H | H | IZ4-539 | PH | Me | BB37 | H | H | H |
IZ4-500 | HHk11 | HHk11 | BB19 | H | H | H | IZ4-540 | Oct | Me | BB37 | H | H | H |
IZ4-501 | Et | Me | BB19 | H | H | H | IZ4-541 | CHM | Me | BB37 | H | H | H |
IZ4-502 | PH | Me | BB19 | H | H | H | IZ4-542 | CH | Me | BB37 | H | H | H |
IZ4-503 | Oct | Me | BB19 | H | H | H | IZ4-543 | BZ | Me | BB37 | H | H | H |
IZ4-504 | CHM | Me | BB19 | H | H | H | IZ4-544 | EOE | Me | BB37 | H | H | H |
IZ4-505 | CH | Me | BB19 | H | H | H | IZ4-545 | ALL | Me | BB37 | H | H | H |
IZ4-506 | EOE | Me | BB19 | H | H | H | IZ4-546 | CBA | Me | BB37 | H | H | H |
IZ4-507 | ALL | Me | BB19 | H | H | H | IZ4-547 | HYE | Me | BB37 | H | H | H |
IZ4-508 | CBA | Me | BB19 | H | H | H | IZ4-548 | NA1 | Me | BB37 | H | H | H |
IZ4-509 | HYE | Me | BB19 | H | H | H | IZ4-549 | HHk8 | Me | BB37 | H | H | H |
IZ4-510 | NA1 | Me | BB19 | H | H | H | IZ4-550 | NA2 | Me | BB37 | H | H | H |
IZ4-511 | HHk8 | Me | BB19 | H | H | H | IZ4-551 | HHk7 | Me | BB37 | H | H | H |
IZ4-512 | NA2 | Me | BB19 | H | H | H | IZ4-552 | HH37 | Me | BB37 | H | H | H |
IZ4-513 | HHk7 | Me | BB19 | H | H | H | IZ4-553 | HHk6 | Me | BB37 | H | H | H |
IZ4-514 | HH37 | Me | BB19 | H | H | H | IZ4-554 | NA3 | Me | BB37 | H | H | H |
IZ4-515 | HHk6 | Me | BB19 | H | H | H | IZ4-555 | HHJ2 | Me | BB37 | H | H | H |
IZ4-516 | NA3 | Me | BB19 | H | H | H | IZ4-556 | HHk11 | Me | BB37 | H | H | H |
IZ4-517 | HHJ2 | Me | BB19 | H | H | H | IZ4-557 | Me | Me | BB58 | H | H | H |
IZ4-518 | HHk11 | Me | BB19 | H | H | H | IZ4-558 | Et | Et | BB58 | H | H | H |
IZ4-519 | Me | Me | BB37 | H | H | H | IZ4-559 | PH | PH | BB58 | H | H | H |
IZ4-520 | Et | Et | BB37 | H | H | H | IZ4-560 | Oct | Oct | BB58 | H | H | H |
IZ4-521 | PH | PH | BB37 | H | H | H | IZ4-561 | CHM | CHM | BB58 | H | H | H |
[ Table 14Z4]
TABLE 14Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | ||
IZ4-562 | CH | CH | BB58 | H | H | H | IZ4-602 | EOE | EOE | BBJ2 | H | H | H |
IZ4-563 | BZ | BZ | BB58 | H | H | H | IZ4-603 | ALL | ALL | BBJ2 | H | H | H |
IZ4-564 | EOE | EOE | BB58 | H | H | H | IZ4-604 | CBA | CBA | BBJ2 | H | H | H |
IZ4-565 | CBA | CBA | BB58 | H | H | H | IZ4-605 | HYE | HYE | BBJ2 | H | H | H |
IZ4-566 | HYE | HYE | BB58 | H | H | H | IZ4-606 | NA1 | NA1 | BBJ2 | H | H | H |
IZ4-567 | NA1 | NA1 | BB58 | H | H | H | IZ4-607 | HHk8 | HHk8 | BBJ2 | H | H | H |
IZ4-568 | HHk8 | HHk8 | BB58 | H | H | H | IZ4-608 | NA2 | NA2 | BBJ2 | H | H | H |
IZ4-569 | NA2 | NA2 | BB58 | H | H | H | IZ4-609 | HHk7 | HHk7 | BBJ2 | H | H | H |
IZ4-570 | HHk7 | HHk7 | BB58 | H | H | H | IZ4-610 | HH37 | HH37 | BBJ2 | H | H | H |
IZ4-571 | HH37 | HH37 | BB58 | H | H | H | IZ4-611 | HHk6 | HHk6 | BBJ2 | H | H | H |
IZ4-572 | HHk6 | HHk6 | BB58 | H | H | H | IZ4-612 | NA3 | NA3 | BBJ2 | H | H | H |
IZ4-573 | NA3 | NA3 | BB58 | H | H | H | IZ4-613 | HHJ2 | HHJ2 | BBJ2 | H | H | H |
IZ4-574 | HHJ2 | HHJ2 | BB58 | H | H | H | IZ4-614 | HHk11 | HHk11 | BBJ2 | H | H | H |
IZ4-575 | HHk11 | HHk11 | BB58 | H | H | H | IZ4-615 | Et | Me | BBJ2 | H | H | H |
IZ4-576 | Et | Me | BB58 | H | H | H | IZ4-616 | PH | Me | BBJ2 | H | H | H |
IZ4-577 | PH | Me | BB58 | H | H | H | IZ4-617 | Oct | Me | BBJ2 | H | H | H |
IZ4-578 | Oct | Me | BB58 | H | H | H | IZ4-618 | CHM | Me | BBJ2 | H | H | H |
IZ4-579 | CHM | Me | BB58 | H | H | H | IZ4-619 | CH | Me | BBJ2 | H | H | H |
IZ4-580 | CH | Me | BB58 | H | H | H | IZ4-620 | BZ | Me | BBJ2 | H | H | H |
IZ4-581 | BZ | Me | BB58 | H | H | H | IZ4-621 | EOE | Me | BBJ2 | H | H | H |
IZ4-582 | EOE | Me | BB58 | H | H | H | IZ4-622 | ALL | Me | BBJ2 | H | H | H |
IZ4-583 | ALL | Me | BB58 | H | H | H | IZ4-623 | CBA | Me | BBJ2 | H | H | H |
IZ4-584 | CBA | Me | BB58 | H | H | H | IZ4-624 | HYE | Me | BBJ2 | H | H | H |
IZ4-585 | HYE | Me | BB58 | H | H | H | IZ4-625 | NA1 | Me | BBJ2 | H | H | H |
IZ4-586 | NA1 | Me | BB58 | H | H | H | IZ4-626 | HHk8 | Me | BBJ2 | H | H | H |
IZ4-587 | HHk8 | Me | BB58 | H | H | H | IZ4-627 | NA2 | Me | BBJ2 | H | H | H |
IZ4-588 | NA2 | Me | BB58 | H | H | H | IZ4-628 | HHk7 | Me | BBJ2 | H | H | H |
IZ4-589 | HHk7 | Me | BB58 | H | H | H | IZ4-629 | HH37 | Me | BBJ2 | H | H | H |
IZ4-590 | HH37 | Me | BB58 | H | H | H | IZ4-630 | HHk6 | Me | BBJ2 | H | H | H |
IZ4-591 | HHk6 | Me | BB58 | H | H | H | IZ4-631 | NA3 | Me | BBJ2 | H | H | H |
IZ4-592 | NA3 | Me | BB58 | H | H | H | IZ4-632 | HHJ2 | Me | BBJ2 | H | H | H |
IZ4-593 | HHJ2 | Me | BB58 | H | H | H | IZ4-633 | HHk11 | Me | BBJ2 | H | H | H |
IZ4-594 | HHk11 | Me | BB58 | H | H | H | IZ4-634 | Me | Me | BBO8 | H | H | H |
IZ4-595 | Me | Me | BBJ2 | H | H | H | IZ4-635 | Et | Et | BBO8 | H | H | H |
IZ4-596 | Et | Et | BBJ2 | H | H | H | IZ4-636 | PH | PH | BBO8 | H | H | H |
IZ4-597 | PH | PH | BBJ2 | H | H | H | IZ4-637 | Oct | Oct | BBO8 | H | H | H |
IZ4-598 | Oct | Oct | BBJ2 | H | H | H | IZ4-638 | CHM | CHM | BBO8 | H | H | H |
IZ4-599 | CHM | CHM | BBJ2 | H | H | H | IZ4-639 | CH | CH | BBO8 | H | H | H |
IZ4-600 | CH | CH | BBJ2 | H | H | H | IZ4-640 | BZ | BZ | BBO8 | H | H | H |
IZ4-601 | BZ | BZ | BBJ2 | H | H | H | IZ4-641 | EOE | EOE | BBO8 | H | H | H |
[ Table 15Z4]
TABLE 15Z4
RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | RN1Z4 | RN2Z4 | Ba1Z4Ba2Z4 | R1Z4 | R6Z4 | R7Z4 | ||
IZ4-642 | ALL | ALL | BBO8 | H | H | H | IZ4-682 | CBA | CBA | BBO10 | H | H | H |
IZ4-643 | CBA | CBA | BBO8 | H | H | H | IZ4-683 | HYE | HYE | BBO10 | H | H | H |
IZ4-644 | HYE | HYE | BBO8 | H | H | H | IZ4-684 | NA1 | NA1 | BBO10 | H | H | H |
IZ4-645 | NA1 | NA1 | BBO8 | H | H | H | IZ4-685 | HHk8 | HHk8 | BBO10 | H | H | H |
IZ4-646 | HHk8 | HHk8 | BBO8 | H | H | H | IZ4-686 | NA2 | NA2 | BBO10 | H | H | H |
IZ4-647 | NA2 | NA2 | BBO8 | H | H | H | IZ4-687 | HHk7 | HHk7 | BBO10 | H | H | H |
IZ4-648 | HHk7 | HHk7 | BBO8 | H | H | H | IZ4-688 | HH37 | HH37 | BBO10 | H | H | H |
IZ4-649 | HH37 | HH37 | BBO8 | H | H | H | IZ4-689 | HHk6 | HHk6 | BBO10 | H | H | H |
IZ4-650 | HHk6 | HHk6 | BBO8 | H | H | H | IZ4-690 | NA3 | NA3 | BBO10 | H | H | H |
IZ4-651 | NA3 | NA3 | BBO8 | H | H | H | IZ4-691 | HHJ2 | HHJ2 | BBO10 | H | H | H |
IZ4-652 | HHJ2 | HHJ2 | BBO8 | H | H | H | IZ4-692 | HHk11 | HHk11 | BBO10 | H | H | H |
IZ4-653 | HHk11 | HHk11 | BBO8 | H | H | H | IZ4-693 | Et | Me | BBO10 | H | H | H |
IZ4-654 | Et | Me | BBO8 | H | H | H | IZ4-694 | PH | Me | BBO10 | H | H | H |
IZ4-655 | PH | Me | BBO8 | H | H | H | IZ4-695 | Oct | Me | BBO10 | H | H | H |
IZ4-656 | Oct | Me | BBO8 | H | H | H | IZ4-696 | CHM | Me | BBO10 | H | H | H |
IZ4-657 | CHM | Me | BBO8 | H | H | H | IZ4-697 | CH | Me | BBO10 | H | H | H |
IZ4-658 | CH | Me | BBO8 | H | H | H | IZ4-698 | BZ | Me | BBO10 | H | H | H |
IZ4-659 | BZ | Me | BBO8 | H | H | H | IZ4-699 | EOE | Me | BBO10 | H | H | H |
IZ4-660 | EOE | Me | BBO8 | H | H | H | IZ4-700 | ALL | Me | BBO10 | H | H | H |
IZ4-661 | ALL | Me | BBO8 | H | H | H | IZ4-701 | CBA | Me | BBO10 | H | H | H |
IZ4-662 | CBA | Me | BBO8 | H | H | H | IZ4-702 | HYE | Me | BBO10 | H | H | H |
IZ4-663 | HYE | Me | BBO8 | H | H | H | IZ4-703 | NA1 | Me | BBO10 | H | H | H |
IZ4-664 | NA1 | Me | BBO8 | H | H | H | IZ4-704 | HHk8 | Me | BBO10 | H | H | H |
IZ4-665 | HHk8 | Me | BBO8 | H | H | H | IZ4-705 | NA2 | Me | BBO10 | H | H | H |
IZ4-666 | NA2 | Me | BBO8 | H | H | H | IZ4-706 | HHk7 | Me | BBO10 | H | H | H |
IZ4-667 | HHk7 | Me | BBO8 | H | H | H | IZ4-707 | HH37 | Me | BBO10 | H | H | H |
IZ4-668 | HH37 | Me | BBO8 | H | H | H | IZ4-708 | HHk6 | Me | BBO10 | H | H | H |
IZ4-669 | HHk6 | Me | BBO8 | H | H | H | IZ4-709 | NA3 | Me | BBO10 | H | H | H |
IZ4-670 | NA3 | Me | BBO8 | H | H | H | IZ4-710 | HHJ2 | Me | BBO10 | H | H | H |
IZ4-671 | HHJ2 | Me | BBO8 | H | H | H | IZ4-711 | HHk11 | Me | BBO10 | H | H | H |
IZ4-672 | HHk11 | Me | BBO8 | H | H | H | IZ4-712 | HH9 | HHf5 | BB2 | H | H | H |
IZ4-673 | Me | Me | BBO10 | H | H | H | IZ4-713 | HHh1 | HHj19 | BB3 | H | H | H |
IZ4-674 | Et | Et | BBO10 | H | H | H | IZ4-714 | HH55 | HH81 | BB4 | H | H | H |
IZ4-675 | PH | PH | BBO10 | H | H | H | IZ4-715 | HHf1 | HHi11 | BB5 | H | H | H |
IZ4-676 | Oct | Oct | BBO10 | H | H | H | IZ4-716 | NA5 | HHJ10 | BB7 | H | H | H |
IZ4-677 | CHM | CHM | BBO10 | H | H | H | IZ4-717 | HHk7 | HHc1 | BB9 | H | H | H |
IZ4-678 | CH | CH | BBO10 | H | H | H | IZ4-718 | HHf11 | HH28 | BB10 | H | H | H |
IZ4-679 | BZ | BZ | BBO10 | H | H | H | IZ4-719 | HH13 | HH46 | BB12 | H | H | H |
IZ4-680 | EOE | EOE | BBO10 | H | H | H | IZ4-720 | HHJ4 | HH78 | BB13 | H | H | H |
IZ4-681 | ALL | ALL | BBO10 | H | H | H | IZ4-721 | HHb3 | HH22 | BB15 | H | H | H |
[ Table 16Z4]
TABLE 16Z4
For example, the compound IZ4-1 is a compound represented by the formula (IZ 4-1).
The compound IZ4 is preferably a compound IZ4-1 to a compound IZ4-234 and a compound IZ4-321 to a compound IZ4-769, more preferably a compound IZ4-1 to a compound IZ4-234 and a compound IZ4-321 to a compound IZ4-711, still more preferably a compound IZ4-1 to a compound IZ4-234, yet more preferably a compound IZ4-1 to a compound IZ4-174, particularly preferably a compound IZ4-1 to a compound IZ4-117,
particularly preferred are the compound IZ4-1 to the compound IZ4-2, the compound IZ4-40 to the compound IZ4-41, and the compound IZ4-79 to the compound IZ 4-80.
Specific examples of the compound IZ4 include compounds represented by table 1Z4, table 2Z4, table 3Z4, table 4Z4, table 5Z4, table 6Z4, table 7Z4, table 8Z4, and tables 11Z4 to 16Z4, in which 1 to 3 hydrogen atoms contained in the compounds are replaced by — SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ4-1 of Table 1Z4 are represented by the following structures. Wherein, in the formula, - (SO)3H) Represents a compound in which any hydrogen atom in compound IZ4-1 of Table 1Z4 is substituted.
In the present invention, it is preferable that 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-234 and the compound IZ4-321 to the compound IZ4-7693M or-CO2More preferably, the compound of M is a compound in which 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-234 and the compound IZ4-321 to the compound IZ4-711 3M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-2343M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-1743M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-1173M or-CO2A compound formed by the reaction of M,
particularly preferably, 1 to 3-SO groups are bonded to the compound IZ4-1 to the compound IZ4-2, the compound IZ4-40 to the compound IZ4-41, and the compound IZ4-79 to the compound IZ4-803M or-CO2M, or a salt thereof.
As the compound (IZ4), the following compounds are preferable:
in the formula (IZ4), RN1Z4And RN2Z4Independently of one another are-CO-R102Z4、-COO-R101Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z4Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2Taking of group consisting of MA substituted hydrocarbon group having 1 to 20 carbon atoms, -SO3M or-CO2M,
R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102Z4、-O-R102Z4、-SO3M or-CO2M,R6Z4And R7Z4Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R102Z4Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R101Z4May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
RN1Z4and RN2Z4Independently of one another are-CO-R102Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z4Is a hydrogen atom, R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z4)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z4、-O-R102Z4、-SO3M or-CO2M,
R6Z4And R7Z4Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R102Z4is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2a C1-10 hydrocarbon group as a substituent in the group consisting of M, R 101Z4May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RN1Z4and RN2Z4Independently of one another are-CO-R102Z4、-CON(R102Z4)2Or may have a structure selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z4is a hydrogen atom, R2Z4~R5Z4Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z4)2Nitro, trifluoromethyl, -O-R102Z4、-SO3M or-CO2M,
R6Z4And R7Z4The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, R102Z4Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R101Z4may have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ4, R1Z4In the case of a hydrogen atom, the compound represented by the formula (pt1Z4) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z4) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z4) and the compound represented by the formula (pt4Z4) in the presence of an acid. In addition, R 1Z4When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z4) to produce a compound IZ 4.
In [ formula (pt1Z4), formula (pt2Z4), formula (pt3Z4), formula (pt4Z4), formula (pt5Z4) and formula (IZ4), RN1Z4、RN2Z4、R1Z4、R2Z4、R3Z4、R4Z4、R5Z4、R6Z4And R7Z4The same meanings as described above are indicated. R14Z4Represents an alkyl group having 1 to 20 carbon atoms. M1Z4Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z4Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z4Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom. The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z4 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z4 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z4, and the compound pt4Z4 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound. The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z4 used, relative to R1Z4The amount of the compound IZ41 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z4 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z4The amount of the compound IZ41 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z4 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z4The amount of the compound IZ 41 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z4 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ4 having no sulfo group or-SO3M2In the case of (3), the compound IZ4 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22。
M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 41 mol of the compound IZ.
The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 41 moles of the compound IZ.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 41 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ4 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 4. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ5 >)
Compound IZ5 is represented by formula (IZ 5).
[ formula (IZ5), RN1Z5represents-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Independently of one another, represents a hydrogen atom, -CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group, R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Each of which may be bonded to each other to form a ring, R2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R 102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5At least one group of them is bonded to form a ring.
R101Z5The alkyl group may have a substituent and has 1 to 40 carbon atoms, or a heterocyclic group may have a substituent.
R102Z5Represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom. R101Z5、R102Z5And when there are a plurality of M, they may be the same or different. The wavy line indicates the E-body or the Z-body.]
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The number of carbon atoms of the optionally substituted hydrocarbon group is 1 to 40, preferably 1 to 401 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, and particularly preferably 1 to 5.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, particularly preferably 1 to 10, further more preferably 1 to 8, and particularly preferably 1 to 5. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms is particularly preferable, and a methyl group, an ethyl group, and a tert-butyl group are particularly preferable.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5A saturated or unsaturated alicyclic hydrocarbon group represented byExamples thereof include cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1, 2-dimethylcyclohexyl group, 1, 3-dimethylcyclohexyl group, 1, 4-dimethylcyclohexyl group, 2, 3-dimethylcyclohexyl group, 2, 4-dimethylcyclohexyl group, 2, 5-dimethylcyclohexyl group, 2, 6-dimethylcyclohexyl group, 3, 4-dimethylcyclohexyl group, 3, 5-dimethylcyclohexyl group, 2-dimethylcyclohexyl group, 3-dimethylcyclohexyl group, 4-dimethylcyclohexyl group, cyclooctyl group, 2,4, 6-trimethylcyclohexyl group, 2,6, 6-tetramethylcyclohexyl group and 3, cycloalkyl groups such as 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further more preferably 6 to 20Preferably 6 to 15.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5Examples of the group represented by the above-mentioned groups, which are a combination of the above-mentioned hydrocarbon groups (e.g., chain hydrocarbon groups and alicyclic hydrocarbon groups), include alkyl groups to which 1 or more alicyclic hydrocarbon groups are bonded, such as cyclopropylmethyl groups, cyclopropylethyl groups, cyclobutylmethyl groups, cyclobutylethyl groups, cyclopentylmethyl groups, cyclopentylethyl groups, cyclohexylmethyl groups, 2-methylcyclohexylmethyl groups, cyclohexylethyl groups, and adamantylmethyl groups. The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group; a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is an alkali metal, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3Or a thiocarbonyl group, -CO-S-C, bonded to an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) 6H5A thiocarbonyl group bonded to an aryl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), etc.), and R's may be the same or different from each other, and may be mutually different Bonded to form a ring);
a group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); and so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; fluorine atomA hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); -SO3M (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent;
a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group having 1 to 40 carbon atoms and having a substituent represented by the formula (I) includes a hydrocarbon group having 1 to 40 carbon atoms and having a substituent having a valence of 1 or 2, preferably a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, and a group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of hydrocarbon groups,
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups having 1 to 20 carbon atoms having a substituent of group s1,
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 1 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include:
monocyclic saturated heterocycles such as aziridine, azetidine, pyrrolidine, piperidine and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole;
a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine;
a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran; fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include:
five-membered ring system saturated heterocycles such as dithiolane;
saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like;
a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran);
fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include monocyclic saturated heterocyclic rings such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole); fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1Z5~R5Z52 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1Z5~R5Z5The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group represented may have a substituent. Examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom. Preferred examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The preferable examples of the substituents which the hydrocarbon group may have are the same.
As RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. As for the above-mentioned first substituent, another substituent (second substituent) may be bonded to the hydrocarbon group contained in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5Of (a) is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, -SO3M、-CO2M is explained.
as-CO-R102Z5Examples thereof include a formyl group; acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, (2-ethyl) hexanoyl, heptanoyl, examples of the carbonyl group include a carbonyl group (in the case where the carbonyl group is an acyl group, the number of carbon atoms is 2 to 41) in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group, and the compounds shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5 correspond to — CO — R.102Z5Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to-CO-R 102Z5And the like.
as-COO-R101Z5Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl and the like, and hydrocarbyl groups having 1 to 40 (preferably 1 to 20) carbon atoms or derived groups thereof (for example, through carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylaminosulfonyl groups having 1 to 10 carbon atoms (preferably through carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom)) are bonded to groups represented by the above formulaeOctyl sulfamoyl) and the like) and the corresponding-COO-R in the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5Preferred examples of the group (b) include oxycarbonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-COO-R102Z5And the like.
as-OCO-R102Z5Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And those shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to-OCO-R 102Z5Preferable examples of the group(s) include a carbonyloxy group (more preferably 2 to 12 carbon atoms when the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponds to-OCO-R102Z5And the like.
as-COCO-R102Z5Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, decyloxyl, undecyloxalyl, dodecyloxalyl, eicosanoyl, cyclopentyloxalyl, cyclohexyloxalyl, phenyloxalyl, p-tolyloxalyl and the like,And oxalyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded to a group represented by the above formula, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponding to-COCO-R 102Z5And the like.
as-O-R102Z5Examples of the group include a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbyl group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or the like, and a group represented by the above chemical formulae), and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to — O — R. 102Z5Preferred examples of the group (b) include an oxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-O-R102Z5And the like.
as-SO2-R101Z5Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, octylsulfonyl, nonyl sulfonyl, decyl sulfonyl, undecyl sulfonyl, dodecyl sulfonyl, eicosyl sulfonyl, phenyl sulfonyl, p-tolyl sulfonyl, and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like is bonded, such as the group represented by the above chemical formula, and-SO corresponds to the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z 5.2-R102Z5Preferable examples of the group (b) include sulfonyl groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-SO 2-R102Z5And the like.
as-SO2N(R102Z5)2Examples thereof include:
a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 correspond to the above groups-SO2NH(R102Z5X) (wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
N, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylsulfamoyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylsulfamoyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diethylsulfamoyl, N, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like, and sulfamoyl groups represented by the above chemical formulae and the like substituted with a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl) and the like), and sulfamoyl groups shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 Corresponding to-SO in the compound 2N(R102Z5X)2(wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof, and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-SO2N(R102Z5)2And the like.
as-CON (R)102Z5)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylA hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, an N-isopropylcarbamoyl group, an N-butylcarbamoyl group, an N-isobutylcarbamoyl group, an N-sec-butylcarbamoyl group, an N-tert-butylcarbamoyl group, an N-pentylcarbamoyl group, an N- (1-ethylpropyl) carbamoyl group, an N-hexylcarbamoyl group, an N- (2-ethyl) hexylcarbamoyl group, an N-heptylcarbamoyl group, an N-octylcarbamoyl group, an N-nonylcarbamoyl group, an N-decylcarbamoyl group, an N-undecylcarbamoyl group, an N-dodecylcarbamoyl group, an N-eicosylcarbamoyl group, an N-phenylcarbamoyl group and the like, and a group represented by the above chemical formula A carbamoyl group substituted with a group derived from sulfo, nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), or the like), and a compound shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 corresponds to-CONH (R is 102Z5X) (wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, n, N-dihexylcarbamoyl group, N-di (2-ethyl) hexylcarbamoyl group, N-diheptylcarbamoyl group, N-octylmethylcarbamoyl group, N-dioctylcarbamoyl group, N-dinonylcarbamoyl group, N-decylmethylcarbamoyl group, N-undecylmethylcarbamoyl group, N-dodecylmethylcarbamoyl group, N-eicosylmethylcarbamoyl group, N-phenylmethylcarbamoyl group, N-diphenylcarbamoyl group, etc., and the above Carbamoyl groups such as the group represented by the above chemical formula, which are substituted with 2C 1-40 (preferably C1-20) hydrocarbon groups or derivative groups thereof (e.g., groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), C1-10 alkylsulfamoyl (preferably octylsulfamoyl), etc.), and compounds shown in tables 1Z 5-7Z 5 and tables 10Z 5-13Z 5 which correspond to-CON (R)102Z5X)2(R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z5 to 7Z5 and 10Z5 to 13Z5 which corresponds to-CON (R)102Z5)2And the like.
as-N (R)102Z5)2Examples thereof include:
an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like) and a compound shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5, wherein the compound corresponds to-NH (R 102Z5X)(R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-t-butylmethylamino group, N-diisobutylamino groupA hydrocarbon group having 2 carbon atoms of 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a di-sec-butylamino group, an N, N-di-tert-butylamino group, an N, N-butylmethylamino group, an N, N-dibutylamino group, an N, N-dipentylamino group, an N, N-di (1-ethylpropyl) amino group, an N, N-dihexylamino group, an N, N-di (2-ethyl) hexylamino group, an N, N-diheptylamino group, an N, N-dioctylamino group, an N, N-dinonylamino group, an N, N-decylmethylamino group, an N, N-undecylmethylamino group, an N, N-dodecylmethylamino group, an N, N-eicosylmethylamino group, an N, N-phenylmethylamino group, an N, N-diphenylamino group, etc., and a group represented by the above chemical formula, A derivative of sulfo, nitro, hydroxy, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), or the like) and a compound shown in tables 1Z5 to 7Z5 and 10Z5 to 13Z5, wherein the compound corresponds to-N (R 102Z5X)2(wherein, R102Z5XIs not a hydrogen atom, other than, and R102Z5The same as defined above) and the like,
preferred examples thereof include amino groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-N (R)102Z5)2And the like.
as-NHCO-R102Z5Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (in the case where the carbonylamino group is an acylamino group, the carbon number is 1 to 40), wherein a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded to an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group, or the like, or a group represented by the above chemical formula), and tables 1Z5 to 7Z5 and tables. 10Z5 to Table 13Z5 correspond to-NHCO-R102Z5And the like,
preferred examples thereof include carbonylamino groups to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5, which correspond to-NHCO-R102Z5And the like.
as-NHCON (R)102Z5)2Examples thereof include the groups listed above and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5 which correspond to-NHCON (R)102Z5)2And the like.
as-NHCOOR102Z5Examples thereof include those corresponding to-NHCOOR among the above-mentioned groups and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5And the like.
as-OCON (R)102Z5)2Examples thereof include those corresponding to-OCON (R) among the above-mentioned groups and the compounds shown in tables 1Z5 to 7Z5 and tables 10Z5 to 13Z5102Z5)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102Z5、-COO-R102Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R102Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCON(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 5). As R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Nitrogen-containing fused heterocycles such as pyridine, phenanthroline, and phenazine, and partial reductants thereof; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2Z5And R3Z5、R3Z5And R4Z5And R4Z5And R5Z5In the case of forming a ring, the ring may have a substituent. Examples of the substituent include N1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent includeN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5、R7Z5、R101Z5And R102Z5The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3Z5And R4Z5When forming a ring, as R2Z5And R5Z5Independently of one another, hydrogen atoms, amino groups and hydroxyl groups are preferred.
R2Z5And R3Z5When a ring is formed, R is preferably4Z5And R5Z5Does not form a ring, more preferably R4Z5And R5Z5Is a hydrogen atom.
R4Z5And R5Z5When a ring is formed, R is preferably2Z5And R3Z5Does not form a ring, more preferably R2Z5And R3Z5Is a hydrogen atom. R1Z5、R6Z5And R7Z5Preferably a hydrogen atom.
RN1Z5preferably-CO-R102Z5、-COO-R101Z5、-CON(R102Z5)2、-N(R102Z5)2、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, more preferably a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, still more preferably a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, particularly preferably a hydrocarbon group having 1 to 6 carbon atoms which may have a substituent or a hydrocarbon group having 1 to 5 carbon atoms which may have a substituent, still more preferably a methyl group, an ethyl group or a phenyl group, and most preferably a methyl group or an ethyl group.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z5、R3Z5、R4Z5And R5Z5At least one of which is-CO-R102Z5、-COO-R101Z5、-OCO-R102Z5、-COCO-R102Z5、-O-R102Z5、-SO2-R101Z5、-SO2N(R102Z5)2、-CON(R102Z5)2、-N(R102Z5)2、-NHCO-R102Z5、-NHCO-N(R102Z5)2、-NHCOOR102Z5、-OCON(R102Z5)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, more preferably a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a halogen atom, -N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M is more preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Alternatively, R is preferred2Z5And R3Z5、R3Z5And R4Z5Or R4Z5And R5Z5Form a ring.
From the viewpoint of reducing the retardation value of the color filter formed from the colored composition, R is preferable2Z5、R3Z5、R4Z5And R5Z5At least one of which is an optionally substituted hydrocarbon group having 1 to 40 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,
More preferably a nitro group or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and still more preferably a nitro group or a tert-butyl group. Among them, it is still more preferable that R 3Z5Is nitro or tert-butyl, R2Z5、R4Z5And R5Z5Is a hydrogen atom; or, R2Z5、R3Z5And R5Z5Is a hydrogen atom, R4Z5Is nitro or tert-butyl.
Specific examples of compound IZ5 include compounds IZ5-1 to IZ5-1 having substituents shown in table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and table 10Z5 to table 13Z5 in formula (IZ5-aa)IZ5-542 or an alkali metal salt thereof. B isa1Z5Ba2Z5The partial structure represented by any one of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) is shown. The formulae (BB2) to (BB60), (BBK2), (BBK3), (BBK4), (BBK14), (BBI1), (BBO8), (BBO10), (BBD1) and (BBJ2) are the same as B representing formula (IZ1-aa)a1Z1Ba2Z1The same structures as (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) described above. B isa1Z5And Ba2Z5Each represents a chemical bond, Ba1Z5B of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2)1When a chemical bond of (A) is present, Ba2Z5To be B2The chemical bond of (a); b isa1Z5B of formulae (BB2) to (BB60), formula (BBK2), formula (BBK3), formula (BBK4), formula (BBK14), formula (BBI1), formula (BBO8), formula (BBO10), formula (BBD1) and formula (BBJ2) 2When a chemical bond of (A) is present, Ba2Z5To be B1The chemical bond of (1). As Ba1Z5Ba2Z5Formula (BB6), formula (BB8), formula (BB11), formula (BB14), formula (BB19), formula (BB37), formula (BB58), formula (BBJ2), formula (BBO8), and formula (BBO10) are preferable, and formula (BB6) and formula (BB19) are more preferable.
Each symbol in table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and tables 10Z5 to table 13Z5 represents the following partial structure. In the partial structure, "Me" represents a methyl group, "Et" represents an ethyl group, "Bu" represents a butyl group, "TBu" represents a tert-butyl group, "Hex" represents a hexyl group, "Oct" represents an octyl group, "2 EH" represents a 2-ethylhexyl group, "CHM" represents a cyclohexylmethyl group, "CH" represents a cyclohexyl group, "PH" represents a phenyl group, "BZ" represents a benzyl group, "NPR" represents a propyl group, "IPR" represents an isopropyl group, "IBu" represents an isobutyl group, and "EOE"represents-CH2CH2OCH2CH3"ALL" represents allyl, "HYE" represents 2-hydroxyethyl, and "COM" represents-CO-CH3And "COE" represents-COO-CH2CH3And "OCM" represents-OCO-CH3And "OME" represents-O-CH3"SOT" represents a tosyl group, and "SNH" represents-SO2NH-CH2CH(CH2CH3)((CH2)3CH3) "SN 2" represents-SO2N(CH3)((CH2)7CH3) "CNM" represents-CONHCH 3And "CN 2" represents-CON (CH)3)C6H5And "NPH" represents-NHC6H5And "NOT" represents-N ((CH)2)7CH3)2And "NCO" represents-NHCO ((CH)2)4CH3) "F" represents a fluorine atom, "Cl" represents a chlorine atom, "Br" represents a bromine atom, "CN" represents a cyano group, "NO 2" represents a nitro group, and "SUA" represents-SO3H, "CBA" means-CO2H, "CHO" means-CHO, "OCH" means-OCOH, "OH" means-OH, "SFM" means-SO2NH2"CBM" represents-CONH2"NH 2" means-NH2"NCH" represents-nhcooh, and represents a chemical bond. In the table, the following partial structures are denoted by symbols.
[ Table 1Z5]
TABLE 1Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-1 | Me | BB6 | H | H | H |
IZ5-2 | Et | BB6 | H | H | H |
IZ5-3 | PH | BB6 | H | H | H |
IZ5-4 | Bu | BB6 | H | H | H |
IZ5-5 | TBu | BB6 | H | H | H |
IZ5-6 | Hex | BB6 | H | H | H |
IZ5-7 | Oct | BB6 | H | H | H |
IZ5-8 | 2EH | BB6 | H | H | H |
IZ5-9 | CHM | BB6 | H | H | H |
IZ5-10 | CH | BB6 | H | H | H |
IZ5-11 | BZ | BB6 | H | H | H |
IZ5-12 | NPR | BB6 | H | H | H |
IZ5-13 | IPR | BB6 | H | H | H |
IZ5-14 | IBu | BB6 | H | H | H |
IZ5-15 | EOE | BB6 | H | H | H |
IZ5-16 | ALL | BB6 | H | H | H |
IZ5-17 | NH2 | BB6 | H | H | H |
IZ5-18 | CBM | BB6 | H | H | H |
IZ5-19 | COM | BB6 | H | H | H |
IZ5-20 | COE | BB6 | H | H | H |
IZ5-21 | CBA | BB6 | H | H | H |
IZ5-22 | HYE | BB6 | H | H | H |
IZ5-23 | Me | BB19 | H | H | H |
IZ5-24 | Et | BB19 | H | H | H |
IZ5-25 | PH | BB19 | H | H | H |
IZ5-26 | Bu | BB19 | H | H | H |
IZ5-27 | TBu | BB19 | H | H | H |
IZ5-28 | Hex | BB19 | H | H | H |
IZ5-29 | Oct | BB19 | H | H | H |
IZ5-30 | 2EH | BB19 | H | H | H |
IZ5-31 | CHM | BB19 | H | H | H |
IZ5-32 | CH | BB19 | H | H | H |
IZ5-33 | BZ | BB19 | H | H | H |
IZ5-34 | NPR | BB19 | H | H | H |
IZ5-35 | IPR | BB19 | H | H | H |
IZ5-36 | IBu | BB19 | H | H | H |
IZ5-37 | EOE | BB19 | H | H | H |
IZ5-38 | ALL | BB19 | H | H | H |
IZ5-39 | NH2 | BB19 | H | H | H |
IZ5-40 | CBM | BB19 | H | H | H |
[ Table 2Z5]
TABLE 2Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-41 | COM | BB19 | H | H | H |
IZ5-42 | COE | BB19 | H | H | H |
IZ5-43 | CBA | BB19 | H | H | H |
IZ5-44 | HYE | BB19 | H | H | H |
IZ5-45 | BZ | BB2 | H | H | H |
IZ5-46 | CHM | BB3 | H | H | H |
IZ5-47 | ALL | BB4 | H | H | H |
IZ5-48 | CBM | BB5 | H | H | H |
IZ5-49 | Me | BB7 | H | H | H |
IZ5-50 | NH2 | BB8 | H | H | H |
IZ5-51 | 2EH | BB9 | H | H | H |
IZ5-52 | Et | BB10 | H | H | H |
IZ5-53 | IPR | BB11 | H | H | H |
IZ5-54 | COM | BB12 | H | H | H |
IZ5-55 | CBA | BB13 | H | H | H |
IZ5-56 | HYE | BB14 | H | H | H |
IZ5-57 | Bu | BB15 | H | H | H |
IZ5-58 | Hex | BB16 | H | H | H |
IZ5-59 | EOE | BB17 | H | H | H |
IZ5-60 | CH | BB18 | H | H | H |
IZ5-61 | PH | BB20 | H | H | H |
IZ5-62 | COE | BB21 | H | H | H |
IZ5-63 | TBu | BB22 | H | H | H |
IZ5-64 | Oct | BB23 | H | H | H |
IZ5-65 | IBu | BB24 | H | H | H |
IZ5-66 | NPR | BB25 | H | H | H |
IZ5-67 | BZ | BB26 | H | H | H |
IZ5-68 | CHM | BB27 | H | H | H |
IZ5-69 | ALL | BB28 | H | H | H |
IZ5-70 | CBM | BB29 | H | H | H |
IZ5-71 | Me | BB30 | H | H | H |
IZ5-72 | NH2 | BB31 | H | H | H |
IZ5-73 | 2EH | BB32 | H | H | H |
IZ5-74 | Et | BB33 | H | H | H |
IZ5-75 | IPR | BB34 | H | H | H |
IZ5-76 | COM | BB35 | H | H | H |
IZ5-77 | CBA | BB36 | H | H | H |
IZ5-78 | HYE | BB37 | H | H | H |
IZ5-79 | Bu | BB38 | H | H | H |
IZ5-80 | Hex | BB39 | H | H | H |
[ Table 3Z5]
TABLE 3Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-81 | EOE | BB40 | H | H | H |
IZ5-82 | CH | BB41 | H | H | H |
IZ5-83 | PH | BB42 | H | H | H |
IZ5-84 | COE | BB43 | H | H | H |
IZ5-85 | TBu | BB44 | H | H | H |
IZ5-86 | Oct | BB45 | H | H | H |
IZ5-87 | IBu | BB46 | H | H | H |
IZ5-88 | NPR | BB47 | H | H | H |
IZ5-89 | BZ | BB48 | H | H | H |
IZ5-90 | CHM | BB49 | H | H | H |
IZ5-91 | ALL | BB50 | H | H | H |
IZ5-92 | CBM | BB51 | H | H | H |
IZ5-93 | Me | BB52 | H | H | H |
IZ5-94 | NH2 | BB53 | H | H | H |
IZ5-95 | 2EH | BB54 | H | H | H |
IZ5-96 | Et | BB55 | H | H | H |
IZ5-97 | IPR | BB56 | H | H | H |
IZ5-98 | COM | BB57 | H | H | H |
IZ5-99 | CBA | BB58 | H | H | H |
IZ5-100 | HYE | BB59 | H | H | H |
IZ5-101 | PH | BB60 | H | H | H |
IZ5-102 | Et | BB2 | H | Et | Et |
IZ5-103 | IPR | BB3 | H | NPR | NPR |
IZ5-104 | COM | BB4 | H | HYE | HYE |
IZ5-105 | CBA | BB5 | H | PH | PH |
IZ5-106 | HYE | BB6 | H | Me | Me |
IZ5-107 | Bu | BB7 | H | ALL | ALL |
IZ5-108 | PH | BB8 | H | 2EH | 2EH |
IZ5-109 | EOE | BB9 | H | CH | CH |
IZ5-110 | BZ | BB10 | H | BZ | H |
IZ5-111 | CHM | BB11 | Me | Me | Me |
IZ5-112 | ALL | BB12 | H | COM | COM |
IZ5-113 | CBM | BB13 | H | NPR | NPR |
IZ5-114 | Me | BB14 | H | IBu | IBu |
IZ5-115 | NH2 | BB15 | H | Oct | Oct |
IZ5-116 | 2EH | BB16 | H | COE | COE |
IZ5-117 | Et | BB17 | H | HYE | HYE |
IZ5-118 | IPR | BB18 | H | EOE | EOE |
IZ5-119 | COM | BB19 | Me | Me | Me |
IZ5-120 | CBA | BB20 | H | Hex | Hex |
[ Table 4Z5]
TABLE 4Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-121 | HYE | BB21 | H | IPR | IPR |
IZ5-122 | Bu | BB22 | H | NH2 | NH2 |
IZ5-123 | Hex | BB23 | H | Et | Et |
IZ5-124 | EOE | BB24 | H | BZ | BZ |
IZ5-125 | CH | BB25 | H | Me | Me |
IZ5-126 | PH | BB26 | H | CBA | CBA |
IZ5-127 | COE | BB27 | H | BZ | H |
IZ5-128 | TBu | BB28 | H | CHM | CHM |
IZ5-129 | Oct | BB29 | H | TBu | TBu |
IZ5-130 | IBu | BB30 | H | PH | PH |
IZ5-131 | NPR | BB31 | H | Bu | Bu |
IZ5-132 | BZ | BB32 | Et | CH | CH |
IZ5-133 | CHM | BB33 | H | ALL | ALL |
IZ5-134 | ALL | BB34 | H | CBM | CBM |
IZ5-135 | CBM | BB35 | H | CH | CH |
IZ5-136 | Me | BB36 | H | 2EH | 2EH |
IZ5-137 | NH2 | BB37 | H | COM | COM |
IZ5-138 | 2EH | BB38 | H | NPR | NPR |
IZ5-139 | Et | BB39 | H | IBu | IBu |
IZ5-140 | IPR | BB40 | H | Oct | Oct |
IZ5-141 | COM | BB41 | H | COE | COE |
IZ5-142 | CBA | BB42 | H | HYE | HYE |
IZ5-143 | HYE | BB43 | H | EOE | EOE |
IZ5-144 | Bu | BB44 | Me | Me | Me |
IZ5-145 | Hex | BB45 | H | Hex | Hex |
IZ5-146 | EOE | BB46 | H | IPR | IPR |
IZ5-147 | CH | BB47 | H | NH2 | NH2 |
IZ5-148 | PH | BB48 | H | Et | Et |
IZ5-149 | COE | BB49 | H | BZ | BZ |
IZ5-150 | TBu | BB50 | H | Me | Me |
IZ5-151 | Oct | BB51 | H | CBA | CBA |
IZ5-152 | IBu | BB52 | H | BZ | H |
IZ5-153 | NPR | BB53 | H | CHM | CHM |
IZ5-154 | BZ | BB54 | H | TBu | TBu |
IZ5-155 | CHM | BB55 | H | PH | PH |
IZ5-156 | ALL | BB56 | H | Bu | Bu |
IZ5-157 | CBM | BB57 | Et | CH | CH |
IZ5-158 | Me | BB58 | H | ALL | ALL |
IZ5-159 | NH2 | BB59 | H | CBM | CBM |
IZ5-160 | 2EH | BB60 | H | CH | CH |
[ Table 5Z5]
TABLE 5Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-161 | ALL | BB2 | SOT | H | H |
IZ5-162 | CBM | BB3 | SNH | H | H |
IZ5-163 | Me | BB4 | TBu | H | H |
IZ5-164 | NH2 | BB5 | SN2 | H | H |
IZ5-165 | 2EH | BB6 | CNM | H | H |
IZ5-166 | Et | BB7 | Hex | H | H |
IZ5-167 | IPR | BB8 | CN2 | H | H |
IZ5-168 | COM | BB9 | NPH | H | H |
IZ5-169 | CBA | BB10 | Oct | H | H |
IZ5-170 | HYE | BB11 | NOT | H | H |
IZ5-171 | Bu | BB12 | NCO | H | H |
IZ5-172 | Hex | BB13 | H | 2EH | H |
IZ5-173 | EOE | BB14 | H | H | F |
IZ5-174 | CH | BB15 | H | Cl | H |
IZ5-175 | PH | BB16 | H | H | CHM |
IZ5-176 | COE | BB17 | H | Br | H |
IZ5-177 | IBu | BB18 | H | H | CN |
IZ5-178 | NPR | BB19 | H | CH | H |
IZ5-179 | BZ | BB20 | H | H | NO2 |
IZ5-180 | CHM | BB21 | H | SUA | H |
IZ5-181 | ALL | BB22 | H | H | PH |
IZ5-182 | CBM | BB23 | H | CBA | H |
IZ5-183 | Me | BB24 | H | H | CHO |
IZ5-184 | NH2 | BB25 | H | BZ | BZ |
IZ5-185 | 2EH | BB26 | H | H | OCH |
IZ5-186 | Et | BB27 | H | NPR | H |
IZ5-187 | IPR | BB28 | H | H | OH |
IZ5-188 | COM | BB29 | H | IPR | H |
IZ5-189 | CBA | BB30 | H | H | SFM |
IZ5-190 | HYE | BB31 | H | IBu | H |
IZ5-191 | Bu | BB32 | H | H | CBM |
IZ5-192 | Hex | BB33 | H | EOE | H |
IZ5-193 | EOE | BB34 | H | H | NH2 |
IZ5-194 | CH | BB35 | H | ALL | H |
IZ5-195 | PH | BB36 | H | H | NCH |
IZ5-196 | COE | BB37 | H | HYE | H |
IZ5-197 | TBu | BB38 | 2EH | H | H |
IZ5-198 | Oct | BB39 | F | H | H |
IZ5-199 | IBu | BB40 | Cl | H | H |
IZ5-200 | NPR | BB41 | CHM | H | H |
[ Table 6Z5]
TABLE 6Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-201 | BZ | BB42 | Br | H | H |
IZ5-202 | CHM | BB43 | CN | H | H |
IZ5-203 | ALL | BB44 | CH | H | H |
IZ5-204 | CBM | BB45 | NO2 | H | H |
IZ5-205 | Me | BB46 | SUA | H | H |
IZ5-206 | NH2 | BB47 | PH | H | H |
IZ5-207 | 2EH | BB48 | CBA | H | H |
IZ5-208 | Et | BB49 | CHO | H | H |
IZ5-209 | IPR | BB50 | BZ | H | H |
IZ5-210 | COM | BB51 | OCH | H | H |
IZ5-211 | CBA | BB52 | NPR | H | H |
IZ5-212 | HYE | BB53 | OH | H | H |
IZ5-213 | Bu | BB54 | IPR | H | H |
IZ5-214 | Hex | BB55 | SFM | H | H |
IZ5-215 | EOE | BB56 | IBu | H | H |
IZ5-216 | CH | BB57 | CBM | H | H |
IZ5-217 | PH | BB58 | EOE | H | H |
IZ5-218 | COE | BB59 | NH2 | H | H |
IZ5-219 | TBu | BB60 | ALL | H | H |
IZ5-220 | Oct | BB2 | NCH | H | H |
IZ5-221 | IBu | BB3 | HYE | H | H |
IZ5-222 | NPR | BB4 | H | Me | H |
IZ5-223 | BZ | BB5 | H | H | COM |
IZ5-224 | CHM | BB6 | H | COE | H |
IZ5-225 | ALL | BB7 | H | H | Et |
IZ5-226 | CBM | BB8 | H | OCM | H |
IZ5-227 | Me | BB9 | H | H | OME |
IZ5-228 | NH2 | BB10 | H | Bu | H |
IZ5-229 | 2EH | BB11 | H | H | SOT |
IZ5-230 | Et | BB12 | H | SNH | H |
IZ5-231 | IPR | BB13 | H | H | TBu |
IZ5-232 | COM | BB14 | H | SN2 | H |
IZ5-233 | CBA | BB15 | H | H | CNM |
IZ5-234 | HYE | BB16 | H | Hex | H |
IZ5-235 | Bu | BB17 | H | H | CN2 |
IZ5-236 | Hex | BB18 | H | NPH | H |
IZ5-237 | EOE | BB19 | H | H | Oct |
IZ5-238 | CH | BB20 | H | NOT | H |
IZ5-239 | PH | BB21 | H | H | NCO |
IZ5-240 | COE | BB22 | Me | H | H |
[ Table 7Z5]
TABLE 7Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | |
IZ5-241 | TBu | BB23 | COM | H | H |
IZ5-242 | Oct | BB24 | COE | H | H |
IZ5-243 | IBu | BB25 | Et | H | H |
IZ5-244 | NPR | BB26 | OCM | H | H |
IZ5-245 | BZ | BB27 | OME | H | H |
IZ5-246 | CHM | BB28 | Bu | H | H |
IZ5-247 | Me | BB8 | H | H | H |
[ Table 10Z5]
TABLE 10Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | ||
IZ5-248 | NA1 | BB6 | H | H | H | IZ5-288 | Hex | BB11 | H | H | H |
IZ5-249 | HHk8 | BB6 | H | H | H | IZ5-289 | Oct | BB11 | H | H | H |
IZ5-250 | NA2 | BB6 | H | H | H | IZ5-290 | 2EH | BB11 | H | H | H |
IZ5-251 | HHk7 | BB6 | H | H | H | IZ5-291 | CHM | BB11 | H | H | H |
IZ5-252 | HH37 | BB6 | H | H | H | IZ5-292 | CH | BB11 | H | H | H |
IZ5-253 | HHk6 | BB6 | H | H | H | IZ5-293 | BZ | BB11 | H | H | H |
IZ5-254 | NA3 | BB6 | H | H | H | IZ5-294 | EOE | BB11 | H | H | H |
IZ5-255 | HHJ2 | BB6 | H | H | H | IZ5-295 | ALL | BB11 | H | H | H |
IZ5-256 | HHk11 | BB6 | H | H | H | IZ5-296 | NH2 | BB11 | H | H | H |
IZ5-257 | Et | BB8 | H | H | H | IZ5-297 | CBM | BB11 | H | H | H |
IZ5-258 | PH | BB8 | H | H | H | IZ5-298 | COM | BB11 | H | H | H |
IZ5-259 | Bu | BB8 | H | H | H | IZ5-299 | COE | BB11 | H | H | H |
IZ5-260 | TBu | BB8 | H | H | H | IZ5-300 | CBA | BB11 | H | H | H |
IZ5-261 | Hex | BB8 | H | H | H | IZ5-301 | HYE | BB11 | H | H | H |
IZ5-262 | Oct | BB8 | H | H | H | IZ5-302 | NA1 | BB11 | H | H | H |
IZ5-263 | 2EH | BB8 | H | H | H | IZ5-303 | HHk8 | BB11 | H | H | H |
IZ5-264 | CHM | BB8 | H | H | H | IZ5-304 | NA2 | BB11 | H | H | H |
IZ5-265 | CH | BB8 | H | H | H | IZ5-305 | HHk7 | BB11 | H | H | H |
IZ5-266 | BZ | BB8 | H | H | H | IZ5-306 | HH37 | BB11 | H | H | H |
IZ5-267 | EOE | BB8 | H | H | H | IZ5-307 | HHk6 | BB11 | H | H | H |
IZ5-268 | ALL | BB8 | H | H | H | IZ5-308 | NA3 | BB11 | H | H | H |
IZ5-269 | CBM | BB8 | H | H | H | IZ5-309 | HHJ2 | BB11 | H | H | H |
IZ5-270 | COM | BB8 | H | H | H | IZ5-310 | HHk11 | BB11 | H | H | H |
IZ5-271 | COE | BB8 | H | H | H | IZ5-311 | Me | BB14 | H | H | H |
IZ5-272 | CBA | BB8 | H | H | H | IZ5-312 | Et | BB14 | H | H | H |
IZ5-273 | HYE | BB8 | H | H | H | IZ5-313 | PH | BB14 | H | H | H |
IZ5-274 | NA1 | BB8 | H | H | H | IZ5-314 | Bu | BB14 | H | H | H |
IZ5-275 | HHk8 | BB8 | H | H | H | IZ5-315 | TBu | BB14 | H | H | H |
IZ5-276 | NA2 | BB8 | H | H | H | IZ5-316 | Hex | BB14 | H | H | H |
IZ5-277 | HHk7 | BB8 | H | H | H | IZ5-317 | Oct | BB14 | H | H | H |
IZ5-278 | HH37 | BB8 | H | H | H | IZ5-318 | 2EH | BB14 | H | H | H |
IZ5-279 | HHk6 | BB8 | H | H | H | IZ5-319 | CHM | BB14 | H | H | H |
IZ5-280 | NA3 | BB8 | H | H | H | IZ5-320 | CH | BB14 | H | H | H |
IZ5-281 | HHJ2 | BB8 | H | H | H | IZ5-321 | BZ | BB14 | H | H | H |
IZ5-282 | HHk11 | BB8 | H | H | H | IZ5-322 | EOE | BB14 | H | H | H |
IZ5-283 | Me | BB11 | H | H | H | IZ5-323 | ALL | BB14 | H | H | H |
IZ5-284 | Et | BB11 | H | H | H | IZ5-324 | NH2 | BB14 | H | H | H |
IZ5-285 | PH | BB11 | H | H | H | IZ5-325 | CBM | BB14 | H | H | H |
IZ5-286 | Bu | BB11 | H | H | H | IZ5-326 | COM | BB14 | H | H | H |
IZ5-287 | TBu | BB11 | H | H | H | IZ5-327 | COE | BB14 | H | H | H |
[ Table 11Z5]
TABLE 11Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | ||
IZ5-328 | CBA | BB14 | H | H | H | IZ5-368 | HHk7 | BB37 | H | H | H |
IZ5-329 | NA1 | BB14 | H | H | H | IZ5-369 | HH37 | BB37 | H | H | H |
IZ5-330 | HHk8 | BB14 | H | H | H | IZ5-370 | HHk6 | BB37 | H | H | H |
IZ5-331 | NA2 | BB14 | H | H | H | IZ5-371 | NA3 | BB37 | H | H | H |
IZ5-332 | HHk7 | BB14 | H | H | H | IZ5-372 | HHJ2 | BB37 | H | H | H |
IZ5-333 | HH37 | BB14 | H | H | H | IZ5-373 | HHk11 | BB37 | H | H | H |
IZ5-334 | HHk6 | BB14 | H | H | H | IZ5-374 | Me | BB58 | H | H | H |
IZ5-335 | NA3 | BB14 | H | H | H | IZ5-375 | Et | BB58 | H | H | H |
IZ5-336 | HHJ2 | BB14 | H | H | H | IZ5-376 | PH | BB58 | H | H | H |
IZ5-337 | HHk11 | BB14 | H | H | H | IZ5-377 | Bu | BB58 | H | H | H |
IZ5-338 | NA1 | BB19 | H | H | H | IZ5-378 | TBu | BB58 | H | H | H |
IZ5-339 | HHk8 | BB19 | H | H | H | IZ5-379 | Hex | BB58 | H | H | H |
IZ5-340 | NA2 | BB19 | H | H | H | IZ5-380 | Oct | BB58 | H | H | H |
IZ5-341 | HHk7 | BB19 | H | H | H | IZ5-381 | 2EH | BB58 | H | H | H |
IZ5-342 | HH37 | BB19 | H | H | H | IZ5-382 | CHM | BB58 | H | H | H |
IZ5-343 | HHk6 | BB19 | H | H | H | IZ5-383 | CH | BB58 | H | H | H |
IZ5-344 | NA3 | BB19 | H | H | H | IZ5-384 | BZ | BB58 | H | H | H |
IZ5-345 | HHJ2 | BB19 | H | H | H | IZ5-385 | EOE | BB58 | H | H | H |
IZ5-346 | HHk11 | BB19 | H | H | H | IZ5-386 | ALL | BB58 | H | H | H |
IZ5-347 | Me | BB37 | H | H | H | IZ5-387 | NH2 | BB58 | H | H | H |
IZ5-348 | Et | BB37 | H | H | H | IZ5-388 | CBM | BB58 | H | H | H |
IZ5-349 | PH | BB37 | H | H | H | IZ5-389 | COM | BB58 | H | H | H |
IZ5-350 | Bu | BB37 | H | H | H | IZ5-390 | COE | BB58 | H | H | H |
IZ5-351 | TBu | BB37 | H | H | H | IZ5-391 | HYE | BB58 | H | H | H |
IZ5-352 | Hex | BB37 | H | H | H | IZ5-392 | NA1 | BB58 | H | H | H |
IZ5-353 | Oct | BB37 | H | H | H | IZ5-393 | HHk8 | BB58 | H | H | H |
IZ5-354 | 2EH | BB37 | H | H | H | IZ5-394 | NA2 | BB58 | H | H | H |
IZ5-355 | CHM | BB37 | H | H | H | IZ5-395 | HHk7 | BB58 | H | H | H |
IZ5-356 | CH | BB37 | H | H | H | IZ5-396 | HH37 | BB58 | H | H | H |
IZ5-357 | BZ | BB37 | H | H | H | IZ5-397 | HHk6 | BB58 | H | H | H |
IZ5-358 | EOE | BB37 | H | H | H | IZ5-398 | NA3 | BB58 | H | H | H |
IZ5-359 | ALL | BB37 | H | H | H | IZ5-399 | HHJ2 | BB58 | H | H | H |
IZ5-360 | NH2 | BB37 | H | H | H | IZ5-400 | HHk11 | BB58 | H | H | H |
IZ5-361 | CBM | BB37 | H | H | H | IZ5-401 | Me | BBJ2 | H | H | H |
IZ5-362 | COM | BB37 | H | H | H | IZ5-402 | Et | BBJ2 | H | H | H |
IZ5-363 | COE | BB37 | H | H | H | IZ5-403 | PH | BBJ2 | H | H | H |
IZ5-364 | CBA | BB37 | H | H | H | IZ5-404 | Bu | BBJ2 | H | H | H |
IZ5-365 | NA1 | BB37 | H | H | H | IZ5-405 | TBu | BBJ2 | H | H | H |
IZ5-366 | HHk8 | BB37 | H | H | H | IZ5-406 | Hex | BBJ2 | H | H | H |
IZ5-367 | NA2 | BB37 | H | H | H | IZ5-407 | Oct | BBJ2 | H | H | H |
[ Table 12Z5] Table 12Z5
RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | RN1Z5 | Ba1Z5Ba2Z5 | R1Z5 | R6Z5 | R7Z5 | ||
IZ5-408 | 2EH | BBJ2 | H | H | H | IZ5-448 | NA1 | BBO8 | H | H | H |
IZ5-409 | CHM | BBJ2 | H | H | H | IZ5-449 | HHk8 | BBO8 | H | H | H |
IZ5-410 | CH | BBJ2 | H | H | H | IZ5-450 | NA2 | BBO8 | H | H | H |
IZ5-411 | BZ | BBJ2 | H | H | H | IZ5-451 | HHk7 | BBO8 | H | H | H |
IZ5-412 | EOE | BBJ2 | H | H | H | IZ5-452 | HH37 | BBO8 | H | H | H |
IZ5-413 | ALL | BBJ2 | H | H | H | IZ5-453 | HHk6 | BBO8 | H | H | H |
IZ5-414 | NH2 | BBJ2 | H | H | H | IZ5-454 | NA3 | BBO8 | H | H | H |
IZ5-415 | CBM | BBJ2 | H | H | H | IZ5-455 | HHJ2 | BBO8 | H | H | H |
IZ5-416 | COM | BBJ2 | H | H | H | IZ5-456 | HHk11 | BBO8 | H | H | H |
IZ5-417 | COE | BBJ2 | H | H | H | IZ5-457 | Me | BBO10 | H | H | H |
IZ5-418 | CBA | BBJ2 | H | H | H | IZ5-458 | Et | BBO10 | H | H | H |
IZ5-419 | HYE | BBJ2 | H | H | H | IZ5-459 | PH | BBO10 | H | H | H |
IZ5-420 | NA1 | BBJ2 | H | H | H | IZ5-460 | Bu | BBO10 | H | H | H |
IZ5-421 | HHk8 | BBJ2 | H | H | H | IZ5-461 | TBu | BBO10 | H | H | H |
IZ5-422 | NA2 | BBJ2 | H | H | H | IZ5-462 | Hex | BBO10 | H | H | H |
IZ5-423 | HHk7 | BBJ2 | H | H | H | IZ5-463 | Oct | BBO10 | H | H | H |
IZ5-424 | HH37 | BBJ2 | H | H | H | IZ5-464 | 2EH | BBO10 | H | H | H |
IZ5-425 | HHk6 | BBJ2 | H | H | H | IZ5-465 | CHM | BBO10 | H | H | H |
IZ5-426 | NA3 | BBJ2 | H | H | H | IZ5-466 | CH | BBO10 | H | H | H |
IZ5-427 | HHJ2 | BBJ2 | H | H | H | IZ5-467 | BZ | BBO10 | H | H | H |
IZ5-428 | HHk11 | BBJ2 | H | H | H | IZ5-468 | EOE | BBO10 | H | H | H |
IZ5-429 | Me | BBO8 | H | H | H | IZ5-469 | ALL | BBO10 | H | H | H |
IZ5-430 | Et | BBO8 | H | H | H | IZ5-470 | NH2 | BBO10 | H | H | H |
IZ5-431 | PH | BBO8 | H | H | H | IZ5-471 | CBM | BBO10 | H | H | H |
IZ5-432 | Bu | BBO8 | H | H | H | IZ5-472 | COM | BBO10 | H | H | H |
IZ5-433 | TBu | BBO8 | H | H | H | IZ5-473 | COE | BBO10 | H | H | H |
IZ5-434 | Hex | BBO8 | H | H | H | IZ5-474 | CBA | BBO10 | H | H | H |
IZ5-435 | Oct | BBO8 | H | H | H | IZ5-475 | HYE | BBO10 | H | H | H |
IZ5-436 | 2EH | BBO8 | H | H | H | IZ5-476 | NA1 | BBO10 | H | H | H |
IZ5-437 | CHM | BBO8 | H | H | H | IZ5-477 | HHk8 | BBO10 | H | H | H |
IZ5-438 | CH | BBO8 | H | H | H | IZ5-478 | NA2 | BBO10 | H | H | H |
IZ5-439 | BZ | BBO8 | H | H | H | IZ5-479 | HHk7 | BBO10 | H | H | H |
IZ5-440 | EOE | BBO8 | H | H | H | IZ5-480 | HH37 | BBO10 | H | H | H |
IZ5-441 | ALL | BBO8 | H | H | H | IZ5-481 | HHk6 | BBO10 | H | H | H |
IZ5-442 | NH2 | BBO8 | H | H | H | IZ5-482 | NA3 | BBO10 | H | H | H |
IZ5-443 | CBM | BBO8 | H | H | H | IZ5-483 | HHJ2 | BBO10 | H | H | H |
IZ5-444 | COM | BBO8 | H | H | H | IZ5-484 | HHk11 | BBO10 | H | H | H |
IZ5-445 | COE | BBO8 | H | H | H | IZ5-485 | HH22 | BB2 | H | H | H |
IZ5-446 | CBA | BBO8 | H | H | H | IZ5-486 | HH40 | BB3 | H | H | H |
IZ5-447 | HYE | BBO8 | H | H | H | IZ5-487 | HHk7 | BB4 | H | H | H |
[ Table 13Z5]
TABLE 13Z5
For example, the compound IZ5-1 is a compound represented by the following formula (IZ 5-1).
The compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-542 are preferable, the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-484 are more preferable, the compound IZ5-1 to the compound IZ5-160 are still more preferable, the compound IZ5-1 to the compound IZ5-101 are still more preferable, and the compound IZ5-1 to the compound IZ5-44 are particularly preferable.
Specific examples of the compound IZ5 include compounds represented by table 1Z5, table 2Z5, table 3Z5, table 4Z5, table 5Z5, table 6Z5, table 7Z5, and tables 10Z5 to 13Z5, in which 1 to 3 hydrogen atoms are replaced by-SO3M or-CO2M is substituted. For example, compounds having 1 to 3 sulfo groups bonded to the compound IZ5-1 of Table 1Z5 are represented by the following structures. Wherein in (SO)3H) Represents a compound in which any hydrogen atom in compound IZ5-1 of Table 1Z5 is substituted.
Preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-5423M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-160 and the compound IZ5-247 to the compound IZ5-4843M or-CO2A compound formed by the reaction of M,
more preferably, 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-1603M or-CO2M, more preferably 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-1013M or-CO2M, particularly preferably 1 to 3-SO groups are bonded to the compound IZ5-1 to the compound IZ5-443M or-CO2M, or a salt thereof.
As the compound (IZ5), the following compounds are preferable:
In the formula (IZ5), RN1Z5is-CO-R102Z5、-COO-R101Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1Z5Is a hydrogen atom and may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,
R6Z5And R7Z5Independently of one another, a hydrogen atom, may have a structure selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group, -SO3M or-CO2M,
R102Z5Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 20 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
More preferred are the following compounds:
RN1Z5is-CO-R102Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1Z5Is a hydrogen atom, R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102Z5、-O-R102Z5、-SO3M or-CO2M,R6Z5And R7Z5Are the same group, are hydrogen atoms, or may have a structure selected from the group consisting of3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R102Z5Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2A compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms, and M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
RN1Z5is-CO-R102Z5、-CON(R102Z5)2Or may have a structure selected from the group consisting of-SO 3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1Z5is a hydrogen atom, R2Z5~R5Z5Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2Nitro, trifluoromethyl, -O-R102Z5、-SO3M or-CO2M,R2Z5~R5Z5At least one of which is a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102Z5)2Nitro, trifluoromethyl, -O-R102Z5、-SO3M or-CO2M,
R6Z5And R7Z5The same group is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms,
R102Z5is a hydrogen atom, or may have a radical selected from the group consisting of-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R101Z5May have a structure selected from the group consisting of-SO3M and-CO2And M is a compound in which the substituent in the group consisting of M is a hydrocarbon group having 1 to 10 carbon atoms and M is a hydrogen atom or an alkali metal atom.
For compound IZ5, R1Z5In the case of a hydrogen atom, the compound represented by the formula (pt1Z5) (hereinafter, may be referred to as a phthalonitrile compound) may be produced by reacting a compound represented by the formula (pt2Z5) (hereinafter, may be referred to as an alkoxide compound), and then further reacting the compound represented by the formula (pt3Z5) and the compound represented by the formula (pt4Z5) in the presence of an acid. In addition, R1Z5When not a hydrogen atom, the compound is further reacted with a compound represented by the formula (pt5Z5) to produce a compound IZ 5.
In [ formula (pt1Z5), formula (pt2Z5), formula (pt3Z5), formula (pt4Z5), formula (pt5Z5) and formula (IZ5), RN1Z5、R1Z5、R2Z5、R3Z5、R4Z5、R5Z5、R6Z5And R7Z5The same meanings as described above are indicated. R14Z5Represents an alkyl group having 1 to 20 carbon atoms. M1Z5Represents an alkali metal atom. LG represents halogenAn elemental atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R14Z5Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z5Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z5 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z5 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z5, and the compound pt4Z5 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z5 used, relative to R1Z5The amount of the compound IZ51 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z5 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; organic metal compounds such as butyl lithium, tert-butyl lithium and phenyl lithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1Z5The amount of the compound IZ51 is usually 1 to 10 mol based on the hydrogen atomThe amount of the organic solvent is preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z5 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1Z5The amount of the compound IZ 51 is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z5 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound IZ5 having no sulfo group or-SO3M2In the case of (3), the compound IZ5 can be reacted with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid to introduce a sulfo group or-SO3M22。M22Represents an alkali metal atom. As M22Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
With respect to SO in oleum3The amount of (b) is usually 1 to 50 mol, preferably 5 to 40 mol, more preferably 5 to 30 mol, and still more preferably 5 to 25 mol based on 51 mol of the compound IZ. The amount of sulfuric acid used in the oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on 51 moles of the compound IZ. The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on 51 moles of the compound IZ.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound IZ5 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, after the reaction is completed, the reaction mixture is filtered to extract the compound IZ 5. The residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
< Compound IZ6 >)
Compound IZ6 is represented by formula (IZ 6).
[ in the formula (IZ6), D represents a structure having an isoindoline skeleton. Z represents-SO3 -or-CO2 -。Ac+Represents a metal cation having a valence of c. a represents an integer of 1 to 10. b represents an integer of 1 or more. c represents an integer of 2 to 10. d represents an integer of 1 or more.
D. Z, a or Ac+When there are a plurality of them, they may be the same or different. The formula (I 'Z6) and the formula (I' Z6) respectively represent partial structures of the formula (IZ6), D, Z, Ac+A, b, c and d represent the same meanings as the corresponding symbols in formula (IZ 6). The partial structure represented by the formula (I' Z6) has the same negative valence as the partial structure represented by the formula (I "Z6) has the same positive valence in absolute value. ]
The integer represented by a is 1 to 10, preferably 1 to 8, more preferably 1 to 6, and further preferably 1 to 4. The integer represented by b is 1 or more, preferably 1 to 10, and more preferably 1 to 8. The integer represented by c is 2 to 10, preferably 2 to 8, more preferably 2 to 6, and further preferably 2 to 4. d represents an integer of 1 or more, preferably 1 to 10, more preferably 1 to 8. Z is preferably-CO2 -。
Ac+Represents a metal cation having a valence of 2 or more. As the metal cation having a valence of 2 or more,
examples thereof include:the cation of a metal of groups 2 to 15 of the periodic Table of the elements is preferably Mg2+、Ca2+、Sr2 +、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+An isovalent 2 metal cation; al (Al)3+、Fe3+And Cr3+An equivalent 3 valent metal cation; sn (tin)4+And Mn4+The metal cation having a valence of 4, more preferably Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+And Mn4+More preferably, Mg is mentioned2+、Ca2 +、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+And Mn4+。
The compound represented by the formula (IZ6) is preferably a compound represented by the formula (IZ6-A) (hereinafter, may be referred to as a compound IZ 6-A.).
[ in the formula (IZ6-A), Ac+B, c and d are as defined above.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2AZ6And R 3AZ6、R3AZ6And R4AZ6、R4AZ6And R5AZ6、RAA1Z6And RAA2Z6And R12AZ6And R13AZ6Each of which may be bonded to each other to form a ring. R101AZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102AZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group. M represents a hydrogen atom or an alkali metal atom.
The formula (IZ6-A ') and the formula (IZ 6-A') each represent a partial structure of the formula (IZ6-A), Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represents the same meaning as the corresponding symbol in the formula (IZ 6-A).
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6、R102AZ6M, c or Ac+When there are plural, they may or may not be the sameThe same is true.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Satisfies at least 1 of (ra-i) to (ra-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(ra-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-SO3 -or-CO2 -。
(ra-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6or-OCON (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(ra-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO 2 -The heterocyclic group of (1). Wherein the hydrocarbon group and the heterocyclic group may have-SO3 -or-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-A') has the same negative valence as the partial structure represented by the formula (IZ6-A ") has the same positive valence in absolute value. The wavy line indicates the E-body or the Z-body. ]
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The number of carbon atoms of the hydrocarbon group is 1 to 40, preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 15, and particularly preferably 1 to 10.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group having 1 to 40 carbon atoms may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group, and the aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic group.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Examples of the saturated or unsaturated chain hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; an isopropyl group,Branched alkyl groups such as isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and further preferably 1 to 15. Among them, a linear or branched alkyl group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 5 carbon atoms is particularly preferable.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, and, Cycloalkyl groups such as 2,2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, particularly preferred is Is cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, a 4-vinylphenyl group, an o-isopropylphenyl group, a m-isopropylphenyl group, a p-isopropylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a mesityl group, a 4-ethylphenyl group, a 4-butylphenyl group, a 4-pentylphenyl group, a 2, 6-bis (2-propyl) phenyl group, a 4-cyclohexylphenyl group, a 2,4, 6-trimethylphenyl group, a 4-octylphenyl group, a 4-vinylphenyl group, a 1-naphthyl group, a 2-naphthyl group, a, Aromatic hydrocarbon groups such as 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, pyrenyl and the like; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may be a combination of the hydrocarbon groups listed above (for example, an aromatic hydrocarbon group, and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group), and examples thereof include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylvinyl (styryl); arylalkynyl groups such as phenylethynyl; a phenyl group having 1 or more phenyl groups bonded thereto, such as a biphenyl group and a terphenyl group; cyclohexylmethylphenyl, benzylphenyl, (dimethyl (phenyl) methyl) phenyl, and the like.
For R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6A group represented byExamples of the group formed by combining the hydrocarbon groups (e.g., the chain hydrocarbon group and the alicyclic hydrocarbon group) include an alkyl group in which 1 or more alicyclic hydrocarbon groups are bonded, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group.
The number of carbon atoms is preferably 4 to 30, more preferably 6 to 30, further preferably 6 to 20, further preferably 4 to 15, and particularly preferably 6 to 15.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group represented may have a substituent. The substituent may have a valence of 1 or 2. For substituents having a valence of 2, preferably 2 chemical bonds are bonded to the same carbon atom to form a double bond.
Examples of the substituent having a valence of 1 include:
methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, (2-ethyl) hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, (2-ethyl) hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, o-tolyloxy group, 2, 3-dimethylphenyloxy group, 2, 4-dimethylphenyloxy group, 2, 5-dimethylphenyloxy group, 2, 6-dimethylphenyloxy group, 3, 4-dimethylphenyloxy group, 3, 5-dimethylphenyloxy group, 2-dicyanophenyloxy group, 2, 3-dicyanophenyloxy group, 2-dicyanophenyloxy group, 2, 4-dicyanophenyloxy group, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, an oxy group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to one side, such as a 2-methoxyphenyloxy group, a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the following chemical formula;
A thio group (sulfo group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) is bonded, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a tert-butylthio group, a pentylthio group, a hexylthio group, (2-ethyl) hexylthio group, a heptylthio group, an octylthio group, a nonylthio group, a decylthio group, an undecylthio group, a dodecylthio group, an eicosylthio group, a phenylthio group, and an o-tolylthio group;
epoxy, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl;
a formyl group;
a carbonyl group (preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 11 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), or an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) bonded thereto, such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, an undecanoyl group, a dodecanoyl group, an heneicosanoyl group, and a benzoyl group;
An oxycarbonyl group in which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded, such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a butoxycarbonyl group, a tert-butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, (2-ethyl) a hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a undecyloxycarbonyl group, a dodecyloxycarbonyl group, an eicosyloxycarbonyl group, a phenyloxycarbonyl group, or an o-tolyloxycarbonyl group represented by the following chemical formula);
an amino group; n-methylamino, N-dimethylamino, N-ethylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-diisopropylamino, N-butylamino, N-dibutylamino, N-isobutylamino, N-diisobutylamino, N-sec-butylamino, N-di-sec-butylamino, N-tert-butylamino, N-di-tert-butylamino, N-pentylamino, N-dipentylamino, N- (1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-dihexylamino, N- (2-ethyl) hexylamino, N-diethylamino, N-propylamino, N-dipropylamino, N-isopropylamino, N-di-sec-butylamino, N-pentylamino, N-dipentylamino, N-1-ethylpropyl) amino, N-di (1-ethylpropyl) amino, N-hexylamino, N-butylamino, N-butylamino, N-di-butylamino, N-butylamino, N, n, N-di (2-ethyl) hexylamino group, N-heptylamino group, N-diheptylamino group, N-octylamino group, N-dioctylamino group, N-nonylamino group, N-dinonylamino group, N-phenylamino group, N-diphenylamino group, N-ethylmethylamino group, N-propylmethylamino group, N-isopropylmethylamino group, N-butylmethylamino group, N-decylamino group, N-decylmethylamino group, N-undecylamino group, N-undecylmethylamino group, N-dodecylamino group, N-dodecylmethylamino group, N-eicosylamino group, N-eicosylmethyl amino group, An amino group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as an N, N-tert-butylmethylamino group, an N, N-phenylmethylamino group, and the like, and groups represented by the following chemical formula);
A sulfamoyl group; n-methylsulfamoyl, N-dimethylsulfamoyl, N-ethylsulfamoyl, N-diethylsulfamoyl, N-propylsulfamoyl, N-dipropylsulfamoyl, N-isopropylsulfamoyl, N-diisopropylsulfamoyl, N-butylsulfamoyl, N-dibutylsulfamoyl, N-isobutylsulfamoyl, N-diisobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-pentylsulfamoyl, N-dipentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-diethylsulfamoyl, N-butylsulfamoyl, N-di (1-ethylpropyl) sulfamoyl, N-butylsulfamoyl, N-di (1-isobutylsulfamoyl), N-dibutylsulfamoyl, N, di (1-di (ethyl, N, N, N-hexylsulfamoyl, N-dihexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-di (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-diheptylsulfamoyl, N-octylsulfamoyl, N-dioctylsulfamoyl, N-octylmethylsulfamoyl, N-nonylsulfamoyl, N-dinonylsulfamoyl, N-phenylsulfamoyl, N-diphenylsulfamoyl, N-ethylmethylsulfamoyl, N-propylmethylsulfamoyl, N-isopropylmethylsulfamoyl, N-butylmethylsulfamoyl, N-decylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 20 (preferably 1 to 10) carbon atoms or derivative groups thereof (for example, groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N-undecylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylsulfamoyl, N-eicosylmethylsulfamoyl, N-tert-butylmethylsulfamoyl, N-phenylmethylsulfamoyl, and the like, and groups represented by the following chemical formulae);
A formylamino group; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, a carbonylamino group (preferably 1 to 12 carbon atoms in the case where the carbonylamino group is an alkanoylamino group), to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 12 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, or a benzoylamino group represented by the following chemical formula;
a hydroxyl group; halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom;
carboxy, -CO2M2(M2Is an alkali metal, preferably lithium, sodium, potassium); sulfo, -SO3M2(M2Is alkali goldGenus, preferably lithium, sodium, potassium); a nitro group; a cyano group;
a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, a carbonyloxy group (preferably 1 to 10 carbon atoms in the case where the carbonyloxy group is an alkanoyloxy group) to which a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)) is bonded, such as an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, a undecanoyloxy group, a dodecanoyloxy group, a heneicosanoyloxy group, a benzoyloxy group, and the like, and a group represented by the following chemical formula;
A sulfonyl group having a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded thereto, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a (2-ethyl) hexylsulfonyl group, a heptylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group, a dodecylsulfonyl group, an eicosylsulfonyl group, a phenylsulfonyl group, a p-tolylsulfonyl group, or the like represented by the following chemical formula;
a carbamoyl group; n-methylcarbamoyl, N-dimethylcarbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-propylcarbamoyl, N-dipropylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-butylcarbamoyl, N-dibutylcarbamoyl, N-isobutylcarbamoyl, N-diisobutylcarbamoyl, N-sec-butylcarbamoyl, N-di-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-di-tert-butylcarbamoyl, N-pentylcarbamoyl, N-dipentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-ethylcarbamoyl, N-diethylcarbamoyl, N-isopropylcarbamoyl, N-diisopropylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-butylcarbamoyl, N-N-butylcarbamoyl, N-t-N-t-butylcarbamoyl, N-t-butylcarbamoyl, N-t, N, N-di (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-di (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-dioctylcarbamoyl, N-nonylcarbamoyl, N-octylmethylcarbamoyl, N-octylbutylcarbamoyl, N-dinonylcarbamoyl, N-phenylcarbamoyl, N-diphenylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylmethylcarbamoyl, N-propylmethylcarbamoyl, N-ethylhexylcarbamoyl, N-dihexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-octylcarbamoyl, N-diheptylcarbamoyl, N-octylcarbamoyl, N-nonylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-octylcarbamoyl, N-octylmethylcarbamoyl, N-nonylcarbamoyl, N-dimethylcarbamoyl, N, a hydrocarbon group having 1 to 2 carbon atoms of 1 to 20 (preferably 1 to 10 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an N, N-isopropylmethylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N-decylmethylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N-undecylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N-dodecylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N-eicosylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, etc., and a group represented by the following chemical formula, etc. (preferably a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), a derivative thereof, A carbamoyl group substituted with an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably, an octylsulfamoyl group) or the like;
A hydrocarbon group having 1 to 20 carbon atoms, which is obtained by substituting all hydrogen atoms with fluorine atoms such as a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, a perfluoroeicosyl group, a perfluorocyclohexyl group, and a perfluorophenyl group;
a hydrocarbon group having 1 to 20 carbon atoms which has, as a substituent, a linear or branched alkyl group having 1 to 20 carbon atoms in which all hydrogen atoms are substituted with fluorine atoms, such as a perfluoroethylmethyl group, a perfluoropropylmethyl group, a perfluoroisopropylmethyl group, a perfluorobutylmethyl group, a perfluoropentylmethyl group, a perfluorohexylmethyl group, a perfluoroheptylmethyl group, a perfluorooctylmethyl group, a perfluorononylmethyl group, a perfluorodecylmethyl group, a perfluoroundecylmethyl group, a perfluorododecylmethyl group, and a perfluoroeicosylmethyl group;
a hydrocarbon group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms) in which some hydrogen atoms are substituted with fluorine, such as a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, and a 2,4, 6-trifluorophenyl group;
-CO-SH、-CO-S-CH3、-CO-S-CH2CH3、-CO-S-CH2-CH2-CH3and-CO-S-CH2-CH2-CH2-CH3An alkylthio carbonyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), -CO-S-C 6H5An arylthiocarbonyl group having 6 to 20 carbon atoms;
a group represented by the following chemical formula, — COCO-R (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group)), or the like);
-NRCONR represented by the following chemical formula2(wherein R represents a hydrogen atom and the number of carbon atoms is 1A hydrocarbyl group of up to 20 (for example, a hydrocarbyl group having 1 to 20 carbon atoms among the above-mentioned hydrocarbyl groups), or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
OCONR represented by the following chemical formula2(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring);
A group represented by the following chemical formula-NRCOOR (wherein R represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group satisfying 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), wherein R may be the same or different from each other, and may be bonded to each other to form a ring);
*-OP(O)(OCH3)2etc.. OP (O) (OR)2(wherein R represents a hydrogen atom and the number of carbon atoms is 1A hydrocarbyl group of up to 20 (for example, a hydrocarbyl group having 1 to 20 carbon atoms among the above-mentioned hydrocarbyl groups), or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), and the like), wherein R's may be the same or different from each other, and may be bonded to each other to form a ring);
*-Si(CH3)3、*-Si(CH2CH3)3、*-Si(C6H5)3and-Si (CH)3)2)3Etc. -SiR3(wherein R is a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms (for example, a hydrocarbon group having 1 to 20 carbon atoms among the hydrocarbon groups listed above), or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and R's may be the same or different from each other and may be bonded to each other to form a ring); -SO 3 -;-CO2 -(ii) a And so on.
Examples of the substituent having a valence of 2 include an oxo group, a thioxo group, an imino group substituted with an alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and an imino group substituted with an aryl group having 6 to 20 carbon atoms. Examples of the imino group substituted with an alkyl group include CH3-N=、CH3-CH2-N=、CH3-(CH2)2-N ═ and CH3-(CH2)3-N ═ and the like. Examples of the imino group substituted with an aryl group include C6H5-N ═ and the like.
As the substituent of the hydrocarbon group having 1 to 40 carbon atoms, preferred is a substituent of group s 1. The derivative group shown below is preferably a derivative group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like.
[ group s1]
An oxy group having a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded;
an amino group; amino substituted by 1 or 2 alkyl with 1-20 carbon atoms or derivative groups thereof; a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a hydroxyl group; a halogen atom; -CO 2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group; a carbonyloxy group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a sulfonyl group to which a hydrocarbon group having 1 to 20 carbon atoms or a derivative thereof is bonded; a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 20 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms; a hydrocarbon group having 1 to 20 carbon atoms, which has a linear or branched alkyl group having 1 to 20 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 20 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group; -SO3 -;-CO2 -。
The substituent of the hydrocarbon group having 1 to 40 carbon atoms is more preferably a substituent of group s 2.
[ group s2]
An oxy group having a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof bonded to one side thereof;
a carbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
an oxycarbonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
An amino group; an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms;
a sulfamoyl group; a sulfamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded; a hydroxyl group; fluorine atom, chlorine atom, bromine atom; -CO2M (preferably carboxyl group) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom);
-SO3m (preferably sulfo) (M represents a hydrogen atom or an alkali metal atom, preferably a hydrogen atom); a nitro group; a cyano group;
a carbonyloxy group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded;
a carbamoyl group; carbamoyl substituted by 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivative groups thereof; a hydrocarbon group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms;
a hydrocarbon group having 1 to 10 carbon atoms, which has a linear or branched alkyl group having 1 to 10 carbon atoms, wherein all hydrogen atoms are substituted with fluorine atoms, as a substituent; a hydrocarbon group having 1 to 10 carbon atoms, wherein a part of hydrogen atoms is substituted with fluorine; an oxo group; -SO 3 -;-CO2 -。
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The substituted hydrocarbon group having 1 to 40 carbon atoms includes a substituted hydrocarbon group having 1 to 40 carbon atoms having a valence of 1 or 2; preferably, the hydrocarbon-based compound includes a saturated or unsaturated chain hydrocarbon group having 1 to 30 carbon atoms and having a substituent having a valence of 1 or 2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 30 carbon atoms and having a substituent having a valence of 1 or 2, an aromatic hydrocarbon group having 6 to 30 carbon atoms and having a substituent having a valence of 1 or 2, or a group having 4 to 30 carbon atoms and having a substituent having a valence of 1 or 2, which are a combination of the hydrocarbon groups;
more preferably, the hydrocarbon group includes a saturated or unsaturated chain hydrocarbon group having 1 to 20 carbon atoms having a substituent of group s1, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 20 carbon atoms having a substituent of group s1, an aromatic hydrocarbon group having 6 to 20 carbon atoms having a substituent of group s1, or a combination of hydrocarbon groups, and the group has 4 to 20 carbon atoms having a substituent of group s 1;
particularly preferred examples thereof include a saturated or unsaturated chain hydrocarbon group having 1 to 15 carbon atoms having a substituent of group s2, a saturated or unsaturated alicyclic hydrocarbon group having 3 to 15 carbon atoms having a substituent of group s2, an aromatic hydrocarbon group having 6 to 15 carbon atoms having a substituent of group s2, or a group having 4 to 15 carbon atoms having a substituent of group s2, which is a combination of hydrocarbon groups.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group represented by (a) may be monocyclic or polycyclic, and is preferably a heterocyclic ring containing a heteroatom as a constituent of the ring. Examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom and the like.
The number of carbon atoms of the heterocyclic group is preferably 3 to 30, more preferably 3 to 22, further preferably 3 to 20, further preferably 3 to 18, further more preferably 3 to 15, and particularly preferably 3 to 14.
Examples of the heterocyclic ring containing a nitrogen atom include monocyclic saturated heterocyclic rings such as aziridine, azetidine, pyrrolidine, piperidine, and piperazine; five-membered ring system unsaturated heterocycles such as pyrrole (e.g., 2, 5-dimethylpyrrole), pyrazole (e.g., 2-methylpyrazole and 3-methylpyrazole), imidazole, 1,2, 3-triazole and 1,2, 4-triazole; a six-membered ring system unsaturated heterocycle such as pyrimidine, pyrazine and 1,3, 5-triazine, for example pyridine, pyridazine and 6-methylpyrimidine; a fused bicyclic heterocycle such as quinoxaline (e.g., indazole, indoline, isoindoline, indole, indolizine, benzimidazole, quinoline, isoquinoline, 5,6,7, 8-tetrahydro (3-methyl) quinoxaline or 3-methylquinoxaline, quinazoline, cinnoline, phthalazine, naphthyridine, purine, pteridine, benzopyrazole or phenylpiperidine; condensed tricyclic heterocycles such as carbazole, acridine and phenazine; and so on.
Examples of the heterocyclic ring containing an oxygen atom include:
monocyclic saturated heterocycles such as oxetane, tetrahydrofuran, tetrahydropyran, 1, 3-dioxane, 1, 4-dioxane and 1-cyclopentyldioxolane; bicyclic saturated heterocycles such as 1, 4-dioxaspiro [4.5] decane and 1, 4-dioxaspiro [4.5] nonane; lactone heterocycles such as α -caprolactone, β -propiolactone, γ -butyrolactone, γ -valerolactone and δ -valerolactone; five-membered ring system unsaturated heterocycles such as furan (e.g., 2, 3-dimethylfuran, 2, 5-dimethylfuran); a six-membered ring system unsaturated heterocycle such as 2H-pyran, 4H-pyran;
fused bicyclic heterocycles such as benzopyrans (e.g., 1-benzofuran and 4-methylbenzopyran), benzodioxole, chroman and isochroman; fused tricyclic heterocycles such as xanthene and dibenzofuran; and so on.
Examples of the heterocyclic ring containing a sulfur atom include a five-membered ring system saturated heterocyclic ring such as dithiolane; saturated heterocyclic rings of six-membered ring systems such as thiacyclohexane, 1, 3-dithiane, 2-methyl-1, 3-dithiane and the like; a five-membered ring system unsaturated heterocycle such as thiophene (e.g., 3-methylthiophene, 2-carboxythiophene), benzothiopyran (e.g., 4H-thiopyran, tetrahydrothiopyran); fused bicyclic heterocycles such as benzothiophene; fused tricyclic heterocycles such as thianthrene and dibenzothiophene; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and an oxygen atom include:
monocyclic saturated heterocycles such as morpholine, 2-pyrrolidone, 2-methyl-2-pyrrolidone, 2-piperidone and 2-methyl-2-piperidone; a monocyclic unsaturated heterocycle such as oxazole (e.g., 4-methyloxazole), isoxazole (e.g., 2-methylisoxazole, and 3-methylisoxazole);
fused bicyclic heterocycles such as benzoxazole, benzisoxazole, benzoxazine, benzodioxane, and benzimidazoline; condensed tricyclic heterocycles such as phenoxazine; and so on.
Examples of the heterocyclic ring containing a nitrogen atom and a sulfur atom include monocyclic heterocyclic rings such as thiazoles, e.g., 3-methylthiazole and 2, 4-dimethylthiazole; fused bicyclic heterocycles such as benzothiazole; fused tricyclic heterocycles such as phenothiazine; and so on.
The heterocyclic ring may be a combination of the above-mentioned hydrocarbon groups, and examples thereof include tetrahydrofurylmethyl and the like.
The heterocyclic ring may be a heterocyclic ring represented by the following chemical formula.
The above heterocyclic group may be R1AZ6~R5AZ62 or more of them are bonded to form a heterocyclic group. Such heterocyclic radicals contain R1AZ6~R5AZ6The bonded benzene ring has a ring structure of 2 or more rings inside. The 2 or more ring structures include, for example, the structures of the following chemical formulae.
The bonding position of the heterocycle is a portion where any hydrogen atom contained in each ring is removed.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group represented may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. In addition, in the case where the above-mentioned heterocyclic ring contains a nitrogen atom as its constituent element, the above-mentioned hydrocarbon group as a substituent may be bonded to the nitrogen atom.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The heterocyclic group having a substituent represented by the formula (i) includes a heterocyclic group having a substituent having a valence of 1 or 2, preferably a heterocyclic group having a substituent of group s1, and more preferably a heterocyclic group having a substituent of group s 2.
The substituent (first substituent) that the hydrocarbon group or heterocyclic group may have may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other. Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
Below, for R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Of (a) is-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M、-CO2M is explained. Examples of-CO-R hereinafter102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Preferably in the range corresponding to R101AZ6、R102AZ6In which a substituent of group s2, in particular-SO3 -、-CO2 -And the like.
as-CO-R102AZ6Examples thereof include a formyl group; a carbonyl group (having 2 to 41 carbon atoms when the carbonyl group is an acyl group), wherein the carbonyl group is a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like) bonded to a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as an acetyl group, a propionyl group, a butyryl group, a 2, 2-dimethylpropionyl group, a pentanoyl group, a hexanoyl group, a (2-ethyl) hexanoyl group, a heptanoyl group, an octanoyl group, a nonanoyl group, a decanoyl group, a undecanoyl group, a dodecanoyl group, a heneicosanoyl group, a benzoyl group, or the group represented by the above chemical formula (i) and the like), and the carbonyl group corresponding to-CO-R-in the compounds represented by Table 1Z6 to Table 4Z6102AZ6Preferable examples of the group(s) include a carbonyl group (more preferably 2 to 12 carbon atoms when the carbonyl group is an alkanoyl group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and compounds represented by tables 1Z6 to 4Z6 corresponding to-CO-R 102AZ6And the like.
as-COO-R101AZ6Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenyloxycarbonyl, eicosyloxycarbonyl and the like, and a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an orthocarbon group bonded to a group represented by the above formula or the likeGroups derived from alkylsulfamoyl (preferably octylsulfamoyl) having 1 to 10 moles) and compounds shown in tables 1Z6 to 4Z6, which correspond to-COO-R102AZ6Preferred examples of the group (b) include oxycarbonyl groups to which a C1-10 hydrocarbon group or a derivative thereof is bonded and compounds represented by tables 1Z6 to 4Z6 corresponding to-COO-R102AZ6And the like.
as-OCO-R102AZ6Examples thereof include a formyloxy group; acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, pentanoyloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy and the like, carbonyloxy (having 2 to 41 carbon atoms in the case where the carbonyloxy group is an acyloxy group), carbonyloxy having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) bonded to a group represented by the above formula) and the like, And the compounds shown in tables 1Z6 to 4Z6 correspond to-OCO-R 102AZ6The group (B) preferably includes a carbonyloxy group (more preferably 2 to 12 carbon atoms in the case where the carbonyloxy group is an acyloxy group) to which a hydrocarbon group having 1 to 11 carbon atoms (more preferably 1 to 10 carbon atoms) or a derivative thereof is bonded, and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-OCO-R102AZ6And the like.
as-COCO-R102Z6Examples thereof include methyloxalyl, ethyloxalyl, propyloxalyl, butyloxalyl, pentyloxalyl, hexyloxalyl, (2-ethyl) hexyloxalyl, heptyloxalyl, octyloxalyl, nonyloxalyl, decyloxyl, undecyloxalyl, dodecyloxalyl, eicosanoyl, cyclopentyloxalyl, cyclohexyloxalyl, phenyloxalyl, p-tolyloxalyl and the like, and a group represented by the above-mentioned chemical formulaAnd an oxalyl group to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded).
as-O-R102AZ6There may be mentioned a hydroxyl group; methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, (2-ethyl) hexyloxy, eicosyloxy, 1-phenylethoxy, 1-methyl-1-phenylethoxy, phenyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 5-dimethylphenyloxy, 2, 6-dimethylphenyloxy, 3, 4-dimethylphenyloxy, 3, 5-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 3-dicyanophenyloxy, 2, 4-dicyanophenyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, decyloxy, 2, 3-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 2, 4-dimethylphenyloxy, 3-dimethylphenyloxy, 2-dicyanophenyloxy, 2, 4-di-yloxy, 2-di-methyl-1-phenylethoxy, 2, 4-di-methyl, and mixtures thereof, 2, 5-dicyanophenyloxy group, 2, 6-dicyanophenyloxy group, 3, 4-dicyanophenyloxy group, 3, 5-dicyanophenyloxy group, 4-methoxyphenyloxy group, 2-methoxyphenyloxy group, examples of the oxygen group include an oxygen group having a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a group derived from a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like bonded thereto, such as a 3-methoxyphenyloxy group, a 4-ethoxyphenyloxy group, a 2-ethoxyphenyloxy group, a 3-ethoxyphenyloxy group, or a group represented by the above chemical formula), and compounds shown in tables 1Z6 to 4Z6, which correspond to — O — R. 102AZ6Preferable examples of the group (b) include an oxy group to which a C1-10 hydrocarbon group or a derivative thereof is bonded, and compounds represented by tables 1Z6 to 4Z6 corresponding to-O-R102AZ6And the like.
as-SO2-R101AZ6Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, (2-ethyl) hexylsulfonyl, heptylsulfonyl, ethylsulfonyl, pentylsulfonyl, ethylsulfonyl, 2-hexylsulfonyl, ethylsulfonyl, ethyl,Octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group, dodecylsulfonyl group, eicosylsulfonyl group, phenylsulfonyl group, p-tolylsulfonyl group and the like, and sulfonyl groups in which a hydrocarbon group having 1 to 40 (preferably 1 to 20) carbon atoms or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group) is bonded such as the group represented by the above chemical formula) and the compounds shown in tables 1Z6 to 4Z6 correspond to-SO2-R102AZ6Preferable examples of the group (b) include a sulfonyl group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded and a group corresponding to-SO in the compounds represented by tables 1Z6 to 4Z6 2-R102AZ6And the like.
as-SO2N(R102AZ6)2Examples thereof include: a sulfamoyl group; n-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N- (1-ethylpropyl) sulfamoyl, N-hexylsulfamoyl, N- (2-ethyl) hexylsulfamoyl, N-heptylsulfamoyl, N-octylsulfamoyl, N-nonylsulfamoyl, N-decylsulfamoyl, N-undecylsulfamoyl, N-dodecylsulfamoyl, N-eicosylsulfamoyl, N-phenylsulfamoyl, etc., and a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) such as a group represented by the above formula, or a derivative thereof Sulfamoyl groups substituted with a raw group (e.g., a group derived from carboxyl group, sulfo group, nitro group, hydroxyl group, halogen (preferably chlorine atom), alkylsulfamoyl group having 1 to 10 carbon atoms (preferably octylsulfamoyl group)), and compounds represented by tables 1Z6 to 4Z6, which correspond to — SO2NH(R102AZ6X)(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.; n, N-dimethylsulfamoyl, N-ethylmethylsulfamoyl, N-diethylsulfamoyl, N-propylmethylsulfamoyl, N-dipropylamido Sulfonyl, N-isopropylmethylsulfamoyl, N-diisopropylsulfamoyl, N-tert-butylmethylsulfamoyl, N-diisobutylaminosulfonyl, N-di-sec-butylsulfamoyl, N-di-tert-butylsulfamoyl, N-butylmethylsulfamoyl, N-dibutylsulfamoyl, N-dipentylsulfamoyl, N-bis (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-bis (2-ethyl) hexylsulfamoyl, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, Sulfamoyl groups substituted with 2 hydrocarbon groups having 1 to 40 (preferably 1 to 20) carbon atoms or derivative groups thereof (e.g., groups derived from carboxyl, sulfo, nitro, hydroxyl, halogen (preferably chlorine atom), alkylsulfamoyl having 1 to 10 carbon atoms (preferably octylsulfamoyl), and the like, such as N, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl, and the like, and groups represented by the above chemical formulae), and sulfamoyl groups derived from compounds represented by tables 1Z6 to 4Z6, which correspond to-SO 2N(R102AZ6X)2(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), and the like, and preferably include sulfamoyl groups substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and compounds represented by tables 1Z6 to 4Z6, which correspond to-SO2N(R102AZ6)2And the like.
as-CON (R)102AZ6)2Examples thereof include:
a carbamoyl group; n-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N- (1-ethylpropyl) carbamoyl, N-hexylcarbamoyl, N- (2-ethyl) hexylcarbamoyl, N-heptylcarbamoyl, N-octylcarbamoyl and N-nonylcarbamoyl, N-decylcarbamoyl, N-decadecadecylcarbamoylMonoalkylcarbamoyl, N-dodecylcarbamoyl, N-eicosylcarbamoyl, N-phenylcarbamoyl and the like, and carbamoyl groups represented by the above chemical formulae which are substituted with a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof with a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) or the like), and a compound represented by one of tables 1Z6 to 4Z6 corresponds to-CONH (R-CONH) 102AZ6X)(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.;
n, N-dimethylcarbamoyl group, N-ethylmethylcarbamoyl group, N-diethylcarbamoyl group, N-propylmethylcarbamoyl group, N-dipropylcarbamoyl group, N-isopropylmethylcarbamoyl group, N-diisopropylcarbamoyl group, N-tert-butylmethylcarbamoyl group, N-diisobutylcarbamoyl group, N-di-sec-butylcarbamoyl group, N-di-tert-butylcarbamoyl group, N-butylmethylcarbamoyl group, N-dibutylcarbamoyl group, N-butyloctylcarbamoyl group, N-dipentylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-diethylcarbamoyl group, N-diisopropylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-t-butylmethylcarbamoyl group, N-di (1-ethylpropyl) carbamoyl group, N-t-butylmethylcarbamoyl group, N-di-isobutylcarbamoyl group, N-di (s-butylmethylcarbamoyl group, N-di-butylmethylcarbamoyl group, N-di-N-butylcarbamoyl group, N, a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, an N, N-di (2-ethyl) hexylcarbamoyl group, an N, N-diheptylcarbamoyl group, an N, N-octylmethylcarbamoyl group, an N, N-dinonylcarbamoyl group, an N, N-decylmethylcarbamoyl group, an N, N-undecylmethylcarbamoyl group, an N, N-dodecylmethylcarbamoyl group, an N, N-eicosylmethylcarbamoyl group, an N, N-phenylmethylcarbamoyl group, an N, N-diphenylcarbamoyl group, etc., and a group represented by the above chemical formula, A carbamoyl group substituted with a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group), or the like), and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-CON (R) 102AZ6X)2(R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above) and the like,
preferred examples thereof include a carbamoyl group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or a derivative thereof and a compound represented by any one of tables 1Z6 to 4Z6 corresponding to-CON (R)102AZ6)2And the like.
as-N (R)102AZ6)2Examples thereof include: an amino group; a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom)), such as an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, an N-tert-butylamino group, an N-pentylamino group, an N-hexylamino group, an N- (2-ethyl) hexylamino group, an N-heptylamino group, an N-octylamino group, an N-nonylamino group, an N-decylamino group, an N-undecylamino group, an N-dodecylamino group, an N-eicosylamino group, an N-phenylamino group, and the like, and a group represented by the above chemical formula, A group derived from an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) and the like) and a compound shown in tables 1Z6 to 4Z6 corresponding to-NH (R102AZ6X) (wherein, R 102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), etc.;
n, N-dimethylamino group, N-ethylmethylamino group, N-diethylamino group, N-propylmethylamino group, N-dipropylamino group, N-isopropylmethylamino group, N-diisopropylamino group, N-tert-butylmethylamino group, N-diisobutylamino group, N-di-sec-butylamino group, N-di-tert-butylamino group, N-butylmethylamino group, N-dibutylamino group, N-dipentylamino group, N-bis (1-ethylpropyl) amino group, N-dihexylamino group, N-bis (2-ethyl) hexylamino group, N-diheptylamino group, N-dioctylamino group, N, n-dinonylamino group, N-decylmethylamino group, N-undecylmethylamino group, N-dodecylmethylamino group, N-eicosylmethyl amino group, N-phenylmethylamino group, N-diphenylamino group, etc., and a group represented by the above chemical formula, etc., having 2 carbon atomsAmino groups substituted with 1 to 40 (preferably 1 to 20 carbon atoms) hydrocarbon groups or derivative groups thereof (for example, groups derived from carboxyl groups, sulfo groups, nitro groups, hydroxyl groups, halogens (preferably chlorine atoms), alkylsulfamoyl groups (preferably octylsulfamoyl groups) having 1 to 10 carbon atoms), and the like, and compounds shown in tables 1Z6 to 4Z6 corresponding to-N (R is 102AZ6X)2(wherein, R102AZ6XIs not a hydrogen atom, other than, and R102AZ6The same as defined above), and the like, and preferably include an amino group substituted with 1 or 2 hydrocarbon groups having 1 to 10 carbon atoms or derivatives thereof and a group corresponding to-N (R) in the compounds shown in tables 1Z6 to 4Z6102AZ6)2And the like.
as-NHCO-R102AZ6Examples thereof include formylamino; acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, valerylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, examples of the carbonylamino group (the number of carbon atoms is 1 to 40 in the case where the carbonylamino group is an acylamino group), to which a hydrocarbon group having 1 to 40 carbon atoms (preferably 1 to 20 carbon atoms) or a derivative thereof (for example, a derivative thereof such as a carboxyl group, a sulfo group, a nitro group, a hydroxyl group, a halogen (preferably a chlorine atom), an alkylsulfamoyl group having 1 to 10 carbon atoms (preferably an octylsulfamoyl group) is bonded such as an octanoylamino group, a nonanoylamino group, a decanoylamino group, a undecanoylamino group, a dodecanoylamino group, a heneicosanoylamino group, a benzoylamino group and the like, and the compounds shown in tables 1Z6 to 4Z6 correspond to-NHCO-R. 102AZ6Preferable examples of the group (b) include a carbonylamino group to which a hydrocarbon group having 1 to 10 carbon atoms or a derivative thereof is bonded (in the case where the carbonylamino group is an alkanoylamino group, the carbon number is more preferably 1 to 10), and compounds represented by tables 1Z6 to 4Z6, wherein the compound corresponds to-NHCO-R102AZ6And the like.
as-NHCON (R)102AZ6)2Examples thereof include the groups listed above and the compounds shown in tables 1Z6 to 4Z6 which correspond to-NHCON (R)102AZ6)2And the like.
as-NHCOOR102AZ6Examples thereof include the groups listed above and the groups corresponding to-NHCOOR among the compounds shown in tables 1Z6 to 4Z6102AZ6And the like.
as-OCON (R)102AZ6)2Examples thereof include those corresponding to-OCON (R) in the above-mentioned groups and the compounds shown in tables 1Z6 to 4Z6102AZ6)2And the like.
The halogen atom is preferably a fluorine atom, a chlorine atom, a bromine atom, an iodine atom or the like.
as-SO3M and-CO2M in M is a hydrogen atom; the alkali metal atom such as lithium atom, sodium atom and potassium atom, preferably hydrogen atom, sodium atom and potassium atom.
The above-mentioned-CO-R102AZ6、-COO-R102AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R102AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCON(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2The number of the substituents (first substituents) contained in (2) may be 1 or 2 or more, and 2 or more substituents may be the same or different and independent of each other.
Further, the first substituent may have another substituent (second substituent) bonded to the hydrocarbon group included in a part thereof. The second substituent may be selected from the same groups as the first substituent.
As R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Preferably a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
As R101AZ6The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent is preferable.
As R102AZ6Preferably, the hydrocarbon group has 1 to 40 carbon atoms and may have a substituent.
R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6The ring formed is fused with the benzene ring of the isoindoline skeleton of the compound represented by the formula (IZ 6). As R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6Examples of the condensed ring structure of the ring formed and the benzene ring include indene, naphthalene, biphenylene, indacene, acenaphthylene, fluorene, phenalene, phenanthrene, anthracene, fluoranthene, acephenanthrene, aceanthrylene, and benzo [9,10 ] ene]Phenanthrene, pyrene,Hydrocarbon-based condensed ring structures such as N-methylphthalimide, N- (1-phenylethyl) phthalimide and butachlor, and partially reduced products thereof (for example, 9, 10-dihydroanthracene, 1,2,3, 4-tetrahydronaphthalene, etc.); indole, isoindole, indazole, quinoline, isoquinoline, phthalazine, quinoxaline, quinazoline, cinnoline, carbazole, carboline, phenanthridine, acridine, quinoline, quinoxaline, quinoline, and/or quinoline derivative,Nitrogen-containing fused heterocycles and partial reductants thereof such as pyridine, phenanthroline and phenazine; oxygen-containing fused heterocycles such as 3-hydrobenzofuran-2-one and partial reductants thereof.
R2AZ6And R3AZ6、R3AZ6And R4AZ6And R4AZ6And R5AZ6In the case of forming a ring, the ring may have a substituent. AsThe substituent includes1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
R3AZ6And R4AZ6In the case of forming a ring, R2AZ6And R5AZ6Independently of one another, hydrogen atoms, amino groups or hydroxyl groups are preferred.
R2AZ6And R3AZ6When a ring is formed, R is preferably4AZ6And R5AZ6Does not form a ring, more preferably R4AZ6And R5AZ6Is a hydrogen atom.
In addition, R4AZ6And R5AZ6When a ring is formed, R is preferably2AZ6And R3AZ6Does not form a ring, more preferably R2AZ6And R3AZ6Is a hydrogen atom.
RAA1Z6And RAA2Z6And R12AZ6And R13AZ6The ring formed is bonded to the exocyclic methylene (C ═ CH) group of the isoindoline skeleton of formula (IZ6)2) Is bonded to contain the exocyclic methylene (C ═ CH)2) In the form of structures within, R is listedAA1Z6And RAA2Z6And R12AZ6And R13AZ6Examples of the ring to be formed include structures in which a carbonyl group, an exocyclic methylene group and a carbonyl group are arranged in this order as shown in the following groups A and B. Represents a bond to the isoindoline backbone.
[ group A ]
[ group B ]
R104AZ6、R105AZ6、R106AZ6And R107AZ6Independently of one another, represents a hydrogen atom, -CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, cyano group, nitro group, -SO 3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
With respect to R104AZ6、R105AZ6、R106AZ6And R107AZ6Represented by-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M and-CO2M, may be exemplified by1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6Represented by-CO-R102AZ6、-COO-R101AZ6、-OCO-R102AZ6、-COCO-R102AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2、-N(R102AZ6)2、-NHCO-R102AZ6、-NHCO-N(R102AZ6)2、-NHCOOR102AZ6、-OCON(R102AZ6)2Halogen atom, -SO3M and-CO2M is the same example.
As R104AZ6、R105AZ6、R106AZ6And R107AZ6The optionally substituted hydrocarbon group having 1 to 40 carbon atoms and the optionally substituted heterocyclic group are represented by1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or the heterocyclic group which may have a substituent are the same.
R104AZ6、R105AZ6、R106AZ6And R107AZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R104AZ6、R105AZ6、R106AZ6And R107AZ6Preferably, R is1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferable example as in (1).
As R104AZ6、R105AZ6、R106AZ6And R107AZ6More preferably, the alkyl group has 1 to 10 carbon atoms and a hydrogen atom, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group, and a phenyl group.
For the groups exemplified in group A and group B, the hydrogen atom bonded to the ring structure may be substituted with a substituent.
Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
R1AZ6Is a hydrogen atom, R2AZ6、R3AZ6、R4AZ6And R5AZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102AZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102AZ6、-O-R102AZ6、-SO3M or-CO2M,
More preferably a hydrogen atom, a tert-butyl group or a nitro group.
R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6Preferably satisfies at least 1 of (raa-i) to (raa-iii), R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(raa-i)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-SO3 -or-CO2 -。
(raa-ii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is-CO-R102AZ6、-COO-R101AZ6、-O-R102AZ6、-SO2-R101AZ6、-SO2N(R102AZ6)2、-CON(R102AZ6)2or-N (R)102AZ6)2R is a hydrogen atom101AZ6And R102AZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(raa-iii)R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO 3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Examples of the groups a and B include rings represented by the formulae (QQ1) to (QQ25) and the formulae (QQA1) to (QQA 36).
The compound represented by the formula (IZ6-A) is preferably a compound represented by the formula (IZ6-B) (hereinafter, may be referred to as a compound IZ 6-B.).
[ formula (IZ6-B) wherein Ac+B, c, d and the wavy line have the same meanings as described above. L is1represents-CO-or-SO2-。R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Independently of one another, represents a hydrogen atom, -CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2、-N(R102BZ6)2、-NHCO-R102BZ6、-NHCO-N(R102BZ6)2、-NHCOOR102BZ6、-OCON(R102BZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2BZ6And R3BZ6、R3BZ6And R4BZ6、R4BZ6And R5BZ6And R12BZ6And R13BZ6Each of which may be bonded to each other to form a ring.
R101BZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102BZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
The formula (IZ6-B ') and the formula (IZ 6-B') each represent a partial structure of the formula (IZ6-B), Ac+、b、c、d、R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-B).
M represents the same meaning as described above.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6、R102BZ6、L1M, c or Ac+When there are a plurality of them, they may be the same or different.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Satisfies at least 1 of (rb-i) to (rb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Is provided withis-SO of3 -or-CO2 -The total number of (a) is a.
(rb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-SO3 -or-CO2 -。
(rb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-OCO-R102BZ6、-COCO-R102BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2、-N(R102BZ6)2、-NHCO-R102BZ6、-NHCO-N(R102BZ6)2、-NHCOOR102BZ6or-OCON (R)102BZ6)2R is a hydrogen atom101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-A). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ6-B ') has the same negative valence as the partial structure represented by the formula (IZ 6-B') has the same positive valence in absolute value. ]
As R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R 101BZ6Examples thereof include the compounds with R101AZ6The same example. As R101BZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1). As R102BZ6Examples thereof include the compounds with R102AZ6The same example. As R102BZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1). R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11BZ6The alkyl group is an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent.
R11BZ6The aliphatic hydrocarbon group has 1 to 40 carbon atoms, preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and further preferably 1 to 15 carbon atoms.
The aliphatic hydrocarbon group may be saturated or unsaturated, and may be a chain or alicyclic ring.
As R11BZ6Examples of the saturated or unsaturated chain aliphatic hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, heptadecyl, octadecyl, and eicosyl; branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, (2-ethyl) butyl, isopentyl, neopentyl, tert-pentyl, (1-methyl) pentyl, (2-methyl) pentyl, (1-ethyl) pentyl, (3-ethyl) pentyl, isohexyl, (5-methyl) hexyl, (2-ethyl) hexyl and (3-ethyl) heptyl; alkenyl groups such as vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl) vinyl, 2-butenyl, 3-butenyl, 1, 3-butadienyl, (1- (2-propenyl)) vinyl, (1, 2-dimethyl) propenyl, and 2-pentenyl; and so on. The number of carbon atoms of the saturated or unsaturated chain hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, further preferably 1 to 15, and particularly preferably 1 to 10.
As R11BZ6Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, and 3-methylcyclohexylCyclohexyl, 4-methylcyclohexyl, 1, 2-dimethylcyclohexyl, 1, 3-dimethylcyclohexyl, 1, 4-dimethylcyclohexyl, 2, 3-dimethylcyclohexyl, 2, 4-dimethylcyclohexyl, 2, 5-dimethylcyclohexyl, 2, 6-dimethylcyclohexyl, 3, 4-dimethylcyclohexyl, cycloalkyl groups such as 3, 5-dimethylcyclohexyl, 2-dimethylcyclohexyl, 3-dimethylcyclohexyl, 4-dimethylcyclohexyl, cyclooctyl, 2,4, 6-trimethylcyclohexyl, 2,6, 6-tetramethylcyclohexyl, 3,5, 5-tetramethylcyclohexyl, 4-pentylcyclohexyl, 4-octylcyclohexyl and 4-cyclohexylcyclohexyl; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl, cyclooctenyl, and the like; norbornyl, adamantyl, bicyclo [2.2.2]An octyl group and the like. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 30, more preferably 3 to 20, still more preferably 4 to 20, yet more preferably 4 to 15, even more preferably 5 to 15, and most preferably 5 to 10. Among them, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl are particularly preferable.
R11BZ6The aliphatic hydrocarbon group represented by (a) may be a group in which a hydrogen atom contained in the above-mentioned aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms or a group in which the above-mentioned aliphatic hydrocarbon groups are combined.
Examples of the aromatic hydrocarbon group include a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2, 3-dimethylphenyl group, a 2, 4-dimethylphenyl group, a 2, 5-dimethylphenyl group, a 2, 6-dimethylphenyl group, a 3, 4-dimethylphenyl group, a 3, 5-dimethylphenyl group, an o-isopropylphenyl group, an m-isopropylphenyl group, a p-isopropylphenyl group, aromatic hydrocarbon groups such as o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, mesityl, 2, 6-bis (2-propyl) phenyl, 2,4, 6-trimethylphenyl, 1-naphthyl, 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, and anthracenyl; and so on. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and further preferably 6 to 15.
Examples of the group in which a hydrogen atom contained in the above-mentioned aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl. Examples of the group formed by combining the above-mentioned aliphatic hydrocarbon groups include (cycloalkyl) alkyl groups such as cyclohexylmethyl groups. The number of carbon atoms of a group in which a hydrogen atom contained in an aliphatic hydrocarbon group is substituted with an aromatic hydrocarbon group having 1 to 40 carbon atoms or a group in which aliphatic hydrocarbon groups are combined is preferably 4 to 30, more preferably 4 to 20, and further preferably 4 to 15.
R11BZ6The aliphatic hydrocarbon group having 1 to 40 carbon atoms, phenyl group, naphthyl group, tetrahydronaphthyl group, thienyl group, furyl group and pyridyl group may have a substituent.
Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
In the compound IZ6-B, R1BZ6Preferably a hydrogen atom.
R2BZ6、R3BZ6、R4BZ6Or R5BZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102BZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102BZ6、-O-R102BZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6Preferably satisfies at least 1 of (rbb-i) to (rbb-iii), R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6、R13BZ6、R101BZ6And R102BZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rbb-i)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-SO3 -or-CO2 -。
(rbb-ii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is-CO-R102BZ6、-COO-R101BZ6、-O-R102BZ6、-SO2-R101BZ6、-SO2N(R102BZ6)2、-CON(R102BZ6)2or-N (R)102BZ6)2R is a hydrogen atom101BZ6And R102BZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -And (ii) an additional substituent.
(rbb-iii)R1BZ6、R2BZ6、R3BZ6、R4BZ6、R5BZ6、R11BZ6、R12BZ6And R13BZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
In the formula (IZ6-B), R12BZ6And R13BZ6When no ring is formed, the compound IZ6-B is preferably a compound represented by the formula (IZ6-C) (hereinafter, may be referred to as a compound IZ 6-C.).
[ formula (IZ6-C) wherein Ac+、b、c、d、L1And the wavy line means the same as described above.
L2represents-CO-or-SO2-。R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Independently of one another, represents a hydrogen atom, -CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6、-OCON(R102CZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2CZ6And R3CZ6、R3CZ6And R4CZ6And R4CZ6And R5CZ6Each of which may be bonded to each other to form a ring.
R101CZ6Independently represent a carbon atom number of 1 to E which may have a substituent40 or a heterocyclic group which may have a substituent.
R102CZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above.
The formula (IZ6-C ') and the formula (IZ 6-C') each represent a partial structure of the formula (IZ6-C), A c+、b、c、d、R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、L1And L2Represents the same meaning as the corresponding symbol in the formula (IZ 6-C).
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6、R102CZ6、L1、L2M, c or Ac+When there are a plurality of them, they may be the same or different.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Satisfies at least 1 of (rc-i) to (rc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-SO3 -or-CO2 -。
(rc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-OCO-R102CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-R102CZ6、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-B). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-C') has the same negative valence as the partial structure represented by the formula (IZ6-C ") has the same positive valence in absolute value. ]
As R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example. As R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6Preferred examples of (3) include 1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R101CZ6Examples thereof include the compounds with R101AZ6The same example. As R101CZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102CZ6Examples thereof include the compounds with R102AZ6The same example. As R102CZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1Or L2preferably-CO-. Preferably, R11CZ6And R14CZ6Are identical radicals, L1And L2Are the same group.
R11CZ6And R14CZ6Independently of each other, it is preferably an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, or a naphthyl group which may have a substituentA furyl group which may have a substituent or a pyridyl group which may have a substituent.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B 11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-C, R1CZ6Preferably a hydrogen atom.
R2CZ6、R3CZ6、R4CZ6And R5CZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102CZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102CZ6、-O-R102CZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably satisfies at least 1 of (rcc-i) to (rcc-iii), R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(rcc-i)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-SO3 -or-CO2 -。
(rcc-ii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is-CO-R102CZ6、-COO-R101CZ6、-COCO-R102CZ6、-O-R102CZ6、-SO2-R101CZ6、-SO2N(R102CZ6)2、-CON(R102CZ6)2、-N(R102CZ6)2、-NHCO-N(R102CZ6)2、-NHCOOR102CZ6or-OCON (R)102CZ6)2R is a hydrogen atom101CZ6And R102CZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO 3 -and-CO2 -And (ii) an additional substituent.
(rcc-iii)R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably, at least 1 of (rc-I) and (rc-II) is satisfied.
(rc-I)R2CZ6、R3CZ6、R4CZ6、R5CZ6At least one of which is-SO3 -or-CO2 -。(rc-II)R1CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -The optionally substituted hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
R1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6Preferably, at least 1 of (rcc-I) and (rcc-II) is satisfied.
(rcc-I)R2CZ6、R3CZ6、R4CZ6、R5CZ6At least one of which is-SO3 -or-CO2 -。
(rcc-II)R1CZ6、R11CZ6And R14CZ6At least one of which is a compound having-SO3 -or-CO2 -The hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Wherein R is1CZ6、R2CZ6、R3CZ6、R4CZ6、R5CZ6、R11CZ6、R14CZ6、R101CZ6And R102CZ6having-SO of3 -or-CO2 -The total number of (a) is a.
In the compound IZ6-B, R12BZ6And R13BZ6When a ring is formed, the compound IZ6-B is preferably a compound represented by the formula (IZ6-D) (hereinafter, may be referred to as a compound IZ 6-D.).
[ formula (IZ6-D) wherein Ac+、b、c、d、L1And the wavy line means the same as described above. R 20DZ6And R30DZ6Bonded to form a ring Q. The ring Q may have a substituent, and is a ring having 5 to 7 ring-constituting elements, and the ring Q may be a hydrocarbon ring or a heterocyclic ring. The following rings may be fused/condensed on ring Q: a monocyclic ring which is selected from hydrocarbon rings and hetero rings and which may have a substituent, wherein the number of constituent elements of the ring is 5 to 7; or 2 or more condensed rings obtained by condensing the monocyclic rings.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Independently of one another, represents a hydrogen atom, -CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6、-OCON(R102DZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -The hydrocarbon group may have a substituent and has 1 to 40 carbon atoms, or the heterocyclic group may have a substituent.
R2DZ6And R3DZ6、R3DZ6And R4DZ6And R4DZ6And R5DZ6Each of which may be bonded to each other to form a ring.
R101DZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102DZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted hydrocarbon groupA heterocyclic group having a substituent.
M represents the same meaning as described above.
The formulae (IZ 6-D') and (IZ6-D ") each represent a partial structure of the formula (IZ6-D), Ac+、b、c、d、R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R20DZ6、R30DZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-D).
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6、L1、M、R20DZ6、R30DZ6Ring Q, c or Ac+When there are a plurality of them, they may be the same or different.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q satisfies at least 1 of (rd-i) to (rd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and-SO of ring Q3 -or-CO2 -The total number of (a) is a.
(rd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-SO3 -or-CO2 -。
(rd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-OCO-R102DZ6、-COCO-R102DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2、-N(R102DZ6)2、-NHCO-R102DZ6、-NHCO-N(R102DZ6)2、-NHCOOR102DZ6or-OCON (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rd-iv) Ring Q has-SO3 -or-CO2 -。
a represents the same meaning as the symbol in the formula (IZ 6-B). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ 6-D') has the same negative valence as the partial structure represented by the formula (IZ6-D ") has the same positive valence in absolute value. ]
The number of ring-constituting elements is preferably 5 to 6.
These monocyclic or condensed rings are preferably bonded to ring Q at 2 positions to form a condensed ring.
Examples of the ring Q and the ring having a monocyclic or condensed ring fused thereto include those similar to those of the above-mentioned group A.
Among them, preferred are formula (Q1), formula (Q4), formula (Q7), formula (Q8) and formula (Q18), and more preferred are formula (Q8) and formula (Q18).
The monocyclic ring (the monocyclic ring is selected from hydrocarbon rings and hetero rings) which may have a substituent, or the condensed ring in which 2 or more of the monocyclic rings are condensed, wherein the number of the constituent elements of the ring Q and the ring which may be condensed/condensed on the ring Q is 5 to 7, may haveHas a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent.
Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
As R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
As R101DZ6Examples thereof include the compounds with R101AZ6The same example. As R101DZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102DZ6Examples thereof include the compounds with R102AZ6The same example. As R102DZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6And R102DZ6Carbon ofThe hydrocarbyl group and the heterocyclic group having 1 to 40 atoms may have a substituent. Examples of the substituent include 1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group may have the same substituent as the substituent. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11DZ6Independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent is preferable.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-D, R1DZ6Preferably a hydrogen atom.
R2DZ6、R3DZ6、R4DZ6And R5DZ6Independently of each otherPreferably a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102DZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102DZ6、-O-R102DZ6、-SO3M or-CO2M, more preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6And ring Q preferably satisfies at least 1 of (rdd-i) to (rdd-iv), R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6、R11DZ6、R101DZ6、R102DZ6and-SO of ring Q3 -or-CO2 -The total number of (a) is a.
(rdd-i)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-SO3 -or-CO2 -。
(rdd-ii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At least one of which is-CO-R102DZ6、-COO-R101DZ6、-O-R102DZ6、-SO2-R101DZ6、-SO2N(R102DZ6)2、-CON(R102DZ6)2or-N (R)102DZ6)2R is a hydrogen atom101DZ6And R102DZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rdd-iii)R1DZ6、R2DZ6、R3DZ6、R4DZ6、R5DZ6And R11DZ6At leastOne is having a-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). The hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(rdd-iv) Ring Q has-SO3 -or-CO2 -。
The compound IZ6-D is more preferably a compound represented by the formula (IZ6-E) (hereinafter, may be referred to as a compound IZ 6-E.).
[ formula (IZ6-E), wherein A isc+、b、c、d、L1And the wavy line means the same as described above.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Independently of one another, represents a hydrogen atom, -CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6、-OCON(R102EZ6)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M、-SO3 -、-CO2 -And can haveA substituted hydrocarbon group having 1 to 40 carbon atoms or a heterocyclic group which may have a substituent.
R2EZ6And R3EZ6、R3EZ6And R4EZ6And R4EZ6And R5EZ6Each of which may be bonded to each other to form a ring.
R101EZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102EZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above.
The formulae (IZ6-E ') and (IZ 6-E') each represent a partial structure of the formula (IZ6-E), Ac+、b、c、d、R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6And L1Represents the same meaning as the corresponding symbol in the formula (IZ 6-E).
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6、R102EZ6、L1M, c or Ac+When there are a plurality of them, they may be the same or different.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6Satisfies at least 1 of (re-i) to (re-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(re-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-SO3 -or-CO2 -。
(re-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-OCO-R102EZ6、-COCO-R102EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2、-N(R102EZ6)2、-NHCO-R102EZ6、-NHCO-N(R102EZ6)2、-NHCOOR102EZ6or-OCON (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO 3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(re-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6-D). When a plurality of a exist, they may be the same or different.
The partial structure represented by the formula (IZ6-E ') has the same negative valence as the partial structure represented by the formula (IZ 6-E') has the same positive valence in absolute value. ]
As R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Examples thereof include the compounds with R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same example.
As R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6Preferred examples of (3) include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6And R13AZ6The same preferred examples as those of (1).
R6EZ6And R7EZ6Independently of each other, a hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a (2-ethyl) hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclohexyl group, a phenyl group and the like is preferable.
As R101EZ6Examples thereof include the compounds with R101AZ6The same example. As R101EZ6Preferred examples of (3) include101AZ6The same preferred examples as those of (1).
As R102EZ6Examples thereof include the compounds with R 102AZ6The same example. As R102EZ6Preferred examples of (3) include102AZ6The same preferred examples as those of (1).
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6The hydrocarbon group and the heterocyclic group having 1 to 40 carbon atoms may have a substituent. Examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The hydrocarbon group represented may haveThe same substituents are used. Preferred examples of the substituent include1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6、R101AZ6And R102AZ6The preferable examples of the substituents which the hydrocarbon group may have are the same.
L1preferably-CO-.
R11EZ6Independently of each other, an aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, a phenyl group which may have a substituent, a naphthyl group which may have a substituent, a tetrahydronaphthyl group which may have a substituent, a thienyl group which may have a substituent, a furyl group which may have a substituent, or a pyridyl group which may have a substituent is preferable.
Examples of the optionally substituted aliphatic hydrocarbon group having 1 to 40 carbon atoms, the optionally substituted phenyl group, the optionally substituted naphthyl group, the optionally substituted tetrahydronaphthyl group, the optionally substituted thienyl group, the optionally substituted furyl group or the optionally substituted pyridyl group include those related to R in the compound IZ6-B 11BZ6Preferable examples of the above-mentioned (a) include the same examples as those of the above-mentioned aliphatic hydrocarbon group having 1 to 40 carbon atoms which may have a substituent(s), the phenyl group which may have a substituent(s), the naphthyl group which may have a substituent(s), the tetrahydronaphthyl group which may have a substituent(s), the thienyl group which may have a substituent(s), the furyl group which may have a substituent(s), and the pyridyl group which may have a substituent(s).
In the compound IZ6-E, R1EZ6Preferably a hydrogen atom.
R2EZ6、R3EZ6、R4EZ6And R5EZ6Independently of each other, a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, -N (R)102EZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3M or-CO2M,
More preferably a hydrogen atom or a nitro group. The number of nitro groups is preferably 0 to 2, more preferably 0 or 1.
R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6Preferably satisfies at least 1 of (ree-i) to (ree-iii), R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6、R11EZ6、R101EZ6And R102EZ6having-SO of3 -or-CO2 -The total number of (a) is a.
(ree-i)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-SO3 -or-CO2 -。
(ree-ii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is-CO-R102EZ6、-COO-R101EZ6、-O-R102EZ6、-SO2-R101EZ6、-SO2N(R102EZ6)2、-CON(R102EZ6)2or-N (R)102EZ6)2R is a hydrogen atom101EZ6And R102EZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(ree-iii)R1EZ6、R2EZ6、R3EZ6、R4EZ6、R5EZ6、R6EZ6、R7EZ6And R11EZ6At least one of which is a compound having-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
Specific examples of compound IZ6 include compounds IFZ6-1 to IFZ6-32, compounds IGZ6-1 to IGZ6-32, compounds IHZ6-1 to IHZ6-32, and compounds IJZ6-1 to IJZ6-32, which are shown in tables 1Z6 to 4Z6, among formula (IFZ6), formula (IGZ6), formula (IHZ6), and formula (IJZ 6).
"-SO in the formulae (IFZ6), (IGZ6), (IHZ6) and (IJZ6)3 -"represents a substitution of any hydrogen atom contained in the partial structure in parentheses, respectively.
[ Table 1Z6]
TABLE 1Z6
R4Z6 | Ac+ | b | d | |
IFZ6-1 | H | Mg2+ | 1 | 1 |
IFZ6-2 | H | Ca2+ | 1 | 1 |
IFZ6-3 | H | Sr2+ | 1 | 1 |
IFZ6-4 | H | Ba2+ | 1 | 1 |
IFZ6-5 | H | Ni2+ | 1 | 1 |
IFZ6-6 | H | Zn2+ | 1 | 1 |
IFZ6-7 | H | Fe2+ | 1 | 1 |
IFZ6-8 | H | Co2+ | 1 | 1 |
IFZ6-9 | H | Sn2+ | 1 | 1 |
IFZ6-10 | H | Mn2+ | 1 | 1 |
IFZ6-11 | H | Al3+ | 3 | 2 |
IFZ6-12 | H | Fe3+ | 3 | 2 |
IFZ6-13 | H | Cr3+ | 3 | 2 |
IFZ6-14 | H | Sn4+ | 2 | 1 |
IFZ6-15 | H | Mn4+ | 2 | 1 |
IFZ6-16 | NO2 | Mg2+ | 1 | 1 |
IFZ6-17 | NO2 | Ca2+ | 1 | 1 |
IFZ6-18 | NO2 | Sr2+ | 1 | 1 |
IFZ6-19 | NO2 | Ba2+ | 1 | 1 |
IFZ6-20 | NO2 | Ni2+ | 1 | 1 |
IFZ6-21 | NO2 | Zn2+ | 1 | 1 |
IFZ6-22 | NO2 | Fe2+ | 1 | 1 |
IFZ6-23 | NO2 | Co2+ | 1 | 1 |
IFZ6-24 | NO2 | Sn2+ | 1 | 1 |
IFZ6-25 | NO2 | Mn2+ | 1 | 1 |
IFZ6-26 | NO2 | Al3+ | 3 | 2 |
IFZ6-27 | NO2 | Fe3+ | 3 | 2 |
IFZ6-28 | NO2 | Cr3+ | 3 | 2 |
IFZ6-29 | NO2 | Sn4+ | 2 | 1 |
IFZ6-30 | NO2 | Mn4+ | 2 | 1 |
IFZ6-31 | H | Cu2+ | 1 | 1 |
IFZ6-32 | NO2 | Cu2+ | 1 | 1 |
[ Table 2Z6]
TABLE 2Z6
R4Z6 | Ac+ | b | d | |
IGZ6-1 | H | Mg2+ | 1 | 1 |
IGZ6-2 | H | Ca2+ | 1 | 1 |
IGZ6-3 | H | Sr2+ | 1 | 1 |
IGZ6-4 | H | Ba2+ | 1 | 1 |
IGZ6-5 | H | Ni2+ | 1 | 1 |
IGZ6-6 | H | Zn2+ | 1 | 1 |
IGZ6-7 | H | Fe2+ | 1 | 1 |
IGZ6-8 | H | Co2+ | 1 | 1 |
IGZ6-9 | H | Sn2+ | 1 | 1 |
IGZ6-10 | H | Mn2+ | 1 | 1 |
IGZ6-11 | H | Al3+ | 3 | 2 |
IGZ6-12 | H | Fe3+ | 3 | 2 |
IGZ6-13 | H | Cr3+ | 3 | 2 |
IGZ6-14 | H | Sn4+ | 2 | 1 |
IGZ6-15 | H | Mn4+ | 2 | 1 |
IGZ6-16 | NO2 | Mg2+ | 1 | 1 |
IGZ6-17 | NO2 | Ca2+ | 1 | 1 |
IGZ6-18 | NO2 | Sr2+ | 1 | 1 |
IGZ6-19 | NO2 | Ba2+ | 1 | 1 |
IGZ6-20 | NO2 | Ni2+ | 1 | 1 |
IGZ6-21 | NO2 | Zn2+ | 1 | 1 |
IGZ6-22 | NO2 | Fe2+ | 1 | 1 |
IGZ6-23 | NO2 | Co2+ | 1 | 1 |
IGZ6-24 | NO2 | Sn2+ | 1 | 1 |
IGZ6-25 | NO2 | Mn2+ | 1 | 1 |
IGZ6-26 | NO2 | Al3+ | 3 | 2 |
IGZ6-27 | NO2 | Fe3+ | 3 | 2 |
IGZ6-28 | NO2 | Cr3+ | 3 | 2 |
IGZ6-29 | NO2 | Sn4+ | 2 | 1 |
IGZ6-30 | NO2 | Mn4+ | 2 | 1 |
IGZ6-31 | H | Cu2+ | 1 | 1 |
IGZ6-32 | NO2 | Cu2+ | 1 | 1 |
[ Table 3Z6]
TABLE 3Z6
R4Z6 | Ac+ | b | d | |
IHZ6-1 | H | Mg2+ | 1 | 1 |
IHZ6-2 | H | Ca2+ | 1 | 1 |
IHZ6-3 | H | Sr2+ | 1 | 1 |
IHZ6-4 | H | Ba2+ | 1 | 1 |
IHZ6-5 | H | Ni2+ | 1 | 1 |
IHZ6-6 | H | Zn2+ | 1 | 1 |
IHZ6-7 | H | Fe2+ | 1 | 1 |
IHZ6-8 | H | Co2+ | 1 | 1 |
IHZ6-9 | H | Sn2+ | 1 | 1 |
IHZ6-10 | H | Mn2+ | 1 | 1 |
IHZ6-11 | H | Al3+ | 3 | 2 |
IHZ6-12 | H | Fe3+ | 3 | 2 |
IHZ6-13 | H | Cr3+ | 3 | 2 |
IHZ6-14 | H | Sn4+ | 2 | 1 |
IHZ6-15 | H | Mn4+ | 2 | 1 |
IHZ6-16 | NO2 | Mg2+ | 1 | 1 |
IHZ6-17 | NO2 | Ca2+ | 1 | 1 |
IHZ6-18 | NO2 | Sr2+ | 1 | 1 |
IHZ6-19 | NO2 | Ba2+ | 1 | 1 |
IHZ6-20 | NO2 | Ni2+ | 1 | 1 |
IHZ6-21 | NO2 | Zn2+ | 1 | 1 |
IHZ6-22 | NO2 | Fe2+ | 1 | 1 |
IHZ6-23 | NO2 | Co2+ | 1 | 1 |
IHZ6-24 | NO2 | Sn2+ | 1 | 1 |
IHZ6-25 | NO2 | Mn2+ | 1 | 1 |
IHZ6-26 | NO2 | Al3+ | 3 | 2 |
IHZ6-27 | NO2 | Fe3+ | 3 | 2 |
IHZ6-28 | NO2 | Cr3+ | 3 | 2 |
IHZ6-29 | NO2 | Sn4+ | 2 | 1 |
IHZ6-30 | NO2 | Mn4+ | 2 | 1 |
IHZ6-31 | H | Cu2+ | 1 | 1 |
IHZ6-32 | NO2 | Cu2+ | 1 | 1 |
[ Table 4Z6]
TABLE 4Z6
R4Z6 | Ac+ | b | d | |
IJZ6-1 | H | Mg2+ | 1 | 1 |
IJZ6-2 | H | Ca2+ | 1 | 1 |
IJZ6-3 | H | Sr2+ | 1 | 1 |
IJZ6-4 | H | Ba2+ | 1 | 1 |
IJZ6-5 | H | Ni2+ | 1 | 1 |
IJZ6-6 | H | Zn2+ | 1 | 1 |
IJZ6-7 | H | Fe2+ | 1 | 1 |
IJZ6-8 | H | Co2+ | 1 | 1 |
IJZ6-9 | H | Sn2+ | 1 | 1 |
IJZ6-10 | H | Mn2+ | 1 | 1 |
IJZ6-11 | H | Al3+ | 3 | 2 |
IJZ6-12 | H | Fe3+ | 3 | 2 |
IJZ6-13 | H | Cr3+ | 3 | 2 |
IJZ6-14 | H | Sn4+ | 2 | 1 |
IJZ6-15 | H | Mn4+ | 2 | 1 |
IJZ6-16 | NO2 | Mg2+ | 1 | 1 |
IJZ6-17 | NO2 | Ca2+ | 1 | 1 |
IJZ6-18 | NO2 | Sr2+ | 1 | 1 |
IJZ6-19 | NO2 | Ba2+ | 1 | 1 |
IJZ6-20 | NO2 | Ni2+ | 1 | 1 |
IJZ6-21 | NO2 | Zn2+ | 1 | 1 |
IJZ6-22 | NO2 | Fe2+ | 1 | 1 |
IJZ6-23 | NO2 | Co2+ | 1 | 1 |
IJZ6-24 | NO2 | Sn2+ | 1 | 1 |
IJZ6-25 | NO2 | Mn2+ | 1 | 1 |
IJZ6-26 | NO2 | Al3+ | 3 | 2 |
IJZ6-27 | NO2 | Fe3+ | 3 | 2 |
IJZ6-28 | NO2 | Cr3+ | 3 | 2 |
IJZ6-29 | NO2 | Sn4+ | 2 | 1 |
IJZ6-30 | NO2 | Mn4+ | 2 | 1 |
IJZ6-31 | H | Cu2+ | 1 | 1 |
IJZ6-32 | NO2 | Cu2+ | 1 | 1 |
For example, compound IFZ6-1 is a compound represented by formula (IFZ 6-1).
The compound IZ6 is preferably the compound IFZ6-1 to the compound IFZ6-4, the compound IFZ6-6 to the compound IFZ6-7, the compound IFZ6-10 to the compound IFZ6-13, the compound IFZ6-15 to the compound IFZ6-19, the compound IFZ6-21 to the compound IFZ6-22, the compound IFZ6-25 to the compound IFZ6-28, or the compound IFZ6-30 to the compound IFZ 6-31; compound IGZ6-1 to compound IGZ6-4, compound IGZ6-6 to compound IGZ6-7, compound IGZ6-10 to compound IGZ6-13, compound IGZ6-15 to compound IGZ6-19, compound IGZ6-21 to compound IGZ6-22, compound IGZ6-25 to compound IGZ6-28, and compound IGZ 6-30; compound IHZ6-1 to compound IHZ6-4, compound IHZ6-6 to compound IHZ6-7, compound IHZ6-10 to compound IHZ6-13, compound IHZ6-15 to compound IHZ6-19, compound IHZ6-21 to compound IHZ6-22, compound IHZ6-25 to compound IHZ6-28, and compound IHZ 6-30; and compounds IJZ6-1 to IJZ6-4, IJZ6-6 to IJZ6-7, IJZ6-10 to IJZ6-13, IJZ6-15 to IJZ6-19, IJZ6-21 to IJZ6-22, IJZ6-25 to IJZ6-28 and IJZ6-30,
More preferably, the compound is IFZ6-1 to IFZ6-4, IFZ6-6 to IFZ6-7, IFZ6-10 to IFZ6-13, IFZ6-15 to IFZ6-19, IFZ6-21 to IFZ6-22, IFZ6-25 to IFZ6-28 or IFZ 6-30; and compound IJZ6-1 to compound IJZ6-4, compound IJZ6-6 to compound IJZ6-7, compound IJZ6-10 to compound IJZ6-13, compound IJZ6-15 to compound IJZ6-19, compound IJZ6-21 to compound IJZ6-22, compound IJZ6-25 to compound IJZ6-28, and compound IJZ6-30 to compound IJZ 6-32.
As the compound (IZ6), the following compounds are preferable:
in the formula (IZ6-C), L1And L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102CZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R 102CZ6、-O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
Ac+is Mg2+、Ca2+、Sr2+、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+Metal cation of equivalent 2 valence, Al3+、Fe3+And Cr3+Equi-3 valent metal cation, Sn4+And Mn4+A compound of an equivalent metal cation having a valence of 4, M being a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
L1and L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102CZ6)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102CZ6、-O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
Ac+is Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2+、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+Or Mn4+M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
L1and L2Are the same group and are-CO-or-SO2-, preferably-CO-, R11CZ6And R14CZ6Are identical radicals, are hydroxy, -O -Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R1CZ6Is a hydrogen atom, R2CZ6~R5CZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102CZ6)2Nitro, trifluoromethyl, -O-R102CZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102CZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+Or Mn4+And M is a hydrogen atom or an alkali metal atom.
As the compound (IZ6), the following compounds are preferable:
in the formula (IZ6-E), L1is-CO-or-SO2-, preferably-CO-, R11EZ6Is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group as a substituent in the group consisting of M, R1EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, a halogen atom, or-N (R)102EZ6)2A C1-20 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO 2A hydrocarbyl group having 1 to 20 carbon atoms as a substituent in the group consisting of M,
R6EZ6and R7EZ6Independently of one another, are hydrogen atoms or may have radicals selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-20 hydrocarbon group, -SO3 -、-CO2 -、-SO3M or-CO2M,
Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Cd2+、Ni2+、Zn2+、Cu2+、Hg2+、Fe2+、Co2+、Sn2+、Pb2+And Mn2+Metal cation of equivalent 2 valence, Al3+、Fe3+And Cr3+Equi-3 valent metal cation, Sn4+And Mn4+And the equivalent of a metal cation having a valence of 4,
a compound in which M is a hydrogen atom or an alkali metal atom;
more preferred are the following compounds:
L1is-CO-or-SO2-, preferably-CO-,
R11EZ6is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1EZ6is a hydrogen atom, R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102EZ6)2A C1-10 hydrocarbon group in which all or a part of the hydrogen atoms are replaced by nitro groups or fluorine atoms, -NHCO-R102EZ6、-O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,
R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R6EZ6and R7EZ6Independently of one another, are hydrogen atoms or may have radicals selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, A c+Is Mg2+、Ca2+、Sr2+、Ba2+、Ni2+、Zn2+、Cu2+、Fe2 +、Co2+、Sn2+、Mn2+、Al3+、Fe3+、Cr3+、Sn4+Or Mn4+M is a hydrogen atom or an alkali metal atom;
further preferred are the following compounds:
L1is-CO-or-SO2-, preferably-CO-, R11EZ6Is hydroxy, -O-Or may have a structure selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A hydrocarbyl group having 1 to 10 carbon atoms as a substituent in the group consisting of M,
R1EZ6is a hydrogen atom, R2EZ6~R5EZ6Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, a halogen atom, or-N (R)102EZ6)2Nitro, trifluoromethyl, -O-R102EZ6、-SO3 -、-CO2 -、-SO3M or-CO2M,R102EZ6Is a hydrogen atom, or may have a radical selected from the group consisting of-SO3 -、-CO2 -、-SO3M and-CO2A C1-10 hydrocarbon group as a substituent in the group consisting of M, R6EZ6And R7EZ6Independently represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, Ac+Is Mg2+、Ca2+、Sr2+、Ba2+、Zn2+、Cu2+、Fe2+、Mn2+、Al3+、Fe3+、Cr3+Or Mn4+And M is a hydrogen atom or an alkali metal atom.
The compound represented by formula (IZ6) can be produced by reacting the compound represented by formula (JZ6) with the compound represented by formula (KZ 6). In particular, 1 or 2 or more compounds of formula (JZ6) and formula (KZ6) may be used.
[ in the formula (JZ6), the formula (KZ6) and the formula (IZ6), a, b, c, D, D, Z and Ac+The same meanings as described above are indicated. ZZ represents-SO3M or-CO2And M. M represents the same meaning as described above. MM denotes the direction of inclusion A c+A metal compound which provides 0 or more and c or less electrons.
When a plurality of compounds represented by the formula (JZ6), D, ZZ, a, MM, and M are present, they may be the same or different. ]
Examples of the compound represented by formula (KZ6) include:
comprises the direction Ac+Inorganic compounds such as chlorides, bromides, iodides, sulfates, nitrates, fluorosulfonates, and phosphates of metals that provide 0 or more and c or less electrons; comprises the direction Ac+Sulfonates such as methanesulfonate, trifluoromethanesulfonate and p-toluenesulfonate of a metal which provide 0 or more and c or less electrons;
comprises the direction Ac+Carboxylates such as acetates, citrates, formates, gluconates, lactates, oxalates, and tartrates of metals that provide 0 or more and c or less electrons;
substituted by alkoxy groups such as methoxy, ethoxy, tert-butoxy, etc. to Ac+A metal providing 0 or more and c or less electrons; substituted by butyl, tert-butyl, phenyl, etc. to Ac+A metal providing 0 or more and c or less electrons;
by substitution of hydroxy groupsIn the direction of Ac+A metal which supplies 0 or more and c or less electrons, and the like.
The amount of the compound represented by the formula (KZ6) used is usually 0.05 to 20 mol, preferably 0.06 to 15 mol, and more preferably 0.1 to 10 mol, based on 1 mol of the compound represented by the formula (JZ 6).
When the compound represented by the formula (JZ6) is reacted with the compound represented by the formula (KZ6), a base is preferably present. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide, organic metal compounds such as butyllithium, tert-butyllithium, and phenyllithium, and inorganic bases such as lithium hydroxide, sodium hydroxide, and potassium hydroxide.
The amount of the base used is usually 0.0001 to 10 moles, preferably 0.0001 to 8 moles, more preferably 0.0001 to 5 moles, and still more preferably 0.0001 to 4 moles, based on 1 mole of the compound represented by formula (JZ 6).
The reaction of the compound represented by the formula (JZ6) with the compound represented by the formula (KZ6) can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; and sulfoxide solvents such as dimethyl sulfoxide, preferably water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably water, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (JZ 6).
The reaction temperature of the compound represented by the formula (JZ6) and the compound represented by the formula (KZ6) is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
When the compound represented by the formula (IZ6) is a compound represented by the formula (IZ6-A), it can be produced in the same manner as described above. Specifically, the compound represented by the formula (JJZ6) can be produced by reacting a compound represented by the formula (KZ 6). In particular, 1 or 2 or more compounds of formula (JJZ6) and (KZ6) may be used, respectively.
[ formula (JJZ6), formula (KZ6) and formula (IZ6-A) wherein Ac+、b、c、d、R1AZ6、R2AZ6、R3AZ6、R4AZ6、R5AZ6、RAA1Z6、RAA2Z6、R12AZ6、R13AZ6And the wavy line means the same as described above.
R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6Independently of one another, represents a hydrogen atom, -CO-R102AAZ6、-COO-R101AAZ6、-OCO-R102AAZ6、-O-R102AAZ6、-SO2-R101AAZ6、-SO2N(R102AAZ6)2、-CON(R102AAZ6)2、-N(R102AAZ6)2、-NHCO-R102AAZ6Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a C1-40 hydrocarbon group which may have a substituent orA heterocyclic group which may have a substituent.
R2AAZ6And R3AAZ6、R3AAZ6And R4AAZ6、R4AAZ6And R5AZ6、RAAA1Z6And RAAA2Z6And R12AAZ6And R13AAZ6Each of which may be bonded to each other to form a ring.
R101AAZ6Independently represent a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent.
R102AAZ6Independently represent a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group.
M represents the same meaning as described above. R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6、R102AAZ6Or when there are a plurality of M, they may be the same or different.
R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6And R102AAZ6Satisfies at least 1 of (j-i) to (j-iii), R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6、R13AAZ6、R101AAZ6And R102AAZ6having-SO of3M or-CO2The total number of M is more than a.
(j-i)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is-SO3M or-CO2M。
(j-ii)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is-CO-R102AAZ6、-COO-R101AAZ6、-OCO-R102AAZ6、-O-R102AAZ6、-SO2-R101AAZ6、-SO2N(R102AAZ6)2、-CON(R102AAZ6)2、-N(R102AAZ6)2or-NHCO-R102AAZ6R is a hydrogen atom101AAZ6And R102AAZ6To have-SO3 -or-CO2 -A hydrocarbon group having 1 to 40 carbon atoms or having-SO3 -or-CO2 -The heterocyclic group of (1). Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
(j-iii)R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6At least one of which is a compound having-SO3M or-CO2M is a hydrocarbon group having 1 to 40 carbon atoms or has-SO3M or-CO2A heterocyclic group of M. Wherein the hydrocarbon group or the heterocyclic group may have-SO3 -and-CO2 -And (ii) an additional substituent.
a represents the same meaning as the symbol in the formula (IZ 6). When a plurality of a exist, they may be the same or different. ]
With respect to the compound represented by the formula (JJZ6) (hereinafter, may be referred to as compound JJZ6), R1AAZ6In the case of a hydrogen atom, the compound represented by the formula (pt1Z6) (hereinafter, may be referred to as a phthalonitrile compound) and the compound represented by the formula (pt2Z6) (hereinafter, may be referred to as an alkoxide compound) are reacted with each other, and then the compound represented by the formula (pt3Z6) (hereinafter, may be referred to as a compound pt3Z6) and the compound represented by the formula (pt4Z6) (hereinafter, may be referred to as a compound pt4Z6) are further reacted with each other in the presence of an acid. In addition, R 1AAZ6When not a hydrogen atom, a compound represented by the formula (pt5Z6) (hereinafter, may be referred to as a compound pt5Z 6).) The reaction to produce a compound represented by formula (JJZ 6). Here, the compounds represented by the formula (pt1Z6), the formula (pt2Z6), the formula (pt3Z6), the formula (pt4Z6) and the formula (pt5Z6) may be independent of each other, individual compounds, or a mixture of different compounds.
In [ formula (pt1Z6), formula (pt2Z6), formula (pt3Z6), formula (pt4Z6), formula (pt5Z6) and formula (JJZ6), R1AAZ6、R2AAZ6、R3AAZ6、R4AAZ6、R5AAZ6、RAAA1Z6、RAAA2Z6、R12AAZ6And R13AAZ6The same meanings as described above are indicated. R50Z6Represents an alkyl group having 1 to 20 carbon atoms. M1Z6Represents an alkali metal atom. LG represents a halogen atom, a mesyloxy group, a tosyloxy group or a trifluormesyloxy group.]
As R50Z6Examples of the alkyl group having 1 to 20 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, and the like, and preferred examples thereof include alkyl groups having 1 to 6 carbon atoms.
As M1Z6Examples of the alkali metal atom include a lithium atom, a sodium atom and a potassium atom.
The amount of the alkoxide compound used is usually 0.1 to 10 moles, preferably 0.2 to 5 moles, more preferably 0.3 to 3 moles, and still more preferably 0.4 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt3Z6 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
The amount of the compound pt4Z6 used is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles, based on 1 mole of the phthalonitrile compound.
Examples of the acid include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, fluorosulfonic acid, and phosphoric acid; sulfonic acids such as methanesulfonic acid, trifluoromethanesulfonic acid, and p-toluenesulfonic acid; examples of the carboxylic acid include acetic acid, citric acid, formic acid, gluconic acid, lactic acid, oxalic acid, tartaric acid, and the like, and preferably include hydrochloric acid, hydrobromic acid, sulfuric acid, methanesulfonic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and carboxylic acid, and more preferably include acetic acid.
The amount of the acid used is usually 1 to 20 moles, preferably 1 to 10 moles, more preferably 1 to 8 moles, and still more preferably 1 to 6 moles, based on 1 mole of the phthalonitrile compound.
The reaction of the phthalonitrile compound, the alkoxide compound, the compound pt3Z6, and the compound pt4Z6 can be usually carried out in the presence of a solvent.
As the solvent, water may be mentioned; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, and 1-octanol; ether solvents such as tetrahydrofuran; ketone solvents such as acetone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide, preferably include water, nitrile solvents, alcohol solvents, ether solvents, ketone solvents, ester solvents, aromatic hydrocarbon solvents, halogenated hydrocarbon solvents, amide solvents and sulfoxide solvents, more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, tetrahydrofuran, acetone, ethyl acetate, toluene, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, still more preferably include water, acetonitrile, methanol, ethanol, 2-propanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide, and particularly preferably include water, methanol, ethanol, methanol, ethanol, butanol, methanol, ethanol, 1-butanol, 1-pentanol, 1-octanol, acetone, dichloromethane, chloroform, N-methylpyrrolidone and dimethyl sulfoxide, Acetonitrile, methanol, ethanol and 2-propanol.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the phthalonitrile compound.
The reaction temperature is usually 0 to 200 ℃, preferably 0 to 100 ℃, more preferably 0 to 70 ℃, and further preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
With respect to the amount of compound pt5Z6 used, relative to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
When the compound pt5Z6 is reacted, a base is preferably coexisted. Examples of the base include organic bases such as triethylamine, 4- (N, N-dimethylamino) pyridine, and piperidine, metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide, and organic metal compounds such as butyllithium, tert-butyllithium, and phenyllithium; inorganic bases such as lithium hydroxide, sodium hydroxide and potassium hydroxide.
As for the amount of the base used, with respect to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 10 moles, preferably 1 to 5 moles, more preferably 1 to 3 moles, and still more preferably 1 to 2 moles.
The reaction of compound pt5Z6 can generally be carried out in the presence of a solvent. The solvent may be selected from the same ranges as described above.
As to the amount of the solvent used, with respect to R1AAZ6The amount of the compound JJZ 61 which is a hydrogen atom is usually 1 to 1000 parts by mass. The reaction temperature of the compound pt5Z6 is usually-90 to 200 ℃, preferably-80 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
Compound JJZ6 is a compound having no-SO3In the case of the compound of M (hereinafter, sometimes referred to as compound JJJZ6), the compound JJJZ6 may be introduced into-SO by reacting it with a sulfonating agent such as fuming sulfuric acid or chlorosulfonic acid3M。
With respect to SO in oleum3The amount of (b) is usually 1 to 50 moles, preferably 5 to 40 moles, more preferably 5 to 30 moles, and still more preferably 5 to 25 moles, based on the moles of the compound jjjjz 61.
The amount of sulfuric acid used in oleum is usually 1 to 200 moles, preferably 10 to 100 moles, more preferably 10 to 75 moles, and still more preferably 10 to 50 moles, based on the moles of compound jjjjz 61 moles.
The amount of chlorosulfonic acid used is usually 1 to 500 moles, preferably 10 to 300 moles, more preferably 10 to 200 moles, and still more preferably 10 to 150 moles, based on the moles of the compound JJJZ 61.
The reaction temperature of sulfonation is usually-20 to 200 ℃, preferably-10 to 100 ℃, and more preferably 0 to 50 ℃. The reaction time is usually 0.5 to 300 hours.
The method for extracting the compound JJZ6 from the reaction mixture is not particularly limited, and it can be extracted by various known methods. For example, compound JJZ6 can be extracted by filtering the reaction mixture after the reaction is completed. Further, the residue obtained after filtration may be subjected to column chromatography, recrystallization, or the like. After the completion of the reaction, the solvent of the reaction mixture may be distilled off and then purified by column chromatography.
The coloring composition of the present invention contains the compound Z and at least one of the resin (B) and the solvent (E), and preferably contains both the resin (B) and the solvent (E) and the compound Z.
The coloring composition of the present invention preferably contains a resin (hereinafter, sometimes referred to as resin (B)). By including the resin (B) in the coloring composition, dispersion stability may be further improved.
< resin (B) >
The resin (B) is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least 1 monomer (a) (hereinafter, sometimes referred to as "(a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride.
The resin (B) is preferably a copolymer having a structural unit derived from a monomer (B) (hereinafter sometimes referred to as "(B)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, and other structural units.
Examples of other structural units include: a structural unit derived from a monomer (c) copolymerizable with the monomer (a) (however, it is different from the monomer (a) and the monomer (b) and may be referred to as "(c)" hereinafter), a structural unit having an ethylenically unsaturated bond, and the like.
Examples of (a) include:
unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, and p-vinylbenzoic acid;
unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5, 6-tetrahydrophthalic acid, 1,2,3, 6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1, 4-cyclohexenedicarboxylic acid;
carboxyl group-containing bicyclic unsaturated compounds such as methyl-5-norbornene-2, 3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene, 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene; carboxylic acid anhydrides such as anhydrides of the above unsaturated dicarboxylic acids other than fumaric acid and mesaconic acid; unsaturated mono [ (meth) acryloyloxyalkyl ] esters of 2-or more-membered polycarboxylic acids such as succinic acid mono [ 2- (meth) acryloyloxyethyl ] ester and phthalic acid mono [ 2- (meth) acryloyloxyethyl ] ester;
And unsaturated acrylates containing a hydroxyl group and a carboxyl group in the same molecule, such as α - (hydroxymethyl) acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an aqueous alkaline solution.
(b) The polymerizable compound has a cyclic ether structure having 2 to 4 carbon atoms (for example, at least 1 selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) Preferably, the monomer has a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
Examples of (b) include: a monomer (b1) (hereinafter sometimes referred to as "(b 1)") having an oxetanyl group and an ethylenically unsaturated bond, a monomer (b2) (hereinafter sometimes referred to as "(b 2)") having an oxetanyl group and an ethylenically unsaturated bond, and a monomer (b3) (hereinafter sometimes referred to as "(b 3)") having a tetrahydrofuranyl group and an ethylenically unsaturated bond.
Examples of (b1) include: a monomer (b1-1) (hereinafter sometimes referred to as "(b 1-1)") having a structure obtained by epoxidizing a linear or branched aliphatic unsaturated hydrocarbon, and a monomer (b1-2) (hereinafter sometimes referred to as "(b 1-2)") having a structure obtained by epoxidizing an alicyclic unsaturated hydrocarbon.
As (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of (b1-1) include glycidyl (meth) acrylate,. beta. -methylglycidyl (meth) acrylate,. beta. -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether,. alpha. -methylvinylbenzyl glycidyl ether, 2, 3-bis (glycidyloxymethyl) styrene, 2, 4-bis (glycidyloxymethyl) styrene, 2, 5-bis (glycidyloxymethyl) styrene, 2, 6-bis (glycidyloxymethyl) styrene, 2,3, 4-tris (glycidyloxymethyl) styrene, 2,3, 5-tris (glycidyloxymethyl) styrene, 2,3, 6-tris (glycidyloxymethyl) styrene, 3,4, 5-tris (glycidyloxymethyl) styrene, 2,4, 6-tris (glycidyloxymethyl) styrene and the like.
Examples of (b1-2) include vinylcyclohexene monooxide, 1, 2-epoxy-4-vinylcyclohexane (for example, CELLOXIDE (registered trademark) 2000 (manufactured by DAicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, CYCLOMER (registered trademark) A400 (manufactured by Daicel Co., Ltd.), (3, 4-epoxycyclohexylmethyl (meth) acrylate (for example, CYCLOMER (registered trademark) M100 (manufactured by Daicel Co., Ltd.)), the compound represented by the formula (BI), and the compound represented by the formula (BII).
[ formula (BI) and formula (BII) wherein RaAnd RbIndependently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, the alkyl groupThe hydrogen atoms contained in the radicals may be substituted by hydroxyl groups. XaAnd XbIndependently of one another, represents a single bond, -Rc-、*-Rc-O-、*-Rc-S-or Rc-NH-。RcRepresents an alkanediyl (alkanediyl) group having 1 to 6 carbon atoms. Denotes a bond to O.]
The compound represented by formula (BI) includes compounds represented by any one of formulae (BI-1) to (BI-15), preferably compounds represented by formulae (BI-1), (BI-3), (BI-5), (BI-7), (BI-9), and (BI-11) to (BI-15), and more preferably compounds represented by formulae (BI-1), (BI-7), (BI-9), and (BI-15).
The compound represented by formula (BII) includes compounds represented by any one of formulae (BII-1) to (BII-15), preferably compounds represented by formulae (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15), and more preferably compounds represented by formulae (BII-1), (BII-7), (BII-9), and (BII-15).
The compound represented by the formula (BI) and the compound represented by the formula (BII) may be used alone or in combination. When they are used in combination, the content ratio of the compound represented by the formula (BI) to the compound represented by the formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20 on a molar basis.
Examples of (c) include: methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, and (meth) acrylic acidLauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, tricyclo [5.2.1.0 (meth) acrylate2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6](meth) acrylates such as decen-9-yl ester, dicyclopentanyl oxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, and benzyl (meth) acrylate;
hydroxyl group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate; bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2 '-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [2.2.1] hept-2-ene, 5, 6-dihydroxybicyclo [2.2.1] hept-2-ene, 5, 6-bis (hydroxymethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-bis (2' -hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5, 6-dimethoxybicyclo [2.2.1] hept-2-ene, 5, 6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, bicyclic unsaturated compounds such as 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonybicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5, 6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene and 5, 6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene; dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl 3-maleimidobenzoate, N-succinimidyl 4-maleimidobutyrate, N-succinimidyl 6-maleimidohexanoate, N-succinimidyl 3-maleimidopropionate and N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, α -methylstyrene, vinyltoluene and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth) acrylamide; esters such as vinyl acetate; dienes such as 1, 3-butadiene, isoprene and 2, 3-dimethyl-1, 3-butadiene; and so on.
Among these, styrene, vinyltoluene, and tricyclo [5.2.1.0 (meth) acrylate are preferable from the viewpoint of copolymerization reactivity and heat resistance2,6]Decan-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decan-9-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-8-yl ester, tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decen-9-yl ester, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1]Hept-2-ene, benzyl (meth) acrylate, and the like.
The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group. The resin having such a structural unit can be obtained by adding a monomer having an ethylenically unsaturated bond in a group reactive with the group (a) and/or (b) to a polymer having a structural unit derived from (a) and/or (b).
Examples of such a structural unit include a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth) acrylate is added to a maleic anhydride unit, and a structural unit in which glycidyl (meth) acrylate is added to a (meth) acrylic acid unit. When these structural units have a hydroxyl group, a structural unit obtained by further adding a carboxylic anhydride may be mentioned as a structural unit having an ethylenically unsaturated bond.
The polymer having a structural unit derived from (a) can be produced, for example, by polymerizing a monomer constituting the structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator and the solvent are not particularly limited, and polymerization initiators and solvents generally used in the art can be used. Examples of the polymerization initiator include azo compounds (e.g., 2 '-azobisisobutyronitrile, 2' -azobis (2, 4-dimethylvaleronitrile), and organic peroxides (e.g., benzoyl peroxide), and any solvent may be used as long as it dissolves the monomers.
The polymer obtained may be used as it is in a solution after the reaction, may be used as a solution obtained by concentration or dilution, or may be used as a copolymer obtained in a solid (powder) form by a method such as reprecipitation.
If necessary, a catalyst for the reaction of a carboxylic acid or a carboxylic anhydride with a cyclic ether (e.g., tris (dimethylaminomethyl) phenol) and a polymerization inhibitor (e.g., hydroquinone) can be used.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5, 6-tetrahydrophthalic anhydride, 1,2,3, 6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5, 6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride.
Specific examples of the resin (B) include a 3, 4-epoxycyclohexylmethyl (meth) acrylate/(meth) acrylic acid copolymer, and a 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/(benzyl (meth) acrylate/(meth) acrylic acid copolymer, glycidyl (meth) acrylate/styrene/(meth) acrylic acid copolymer, and 3, 4-epoxytricyclo [5.2.1.0 ] meth) acrylic acid2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid) 2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid 2-ethylhexyl esterEster copolymer, 3, 4-epoxy tricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid tricyclo [5.2.1.02,6]Decenyl ester/(meth) acrylic acid/N-cyclohexylmaleimide copolymer, 3-methyl-3- (meth) acryloyloxymethyloxetane/(meth) acrylic acid/styrene copolymer, benzyl (meth) acrylate/(meth) acrylic acid copolymer, styrene/(meth) acrylic acid copolymer, and resins described in each of Japanese patent application laid-open Nos. 9-106071, 2004-29518 and 2004-361455.
Among these, the resin (B) is preferably a copolymer containing a structural unit derived from (a) and a structural unit derived from (B).
In the case where 2 or more species are combined with the resin (B), it is preferable that the resin (B) contains at least 3, 4-epoxytricyclo [5.2.1.0 ] selected from (meth) acrylic acid2,6]Decyl ester/(meth) acrylic acid copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]Decyl ester/(meth) acrylic acid/N-cyclohexylmaleimide/(meth) acrylic acid 2-hydroxyethyl ester copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid) 2,6]Decyl ester/(meth) acrylic acid/vinyltoluene copolymer, 3, 4-epoxytricyclo [5.2.1.0 ] meth (acrylic acid)2,6]1 or more of decyl ester/(meth) acrylic acid 2-ethylhexyl ester copolymer.
The weight average molecular weight (Mw) of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. The dispersity [ weight average molecular weight (Mw)/number average molecular weight (Mn) ] of the resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.
The acid value (in terms of solid content) of the resin (B) is preferably 10 to 300mg-KOH/g, more preferably 20 to 250mg-KOH/g, and still more preferably 30 to 200 mg-KOH/g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required for neutralizing 1g of the resin (B), and can be determined, for example, by titration using an aqueous potassium hydroxide solution.
The content of the resin (B) in the coloring composition is preferably 3 to 99% by mass, more preferably 5 to 99% by mass, and still more preferably 7 to 95% by mass, based on the total amount of the solid components.
The coloring composition of the present invention preferably contains a solvent (hereinafter, sometimes referred to as "solvent (E)"). By including the solvent (E) in the coloring composition, the dispersion stability may be further improved.
< solvent (E) >
Examples of the solvent (E) include an ester solvent (a solvent containing-COO-and not containing-O-in the molecule), an ether solvent (a solvent containing-O-and not containing-COO-in the molecule), an ether ester solvent (a solvent containing-COO-and not containing-O-in the molecule), a ketone solvent (a solvent containing-CO-and not containing-COO-in the molecule), an alcohol solvent (a solvent containing OH and not containing-O-, -CO-, and-COO-in the molecule), an aromatic hydrocarbon solvent, an amide solvent, and dimethyl sulfoxide.
Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ -butyrolactone.
Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1, 4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methyl anisole.
Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, and mixtures thereof, Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol methyl ether acetate, and the like.
Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.
Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, glycerin, and the like.
Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, mesitylene, and the like.
Examples of the amide solvent include N, N-dimethylformamide, N-dimethylacetamide, and N-methylpyrrolidone.
These solvents may be used in combination of 2 or more.
The content of the solvent (E) is preferably 40 to 99% by mass, and more preferably 50 to 95% by mass, based on the total amount of the coloring composition.
In the coloring composition of the present invention, the compound Z is preferably dispersed in the solvent (E).
For the compound Z, the following treatments may be carried out, as required: rosin treatment; surface treatment using a derivative or the like into which an acidic group or a basic group is introduced; grafting treatment of the surface of the compound Z with a polymer compound or the like; micronization treatment by sulfuric acid micronization method; washing treatment with an organic solvent, water or the like for removing impurities; and a treatment of removing ionic impurities by an ion exchange method or the like. Preferably, the particle size of the compound Z is substantially uniform. The compound Z can be dispersed uniformly in the dispersion liquid by adding a dispersant and performing a dispersion treatment.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamine, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical industries, Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF (manufactured by Kyoho Co., Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Technio Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by Co., Ltd.), and the like.
When a dispersant is used, the amount of the dispersant (solid component) used is preferably 300 parts by mass or less, and more preferably 5 parts by mass or more and 100 parts by mass or less, relative to 100 parts by mass of the compound Z. When the amount of the dispersant used is within the above range, a colored composition having a more uniform dispersion state tends to be obtained.
The content of the compound Z in the coloring composition is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass, based on the total amount of the coloring composition.
The content of the compound Z in the coloring composition is usually 1 mass% to 90 mass%, preferably 1 mass% to 80 mass%, and more preferably 2 mass% to 75 mass% with respect to the total amount of the solid content.
When the coloring composition of the present invention contains the compound Z, the coloring composition may further contain a colorant other than the compound Z (that is, the above-mentioned colorant A1Z1, colorant A1Z2, colorant A1Z3, colorant A1Z4, colorant A1Z5, colorant A1Z6, and the like). Hereinafter, the colorant A1Z1, the colorant A1Z2, the colorant A1Z3, the colorant A1Z4, the colorant A1Z5, and the colorant A1Z6 may be collectively referred to as "colorant ZZ". The coloring agent ZZ may contain 1 or 2 or more coloring agents. The colorant ZZ preferably comprises a yellow colorant or a green colorant.
< colorant ZZ >
The coloring agent ZZ may be a dye or a pigment. As The dye, known dyes can be used, and there can be mentioned dyes described in The index of dyes (published by The Society of Dyers and Colourists) and Dyeing notes (color Dyeing company). Further, depending on the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, and the like can be given. These dyes may be used alone, or 2 or more of them may be used in combination.
Specifically, the following dyes are given by the color index (c.i.) number. C.i. solvent yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
c.i. acid yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
c.i. reactive yellow 2, 76, 116;
C.i. direct yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
c.i. disperse yellow 51, 54, 76;
c.i. solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
c.i. acid orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
c.i. reactive orange 16;
c.i. direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
c.i. solvent red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247;
c.i. acid red 52, 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;
c.i. acid violet 34, 102;
c.i. disperse violet 26, 27;
c.i. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
c.i. solvent blue 14, 18, 35, 36, 45, 58, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C.i. acid blue 25, 27, 40, 45, 78, 80, 112;
c.i. direct blue 40;
c.i. disperse blue 1, 14, 56, 60;
c.i. solvent green 1, 3, 5, 28, 29, 32, 33;
c.i. acid green 3, 5, 9, 25, 27, 28, 41;
c.i. alkaline green 1;
c.i. vat green 1, etc.
As The Pigment, known pigments can be used, and for example, pigments classified as "pigments (pigments)" in The color index (published by The Society of Dyers and Colourists) can be cited. These may be used alone, or 2 or more of them may be used in combination.
Specifically, there may be mentioned:
c.i. pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 and the like;
orange pigments such as c.i. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
red pigments such as c.i. pigment red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and the like;
c.i. pigment blue 15, 15:3, 15:4, 15:6, 60, etc.;
C.i. pigment violet 1, 19, 23, 29, 32, 36, 38 and the like violet pigment;
c.i. pigment green 7, 36, 58, 59 and the like.
The colorant ZZ is preferably a yellow dye and a yellow pigment (hereinafter, these may be collectively referred to as "yellow colorant"), a green dye and a green pigment (hereinafter, these may be collectively referred to as "green colorant"), more preferably a yellow pigment and a green pigment, and still more preferably a green pigment.
Examples of the yellow dye include dyes of which hue is classified as yellow among the dyes, and examples of the yellow pigment include pigments of which hue is classified as yellow among the pigments.
Among the yellow pigments, quinophthalone yellow pigment, metal-containing yellow pigment, and isoindoline yellow pigment are preferable, c.i. pigment yellow 129, 138, 139, 150, and 185 are more preferable, and c.i. pigment yellow 138, 139, 150, and 185 are further preferable.
Examples of the green dye include dyes of which hue is classified as green among the dyes, and examples of the green pigment include pigments of which hue is classified as green among the pigments.
Among the green pigments, phthalocyanine pigments are preferable, at least one selected from the group consisting of halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments is more preferable, and at least one selected from the group consisting of c.i. pigment green 7, 36, 58 and 59 is further preferable.
In the case where the coloring composition of the present invention contains the colorant ZZ and the solvent (E), a liquid containing the colorant ZZ, which contains the colorant ZZ and the solvent (E), may be prepared in advance, and then the coloring composition may be prepared using the liquid containing the colorant ZZ. In the case where the colorant ZZ is insoluble in the solvent (E), a liquid containing the colorant ZZ may be prepared by dispersing the colorant ZZ in the solvent (E) and mixing them. The liquid containing the colorant ZZ may contain a part or all of the solvent (E) contained in the coloring composition.
Preferably, the coloring composition of the present invention can be produced by mixing the compound Z, the resin (B), and a liquid containing the colorant ZZ and the solvent (E), or by mixing the compound Z, the solvent (E), and a liquid containing the colorant ZZ and the solvent (E), or by mixing the compound Z, the resin (B), the solvent (E), and a liquid containing the colorant ZZ and the solvent (E).
As the above-mentioned production method, the following methods are preferred: a method in which a coloring composition is prepared by mixing the compound Z and the resin (B) using a bead mill or the like, and the obtained coloring composition is mixed with a liquid containing the coloring agent ZZ and containing the solvent (E); alternatively, a method in which the compound Z and the solvent (E) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is mixed with a liquid containing the coloring agent ZZ and containing the solvent (E); alternatively, a method in which the compound Z, the resin (B) and the solvent (E) are mixed by a bead mill or the like to prepare a coloring composition, and the obtained coloring composition is mixed with a liquid containing the colorant ZZ and the solvent (E).
The colorant ZZ preferably contains 1 or more colorants selected from a green colorant and a yellow colorant.
For the coloring agent ZZ, the following treatments may be carried out, as necessary: rosin treatment; surface treatment using a colorant derivative or the like into which an acidic group or a basic group has been introduced; grafting treatment of the surface of the coloring agent ZZ with a high molecular compound or the like; micronization treatment by sulfuric acid micronization method; washing treatment with an organic solvent, water or the like for removing impurities; and a treatment of removing ionic impurities by an ion exchange method or the like. Preferably, the particle size of the colouring agent ZZ is substantially uniform. In the case of the colorant ZZ, the colorant ZZ is dispersed in a liquid containing the colorant ZZ uniformly by the dispersion treatment with the dispersant. The colorant ZZ may be dispersed separately or in a mixture of two or more.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamine, acrylic and other surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant include KP (manufactured by shin-Etsu chemical industries, Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), SOLSPERSE (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF (manufactured by Kyoho Co., Ltd.), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Technio Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie (manufactured by Co., Ltd.), and the like.
When a dispersant is used for the preparation of the liquid containing the colorant ZZ, the amount of the dispersant (solid component) used is preferably 300 parts by mass or less, more preferably 5 parts by mass or more and 100 parts by mass or less, based on 100 parts by mass of the colorant ZZ. When the amount of the dispersant used is within the above range, a liquid containing the colorant ZZ in a more uniform dispersion state tends to be obtained.
The content of the coloring agent ZZ in the liquid containing the coloring agent ZZ is usually 0.1 to 60% by mass, preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass, of the total amount of the liquid containing the coloring agent ZZ.
The content of the colorant ZZ in the liquid containing the colorant ZZ is usually 1% by mass or more and 90% by mass or less, preferably 1% by mass or more and 80% by mass or less, and more preferably 2% by mass or more and 75% by mass or less, based on the total amount of the solid components.
The coloring composition of the invention comprises a resin (B), and in the case where a liquid containing a colorant ZZ, which comprises the colorant ZZ and a solvent, is prepared in advance, and then the coloring composition of the invention is prepared using the liquid containing the colorant ZZ, the liquid containing the colorant ZZ may comprise in advance a part or all, preferably a part, of the resin (B) contained in the coloring composition.
By containing the resin (B) in advance, the dispersion stability of the liquid containing the colorant ZZ can be further improved.
The content of the resin (B) in the liquid containing the colorant ZZ is, for example, 1 to 500 parts by mass, preferably 5 to 200 parts by mass, and more preferably 10 to 100 parts by mass with respect to 100 parts by mass of the colorant ZZ.
The content of the colorant ZZZ in the coloring composition, which is a mixture of the compound Z and the colorant ZZ, is usually 1 mass% or more and 90 mass% or less, preferably 1 mass% or more and 80 mass% or less, and more preferably 2 mass% or more and 75 mass% or less, based on the total amount of the solid components.
The content of the compound Z is usually 0.001 mass% or more, preferably 0.003 mass% or more, and more preferably 0.005 mass% or more, and the upper limit is 100 mass% or less, preferably 99.999 mass% or less, and more preferably 99.997 mass% or less, in the total amount of the colorant ZZZ.
The content of the compound Z is usually 0.001 mass% or more, preferably 40 mass% or more, more preferably 50 mass% or more, still more preferably 60 mass% or more, and particularly preferably 70 mass% or more, in the total amount of the yellow coloring agent, and the upper limit is 100 mass% or less, preferably 99.999 mass% or less, and more preferably 99.997 mass% or less.
In the case where the colorant ZZ is contained, the content of the colorant ZZ is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more, further preferably 1 part by mass or more, preferably 10000 parts by mass or less, and more preferably 5000 parts by mass or less with respect to 100 parts by mass of the compound Z.
The colored curable composition of the present invention comprises: a compound Z; at least one of a resin (B) and a solvent (E); and a polymerizable compound (C).
< polymerizable Compound (C) >)
The polymerizable compound (C) is a compound polymerizable by an active radical and/or an acid generated by the polymerization initiator (D), and is, for example, a compound having a polymerizable ethylenically unsaturated bond, and is preferably a (meth) acrylate compound.
Examples of the polymerizable compound having 1 ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone, and the above-mentioned monomer (a), monomer (b), and monomer (c).
Examples of the polymerizable compound having 2 ethylenically unsaturated bonds include 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol a, and 3-methylpentanediol di (meth) acrylate.
Among them, the polymerizable compound (C) is preferably a polymerizable compound having 3 or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) The acrylic acid ester and the like are preferably dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate.
The weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.
The content of the polymerizable compound (C) in the colored curable composition is preferably 1 to 65% by mass, more preferably 3 to 60% by mass, and still more preferably 5 to 55% by mass, based on the total amount of the solid components.
The colored curable composition of the invention may contain a polymerization initiator (D).
< polymerization initiator (D) >)
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating an active radical, an acid, or the like by the action of light or heat, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine oxide compound.
Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanyl) phenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanyl) phenyl) octan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanyl phenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1- (4-phenylsulfanyl phenyl) -3-cyclohexylpropane-1-one-2-imine -imine, N-acetyloxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine, N-acetyloxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxopentylmethyloxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, N-acetyloxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-imine and N-benzoyloxy-1- [ 9-Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] -3-cyclopentylpropane-1-one-2-imine, and the like. Further, as the O-acyloxime compound, commercially available products such as IRGACURE OXE01, OXE02 (manufactured by BASF corporation), N-1919 (manufactured by ADEKA corporation), and the like can be used. Among them, as the O-acyloxime compound, at least 1 selected from the group consisting of N-benzoyloxy-1- (4-phenylthiophenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylthiophenyl) octan-1-one-2-imine, and N-benzoyloxy-1- (4-phenylthiophenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1- (4-phenylthiophenyl) octan-1-one-2-imine is more preferable.
Examples of the alkylphenone compound include 2-methyl-2-morpholino (morpholino) -1- (4-methylthiophenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [4- (4-morpholino (morpholino)) phenyl ] butan-1-one. As the alkylphenone compound, commercially available products such as IRGACURE 369, 907 and 379 (manufactured by BASF corporation) can be used.
Examples of the alkylphenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α -diethoxyacetophenone and benzildimethylketal.
Examples of the biimidazole compound include 2,2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenylbiimidazole, 2 ' -bis (2, 3-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenylbiimidazole (see, for example, japanese patent application laid-open No. 6-75372, japanese patent application laid-open No. 6-75373, etc.), 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (alkoxyphenyl) biimidazole, 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (dialkoxyphenyl) biimidazole, 2 ' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetrakis (trialkoxyphenyl) biimidazole (for example, see, for example, Japanese patent application laid-open No. 48-38403 and Japanese patent application laid-open No. 62-174204) and imidazole compounds in which the phenyl group at the 4,4 ', 5, 5' -position is substituted with an alkoxycarbonyl group (e.g., Japanese patent application laid-open No. 7-10913).
Examples of the triazine compound include 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (5-methylfuran-2-yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (furan-2-yl) vinyl ] -one 1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [ 2- (4-diethylamino-2-methylphenyl) vinyl ] -1,3, 5-triazine, and 2, 4-bis (trichloromethyl) -6- [ 2- (3, 4-dimethoxyphenyl) vinyl ] -1,3, 5-triazine.
Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and the like.
Examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2,4, 6-trimethylbenzophenone; quinone compounds such as 9, 10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl benzoylformate, titanocene compound, and the like.
These are preferably used in combination with the polymerization initiation assistant (D1) (particularly amines) described later.
The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a bisimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.
The content of the polymerization initiator (D) is preferably 0.001 to 40% by mass, and more preferably 0.01 to 30% by mass, based on the total amount of solid components in the colored curable composition.
The colored curable composition of the invention may contain a polymerization initiator aid (D1).
< polymerization initiation assistant (D1) >)
The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting the polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator. In the case of containing the polymerization initiation aid (D1), generally, it may be used in combination with the polymerization initiator (D).
Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.
Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N-dimethyl-p-toluidine, 4 ' -bis (dimethylamino) benzophenone (known as Michler's ketone), 4 ' -bis (diethylamino) benzophenone, and 4,4 ' -bis (ethylmethylamino) benzophenone, and 4,4 ' -bis (diethylamino) benzophenone is preferable. As the amine compound, a commercially available compound such as EAB-F (manufactured by UK chemical Co., Ltd.) can be used.
Examples of the alkoxyanthracene compound include 9, 10-dimethoxyanthracene, 2-ethyl-9, 10-dimethoxyanthracene, 9, 10-diethoxyanthracene, 2-ethyl-9, 10-diethoxyanthracene, 9, 10-dibutoxyanthracene, and 2-ethyl-9, 10-dibutoxyanthracene.
Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
Examples of the carboxylic acid compound include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid and the like.
When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, based on the total amount of solid components in the colored curable composition.
The coloring composition of the present invention may further contain a leveling agent (F) and an antioxidant.
< leveling agent (F) >
Examples of the leveling agent (F) include a silicone surfactant, a fluorine surfactant, and a silicone surfactant having a fluorine atom. They may have a polymerizable group in a side chain.
Examples of the silicone surfactant include surfactants having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, Toray Silicone SH7PA, Toray Silicone DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicone SH29PA, Toray Silicone SH30PA, Toray Silicone SH8400 (trade name; manufactured by Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical Co., Ltd.), TSF400, TSF401, TSF410, F4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Moive Performance Materials Japan Co., Ltd.) can be mentioned.
Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, examples thereof include Fluorad (registered trademark) FC430, Fluorad FC431 (manufactured by Sumitomo 3M Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718K (manufactured by DIC corporation), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352(Mitsubishi Materials Electronic Chemicals Co., manufactured by Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asnitro corporation) and E5844 (Danin fire K., manufactured by Kenkyu K).
Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specifically, there may be mentioned MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFAC F475, MEGAFAC F477, and MEGAFAC F443 (available from DIC Co., Ltd.).
When the leveling agent (F) is contained, the content thereof is usually 0.0005 mass% or more and 1 mass% or less, preferably 0.001 mass% or more and 0.5 mass% or less, more preferably 0.001 mass% or more and 0.2 mass% or less, further preferably 0.002 mass% or more and 0.1 mass% or less, and particularly preferably 0.005 mass% or more and 0.1 mass% or less, based on the total amount of the coloring composition. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
< antioxidant >
The antioxidant may be used alone or in combination of 2 or more from the viewpoint of improving the heat resistance and light resistance of the colorant. The antioxidant is not particularly limited as long as it is an industrially commonly used antioxidant, and a phenol-based antioxidant, a phosphorus-based antioxidant, a sulfur-based antioxidant, and the like can be used.
Examples of the phenolic antioxidant include Irganox 1010(イルガノックス 1010: pentaerythritol tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF corporation), Irganox 1076(イルガノックス 1076: octadecyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate, manufactured by BASF corporation), Irganox 1330(イルガノックス 1330: 3,3 ', 5,5 ' -hexa-tert-butyl-a, a ' - (mesitylene-2, 4, 6-triyl) tri-p-cresol, manufactured by BASF corporation), Irganox 3114(イルガノックス 3114: 1,3, 5-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, manufactured by BASF corporation), Irganox 3790(イルガノックス 3790: 1,3, 5-tris ((4-tert-butyl-3-hydroxy-2, 6-xylyl) methyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, manufactured by BASF (ltd.), Irganox 1035(イルガノックス 1035: thiodiethylene bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF corporation), Irganox 1135(イルガノックス 1135: C7-C9 side chain alkyl ester of 3, 5-bis (1, 1-dimethylethyl) -4-hydroxypropionic acid, manufactured by BASF (ltd.), Irganox 1520L (イルガノックス 1520L: 4, 6-bis (octylthiomethyl) o-cresol, manufactured by BASF corporation), Irganox 3125(イルガノックス 3125, manufactured by BASF corporation), Irganox 565(イルガノックス 565: 2, 4-bis (n-octylthio) -6- (4-hydroxy-3 ', 5' -di-tert-butylanilino) -1,3, 5-triazine manufactured by BASF (ltd)), Adekastab AO-80(アデカスタブ AO-80: 3, 9-bis (2- (3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy) -1, 1-dimethylethyl) -2,4,8, 10-tetraoxaspiro (5,5) undecane (manufactured by ADEKA), Sumilizer BHT (スミライザー BHT, manufactured by Sumilizer chemical corporation), Sumilizer GA-80(スミライザー GA-80, manufactured by Sumilizer chemical corporation), Sumilizer GS (スミライザー GS, manufactured by Sumilizer chemical corporation), Cyanox 1790(シアノックス 1790 (manufactured by Cytec), vitamin E (Eisai co., ltd.).
Examples of the phosphorus-based antioxidant include Irgafos 168(イルガフォス 168: tris (2, 4-di-t-butylphenyl) phosphite, manufactured by BASF corporation), Irgafos 12(イルガフォス 12: tris [2- [ [2,4,8, 10-tetra-t-butyldibenzo [ d, f ] [1,3,2] dioxaphosphorin-6-yl ] oxy ] ethyl ] amine, manufactured by BASF corporation), Irgafos 38(イルガフォス 38: bis (2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl) ethyl phosphite, manufactured by BASF corporation), Adekastab 329K (manufactured by ADEKA), Adekastab PEP36 (manufactured by ADEKA), Adekastab PEP-8 ((manufactured by SanEKA), dstab P-EPQ (manufactured by Clariant), Weston 618 (618, manufactured by Weston GE corporation), manufactured by ウェストン 618, manufactured by SAEK, Weston 619G (ウェストン 619G, GE Co., Ltd.), Ultranox 626(ウルトラノックス 626, GE Co., Ltd.), Sumilizer GP (スミライザー GP: 6- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propoxy ] -2,4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1.3.2] dioxaphosphepin (dioxiphospin)) (manufactured by Sumitomo chemical Co., Ltd.), and the like.
Examples of the sulfur-based antioxidant include dialkyl thiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl thiodipropionate and distearyl thiodipropionate, and β -alkylmercaptopropionate compounds of polyhydric alcohols such as tetrakis [ methylene (3-dodecylthio) propionate ] methane.
< other ingredients >
The coloring composition of the present invention may contain additives known in the art, such as a filler, another polymer compound, an adhesion promoter, a light stabilizer, and a chain transfer agent, as required.
Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, 3-glycidyloxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and the like, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltriethoxysilane, etc.
< color filter >
The color filter can be formed from the colored composition or the colored curable composition of the invention. As a method for forming a colored pattern, a photolithography method, an ink jet method, a printing method, and the like can be mentioned, and a photolithography method can be preferably mentioned. The photolithography method is as follows: the colored curable composition is applied to a substrate and dried to form a colored curable composition layer, and the colored curable composition layer is exposed to light through a photomask and developed. In the photolithography method, the colored curable composition preferably contains a polymerization initiator (D). A colored coating film which is a cured product of the colored curable composition layer can be formed by a photolithography method without using a photomask and/or without performing development during exposure. The colored pattern and the colored coating film formed as described above can be used as the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited, and may be suitably adjusted according to the purpose, use, and the like, and is, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.
As the substrate, a glass plate, a resin plate, silicon, a substrate obtained by forming a thin film of aluminum, silver/copper/palladium alloy, or the like on the above substrate, or the like can be used. Other color filter layers, resin layers, transistors, circuits, and the like may be formed on these substrates.
The formation of each color pixel by photolithography can be performed by using a known or commonly used apparatus and conditions. For example, the following method can be used.
First, a colored curable composition is applied onto a substrate, and dried by removing volatile components such as a solvent by heat drying (prebaking) and/or drying under reduced pressure, thereby obtaining a smooth colored curable composition layer.
Examples of the coating method include spin coating, slit and spin coating (slit and spin coating).
Next, the colored curable composition layer is exposed to light through a photomask for forming a target colored pattern. In order to uniformly irradiate the entire exposure surface with parallel light or to accurately align the photomask with the substrate on which the colored curable composition layer is formed, an exposure apparatus such as a mask aligner or a stepper is preferably used.
The exposed colored curable composition layer is brought into contact with a developer to develop the layer, whereby a colored pattern can be formed on the substrate. By the development, the unexposed portion of the colored curable composition layer is dissolved in a developing solution and removed.
As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable.
The developing method may be any of spin immersion (dip method), immersion method, spray method, and the like. In addition, the substrate may be inclined at an arbitrary angle at the time of development.
The developed substrate is preferably washed with water.
Further, the obtained colored pattern is preferably subjected to post-baking.
The color filter is useful as a color filter used in a display device (a liquid crystal display device, an organic EL device, electronic paper, or the like) or a solid-state imaging device, particularly as a color filter used in a liquid crystal display device.
[ examples ]
Hereinafter, "part" means "part by mass" and "%" means "% by mass" unless otherwise specified.
In the following synthesis examples, the structure of the compound was confirmed by NMR (JMM-ECA-500; manufactured by Japan Electron Ltd.) or MASS spectrometry (LC; model 1200 manufactured by Agilent, MASS; model LC/MSD6130 manufactured by Agilent).
The weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin in terms of polystyrene were measured by GPC under the following conditions.
The device comprises the following steps: HLC-8120GPC (manufactured by Tosoh corporation)
Column: TSK-GELG2000HXL
Column temperature: 40 deg.C
Solvent: tetrahydrofuran (THF)
Flow rate: 1.0 mL/min
Solid content concentration of analysis sample: 0.001 to 0.01% by mass
Sample introduction amount: 50 μ L
A detector: RI (Ri)
Calibration standard substance: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh corporation)
The ratio (Mw/Mn) of the weight average molecular weight (Mw) and the number average molecular weight (Mn) in terms of polystyrene obtained in the above manner was defined as the degree of dispersion.
Example Z1
Example 1Z1
36.2 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 526 parts of methanol were mixed.
While keeping the temperature at 5 ℃, a mixture of 20.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 10 parts of methanol was added dropwise to the obtained mixture over 1 hour.
The resulting mixture was stirred at 5 ℃ for 4 hours.
To the obtained mixture were added 13.1 parts of acetic acid and 23.7 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) while keeping the temperature at 5 ℃ or lower.
The resulting mixture was stirred at 5 ℃ for 1 hour and then at room temperature for 3 days.
To the obtained mixture were added 2.37 parts of ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.) and 231 parts of methanol, and the mixture was stirred at room temperature for 1 day. To the obtained mixture were added 0.496 parts of ethyl cyanoacetate (manufactured by tokyo chemical industry co.) and 26 parts of methanol, and the mixture was stirred at 40 ℃ for 2 hours and 30 minutes.
To the obtained mixture were added 17.1 parts of acetic acid, 26.9 parts of barbituric acid and 793 parts of water, and the mixture was stirred at 40 ℃ for 2 hours.
To the resulting mixture were added 17.0 parts of acetic acid, 26.9 parts of barbituric acid, 12 parts of methanol, and 12 parts of water, and the mixture was stirred at 40 ℃ for 30 minutes and then at room temperature for 2 days.
The resulting mixture was filtered, and the residue was washed 1 time with 915 parts of 50% aqueous methanol solution, 1 time with 950 parts of 50% aqueous methanol solution, 1 time with 1600 parts of 50% aqueous methanol solution, and 1 time with 1800 parts of water.
The obtained residue was recrystallized from N, N-dimethylformamide to obtain 30.7 parts of a mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ 1-39).
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+384
Exact molecular weight (Exact masses): 383
Identification of Compound represented by the formula (IZ1-39)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+398
Exact molecular weight (Exact masses): 397
Example 2Z1
A mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) was obtained in the same manner as in example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Identification of Compound represented by the formula (IZ1-21)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+409
Exact molecular weight (Exact masses): 408
Example 3Z1
A mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) was obtained in the same manner as in example 1Z1, except that 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Identification of Compound represented by the formula (IZ1-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 4Z1
A compound represented by the formula (IZ1-38) was obtained in the same manner as in example 1Z1, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with methyl cyanoacetate (manufactured by tokyo chemical industry co.).
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+384
Exact molecular weight (Exact masses): 383
Example 5Z1
The procedure of example 1Z1 was repeated except for replacing 4-nitrophthalonitrile (manufactured by tokyo chemical industry co., ltd.) with 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co., ltd.) and replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.) with methyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.), thereby obtaining a compound represented by formula (IZ 1-20).
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Example 6Z1
The procedure of example 1Z1 was repeated except for replacing 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) with phthalonitrile (manufactured by tokyo chemical industry co.) and replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co.) with methyl cyanoacetate (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 1-2).
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Example 7Z1XXX (tBu)
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 6.14 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 3.07 parts of ethyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ 1-21).
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Identification of Compound represented by the formula (IZ1-21)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+409
Exact molecular weight (Exact masses): 408
Example 8Z1XXX (542)
2.57 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 24.5 parts of methanol were mixed. To the resulting mixture, 2.00 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) was added at room temperature. The resulting mixture was stirred at 43 ℃ for 1 hour and 30 minutes.
To the resulting mixture, 2.53 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.), 1.26 parts of acetic acid and 54.5 parts of methanol were added, and the mixture was stirred at 40 ℃ for 1 hour and 30 minutes. To the obtained mixture, 2.84 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.), 1.63 parts of acetic acid and 9 parts of methanol were added, and the mixture was stirred at 40 ℃ for 1 hour. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ 1-3).
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Identification of Compound represented by the formula (IZ1-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 9Z1XXX (NO2)
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 5.72 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 2.86 parts of methyl cyanoacetate (manufactured by tokyo chemical industries, ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol. To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 1-38).
Identification of Compound represented by the formula (IZ1-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+384
Exact molecular weight (Exact masses): 383
Example 10Z1XXX (tBu)
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 5.38 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 2.69 parts of methyl cyanoacetate (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 1-20).
Identification of Compound represented by the formula (IZ1-20)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+395
Exact molecular weight (Exact masses): 394
Example 11Z1XXX (645)
60.0 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 501 parts of methanol were mixed. To the resulting mixture, 46.7 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise over 15 minutes while keeping the temperature at 2 ℃. The resulting mixture was stirred for 5 hours while being maintained at 2 to 6 ℃. 556 parts of methanol was added to the mixture while keeping the temperature at 5 ℃ or lower. To the mixture were added 29.3 parts of acetic acid, 46.5 parts of methyl cyanoacetate, and 22 parts of methanol. The mixture was stirred at room temperature for 12 hours and then at 40 ℃ for 3 hours and 20 minutes. This mixture was mixed with 3.00 parts of acetic acid and 4.71 parts of methyl cyanoacetate, and stirred at 40 ℃ for 1 hour and 25 minutes. This mixture was mixed with 2.98 parts of acetic acid and 4.71 parts of methyl cyanoacetate, and stirred at 40 ℃ for 2 hours. This mixture was mixed with 2.96 parts of acetic acid and 4.70 parts of methyl cyanoacetate, and stirred at 40 ℃ for 2 hours. This mixture was mixed with 1.50 parts of acetic acid and 2.40 parts of methyl cyanoacetate.
In addition, a total of 111 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The resulting mixture was stirred at 40 ℃ for 1 hour and 40 minutes. To the resulting mixture, 38.1 parts of acetic acid and 60.6 parts of barbituric acid were added, and the mixture was stirred at 40 ℃ for 42 hours. In addition, up to this point in time, a total of 66 parts of methanol was added in addition to the above-mentioned methanol. The mixture was filtered and the residue was washed 6 times with 400 parts of methanol. The residue was purified by column chromatography to give a compound represented by the formula (IZ 1-2).
Identification of Compound represented by the formula (IZ1-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+339
Exact molecular weight (Exact masses): 338
Example 12Z1
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. Methyl cyanoacetate 1.5 times the molar amount of 5.0 parts of 4, 5-dichlorophthalonitrile and 6.1 parts of acetic acid were added to the mixture while keeping the temperature at 5 ℃ or lower.
The mixture was stirred at 65 ℃ for 3 days. This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. The solvent was distilled off from the mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.297 parts of a compound represented by the formula (IZ 1-258).
Identification of Compound represented by the formula (IZ1-258)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+407
Exact molecular weight (Exact masses): 406
Example 13Z1XXX (659)
25.9 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 513 parts of methanol were mixed. 30.3 parts of a 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 12 parts of methanol were added dropwise to the obtained mixture over 10 minutes while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred for 6 hours while being maintained at 3 to 5 ℃. To the obtained mixture were added 19.8 parts of acetic acid, 28.5 parts of t-butyl cyanoacetate and 26 parts of methanol while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred at room temperature for 2 days, and then at 40 ℃ for 3 hours. To the resulting mixture were added 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetate, and the mixture was stirred at 40 ℃ for 4 hours. To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetate and 38 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours. To the resulting mixture were added 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water, and the mixture was stirred at 40 ℃ for 3 hours.
The resulting mixture was filtered to give a residue. The residue was purified by column chromatography to give a compound represented by the formula (IZ 1-5).
Identification of Compound represented by the formula (IZ1-5)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 14Z1XXX (661)
15.1 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 284 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.81 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture over 10 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower.
To the obtained mixture, 5.55 parts of acetic acid was added while keeping the temperature at 5 ℃ or lower, and the mixture was stirred for 30 minutes. This mixture was mixed with 12.3 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 14 hours. This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 4 hours. This mixture was mixed with 0.613 part of acetic acid and 1.23 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate. Further, up to this point, a total of 89 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid and 508 parts of water. Up to this point, a total of 117 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 24 hours. This mixture was mixed with 3.65 parts of acetic acid and 5.61 parts of barbituric acid, and stirred at 40 ℃ for 9 hours and at room temperature for 2 days. The mixture was filtered and the residue was washed 3 times with 1330 parts of 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 1-41).
Identification of Compound represented by the formula (IZ1-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+426
Exact molecular weight (Exact masses): 425
Synthesis example 1
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 80 ℃ with stirring. Then, 38 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 5 hours2,6]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 289 parts of a mixture of decane-9-yl esters and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, a mixed solution obtained by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at this temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution having a solid content of 35.0%. The resulting resin B1 had a weight average molecular weight (Mw) of 8800, a dispersity of 2.1, and an acid value of the solution of 28 mg-KOH/g.
Synthesis example 2
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, and 371 parts of propylene glycol monomethyl ether acetate was charged and heated to 85 ℃ with stirring. Then, 54 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 4 hours 2,6]Decan-8-yl ester and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 225 parts of a mixture of decane-9-yl ester, 81 parts of vinyltoluene (isomer mixture) and 80 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 30 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, in 160 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the end of the dropwise addition of the initiator solution, the temperature was maintained for 4 hours and then cooledThe temperature was then cooled to room temperature, whereby a copolymer (resin B3) solution containing 37.5% of solid matter was obtained. The resulting resin B3 had a weight-average molecular weight (Mw) of 10600, a dispersity of 2.01, and an acid value of 43 mg-KOH/g.
Synthesis example 3
An appropriate amount of nitrogen was introduced into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, and the atmosphere was replaced with nitrogen, 350 parts of propylene glycol monomethyl ether acetate was charged, and the mixture was heated to 85 ℃ with stirring. Subsequently, 70 parts of acrylic acid and 3, 4-epoxytricyclo [5.2.1.0 ] acrylic acid were added dropwise over 4 hours2,6]Decane-8-yl ester or/and acrylic acid 3, 4-epoxytricyclo [5.2.1.02,6]A mixed solution of 202 parts of a mixture of decane-9-yl ester, 78 parts of vinyltoluene (isomer mixture) and 100 parts of propylene glycol monomethyl ether acetate. On the other hand, a solution obtained by dissolving 33 parts of 2, 2-azobis (2, 4-dimethylvaleronitrile), a polymerization initiator, in 167 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. After the completion of the dropwise addition of the initiator solution, the mixture was held at this temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin B5) solution having a solid content of 38.1%. The obtained resin B5 had a weight-average molecular weight (Mw) of 10400, a dispersity of 2.03 and an acid value of 53 mg-KOH/g.
Example 101Z1
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 1) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 1: 50 parts of a mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39),
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39) was dispersed using a bead mill, to thereby obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z1,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 1);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z1 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a line and space pattern (li) having a thickness of 100 μm was used ne-and-space pattern). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z1 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored coating film was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle (angle あおり Japanese) of the colored coating film of 45 ℃ was measured using an ellipsometer (model M-220 spectroscopic ellipsometer; manufactured by Nippon corporation). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 8Z 1.
Example 102Z1
A colored curable composition 2Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 103Z1
A colored curable composition 3Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 104Z1
A colored curable composition 4Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 105Z1
A colored curable composition 5Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 106Z1
A colored curable composition 6Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 107Z1
A colored curable composition 7Z1 was obtained and a colored pattern was obtained in the same manner as in example 101Z1, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 108Z1
A colored curable composition 8Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 109Z1
A colored curable composition 9Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 110Z1
A colored curable composition 10Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 111Z1
A colored curable composition 11Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 112Z1
A colored curable composition 12Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 113Z1
A colored curable composition 13Z1 was obtained in the same manner as in example 101Z1 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 114Z1
A colored curable composition 14Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-20) and the compound represented by the formula (IZ1-21) obtained in example 2Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 115Z1
A colored curable composition 15Z1 was obtained in the same manner as in example 101Z1 and a colored pattern was obtained in the same manner as in example 101Z1, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the mixture of the compound represented by the formula (IZ1-2) and the compound represented by the formula (IZ1-3) obtained in example 3Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 116Z1
A colored curable composition 16Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-38) obtained in example 4Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 117Z1
A colored curable composition 17Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-20) obtained in example 5Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Example 118Z1
A colored curable composition 18Z1 was obtained in the same manner as in example 101Z1 except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59 and the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound represented by the formula (IZ1-2) obtained in example 6Z1, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 1Z1
A colored curable composition C1Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment yellow 185, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 2Z1
A colored curable composition C2Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment green 7 and the mixture was replaced with c.i. pigment yellow 185, thereby obtaining a colored pattern, instead of c.i. pigment green 58. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
Comparative example 3Z1
A colored curable composition C3Z1 was obtained in the same manner as in example 101Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with c.i. pigment green 58 and the mixture was replaced with c.i. pigment yellow 185, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 1.
[ Table 8Z1]
TABLE 8Z1
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z1 | 2.3 | 3 |
Example 102Z1 | 2.3 | 3 |
Example 103Z1 | 2.3 | 4 |
Practice ofExample 104Z1 | 2.3 | 3 |
Example 105Z1 | 2.3 | 3 |
Example 106Z1 | 2.3 | 4 |
Example 107Z1 | 2.3 | 3 |
Example 108Z1 | 2.3 | 3 |
Example 109Z1 | 2.3 | 4 |
Example 110Z1 | 2.3 | 3 |
Example 111Z1 | 2.3 | 3 |
Example 112Z1 | 2.3 | 4 |
Example 113Z1 | 2.3 | 3 |
Example 114Z1 | 2.3 | 3 |
Example 115Z1 | 2.3 | 4 |
Example 116Z1 | 2.3 | 3 |
Example 117Z1 | 2.3 | 3 |
Example 118Z1 | 2.3 | 4 |
Comparative example 1Z1 | 2.3 | 15 |
Comparative example 2Z1 | 2.3 | 15 |
Comparative example 3Z1 | 2.3 | 15 |
Example 119Z1
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 1) was prepared by dispersing the pigment using a bead mill.
In addition, the following substances were mixed,
colorant AZ 1: 50 parts of a mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IZ1-38) obtained in example 1Z1 and the compound represented by the formula (IZ1-39) was dispersed using a bead mill, to thereby obtain a colored composition.
Next, the following were mixed to obtain a colored curable composition 19Z1,
The total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 1);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z1 except that a colored curable composition 19Z1 was used instead of the colored curable composition 1Z 1. A colored coating film was obtained in the same manner as in example 101Z1 except that a colored curable composition 19Z1 was used in place of the colored curable composition 1Z1, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 1.
Example 120Z1 to example 127Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the colorant shown in the column of "colorant" in table 9Z 1. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
Example 128Z1 to example 136Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound shown in the column of "colorant" in table 9Z1, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
Example 137Z1 to example 145Z1
A colored pattern was obtained in the same manner as in example 119Z1 except that the mixture of the compound represented by the formula (IZ1-38) and the compound represented by the formula (IZ1-39) obtained in example 1Z1 was replaced with the compound shown in the column of "colorant" in table 9Z1, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 1.
[ Table 9Z1]
TABLE 9Z1
In the examination of example Z1, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z2
Example 1Z2
5.02 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 22 parts of methanol were mixed. To the resulting mixture, 2.90 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) was added, and the mixture was stirred at 25 ℃ for 3 hours.
To the obtained mixture were added 3.67 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.), 1.83 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 25 ℃ for 1 hour and 30 minutes.
To the obtained mixture were added 3.62 parts of ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.), 2.37 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 63 ℃ for 3 hours.
To the obtained mixture were added 3.63 parts of ethyl cyanoacetate (manufactured by tokyo chemical industry co., ltd.), 2.36 parts of acetic acid and 30 parts of methanol, and the mixture was stirred at 63 ℃ for 2 hours.
To the obtained mixture were added 3.62 parts of ethyl cyanoacetate (manufactured by Tokyo chemical industry Co., Ltd.) and 2.40 parts of acetic acid, and the mixture was stirred at 63 ℃ for 1 hour, at room temperature for 11 hours and at 63 ℃ for 6 hours.
The temperature of the resulting mixture was lowered to room temperature, followed by filtration.
The obtained residue was dried to obtain 10.0 parts of a mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ 2-149).
Identification of Compound represented by the formula (IaZ2-39)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Identification of Compound represented by the formula (IaZ2-38)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+355
Exact molecular weight (Exact masses): 354
Identification of Compound represented by the formula (IaZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 2Z2
A compound represented by formula (IbZ2-125) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyanoacetamide (manufactured by tokyo chemical industry co.).
Identification of Compound represented by the formula (IbZ2-125)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+325
Exact molecular weight (Exact masses): 324
Example 3Z2
The procedure of example 1Z2 was repeated except for replacing ethyl cyanoacetate (manufactured by tokyo chemical industries, ltd.) with 2-cyano-N-methylacetamide to obtain compounds represented by the formula (IbZ 2-126).
Identification of Compound represented by the formula (IbZ2-126)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 4Z2
A compound represented by formula (IbZ2-148) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.).
Identification of Compound represented by the formula (IbZ2-148)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 5Z2
A compound represented by formula (IbZ2-149) was obtained in the same manner as in example 1Z2, except that ethyl cyanoacetate (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.).
Identification of Compound represented by the formula (IbZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+437
Exact molecular weight (Exact masses): 436
Example 6Z2
The procedure of example 1Z2 was repeated except for replacing ethyl cyanoacetate (manufactured by tokyo chemical industry co.) with 2-cyanoacetanilide (2-cyanoacetanilide) (manufactured by tokyo chemical industry co.) to obtain compounds represented by the formulae (IbZ2 to 128).
Identification of Compound represented by the formula (IbZ2-128)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+477
Exact molecular weight (Exact masses): 476
Example 7Z2XXX (662)
2.55 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a mixture of 1.47 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 30 parts of methanol was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2.16 parts of acetic acid, 2.92 parts of 2-cyano-N-methylacetamide and 21 parts of methanol, and the mixture was stirred at 40 ℃ for 3 hours.
To the mixture was added 13.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.), and the mixture was stirred at 40 ℃ for 12 hours and at 62 ℃ for 9 hours.
To the mixture were added 1.50 parts of 2-cyano-N-methylacetamide and 3.05 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.), and the mixture was stirred at 62 ℃ for 5 hours and at 40 ℃ for 17 hours. In addition, up to this point in time, 6 parts in total of methanol were added in addition to the above-mentioned methanol. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-126).
Identification of Compound represented by the formula (IbZ2-126)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+353
Exact molecular weight (Exact masses): 352
Example 8Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours.
To the mixture were added 16 parts of acetic acid and 2-cyanoacetamide in an amount of 3.3 times the molar amount of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-125).
Identification of Compound represented by the formula (IbZ2-125)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+325
Exact molecular weight (Exact masses): 324
Example 9Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours.
To the mixture were added 16 parts of acetic acid and 2-cyano-N, N-dimethylacetamide in an amount of 3.3 times the number of moles of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-148).
Identification of Compound represented by the formula (IbZ2-148)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+381
Exact molecular weight (Exact masses): 380
Example 10Z2
10 parts of 4-nitrophthalonitrile and 80 parts of methanol are mixed. While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 10 parts was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 16 parts of acetic acid and 2-cyano-N, N-diethylacetamide in an amount of 3.3 times the number of moles of 10 parts of 4-nitrophthalonitrile, and the mixture was stirred at 60 ℃ for 21 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-149).
Identification of Compound represented by the formula (IbZ2-149)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+437
Exact molecular weight (Exact masses): 436
Example 11Z2XXX (660)
1.25 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 41 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 0.722 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 19 parts of methanol was added dropwise to the obtained mixture over 5 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 1.21 parts of acetic acid, 2.33 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 18 parts of methanol were added. The resulting mixture was stirred at 40 ℃ for 21 hours. To the obtained mixture were added 0.596 parts of acetic acid, 1.17 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 17 parts of methanol. The resulting mixture was stirred at 40 ℃ for 3 hours. To the resulting mixture, 2.09 parts of acetic acid was added, and stirring was performed at 50 ℃ for 2 hours, at 60 ℃ for 2 hours, at room temperature for 15 hours, and at 62 ℃ for 3 hours.
To the resulting mixture, 0.981 part of trifluoroacetic acid was added, and stirring was performed at 62 ℃ for 2 hours.
To the resulting mixture, 11.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added, and the mixture was stirred at 62 ℃ for 2 hours, at room temperature for 14 hours, and at 62 ℃ for 5 hours. In addition, 10 parts in total of methanol other than the above-mentioned methanol was added up to this point. The resulting mixture was cooled to 23 ℃ and added to 1100 parts of 50% aqueous acetic acid.
To the resulting mixture, 40 parts of methanol and 400 parts of 50% aqueous acetic acid were added.
The resulting mixture was filtered, and the resulting residue was washed 6 times with 250 parts of 50% aqueous acetic acid solution and 3 times with 250 parts of water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 3.32 parts of a compound represented by the formula (IbZ 2-128).
Identification of Compound represented by the formula (IbZ2-128)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+477
Exact molecular weight (Exact masses): 476
Example 12Z2XXX (653)
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, and stirring was performed at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. In addition, a total of 201 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. To the resulting mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 53 hours.
The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-64).
Identification of Compound represented by the formula (IbZ2-64)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+364
Exact molecular weight (Exact masses): 363
Example 13Z2XXX (659)
25.9 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 513 parts of methanol were mixed. 30.3 parts of a 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 12 parts of methanol were added dropwise to the obtained mixture over 10 minutes while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred for 6 hours while being maintained at 3 to 5 ℃.
To the obtained mixture were added 19.8 parts of acetic acid, 28.5 parts of t-butyl cyanoacetate and 26 parts of methanol while maintaining the temperature at 3 to 5 ℃. The resulting mixture was stirred at room temperature for 2 days, and then at 40 ℃ for 3 hours. To the resulting mixture were added 5.09 parts of acetic acid and 7.17 parts of tert-butyl cyanoacetate, and the mixture was stirred at 40 ℃ for 4 hours.
To the resulting mixture were added 4.95 parts of acetic acid, 7.15 parts of tert-butyl cyanoacetate and 38 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours. To the resulting mixture were added 19.9 parts of acetic acid, 25.8 parts of barbituric acid, 209 parts of methanol, and 800 parts of water, and the mixture was stirred at 40 ℃ for 3 hours. The resulting mixture was filtered to give a residue. The residue was purified by column chromatography to give a compound represented by the formula (IaZ 2-5).
Identification of Compound represented by the formula (IaZ2-5)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 14Z2XXX (661)
15.1 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 284 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.81 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 18 parts of methanol was added dropwise to the obtained mixture over 10 minutes. The resulting mixture was stirred for 4 hours while being kept at 5 ℃ or lower. To the obtained mixture, 5.55 parts of acetic acid was added while keeping the temperature at 5 ℃ or lower, and the mixture was stirred for 30 minutes. This mixture was mixed with 12.3 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 14 hours.
This mixture was mixed with 0.654 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 4 hours. This mixture was mixed with 0.613 part of acetic acid and 1.23 parts of t-butyl cyanoacetate, and stirred at 40 ℃ for 3 hours. This mixture was mixed with 0.647 parts of acetic acid and 1.24 parts of t-butyl cyanoacetate. Further, up to this point, a total of 89 parts of methanol was added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 17 hours. This mixture was mixed with 7.14 parts of acetic acid, 11.3 parts of barbituric acid and 508 parts of water. In addition, up to this point in time, 117 parts in total of methanol were added in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 24 hours. This mixture was mixed with 3.65 parts of acetic acid and 5.61 parts of barbituric acid, and stirred at 40 ℃ for 9 hours and at room temperature for 2 days. The mixture was filtered and the residue was washed 3 times with 1330 parts of 50% aqueous methanol solution. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IaZ 1-41).
Identification of Compound represented by the formula (IaZ1-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+439
Exact molecular weight (Exact masses): 438
Example 15Z2XXX (520)
5.41 parts of 3,4,5, 6-tetrafluorophthalonitrile and 23.6 parts of methanol were mixed. To the mixture was added a mixture of 2.70 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) and 10 parts of methanol at 20 to 25 ℃.
The mixture was stirred at 20 to 25 ℃ for 4 hours and 20 minutes. To the mixture were added 3.36 parts of acetic acid, 5.99 parts of methyl cyanoacetate, and 7.5 parts of methanol. The mixture was stirred at 63 ℃ for 2 hours. The solvent was distilled off from the obtained mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IaZ 2-223).
Identification of Compound represented by the formula (IaZ2-223)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+382
Exact molecular weight (Exact masses): 381
Example 16Z2XXX (538)
2.52 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 22.8 parts of methanol were mixed. To the mixture was added 1.98 parts of 28% sodium methoxide methanol solution (Wako pure chemical industries, Ltd.) at room temperature. The mixture was stirred at 38 ℃ for 3 hours.
To the mixture were added 2.79 parts of cyanoacetylurea (manufactured by tokyo chemical industries, ltd.) and 1.26 parts of acetic acid. The mixture was stirred at 40 ℃ for 1 hour and 30 minutes.
To the mixture were added 2.77 parts of cyanoacetylurea (manufactured by tokyo chemical industries, ltd.) and 1.61 parts of acetic acid. In addition, a total of 39.2 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The mixture was stirred at 40 ℃ for 1 hour. To the mixture was added 65.2 parts of water, and the mixture was stirred at 40 ℃ for 2 hours and 30 minutes. To the mixture were added 2.80 parts of cyanoacetylurea (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 1.60 parts of acetic acid, and the mixture was stirred at 40 ℃ for 20 hours. In addition, up to this point in time, a total of 31 parts of methanol was added in addition to the above-mentioned methanol. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IbZ 2-19).
Identification of Compound represented by the formula (IbZ2-19)
(Mass Spectrometry) ionization mode ESI +: m-z=[M+H]+366
Exact molecular weight (Exact masses): 365
Example 17Z2
8 parts of phthalonitrile and 63 parts of ethanol are mixed.
To the mixture was added a 21% sodium ethoxide ethanol solution containing sodium ethoxide in a molar amount 1 times that of 8 parts of phthalonitrile. The mixture was stirred at room temperature for 2 hours. To the mixture were added 25 parts of acetic acid and a compound represented by the formula (ppp1) in an amount of 2.3 times the mole number of 8 parts of phthalonitrile, and the mixture was stirred at 90 ℃ for 64 hours.
The mixture was cooled to room temperature and filtered. The obtained residue was washed with 160 parts of methanol and dried. The obtained residue 24 parts and N, N-dimethylformamide 230 parts were mixed.
To the mixture was added 210 parts of acetic acid. The mixture was filtered.
The obtained residue was washed with 79 parts of methanol and dried to obtain 17 parts of a compound represented by the formula (IbZ 2-311).
Identification of Compound represented by the formula (IbZ2-311)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+508
Exact molecular weight (Exact masses): 507
To 15 parts of the compound represented by the formula (IbZ2-311), 200 parts of methylene chloride and 150 parts of trifluoroacetic acid were added, and the mixture was stirred at room temperature for 50 hours.
To the resulting mixture was added 160 parts of methanol, followed by filtration.
The obtained residue was dried to obtain 13 parts of a residue.
The residue 12 parts and N, N-dimethylformamide 230 parts were mixed, stirred for 1 hour, and then filtered. The obtained residue was mixed with 160 parts of methanol and stirred at 70 ℃.
The resulting mixture was filtered. The residue was dried to obtain 9 parts of a compound represented by the formula (IbZ 2-317).
Identification of Compound represented by the formula (IbZ2-317)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-394
Exact molecular weight (Exact masses): 395
Example 18Z2
5 parts of 4-nitrophthalonitrile and 39 parts of ethanol are mixed.
While the mixture was kept at 0 ℃, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in an amount of 0.5 times the mole of 5 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 16 parts of acetic acid and a compound represented by the formula (ppp1) in a molar amount of 3.3 times that of 5 parts of 4-nitrophthalonitrile. The mixture was sealed in a tube and stirred at 90 ℃ for 56 hours. The mixture was cooled to room temperature and filtered. The residue was washed with ethanol to give residue A8 parts. 10 parts of 4-nitrophthalonitrile and 79 parts of ethanol are mixed. While the mixture was kept at 0 ℃, a 21% sodium ethoxide ethanol solution containing sodium ethoxide in an amount of 0.5 times the mole number of 10 parts of 4-nitrophthalonitrile was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 31 parts of acetic acid and a compound represented by the formula (ppp1) in a molar amount of 3.3 times that of 10 parts of 4-nitrophthalonitrile. The mixture was sealed in a tube and stirred at 90 ℃ for 56 hours. The mixture was cooled to room temperature and filtered. The obtained residue was washed with ethanol to obtain 15 parts of a residue B. The residue A4 parts and the residue B14 parts were mixed together with 170 parts of N, N-dimethylformamide.
The mixture was mixed with 710 parts of methanol and stirred at room temperature for 16 hours.
The mixture was filtered to obtain 13 parts of a residue containing the compound represented by the formula (IbZ 2-312).
Identification of Compound represented by the formula (IbZ2-312)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+553
Exact molecular weight (Exact masses): 552
The residue containing the compound represented by the formula (IbZ2-312) (13 parts) was mixed with dichloromethane (170 parts) and trifluoroacetic acid (130 parts) and stirred at room temperature for 16 hours.
To the mixture, the solvent was distilled off, 190 parts of N, N-dimethylformamide was added to 12 parts of the obtained residue, and the mixture was stirred at 90 ℃ for 10 minutes and then filtered. The resulting filtrate was allowed to stand at room temperature for 16 hours. The filtrate was filtered to obtain 8.0 parts of a residue. This residue 8.0 parts and tetrahydrofuran 22 parts were mixed, stirred at 70 ℃ for 3 hours, and then filtered.
The obtained residue 7.2 parts and acetic acid 21 parts were mixed, stirred at 80 ℃ for 2 hours, and then filtered.
The obtained residue 6.2 parts and toluene 170 parts were mixed, stirred at 95 ℃ for 3 hours, and then filtered.
The obtained residue 5.6 parts and water 50 parts were mixed, stirred at 90 ℃ for 16 hours, and then filtered.
The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ 2-515).
Identification of Compound represented by the formula (IbZ2-515)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-439
Exact molecular weight (Exact masses): 440
Example 19Z2
2 parts of phthalonitrile and 16 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of phthalonitrile 2 parts was added.
The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 4.2 parts by mole of a compound represented by the formula (ppp2) in an amount of 3.3 times the mole of 2 parts by mole of phthalonitrile, and the mixture was stirred at 60 ℃ for 6 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 4 parts of a residue Aa containing the compound represented by the formula (IbZ 2-313). 8 parts of phthalonitrile and 63 parts of methanol are mixed. While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the mole of 8 parts of phthalonitrile was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added 17 parts of acetic acid and a compound represented by the formula (ppp2) in an amount of 3.3 times the number of moles of 8 parts of phthalonitrile, and the mixture was stirred at 60 ℃ for 10 days.
The mixture was cooled to room temperature and filtered. The obtained residue was washed with methanol to obtain 16 parts of a residue Bb containing the compound represented by formula (IbZ 2-313).
Identification of Compound represented by the formula (IbZ2-313)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+536
Exact molecular weight (Exact masses): 535
The residue Aa 2 parts containing the compound represented by the formula (IbZ2-313) was mixed with 27 parts of methylene chloride and 22 parts of trifluoroacetic acid, and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain a residue Aaa 2 parts. The residue Aa 2 parts containing the compound represented by the formula (IbZ2-313), the residue Bb 16 parts containing the compound represented by the formula (IbZ2-313), 240 parts of methylene chloride and 190 parts of trifluoroacetic acid were mixed and stirred at room temperature for 16 hours.
The solvent of the mixture was distilled off to obtain 16 parts of residue Ccc.
1.7 parts of residue Aaa, 16 parts of residue Ccc and 210 parts of acetic acid were mixed and stirred at 80 ℃ for 16 hours. The mixture was filtered to obtain 13 parts of a residue. The residue was mixed with 71 parts of diethyl ether and stirred at room temperature for 16 hours. The mixture was filtered, and the obtained residue was dried to obtain 12 parts of a compound represented by the formula (IbZ 2-318).
Identification of Compound represented by the formula (IbZ2-318)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-422
Exact molecular weight (Exact masses): 423
Example 20Z2
2 parts of 4-nitrophthalonitrile and 16 parts of methanol are mixed.
While the mixture was kept at 0 ℃, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 4-nitrophthalonitrile 2 parts was added. The mixture was stirred at 0 ℃ for 3 hours. To the mixture were added 2.1 parts by mole of a compound represented by the formula (ppp2) 3.3 times the mole of 2 parts by mole of 4-nitrophthalonitrile and 2.1 parts by mole of acetic acid, and the mixture was stirred at 60 ℃ for 15 days. The mixture was cooled to room temperature and filtered. The obtained residue was washed with 48 parts of methanol to obtain 8.4 parts of a residue containing the compound represented by the formula (IbZ 2-314).
Identification of Compound represented by the formula (IbZ2-314)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+581
Exact molecular weight (Exact masses): 580
The residue containing the compound represented by the formula (IbZ2-314) (8.4 parts) was mixed with dichloromethane (110 parts) and trifluoroacetic acid (89 parts) and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain 6.9 parts of a residue. This residue 6.1 parts and 34 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 5 minutes. The mixture was mixed with 190 parts of acetic acid, and stirred at room temperature for 30 minutes. The mixture was mixed with 290 parts of methanol and stirred at room temperature for 1 hour. The mixture was filtered to give a residue of 5.7 parts. The residue 5.6 parts and water 150 parts were mixed, stirred at 80 ℃ for 2 hours, and filtered.
The obtained residue was dried to obtain 5.4 parts of a compound represented by the formula (IbZ 2-516).
< identification of Compound represented by formula (IbZ2-516 >
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-467
Exact molecular weight (Exact masses): 468
Example 21Z2
A compound represented by the formula (ppp3) in an amount of 1.1 times the mole of 6 parts of phthalonitrile, 66 parts of dimethyl sulfoxide and 1 time the mole of potassium tert-butoxide in an amount of 6 parts of phthalonitrile were mixed and stirred at room temperature for 10 minutes. To the mixture was added 6 parts of phthalonitrile, and the mixture was stirred at 80 ℃ for 2 hours. To the mixture was added a compound represented by the formula (ppp3) in an amount of 1.1 times the mole of 6 parts of phthalonitrile, and the mixture was stirred at 180 ℃ for 2 hours. The mixture was cooled to room temperature and filtered to obtain 5.3 parts of a residue. This residue 5.0 parts was mixed with 55 parts of dimethyl sulfoxide and 47 parts of N, N-dimethylformamide, and stirred at 80 ℃ for 30 minutes.
This mixture was mixed with 240 parts of methanol and stirred at 80 ℃ for 30 minutes.
The mixture was cooled to room temperature and filtered. The obtained residue was mixed with 55 parts of dimethyl sulfoxide and 47 parts of N, N-dimethylformamide, and stirred at 80 ℃ for 30 minutes. This mixture was mixed with 240 parts of methanol and stirred at 80 ℃ for 30 minutes. The mixture was cooled to room temperature and filtered to obtain 4.6 parts of a residue. The residue was mixed with methanol and stirred at 80 ℃ for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 4.5 parts of a compound represented by the formula (IbZ 2-319).
Identification of Compound represented by the formula (IbZ2-319)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-518
Exact molecular weight (Exact masses): 519
Example 22Z2
50 parts of 4-aminomethylbenzoic acid, cyanoacetic acid in an amount of 1.2 times the molar amount of 50 parts of 4-aminomethylbenzoic acid, N' -dicyclohexylcarbodiimide in an amount of 0.9 times the molar amount of 50 parts of 4-aminomethylbenzoic acid, and 890 parts of tetrahydrofuran were mixed and stirred at room temperature for 16 hours. The mixture was filtered, and the solvent of the filtrate was distilled off to obtain a residue.
The obtained residue was mixed with 270 parts of ethyl acetate and filtered.
The obtained residue was dried to obtain 30 parts of a compound represented by the formula (ppp 4).
Identification of Compound represented by the formula (ppp4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-217
Exact molecular weight (Exact masses): 218
In addition, 3 parts of phthalonitrile and 110 parts of ethylene glycol were mixed. To the mixture was added 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 1.5 times the mole of 3 parts of phthalonitrile at room temperature.
The mixture was stirred at room temperature for 4 hours. To the mixture were added 110 parts of a compound represented by the formula (ppp4) in an amount of 3.1 times the mole of 3 parts of phthalonitrile and 110 parts of ethylene glycol, and the mixture was stirred at 110 ℃ for 16 hours. After the mixture was cooled to room temperature, 630 parts of methanol was added. The mixture was mixed with 26 parts of acetic acid. The mixture was filtered to obtain 11 parts of a residue. The residue was mixed with 220 parts of dimethyl sulfoxide. This mixture was mixed with 630 parts of methanol. The mixture was filtered to give a residue of 9.5 parts. The residue was mixed with 220 parts of dimethyl sulfoxide. This mixture was mixed with 630 parts of methanol. The mixture was filtered to obtain 9 parts of a residue. The residue was mixed with 200 parts of water and stirred at 80 ℃ for 2 hours. The mixture was mixed with 2.1 parts of acetic acid. The mixture was filtered to give 8.5 parts of a residue. The residue (8.1 parts) and dimethyl sulfoxide (260 parts) were mixed and stirred at 60 ℃ for 20 minutes. The mixture was cooled to room temperature, allowed to stand at room temperature for 2 hours, and filtered.
The obtained residue was washed with 2% aqueous acetic acid solution to obtain 6.2 parts of a residue. The residue was mixed with 150 parts of water and stirred at 80 ℃ for 30 minutes. The mixture was cooled to room temperature and filtered.
The obtained residue was washed with 200 parts of water. The residue was dried to obtain 6 parts of a compound represented by the formula (IbZ 2-320).
Identification of Compound represented by the formula (IbZ2-320)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-546
Exact molecular weight (Exact masses): 547
Example 23Z2
5 parts of 4, 5-dibromophthalonitrile and 93 parts of 2-ethoxyethanol are mixed.
To the mixture was added a 25% sodium methoxide methanol solution containing 1 time by mole of sodium methoxide as much as 5 parts by mole of 4, 5-dibromophthalonitrile. The mixture was stirred at room temperature for 6 hours. To the mixture was added a compound represented by the formula (ppp1) in an amount of 6 times the mole number of 5 parts of 4, 5-dibromophthalonitrile, and the mixture was stirred at 90 ℃ for 65 hours and then at 100 ℃ for 10 hours. This mixture was mixed with 300 parts of water and 21 parts of acetic acid. The mixture was filtered to obtain 10 parts of a residue. The residue was mixed with 120 parts of methanol and 10 parts of acetic acid. The mixture was filtered to obtain 5.5 parts of a residue containing the compound represented by the formula (IbZ 2-315).
Identification of Compound represented by the formula (IbZ2-315)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+664
Exact molecular weight (Exact masses): 663
The residue containing the compound represented by the formula (IbZ2-315) (5.5 parts) was mixed with trifluoroacetic acid (45 parts) and dichloromethane (80 parts), and stirred at room temperature for 16 hours. The solvent of the mixture was distilled off to obtain 6 parts of a residue. The residue was mixed with 79 parts of methanol. The mixture was filtered to obtain 4 parts of a residue.
This residue was mixed with 0.24 part of lithium hydroxide, 36 parts of tetrahydrofuran and 12 parts of water, and stirred at room temperature for 6 hours. Tetrahydrofuran was distilled off from the mixture using an evaporator. To the resulting mixture, water and 1.5N hydrochloric acid were added. The mixture was filtered to give a residue of 3.5 parts. The residue was mixed with 40 parts of methanol. The mixture was filtered, and the residue was washed with 13 parts of hexane to give 3 parts of residue. This residue 2.8 parts and dimethyl sulfoxide 33 parts were mixed and stirred at 70 ℃ for 20 minutes. The mixture was cooled to room temperature and filtered.
The obtained residue was washed with 40 parts of methanol and then 50 parts of water.
The residue was dried to obtain 1.8 parts of a compound represented by the formula (IbZ 2-706).
Identification of Compound represented by the formula (IbZ2-706)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-550
Exact molecular weight (Exact masses): 551
Example 24Z2
13 parts of 4, 5-dichlorophthalonitrile and 160 parts of methanol were mixed.
While the mixture was kept at 0 ℃ a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the mole number of 13 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 0 ℃ for 5 hours. To the mixture were added a compound represented by the formula (ppp1) in an amount of 4.4 times the mole number of 13 parts of 4, 5-dichlorophthalonitrile and 16 parts of acetic acid, and the mixture was stirred at 75 ℃ for 7 days. To the mixture were added 14 parts of acetic acid and a compound represented by the formula (ppp1) in an amount of 3 times the mole number of 13 parts of 4, 5-dichlorophthalonitrile, and the mixture was stirred at 75 ℃ for 11 days.
The mixture was filtered. The obtained residue was washed with 320 parts of methanol to obtain 26 parts of a residue.
13 parts of this residue was mixed with 100 parts of methanol, 16 parts of acetic acid and 26.3 parts of a compound represented by the formula (ppp1), and stirred at 75 ℃ for 48 hours. The mixture was filtered. The obtained residue was washed with 40 parts of methanol to obtain 12 parts of a residue containing the compound represented by the formula (IbZ 2-316).
Identification of Compound represented by the formula (IbZ2-316)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+576
Exact molecular weight (Exact masses): 575
The residue containing the compound represented by the formula (IbZ2-316) (12 parts) was mixed with dichloromethane (160 parts) and trifluoroacetic acid (130 parts), and the mixture was stirred at room temperature for 16 hours. The mixture was filtered to obtain 6.2 parts of a residue. The residue was mixed with 73 parts of acetic acid and stirred at 80 ℃ for 2 hours. The mixture was filtered to give 5.3 parts of a residue. The residue was mixed with 60 parts of water and stirred at 80 ℃ for 2 hours. The mixture was filtered, and the obtained residue was dried to obtain 5 parts of a compound represented by the formula (IbZ 2-389).
Identification of Compound represented by the formula (IbZ2-389)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-462
Exact molecular weight (Exact masses): 463
Example 101Z2
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 2) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
Colorant AZ 2: 50 parts of a mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain colored curable composition 1Z2,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 2);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A2-inch square glass substrate (EAGLE XG; manufactured by Corning Inc.) was coated with a colored curable composition 1Z2 by spin coating, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z2 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 23Z 2.
Example 102Z2
A colored curable composition 2Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-125) obtained in example 2Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 103Z2
A colored curable composition 3Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 104Z2
A colored curable composition 4Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 105Z2
A colored curable composition 5Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 106Z2
A colored curable composition 6Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by the formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 107Z2
A colored curable composition 7Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 108Z2
A colored curable composition 8Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-125) obtained in example 2Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 109Z2
A colored curable composition 9Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 110Z2
A colored curable composition 10Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 111Z2
A colored curable composition 11Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 112Z2
A colored curable composition 12Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 113Z2
A colored curable composition 13Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 114Z2
A colored curable composition 14Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-125) obtained in example 2Z2, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 115Z2
A colored curable composition 15Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-126) obtained in example 3Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 116Z2
A colored curable composition 16Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-148) obtained in example 4Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 117Z2
A colored curable composition 17Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-149) obtained in example 5Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Example 118Z2
A colored curable composition 18Z2 was obtained in the same manner as in example 101Z2 and a colored pattern was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38) and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound represented by formula (IbZ2-128) obtained in example 6Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 1Z2
A colored curable composition C1Z2 was obtained and a colored pattern was obtained in the same manner as in example 101Z2 except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 2Z2
A colored curable composition C2Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
Comparative example 3Z2
A colored curable composition C3Z2 was obtained in the same manner as in example 101Z2 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the mixture of the compound represented by formula (IaZ2-39), the compound represented by formula (IaZ2-38), and the compound represented by formula (IaZ2-149) obtained in example 1Z2 was replaced with c.i. pigment yellow 185, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 23Z 2.
[ Table 23Z2]
TABLE 23Z2
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z2 | 2.3 | 3 |
Example 102Z2 | 2.3 | 4 |
Example 103Z2 | 2.3 | 3 |
Example 104Z2 | 2.3 | 3 |
Example 105Z2 | 2.3 | 3 |
Example 106Z2 | 2.3 | 3 |
Example 107Z2 | 2.3 | 3 |
Example 108Z2 | 2.3 | 3 |
Example 109Z2 | 2.3 | 3 |
Practice ofExample 110Z2 | 2.3 | 3 |
Example 111Z2 | 2.3 | 4 |
Example 112Z2 | 2.3 | 3 |
Example 113Z2 | 2.3 | 3 |
Example 114Z2 | 2.3 | 3 |
Example 115Z2 | 2.3 | 3 |
Example 116Z2 | 2.3 | 3 |
Example 117Z2 | 2.3 | 3 |
Example 118Z2 | 2.3 | 3 |
Comparative example 1Z2 | 2.3 | 15 |
Comparative example 2Z2 | 2.3 | 15 |
Comparative example 3Z2 | 2.3 | 15 |
Example 119Z2
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 2) was prepared by dispersing the pigment using a bead mill.
In addition, the following substances were mixed,
colorant AZ 2: 50 parts of a mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2,
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
A mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38) and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain a colored curable composition 19Z2,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 2);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
Polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z2 except that a colored curable composition 19Z2 was used instead of the colored curable composition 1Z 2. A colored coating film was obtained in the same manner as in example 101Z2 except that a colored curable composition 19Z2 was used in place of the colored curable composition 1Z2, and the film thickness and the retardation value were measured. The results are shown in Table 24Z 2.
Example 120Z2 to example 138Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the colorant shown in the column of "colorant" in table 24Z 2. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 24Z 2.
Example 139Z2 to example 158Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound shown in the column of "colorant" in table 24Z2, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 25Z 2.
Example 159Z2 to example 178Z2
A colored pattern was obtained in the same manner as in example 119Z2, except that the mixture of the compound represented by the formula (IaZ2-39), the compound represented by the formula (IaZ2-38), and the compound represented by the formula (IaZ2-149) obtained in example 1Z2 was replaced with the compound shown in the column of "colorant" in table 24Z2, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 26Z 2.
[ Table 24Z2]
TABLE 24Z2
[ Table 25Z2]
TABLE 25Z2
[ Table 26Z2]
TABLE 26Z2
Chemical formulas of compounds represented by formula (IaZ2-1) in tables 24Z2, 25Z2, and 26Z2 are shown.
In the examination of example Z2, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z3
Example 1Z3
10.3 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44.8 parts of methanol were mixed. While keeping the temperature at 20 to 25 ℃, 8.01 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture.
The resulting mixture was stirred at 20 to 25 ℃ for 2 hours.
10 parts of methanol was added to the obtained mixture while keeping the temperature at 20 to 25 ℃.
The resulting mixture was stirred at 20-25 ℃ for 2 hours.
To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by tokyo chemical industries, Ltd.) and 4.98 parts of acetic acid were added, and the obtained mixture was stirred at 40 ℃ for 2 hours and at 65 ℃ for 2 hours.
To the obtained mixture were added 11.3 parts of barbituric acid (manufactured by tokyo chemical industry corporation), 6.53 parts of acetic acid, and 160 parts of water, and the obtained mixture was stirred at 65 ℃ for 3 hours, at room temperature for 2 days, and at 75 ℃ for 5 hours.
To the resulting mixture was added 230 parts of methanol at room temperature.
The obtained compound was filtered, and the obtained residue was washed with 170 parts of methanol 1 time, 400 parts of methanol 2 times, 1000 parts of water 1 time, and 200 parts of methanol 11 times.
To the resulting residue was added 641 parts of a 5% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 1000 parts of water.
To the resulting residue was added 478 parts of water, followed by stirring at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 500 parts of water.
The obtained residue was dried to obtain 19.1 parts of a compound represented by the formula (IZ 3-1).
Identification of Compound represented by the formula (IZ3-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+324
Exact molecular weight (Exact masses): 323
Example 2Z3
The procedure of example 1Z3 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) to obtain a compound represented by the formula (IZ 3-19).
Identification of Compound represented by the formula (IZ3-19)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 3Z3
A compound represented by the formula (IZ3-6) was obtained in the same manner as in example 1Z3, except that phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Identification of Compound represented by the formula (IZ3-6)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 4Z3XXX (516)
10.3 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44.8 parts of methanol were mixed.
While keeping the temperature at 20 to 25 ℃, 8.01 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture.
The resulting mixture was stirred at 20 to 25 ℃ for 2 hours.
10 parts of methanol was added to the obtained mixture while keeping the temperature at 20 to 25 ℃.
The resulting mixture was stirred at 20-25 ℃ for 2 hours.
To the obtained mixture, 7.49 parts of 2-cyanoacetamide (manufactured by tokyo chemical industries, Ltd.) and 4.98 parts of acetic acid were added, and the obtained mixture was stirred at 40 ℃ for 2 hours and at 65 ℃ for 2 hours.
To the obtained mixture were added 11.3 parts of barbituric acid (manufactured by tokyo chemical industry corporation), 6.53 parts of acetic acid, and 160 parts of water, and the obtained mixture was stirred at 65 ℃ for 3 hours, at room temperature for 2 days, and at 75 ℃ for 5 hours.
To the resulting mixture was added 230 parts of methanol at room temperature.
The obtained compound was filtered, and the obtained residue was washed with 170 parts of methanol 1 time, 400 parts of methanol 2 times, 1000 parts of water 1 time, and 200 parts of methanol 11 times.
To the resulting residue was added 641 parts of a 5% aqueous sodium hydroxide solution, and the mixture was stirred at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 1000 parts of water.
To the resulting residue was added 478 parts of water, followed by stirring at room temperature.
The resulting mixture was filtered, and the resulting residue was washed with 500 parts of water.
The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 3-1).
Identification of Compound represented by the formula (IZ3-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+324
Exact molecular weight (Exact masses): 323
Example 5Z3XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 4.86 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.88 parts of acetic acid and 2.43 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol.
To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 3-19).
Identification of Compound represented by the formula (IZ3-19)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+369
Exact molecular weight (Exact masses): 368
Example 6Z3XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 4.56 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the obtained mixture were added 2.69 parts of acetic acid and 2.28 parts of 2-cyanoacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 3-6).
Identification of Compound represented by the formula (IZ3-6)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 7Z3
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2-cyanoacetamide (manufactured by Tokyo chemical industries, Ltd.) in an amount of 1.5 times the molar amount of 4, 5-dichlorophthalonitrile 5.0 parts and 6.1 parts of acetic acid while keeping the temperature at 5 ℃ or lower. The mixture was stirred at 65 ℃ for 3 days.
This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days.
After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 3-8).
Identification of Compound represented by the formula (IZ3-8)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+392
Exact molecular weight (Exact masses): 391
Example 101Z3
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 3) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 3: 50 parts of the compound represented by the formula (IZ3-1) obtained in example 1Z3,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ3-1) obtained in example 1Z3 was dispersed using a bead mill to obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z3,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 3);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z3 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere 2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure is mixed with a nonionic surfactant at 25 deg.CThe resultant was immersed in an aqueous solution containing 0.12% surfactant and 0.04% potassium hydroxide for 70 seconds to develop the resist, and then washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z3 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation). The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 7Z 3.
Example 102Z3
A colored curable composition 2Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the compound represented by the formula (IZ3-19) obtained in example 2Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 103Z3
A colored curable composition 3Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 104Z3
A colored curable composition 4Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 105Z3
A colored curable composition 5Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-19) obtained in example 2Z3 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 106Z3
A colored curable composition 6Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-1) obtained in example 3Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z3, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 107Z3
A colored curable composition 7Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3, except that c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 108Z3
A colored curable composition 8Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-19) obtained in example 2Z3 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Example 109Z3
A colored curable composition 9Z3 was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ3-1) obtained in example 3Z3 was replaced with the compound represented by the formula (IZ3-6) obtained in example 3Z 3826, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 1Z3
A colored curable composition C1Z3 was obtained and a colored pattern was obtained in the same manner as in example 101Z3 except that the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 2Z3
A colored curable composition C2Z3 was obtained in the same manner as in example 101Z3, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
Comparative example 3Z3
A colored curable composition C3Z3 was obtained in the same manner as in example 101Z3, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ3-1) obtained in example 1Z3 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z3, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 3.
[ Table 7Z3]
TABLE 7Z3
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z3 | 2.3 | 4 |
Example 102Z3 | 2.3 | 3 |
Example 103Z3 | 2.3 | 3 |
Example 104Z3 | 2.3 | 4 |
Example 105Z3 | 2.3 | 3 |
Example 106Z3 | 2.3 | 3 |
Example 107Z3 | 2.3 | 4 |
Example 108Z3 | 2.3 | 3 |
Example 109Z3 | 2.3 | 3 |
Comparative example 1Z3 | 2.3 | 15 |
Comparative example 2Z3 | 2.3 | 15 |
Comparative example 3Z3 | 2.3 | 15 |
Example 110Z3
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
Resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 3) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 3: 50 parts of a compound represented by the formula (IZ3-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ3-1) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain a colored curable composition 10Z3,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 3);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z3 except that a colored curable composition 10Z3 was used instead of the colored curable composition 1Z 3. A colored coating film was obtained in the same manner as in example 101Z3 except that a colored curable composition 10Z3 was used in place of the colored curable composition 1Z3, and the film thickness and the retardation value were measured. The results are shown in Table 8Z 3.
Example 111Z3 to example 113Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by the formula (IZ3-1) was replaced with the colorant shown in the column of "colorant" of table 8Z 3. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
Example 114Z3 to example 117Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by formula (IZ3-1) was replaced with the compound shown in the column of "colorant" in table 8Z3, and c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
Example 118Z3 to example 121Z3
A colored pattern was obtained in the same manner as in example 110Z3, except that the compound represented by formula (IZ3-1) was replaced with the compound shown in the column of "colorant" in table 8Z3, and c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 3.
[ Table 8Z3]
TABLE 8Z3
Coloring agent | Film thickness (mum) | Phase difference value (nm) | |
Example 110Z3 | A compound represented by the formula (IZ3-1) | 2.3 | 4 |
Example 111Z3 | A compound represented by the formula (IZ3-19) | 2.3 | 3 |
Example 112Z3 | A compound represented by the formula (IZ3-6) | 2.3 | 3 |
Example 113Z3 | A compound represented by the formula (IZ3-8) | 2.3 | 3 |
Example 114Z3 | A compound represented by the formula (IZ3-1) | 2.3 | 4 |
Example 115Z3 | A compound represented by the formula (IZ3-19) | 2.3 | 3 |
Example 116Z3 | A compound represented by the formula (IZ3-6) | 2.3 | 3 |
Example 117Z3 | A compound represented by the formula (IZ3-8) | 2.3 | 3 |
Example 118Z3 | A compound represented by the formula (IZ3-1) | 2.3 | 4 |
Example 119Z3 | A compound represented by the formula (IZ3-19) | 2.3 | 3 |
Example 120Z3 | A compound represented by the formula (IZ3-6) | 2.3 | 3 |
Example 121Z3 | A compound represented by the formula (IZ3-8) | 2.3 | 3 |
In example Z3, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z4
Example 1Z4
20.5 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 171 parts of methanol were mixed. While keeping the temperature at 5 ℃ for 1 hour and 20 minutes, a mixture of 23.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture.
The resulting mixture was stirred at 2-6 ℃ for 7 hours.
To the obtained mixture were added acetic acid (15.6 parts), 2-cyano-N, N-dimethylacetamide (17.9 parts, manufactured by Tokyo chemical industry Co., Ltd.) and methanol (118 parts), and the mixture was stirred at 40 ℃ for 15 hours and at 65 ℃ for 7 hours. To the obtained mixture were added 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 80 parts of methanol, and the mixture was stirred at 40 ℃ for 17 hours and at 65 ℃ for 4 hours. To the obtained mixture were added 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 104 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours and at 60 ℃ for 9 hours. To the obtained mixture were added acetic acid 6.32 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) 7.19 parts, and methanol 40 parts, and the mixture was stirred at 60 ℃ for 3 hours and at room temperature for 59 hours. To the obtained mixture were added acetic acid 15.7 parts, barbituric acid (manufactured by tokyo chemical industry corporation) 20.5 parts, methanol 16 parts, and water 744 parts, and the mixture was stirred at 60 ℃ for 24 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 43.1 parts of a compound represented by the formula (IZ 4-1).
Identification of Compound represented by the formula (IZ4-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+352
Exact molecular weight (Exact masses): 351
Example 2Z4
The procedure of example 1Z4 was repeated except for replacing 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.), to obtain a compound represented by the formula (IZ 4-2).
Identification of Compound represented by the formula (IZ4-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 3Z4
The procedure of example 1Z4 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) to obtain compounds represented by the formula (IZ 4-79).
Identification of Compound represented by the formula (IZ4-79)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+397
Exact molecular weight (Exact masses): 396
Example 4Z4
A compound represented by formula (IZ4-80) was obtained in the same manner as in example 1Z4, except that phthalonitrile (manufactured by tokyo chemical industry co.) was replaced with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) and 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) was replaced with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.).
Identification of Compound represented by the formula (IZ4-80)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+425
Exact molecular weight (Exact masses): 424
Example 5Z4
A compound represented by the formula (IZ4-40) was obtained in the same manner as in example 1Z4, except that phthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-tert-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Identification of Compound represented by the formula (IZ4-40)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+408
Exact molecular weight (Exact masses): 407
Example 6Z4
The procedure of example 1Z4 was repeated except for replacing phthalonitrile (manufactured by tokyo chemical industry co.) with 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co.) and replacing 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) with 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 4-41).
Identification of Compound represented by the formula (IZ4-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+436
Exact molecular weight (Exact masses): 435
Example 7Z4XXX (651)
20.5 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 171 parts of methanol were mixed.
While maintaining the temperature at 2 to 5 ℃, a mixture of 23.9 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 215 parts of methanol was added dropwise to the obtained mixture over 1 hour and 20 minutes. The resulting mixture was stirred at 2-6 ℃ for 7 hours. To the obtained mixture were added acetic acid 15.6 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) 17.9 parts, and methanol 46.9 parts. Further, up to this point in time, a total of 71 parts of methanol was added in addition to the above-mentioned methanol. The resulting mixture was stirred at 40 ℃ for 15 hours and at 65 ℃ for 7 hours. To the obtained mixture were added 7.82 parts of acetic acid, 8.97 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 80 parts of methanol, and the mixture was stirred at 40 ℃ for 17 hours and at 65 ℃ for 4 hours. To the obtained mixture were added 12.6 parts of acetic acid, 14.3 parts of 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) and 104 parts of methanol, and the mixture was stirred at 40 ℃ for 16 hours and at 60 ℃ for 9 hours. To the obtained mixture were added acetic acid 6.32 parts, 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) 7.19 parts, and methanol 40 parts, and the mixture was stirred at 60 ℃ for 3 hours and at room temperature for 59 hours. To the obtained mixture were added acetic acid 15.7 parts, barbituric acid (manufactured by tokyo chemical industry co., ltd.) 20.5 parts, methanol 16 parts, and water 744 parts, and the mixture was stirred at 60 ℃ for 9 days.
The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol.
The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-1).
Identification of Compound represented by the formula (IZ4-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+352
Exact molecular weight (Exact masses): 351
Example 8Z4XXX
10.0 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 83 parts of methanol were mixed.
To the obtained mixture, a mixture of 11.7 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 105 parts of methanol was added dropwise over 1 hour and 30 minutes while maintaining the temperature at 2 to 5 ℃. The resulting mixture was stirred at 2-6 ℃ for 7 hours. To the obtained mixture were added 7.62 parts of acetic acid, 10.9 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co., ltd.) and 140 parts of methanol. In addition, up to this point, a total of 35 parts of methanol was added in addition to the above-mentioned methanol.
The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 3.82 parts of acetic acid and 5.48 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 7.65 parts of acetic acid, 10.0 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and the obtained residue was purified by column chromatography in the same manner as in example 1Z4 to obtain a compound represented by the formula (IZ 4-2).
Identification of Compound represented by the formula (IZ4-2)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+380
Exact molecular weight (Exact masses): 379
Example 9Z4XXX (529)
2.56 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 22 parts of methanol were mixed. To the obtained mixture was added 2.96 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred for 3 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 1.84 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry) and 1.90 parts of acetic acid were added. The resulting mixture was stirred at 40 ℃ for 1 hour and at 65 ℃ for 1 hour. To the obtained mixture, 2.09 parts of barbituric acid (manufactured by tokyo chemical industry Co., Ltd.), 2.48 parts of acetic acid and 41 parts of water were added. In addition, a total of 24 parts of methanol was added up to this time point, in addition to the above-mentioned methanol. The resulting mixture was stirred at 65 ℃ for 15 hours. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-79).
Identification of Compound represented by the formula (IZ4-79)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+397
Exact molecular weight (Exact masses): 396
Example 10Z4XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower. While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 8.10 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 4.05 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industry co.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol. To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-80).
Identification of Compound represented by the formula (IZ4-80)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+425
Exact molecular weight (Exact masses): 424
Example 11Z4XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the obtained mixture, 5.42 parts of acetic acid and 6.09 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.69 parts of acetic acid and 3.04 parts of 2-cyano-N, N-dimethylacetamide (manufactured by tokyo chemical industry co., ltd.) and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-40).
Identification of Compound represented by the formula (IZ4-40)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+408
Exact molecular weight (Exact masses): 407
Example 12Z4XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the obtained mixture, 5.42 parts of acetic acid and 7.61 parts of 2-cyano-N, N-diethylacetamide (manufactured by tokyo chemical industries, ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.69 parts of acetic acid and 3.80 parts of 2-cyano-N, N-diethylacetamide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-41).
Identification of Compound represented by the formula (IZ4-41)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+436
Exact molecular weight (Exact masses): 435
Example 13Z4
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed. While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added.
The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture, while keeping the temperature at 5 ℃ or lower, 2-cyano-N, N-dimethylacetamide (manufactured by Tokyo chemical industry Co., Ltd.) having a molar amount 1.5 times that of 5.0 parts of 4, 5-dichlorophthalonitrile and 6.1 parts of acetic acid were added. The mixture was stirred at 65 ℃ for 3 days. This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. The solvent was distilled off from the mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 4-321).
Identification of Compound represented by the formula (IZ4-321)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H ]+420
Exact molecular weight (Exact masses): 419
Example 101Z4
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 4) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 4: 50 parts of the compound represented by the formula (IZ4-1) obtained in example 1Z4,
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ4-1) obtained in example 1Z4 was dispersed using a bead mill to obtain a colored composition. Next, the following were mixed to obtain colored curable composition 1Z4,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 4);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
Polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z4 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z4 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a coloringAnd (6) coating.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 9Z 4.
Example 102Z4
A colored curable composition 2Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 103Z4
A colored curable composition 3Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-79) obtained in example 3Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 104Z4
A colored curable composition 4Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-80) obtained in example 4Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 105Z4
A colored curable composition 5Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-40) obtained in example 5Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 106Z4
A colored curable composition 6Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-41) obtained in example 6Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 107Z4
A colored curable composition 7Z4 was obtained and a colored pattern was obtained in the same manner as in example 101Z4, except that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 108Z4
A colored curable composition 8Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-1) obtained in example 2Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 109Z4
A colored curable composition 9Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-79) obtained in example 3Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 110Z4
A colored curable composition 10Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-1) obtained in example 4Z4 was replaced with the compound represented by the formula (IZ4-80) obtained in example 4Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 111Z4
A colored curable composition 11Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-40) obtained in example 5Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 112Z4
A colored curable composition 12Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-41) obtained in example 6Z4 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 113Z4
A colored curable composition 13Z4 was obtained in the same manner as in example 101Z4 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 114Z4
A colored curable composition 14Z4 was obtained in the same manner as in example 101Z4 except that c.i. pigment green 58 was replaced with c.i. pigment green 59 and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the compound represented by the formula (IZ4-2) obtained in example 2Z4, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 115Z4
A colored curable composition 15Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-79) obtained in example 3Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 116Z4
A colored curable composition 16Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-80) obtained in example 4Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 117Z4
A colored curable composition 17Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-40) obtained in example 5Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Example 118Z4
A colored curable composition 18Z4 was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ4-41) obtained in example 6Z4 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 1Z4
A colored curable composition C1Z4 was obtained and a colored pattern was obtained in the same manner as in example 101Z4 except that the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 2Z4
A colored curable composition C2Z4 was obtained in the same manner as in example 101Z4, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
Comparative example 3Z4
A colored curable composition C3Z4 was obtained in the same manner as in example 101Z4, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ4-1) obtained in example 1Z4 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z4, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 4.
[ Table 9Z4]
TABLE 9Z4
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z4 | 2.3 | 4 |
Example 102Z4 | 2.3 | 4 |
Example 103Z4 | 2.3 | 3 |
Example 104Z4 | 2.3 | 3 |
Example 105Z4 | 2.3 | 3 |
Example 106Z4 | 2.3 | 3 |
Example 107Z4 | 2.3 | 4 |
Example 108Z4 | 2.3 | 4 |
Example 109Z4 | 2.3 | 3 |
Example 110Z4 | 2.3 | 3 |
Example 111Z4 | 2.3 | 3 |
Example 112Z4 | 2.3 | 3 |
Example 113Z4 | 2.3 | 4 |
Example 114Z4 | 2.3 | 4 |
Example 115Z4 | 2.3 | 3 |
Example 116Z4 | 2.3 | 3 |
Example 117Z4 | 2.3 | 3 |
Example 118Z4 | 2.3 | 3 |
Comparative example 1Z4 | 2.3 | 15 |
Comparative example 2Z4 | 2.3 | 15 |
Comparative example 3Z4 | 2.3 | 15 |
Example 119Z4
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 4) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 4: 50 parts of a compound represented by the formula (IZ4-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ4-1) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain a colored curable composition 19Z4,
The total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 4);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z4 except that a colored curable composition 19Z4 was used instead of the colored curable composition 1Z 4. A colored coating film was obtained in the same manner as in example 101Z4 except that a colored curable composition 19Z4 was used in place of the colored curable composition 1Z4, and the film thickness and the retardation value were measured. The results are shown in Table 10Z 4.
Example 120Z4 to example 125Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the colorant shown in the column of "colorant" in table 10Z 4. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
Example 126Z4 to example 132Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the compound shown in the column of "colorant" in table 10Z4 and the c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
Example 133Z4 to example 139Z4
A colored pattern was obtained in the same manner as in example 119Z4 except that the compound represented by the formula (IZ4-1) was replaced with the compound shown in the column of "colorant" in table 10Z4 and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 4.
[ Table 10Z4]
TABLE 10Z4
Coloring agent | Film thickness (mum) | Phase difference value (nm) | |
Example 119Z4 | A compound represented by the formula (IZ4-1) | 2.3 | 4 |
Example 120Z4 | A compound represented by the formula (IZ4-2) | 2.3 | 4 |
Example 121Z4 | A compound represented by the formula (IZ4-79) | 2.3 | 3 |
Example 122Z4 | A compound represented by the formula (IZ4-80) | 2.3 | 3 |
Example 123Z4 | A compound represented by the formula (IZ4-40) | 2.3 | 3 |
Example 124Z4 | A compound represented by the formula (IZ4-41) | 2.3 | 3 |
Example 125Z4 | A compound represented by the formula (IZ4-321) | 2.3 | 3 |
Example 126Z4 | A compound represented by the formula (IZ4-1) | 2.3 | 4 |
Example 127Z4 | A compound represented by the formula (IZ4-2) | 2.3 | 4 |
Example 128Z4 | A compound represented by the formula (IZ4-79) | 2.3 | 3 |
Example 129Z4 | A compound represented by the formula (IZ4-80) | 2.3 | 3 |
Example 130Z4 | A compound represented by the formula (IZ4-40) | 2.3 | 3 |
Example 131Z4 | A compound represented by the formula (IZ4-41) | 2.3 | 3 |
Example 132Z4 | A compound represented by the formula (IZ4-321) | 2.3 | 3 |
Example 133Z4 | A compound represented by the formula (IZ4-1) | 2.3 | 4 |
Example 134Z4 | A compound represented by the formula (IZ4-2) | 2.3 | 4 |
Example 135Z4 | A compound represented by the formula (IZ4-79) | 2.3 | 3 |
Example 136Z4 | A compound represented by the formula (IZ4-80) | 2.3 | 3 |
Example 137Z4 | A compound represented by the formula (IZ4-40) | 2.3 | 3 |
Example 138Z4 | A compound represented by the formula (IZ4-41) | 2.3 | 3 |
Example 139Z4 | A compound represented by the formula (IZ4-321) | 2.3 | 3 |
In example Z4, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z5
Example 1Z5
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid, 6.75 parts of 2-cyano-N-methylacetamide and 201 parts of methanol were added, and the mixture was stirred at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. To the obtained mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 52 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 49.9 parts of a compound represented by the formula (IZ 5-1).
Identification of Compound represented by the formula (IZ5-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 2Z5
The procedure of example 1Z5 was repeated except for replacing 2-cyano-N-methylacetamide with 2-cyanoacetanilide (manufactured by tokyo chemical industry co., ltd.) to obtain a compound represented by the formula (IZ 5-3).
Identification of Compound represented by the formula (IZ5-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+456
Exact molecular weight (Exact masses): 455
Example 3Z5
A compound represented by the formula (IZ5-23) was obtained in the same manner as in example 1Z5, except that 4-t-butylphthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.) was replaced with 4-nitrophthalonitrile (manufactured by Tokyo chemical industry Co., Ltd.).
Identification of Compound represented by the formula (IZ5-23)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Example 4Z5
The procedure of example 1Z5 was repeated except for replacing 4-tert-butylphthalonitrile (manufactured by tokyo chemical industry co.) with 4-nitrophthalonitrile (manufactured by tokyo chemical industry co.) and replacing 2-cyano-N-methylacetamide with 2-cyanoacetanilide (manufactured by tokyo chemical industry co.) to obtain a compound represented by formula (IZ 5-25).
Identification of Compound represented by the formula (IZ5-25)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+445
Exact molecular weight (Exact masses): 444
Example 5Z5XXX (653)
25.2 parts of 4-tert-butylphthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 212 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 20.5 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 184 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days. To the resulting mixture, 13.7 parts of acetic acid and 13.5 parts of 2-cyano-N-methylacetamide were added at 10 to 20 ℃. The obtained mixture was stirred at 10 to 20 ℃ for 5 hours and then at 40 ℃ for 16 hours. To the resulting mixture, 6.79 parts of acetic acid and 6.75 parts of 2-cyano-N-methylacetamide were added, and stirring was performed at 40 ℃ for 6 hours and at 50 ℃ for 65 hours. In addition, a total of 201 parts of methanol was added up to this time point, in addition to the above-mentioned methanol.
To the resulting mixture were added 13.5 parts of acetic acid, 18.3 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 604 parts of water, and the mixture was stirred at 40 ℃ for 53 hours. The resulting mixture was filtered, and the residue was washed with 50% aqueous methanol. The obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-1).
Identification of Compound represented by the formula (IZ5-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+394
Exact molecular weight (Exact masses): 393
Example 6Z5XXX
10.0 parts of 4-tert-butyl phthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 84 parts of methanol were mixed. While keeping the temperature at 5 ℃ or lower, a mixture of 8.15 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 73 parts of methanol was added dropwise to the obtained mixture over 1 hour. The resulting mixture was stirred at 5-20 ℃ for 2 days.
To the obtained mixture, 5.42 parts of acetic acid and 8.69 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were added at 10 to 20 ℃. The resulting mixture was stirred at 65 ℃ for 3 days.
To the resulting mixture were added 2.69 parts of acetic acid and 4.35 parts of 2-cyanoacetanilide (manufactured by Tokyo chemical industry Co., Ltd.), and the mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 206 parts of methanol were added in addition to the above-mentioned methanol. To the obtained mixture were added 5.36 parts of acetic acid, 7.25 parts of barbituric acid (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days.
The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-3).
Identification of Compound represented by the formula (IZ5-3)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+456
Exact molecular weight (Exact masses): 455
Example 7Z5XXX (654)
25.2 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 376 parts of methanol were mixed together. 14.8 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes while keeping the temperature at 2 to 6 ℃. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 9.31 parts of acetic acid and 14.4 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at room temperature for 14 hours and at 40 ℃ for 29 hours.
To the resulting mixture, 1.50 parts of acetic acid and 2.24 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 19 hours.
To the resulting mixture, 4.83 parts of acetic acid and 7.36 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 79 hours.
To the resulting mixture, 4.60 parts of acetic acid and 7.30 parts of 2-cyano-N-methylacetamide were added. The resulting mixture was stirred at 40 ℃ for 24 hours. In addition, a total of 259 parts of methanol were added to the reaction mixture up to this point in time, in addition to the above-mentioned methanol. To the resulting mixture were added 12.1 parts of acetic acid, 19.1 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.), 635 parts of water, 14.2 parts of methanol and 20 parts of 50% methanol aqueous solution, followed by stirring at 40 ℃ for 21 hours and at 63 ℃ for 5 hours.
To the resulting mixture was added 23.4 parts of acetic acid, and the mixture was stirred at 63 ℃ for 18 hours. To the resulting mixture were added 24.9 parts of acetic acid, 19.4 parts of barbituric acid and 32.8 parts of methanol, and the mixture was stirred at 63 ℃ for 7 hours. To the resulting mixture was added 259 parts of a 50% methanol aqueous solution, and the mixture was stirred at 63 ℃ for 7 days. The resulting mixture was filtered. To the resulting residue, 902 parts of tetrahydrofuran was added, and the mixture was stirred at room temperature. The mixture was filtered, and the resulting residue was purified by column chromatography to give a compound represented by the formula (IZ 5-23).
Identification of Compound represented by the formula (IZ5-23)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+383
Exact molecular weight (Exact masses): 382
Example 8Z5XXX
10.0 parts of 4-nitrophthalonitrile (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 149 parts of methanol were mixed. While keeping the temperature at 2 to 6 ℃, 5.86 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) was added dropwise to the obtained mixture over 20 minutes. The resulting mixture was stirred for 5 hours while being kept at 5 ℃ or lower.
While the resulting mixture was kept at 5 ℃ or lower, 5.79 parts of acetic acid, 9.25 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 74 parts of methanol were added. The resulting mixture was stirred at 65 ℃ for 3 days. To the obtained mixture were added 2.88 parts of acetic acid and 4.63 parts of 2-cyanoacetanilide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). The resulting mixture was stirred at 65 ℃ for 3 days. In addition, up to this point in time, a total of 140 parts of methanol was added in addition to the above-mentioned methanol.
To the obtained mixture were added 24.0 parts of acetic acid, 15.3 parts of barbituric acid (manufactured by Tokyo chemical industry Co., Ltd.) and 363 parts of water, and the mixture was stirred at 65 ℃ for 9 days. The solvent of the resulting mixture was distilled off by a rotary evaporator, and then the resulting residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-25).
Identification of Compound represented by the formula (IZ5-25)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+445
Exact molecular weight (Exact masses): 444
Example 9Z5
5.0 parts of 4, 5-dichlorophthalonitrile and 62 parts of methanol were mixed.
While the mixture was kept at 5 ℃ or lower, a 25% sodium methoxide methanol solution containing sodium methoxide in an amount of 0.5 times the molar amount of 5.0 parts by mole of 4, 5-dichlorophthalonitrile was added. The mixture was stirred at 5 ℃ or below for 5 hours. To the mixture were added 2-cyano-N-methylacetamide and 6.1 parts of acetic acid in an amount of 1.5 times the molar amount of 5.0 parts of 4, 5-dichlorophthalonitrile, while keeping the mixture at 5 ℃ or lower. The mixture was stirred at 65 ℃ for 3 days.
This mixture was mixed with 4.2 parts of acetic acid, 5.2 parts of barbituric acid, 500 parts of methanol and 562 parts of water, and stirred at 65 ℃ for 9 days. After the solvent was distilled off from the mixture by a rotary evaporator, the obtained residue was purified by column chromatography to obtain a compound represented by the formula (IZ 5-247).
Identification of Compound represented by the formula (IZ5-247)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+406
Exact molecular weight (Exact masses): 405
Example 101Z5
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 5) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 5: the compound represented by the formula (IZ5-1) obtained in example 1Z5
50 parts of (a) a mixture of (b),
dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.)
58 parts of (a) to (b),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by the formula (IZ5-1) obtained in example 1Z5 was dispersed using a bead mill to obtain a colored composition.
Next, the following were mixed to obtain colored curable composition 1Z5,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 5);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): n-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01, manufactured by BASF corporation)
15 parts of (1);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z5 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. Exposing the colored curable composition layer to a solution containing a nonionic surfactant 0.12 at 25 deg.C % and 0.04% potassium hydroxide aqueous solution for 70 seconds, followed by development and water washing. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z5 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 8Z 5.
Example 102Z5
A colored curable composition 2Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 103Z5
A colored curable composition 3Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 104Z5
A colored curable composition 4Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the compound represented by the formula (IZ5-25) obtained in example 4Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 105Z5
A colored curable composition 5Z5 was obtained in the same manner as in example 101Z5 except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 106Z5
A colored curable composition 6Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 2Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 107Z5
A colored curable composition 7Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 3Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 108Z5
A colored curable composition 8Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-25) obtained in example 4Z5 was replaced with c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 109Z5
A colored curable composition 9Z5 was obtained in the same manner as in example 101Z5 except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 110Z5
A colored curable composition 10Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 2Z5 was replaced with the compound represented by the formula (IZ5-3) obtained in example 2Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 111Z5
A colored curable composition 11Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-1) obtained in example 3Z5 was replaced with the compound represented by the formula (IZ5-23) obtained in example 3Z5, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Example 112Z5
A colored curable composition 12Z5 was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment green 58 and the compound represented by the formula (IZ5-25) obtained in example 4Z5 was replaced with c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 1Z5
A colored curable composition C1Z5 was obtained and a colored pattern was obtained in the same manner as in example 101Z5 except that the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 2Z5
A colored curable composition C2Z5 was obtained in the same manner as in example 101Z5, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 7, and the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C2Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
Comparative example 3Z5
A colored curable composition C3Z5 was obtained in the same manner as in example 101Z5, except that the c.i. pigment green 58 was replaced with the c.i. pigment green 59, and the compound represented by the formula (IZ5-1) obtained in example 1Z5 was replaced with the c.i. pigment yellow 185, to obtain a colored curable composition C3Z5, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 5.
[ Table 8Z5]
TABLE 8Z5
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z5 | 2.3 | 3 |
Example 102Z5 | 2.3 | 3 |
Example 103Z5 | 2.3 | 3 |
Example 104Z5 | 2.3 | 3 |
Example 105Z5 | 2.3 | 3 |
Example 106Z5 | 2.3 | 3 |
Example 107Z5 | 2.3 | 3 |
Example 108Z5 | 2.3 | 3 |
Example 109Z5 | 2.3 | 3 |
Example 110Z5 | 2.3 | 3 |
Example 111Z5 | 2.3 | 3 |
Example 112Z5 | 2.3 | 3 |
Comparative example 1Z5 | 2.3 | 15 |
Comparative example 2Z5 | 2.3 | 15 |
Comparative example 3Z5 | 2.3 | 15 |
Example 113Z5
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 5) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 5: 50 parts of a compound represented by the formula (IZ5-1),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IZ5-1) was dispersed using a bead mill to obtain a coloring composition.
Next, the following were mixed to obtain a colored curable composition 13Z5,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 5);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z5 except that a colored curable composition 13Z5 was used instead of the colored curable composition 1Z 5. A colored coating film was obtained in the same manner as in example 101Z5 except that a colored curable composition 13Z5 was used in place of the colored curable composition 1Z5, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 5.
Example 114Z5 to example 117Z5
A colored pattern was obtained in the same manner as in example 113Z5, except that the compound represented by the formula (IZ5-1) was replaced with the colorant shown in the column of "colorant" in table 9Z 5. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
Example 118Z5 to example 122Z5
A colored pattern was obtained in the same manner as in example 113Z5 except that the compound represented by the formula (IZ5-1) was replaced with the compound shown in the column of "colorant" in table 9Z5 and the c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
Example 123Z5 to example 127Z5
A colored pattern was obtained in the same manner as in example 113Z5 except that the compound represented by the formula (IZ5-1) was replaced with the compound shown in the column of "colorant" in table 9Z5 and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 5.
[ Table 9Z5]
TABLE 9Z5
Coloring agent | Film thickness (mum) | Phase difference value (nm) | |
Example 113Z5 | A compound represented by the formula (IZ5-1) | 2.3 | 3 |
Example 114Z5 | A compound represented by the formula (IZ5-3) | 2.3 | 3 |
Example 115Z5 | A compound represented by the formula (IZ5-23) | 2.3 | 3 |
Example 116Z5 | A compound represented by the formula (IZ5-25) | 2.3 | 3 |
Example 117Z5 | A compound represented by the formula (IZ5-247) | 2.3 | 3 |
Example 118Z5 | A compound represented by the formula (IZ5-1) | 2.3 | 3 |
Example 119Z5 | A compound represented by the formula (IZ5-3) | 2.3 | 3 |
Example 120Z5 | A compound represented by the formula (IZ5-23) | 2.3 | 3 |
Example 121Z5 | A compound represented by the formula (IZ5-25) | 2.3 | 3 |
Example 122Z5 | A compound represented by the formula (IZ5-247) | 2.3 | 3 |
Example 123Z5 | A compound represented by the formula (IZ5-1) | 2.3 | 3 |
Example 124Z5 | A compound represented by the formula (IZ5-3) | 2.3 | 3 |
Example 125Z5 | A compound represented by the formula (IZ5-23) | 2.3 | 3 |
Example 126Z5 | A compound represented by the formula (IZ5-25) | 2.3 | 3 |
Example 127Z5 | A compound represented by the formula (IZ5-247) | 2.3 | 3 |
In example Z5, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Example Z6
Example 1Z6
7.02 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 61.6 parts of methanol were mixed. While the temperature of the obtained mixture was kept at 2 ℃, a mixture of 8.20 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 74.6 parts of methanol was added dropwise over 1 hour and 30 minutes. The resulting mixture was stirred at 2 ℃ for 6 hours and 15 minutes. While the temperature of the obtained mixture was kept at 4 ℃ or lower, 10.7 parts of acetic acid was added. To the resulting mixture, 17.6 parts of benzoylacetonitrile (benzophenonitrile) (manufactured by tokyo chemical industry Co., Ltd.) was added, and the mixture was stirred at room temperature for 44 hours. The resulting mixture was filtered, and the residue was washed with 800 parts of methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 18.0 parts of a compound represented by the formula (IFFZ 6-1).
Identification of Compound represented by the formula (IFFZ6-1)
(Mass Spectrometry) ionization mode ESI +: m/z ═ M + H]+402
Exact molecular weight (Exact masses): 401
While 7.6 parts of fuming sulfuric acid (25%) at 3 ℃ (manufactured by Wako pure chemical industries, Ltd.) was stirred, 0.513 part of the compound represented by the formula (IFFZ6-1) obtained in example 2Z6 was added. To the resulting mixture was added 3.8 parts of fuming sulfuric acid (25%) (manufactured by Wako pure chemical industries, Ltd.). The resulting mixture was stirred and heated to 15 ℃ over 3 hours and 30 minutes. 139 parts of ice water and 38.2 parts of sodium chloride were added to the obtained mixture. The resulting mixture was filtered, and the resulting residue was washed with 64 parts of a 21.5% aqueous sodium chloride solution. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 1.02 parts of a compound represented by the formula (IFFZ 6-2).
Identification of Compound represented by the formula (IFFZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-560
Exact molecular weight (Exact masses): 561
5.11 parts of a compound represented by the formula (IFFZ6-2) and 511 parts of water were mixed at room temperature. To the obtained mixture, a mixture of 6.72 parts of barium chloride dihydrate (manufactured by Wako pure chemical industries, Ltd.) and 60 parts of water was added. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 2.98 parts of a compound represented by the formula (IFZ 6-4).
Identification of Compound represented by the formula (IFZ6-4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ba++H]-560
Exact molecular weight (Exact masses): 697
Example 2Z6
10.0 parts of a compound represented by the formula (IFFZ6-2) and 1000 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 87.0 parts of a 10% aqueous solution of barium chloride dihydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 9.43 parts of a compound represented by the formula (IFZ 6-4).
Identification of Compound represented by the formula (IFZ6-4)
(Mass Spectrometry) ionization modeThe formula is ESI-: m/z ═ M-Ba + H]-560
Exact molecular weight (Exact masses): 697
Example 3Z6
5.02 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of a 50% aqueous methanol solution were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 95.0 parts of a 10% strontium chloride hexahydrate aqueous solution. The resulting mixture was filtered, and the resulting residue was washed with 50% aqueous methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 4.00 parts of a compound represented by the formula (IFZ 6-3).
Identification of Compound represented by the formula (IFZ6-3)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Sr + H]-560
Exact molecular weight (Exact masses): 647
Example 4Z6
0.501 part of a compound represented by the formula (IFFZ6-2) and 50.0 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 12.6 parts of a 10% aqueous calcium chloride solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.024 part of a compound represented by the formula (IFZ 6-2).
Identification of Compound represented by the formula (IFZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ca + H]-560
Exact molecular weight (Exact masses): 599
Example 5Z6
0.500 parts of a compound represented by the formula (IFFZ6-2) and 50.0 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 3.52 parts of a 10% aqueous solution of manganese chloride tetrahydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.015 part of a compound represented by the formula (IFZ 6-10).
Identification of Compound represented by the formula (IFZ6-10)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mn + H]-560
Exact molecular weight (Exact masses): 614
Example 6Z6
A compound represented by the formula (IFZ6-6) was obtained in the same manner as in example 2Z6, except that barium chloride dihydrate was replaced with zinc nitrate hexahydrate.
Identification of Compound represented by the formula (IFZ6-6)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Zn + H]-560
Exact molecular weight (Exact masses): 623
Example 7Z6
5.00 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 23.7 parts of a 10% aqueous aluminum chloride solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.474 parts of a compound represented by the formula (IFZ 6-11).
Identification of Compound represented by the formula (IFZ6-11)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Al)/3+ H]-560
Exact molecular weight (Exact masses): 1731
Example 8Z6
5.01 parts of a compound represented by the formula (IFFZ6-2) and 500 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 36.0 parts of a 10% aqueous solution of ferric nitrate nonahydrate. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 3.80 parts of a compound represented by the formula (IFZ 6-12).
Identification of Compound represented by the formula (IFZ6-12)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Fe)/3+ H]-560
Exact molecular weight (Exact masses): 1789
Example 9Z6
0.498 part of the compound represented by the formula (IFFZ6-2) and 49.9 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the homogeneous solution was added 4.45 parts of a 10% aqueous copper sulfate pentahydrate solution. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 0.018 parts of a compound represented by the formula (IFZ 6-31).
Identification of Compound represented by the formula (IFZ6-31)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Cu + H]-560
Exact molecular weight (Exact masses): 622
Example 10Z6
The procedure was carried out in the same manner as in example 1Z6 except that benzoylacetonitrile was replaced with 4-cyanoacetylbenzoic acid to give a compound represented by the formula (IFFZ6-1), thereby giving a compound represented by the formula (IJZ 6-1).
Identification of Compound represented by the formula (IJJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-488
Exact molecular weight (Exact masses): 489
16.3 parts of a compound represented by the formula (IJZ 6-1) and 1630 parts of water were mixed at room temperature. To the resulting mixture, a 5% aqueous solution of sodium hydroxide was added dropwise to obtain a homogeneous solution. To the resulting homogeneous solution, 163 parts of a 10% barium chloride dihydrate aqueous solution was added. The resulting mixture was filtered, and the resulting residue was washed with water. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 7.49 parts of a compound represented by the formula (IJZ 6-4).
Identification of Compound represented by the formula (IJZ6-4)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ba + H]-488
Exact molecular weight (Exact masses): 625
Example 11Z6
A compound represented by the formula (IJZ6-3) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with strontium chloride hexahydrate.
Identification of Compound represented by the formula (IJZ6-3)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Sr + H]-488
Exact molecular weight (Exact masses): 575
Example 12Z6
A compound represented by the formula (IJZ6-2) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with calcium chloride.
Identification of Compound represented by the formula (IJZ6-2)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Ca + H ]-488
Exact molecular weight (Exact masses): 527
Example 13Z6
A compound represented by the formula (IJZ6-10) was obtained by the same operation as in example 10Z6, except that barium chloride dihydrate was replaced with manganese chloride tetrahydrate.
Identification of Compound represented by the formula (IJZ6-10)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mn + H]-488
Exact molecular weight (Exact masses): 542
Example 14Z6
A compound represented by the formula (IJZ6-31) was obtained by the same operation as in example 10Z6, except that barium chloride dihydrate was replaced with copper sulfate pentahydrate.
Identification of Compound represented by the formula (IJZ6-31)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Cu + H]-488
Exact molecular weight (Exact masses): 550
Example 15Z6
A compound represented by the formula (IJZ6-6) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with zinc nitrate hexahydrate.
Identification of Compound represented by the formula (IJZ6-6)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Zn + H]-488
Exact molecular weight (Exact masses): 551
Example 16Z6
A compound represented by the formula (IJZ6-11) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with aluminum chloride.
Identification of Compound represented by the formula (IJZ6-11)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Al)/3+ H]-488
Exact molecular weight (Exact masses): 1515
Example 17Z6
A compound represented by the formula (IJZ6-12) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with iron nitrate nonahydrate.
Identification of Compound represented by the formula (IJZ6-12)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ [ (M-2Fe)/3+ H]-488
Exact molecular weight (Exact masses): 1573
Example 18Z6
A compound represented by the formula (IJZ6-1) was obtained in the same manner as in example 10Z6, except that barium chloride dihydrate was replaced with magnesium chloride.
Identification of Compound represented by the formula (IJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-Mg + H]-488
Exact molecular weight (Exact masses): 511
Example 19Z6
5.00 parts of phthalonitrile (manufactured by Tokyo chemical Co., Ltd.) and 44 parts of methanol were mixed. To the obtained mixture, a mixture of 5.84 parts of 28% sodium methoxide methanol solution (manufactured by Wako pure chemical industries, Ltd.) and 54 parts of methanol was added dropwise over 1 hour and 30 minutes while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred at 5 ℃ or lower for 12 hours. To the resulting mixture, 11.5 parts of acetic acid, 24.5 parts of 4-cyanoacetylbenzoic acid and 712 parts of methanol were added while keeping the temperature at 5 ℃ or lower. The resulting mixture was stirred at room temperature for 4 hours and then at 40 ℃ for 96 hours. The solvent was distilled off from the obtained mixture by a rotary evaporator, and the obtained residue was purified by column chromatography to obtain 0.471 part of a compound represented by the formula (IJJZ 6-1).
Identification of Compound represented by the formula (IJJZ6-1)
(Mass Spectrometry) ionization mode-ESI-: m/z ═ M-H]-488
Exact molecular weight (Exact masses): 489
Example 101Z6
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 6) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 6: 50 parts of a compound represented by the formula (IFZ6-4),
58 parts of a dispersant (BYK-LPN 6919; manufactured by BYK-Chemie Japan, Ltd.),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IFZ6-4) was dispersed using a bead mill, to thereby obtain a coloring composition. Next, the following were mixed to obtain colored curable composition 1Z6,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 6);
400 parts of the obtained coloring composition;
Resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
[ preparation of colored Pattern ]
A colored curable composition 1Z6 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, the substrate on which the colored curable composition layer was formed and a photomask made of quartz glass were spaced at a distance of 200 μm, and exposed to an exposure apparatus (TME-150 RSK; manufactured by Topcon Corporation) at a rate of 80mJ/cm in an atmospheric atmosphere2Exposure was carried out with the exposure amount (based on 365 nm). As the photomask, a photomask in which a line-and-space pattern of 100 μm was formed was used. The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, and washed with water. The colored curable composition layer was post-baked at 230 ℃ for 30 minutes, whereby a colored pattern was obtained.
[ measurement of phase difference value ]
A colored curable composition 1Z6 was applied to a 2-inch square glass substrate (EAGLE XG; manufactured by Corning corporation) by a spin coating method, and then prebaked at 100 ℃ for 3 minutes to form a colored curable composition layer. After cooling, an exposure machine (TME-150 RSK; manufactured by Topcon Corporation) was used for the colored curable composition layer under an atmospheric atmosphere at 80mJ/cm2Exposure was carried out with the exposure amount (based on 365 nm). The colored curable composition layer after exposure was immersed in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ℃ for 70 seconds, developed, washed with water, and dried. Subjecting the dried colored curable composition layer to 3 at 230 ℃And baked after 0 minute, thereby obtaining a colored coating film.
The film thickness of the obtained colored coating film was measured using DEKTAK3 (manufactured by japan vacuum technology corporation).
The phase difference value at an inclination angle of 45 ° of the colored coating film was measured using an ellipsometer (M-220 type spectroscopic ellipsometer; manufactured by japan spectro (ltd.)). For the measurement of the retardation value, light having a wavelength of 550nm was used. The results are shown in Table 5Z 6.
Example 102Z6
A colored curable composition 2Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-2). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 103Z6
A colored curable composition 3Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-3). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 104Z6
A colored curable composition 4Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-6). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 105Z6
A colored curable composition 5Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-10). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 106Z6
A colored curable composition 6Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-11). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 107Z6
A colored curable composition 7Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-12). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 108Z6
A colored curable composition 8Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ 6-31). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 109Z6
A colored curable composition 9Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-1). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 110Z6
A colored curable composition 10Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-2). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 111Z6
A colored curable composition 11Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-3). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 112Z6
A colored curable composition 12Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-4). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 113Z6
A colored curable composition 13Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-6). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 114Z6
A colored curable composition 14Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-10). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 115Z6
A colored curable composition 15Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-11). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 116Z6
A colored curable composition 16Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-12). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 117Z6
A colored curable composition 17Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ 6-31). Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 5Z 6.
Example 118Z6
A colored curable composition 18Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 119Z6
A colored curable composition 19Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 120Z6
A colored curable composition 20Z6 was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 7, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 121Z6
A colored curable composition 21Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 122Z6
A colored curable composition 22Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 123Z6
A colored curable composition 23Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-11) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 124Z6
A colored curable composition 24Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 125Z6
A colored curable composition 25Z6 was obtained in the same manner as in example 101Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 126Z6
A colored curable composition 26Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-1) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 127Z6
A colored curable composition 27Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 128Z6
A colored curable composition 28Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 129Z6
A colored curable composition 29Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-4) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 130Z6
A colored curable composition 30Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 131Z6
A colored curable composition 31Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 132Z6
A colored curable composition 32Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-11) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 133Z6
A colored curable composition 33Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 134Z6
A colored curable composition 34Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 6Z 6.
Example 135Z6
A colored curable composition 35Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 136Z6
A colored curable composition 36Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 137Z6
A colored curable composition 37Z6 was obtained in the same manner as in example 101Z6 except that the c.i. pigment green 58 was replaced with c.i. pigment green 59, and a colored pattern was obtained. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 138Z6
A colored curable composition 38Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 139Z6
A colored curable composition 39Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 140Z6
A colored curable composition 40Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-11), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 141Z6
A colored curable composition 41Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-12) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 142Z6
A colored curable composition 42Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IFZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 143Z6
A colored curable composition 43Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-1) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 144Z6
A colored curable composition 44Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-2) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 145Z6
A colored curable composition 45Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-3) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 146Z6
A colored curable composition 46Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-4), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 147Z6
A colored curable composition 47Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-6) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 148Z6
A colored curable composition 48Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-10) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 149Z6
A colored curable composition 49Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-11), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 150Z6
A colored curable composition 50Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-12), and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, to obtain a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Example 151Z6
A colored curable composition 51Z6 was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with the compound represented by the formula (IJZ6-31) and the c.i. pigment green 58 was replaced with the c.i. pigment green 59, thereby obtaining a colored pattern. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 7Z 6.
Comparative example 1Z6
A colored curable composition C1Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that the compound represented by the formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
Comparative example 2Z6
A colored curable composition C2Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 7 and the compound represented by formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
Comparative example 3Z6
A colored curable composition C3Z6 was obtained and a colored pattern was obtained in the same manner as in example 101Z6, except that c.i. pigment green 58 was replaced with c.i. pigment green 59, and the compound represented by formula (IFZ6-4) was replaced with c.i. pigment yellow 185. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 8Z 6.
[ Table 5Z6]
TABLE 5Z6
Film thickness (mum) | Phase difference value (nm) | |
Example 101Z6 | 2.3 | 2 |
Example 102Z6 | 2.3 | 3 |
Example 103Z6 | 2.3 | 2 |
Example 104Z6 | 2.3 | 3 |
Example 105Z6 | 2.3 | 2 |
Example 106Z6 | 2.3 | 2 |
Example 107Z6 | 2.3 | 3 |
Example 108Z6 | 2.3 | 3 |
Example 109Z6 | 2.3 | 2 |
Example 110Z6 | 2.3 | 2 |
Example 111Z6 | 2.3 | 2 |
Example 112Z6 | 2.3 | 2 |
Example 113Z6 | 2.3 | 2 |
Example 114Z6 | 2.3 | 2 |
Example 115Z6 | 2.3 | 2 |
Example 116Z6 | 2.3 | 3 |
Example 117Z6 | 2.3 | 3 |
[ Table 6Z6]
TABLE 6Z6
Film thickness (mum) | Phase difference value (nm) | |
Example 118Z6 | 2.3 | 2 |
Example 119Z6 | 2.3 | 3 |
Example 120Z6 | 2.3 | 2 |
Example 121Z6 | 2.3 | 2 |
Example 122Z6 | 2.3 | 2 |
Example 123Z6 | 2.3 | 2 |
Example 124Z6 | 2.3 | 2 |
Example 125Z6 | 2.3 | 3 |
Example 126Z6 | 2.3 | 2 |
Example 127Z6 | 2.3 | 2 |
Example 128Z6 | 2.3 | 2 |
Example 129Z6 | 2.3 | 2 |
Example 130Z6 | 2.3 | 3 |
Example 131Z6 | 2.3 | 3 |
Example 132Z6 | 2.3 | 2 |
Example 133Z6 | 2.3 | 2 |
Example 134Z6 | 2.3 | 3 |
[ Table 7Z6]
TABLE 7Z6
Film thickness (mum) | Phase difference value (nm) | |
Example 135Z6 | 2.3 | 2 |
Example 136Z6 | 2.3 | 2 |
Example 137Z6 | 2.3 | 2 |
Example 138Z6 | 2.3 | 2 |
Example 139Z6 | 2.3 | 2 |
Example 140Z6 | 2.3 | 2 |
Example 141Z6 | 2.3 | 2 |
Example 142Z6 | 2.3 | 3 |
Example 143Z6 | 2.3 | 2 |
Example 144Z6 | 2.3 | 2 |
Example 145Z6 | 2.3 | 2 |
Example 146Z6 | 2.3 | 2 |
Example 147Z6 | 2.3 | 2 |
Example 148Z6 | 2.3 | 2 |
Example 149Z6 | 2.3 | 2 |
Example 150Z6 | 2.3 | 2 |
Example 151Z6 | 2.3 | 2 |
[ Table 8Z6]
TABLE 8Z6
Film thickness (mum) | Phase difference value (nm) | |
Comparative example 1Z6 | 2.3 | 15 |
Comparative example 2Z6 | 2.3 | 15 |
Comparative example 3Z6 | 2.3 | 15 |
Example 152Z6
The following substances are mixed together and then,
pigment: 5860 portions of C.I. pigment green,
8.1 parts of acrylic pigment dispersing agent,
resin (B): 73 parts of resin B5 solution, and
solvent (E): 290 parts of propylene glycol monomethyl ether acetate
The pigment dispersion liquid (liquid containing colorant A1Z 6) was prepared by dispersing the pigment using a bead mill. In addition, the following substances were mixed,
colorant AZ 6: 50 parts of a compound represented by the formula (IFZ6-4),
58 parts of a dispersant solution (solid content: 60%),
resin (B): 93 parts of resin B3 solution, and
solvent (E): propylene glycol monomethyl ether acetate 800 parts
The compound represented by formula (IFZ6-4) was dispersed using a bead mill to obtain a coloring composition. Next, the following were mixed to obtain colored curable composition 52Z6,
the total amount of the obtained pigment dispersion (the liquid containing the colorant A1Z 6);
400 parts of the obtained coloring composition;
resin (B): 45 parts of resin B1 solution;
polymerizable compound (C): 25 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kagaku Co., Ltd.);
polymerization initiator (D): 15 parts of N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine (Irgacure (registered trademark) OXE-01; manufactured by BASF corporation);
Solvent (E): 86 parts of propylene glycol monomethyl ether acetate; and
leveling agent: 0.12 part of polyether-modified Silicone oil (Toray Silicone SH 8400; manufactured by Dow Corning Toray Co., Ltd.).
A colored pattern was produced in the same manner as in example 101Z6 except that a colored curable composition 52Z6 was used instead of the colored curable composition 1Z 6. A colored coating film was obtained in the same manner as in example 101Z6 except that a colored curable composition 52Z6 was used in place of the colored curable composition 1Z6, and the film thickness and the retardation value were measured. The results are shown in Table 9Z 6.
Example 153Z6 to example 168Z6
A colored pattern was obtained in the same manner as in example 152Z6 except that the compound represented by the formula (IFZ6-4) was replaced with the colorant shown in the column of "colorant" in table 9Z 6. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 9Z 6.
Example 169Z6 to example 185Z6
A colored pattern was obtained in the same manner as in example 152Z6, except that the compound represented by formula (IFZ6-4) was replaced with the compound shown in the column of "colorant" in table 10Z6, and that c.i. pigment green 58 was replaced with c.i. pigment green 7. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 10Z 6.
Example 186Z6 to example 202Z6
A colored pattern was obtained in the same manner as in example 152Z6, except that the compound represented by formula (IFZ6-4) was replaced with the compound shown in the column of "colorant" in table 11Z6, and that c.i. pigment green 58 was replaced with c.i. pigment green 59. Further, a colored coating film was obtained, and film thickness measurement and retardation value measurement were performed. The results are shown in Table 11Z 6.
[ Table 9Z6]
TABLE 9Z6
Film thickness (mum) | Phase difference value (nm) | ||
Example 186Z6 | A compound represented by the formula (IFZ6-4) | 2.3 | 3 |
Example 187Z6 | A compound represented by the formula (IFZ6-2) | 2.3 | 3 |
Example 188Z6 | A compound represented by the formula (IFZ6-3) | 2.3 | 3 |
Example 189Z6 | A compound represented by the formula (IFZ6-6) | 2.3 | 3 |
Example 190Z6 | A compound represented by the formula (IFZ6-10) | 2.3 | 3 |
Example 191Z6 | A compound represented by the formula (IFZ6-11) | 2.3 | 3 |
Example 192Z6 | A compound represented by the formula (IFZ6-12) | 2.3 | 3 |
Example 193Z6 | A compound represented by the formula (IFZ6-31) | 2.3 | 3 |
Example 194Z6 | A compound represented by the formula (IJZ6-1) | 2.3 | 3 |
Example 195Z6 | A compound represented by the formula (IJZ6-2) | 2.3 | 3 |
Example 196Z6 | A compound represented by the formula (IJZ6-3) | 2.3 | 3 |
Example 197Z6 | A compound represented by the formula (IJZ6-4) | 2.3 | 3 |
Example 198Z6 | A compound represented by the formula (IJZ6-6) | 2.3 | 3 |
Example 199Z6 | A compound represented by the formula (IJZ6-10) | 2.3 | 3 |
Example 200Z6 | A compound represented by the formula (IJZ6-11) | 2.3 | 3 |
Example 201Z6 | A compound represented by the formula (IJZ6-12) | 2.3 | 3 |
Example 202Z6 | A compound represented by the formula (IJZ6-31) | 2.3 | 3 |
[ Table 10Z6]
TABLE 10Z6
Film thickness (mum) | Phase difference value (nm) | ||
Example 169Z6 | A compound represented by the formula (IFZ6-4) | 2.3 | 3 |
Example 170Z6 | A compound represented by the formula (IFZ6-2) | 2.3 | 3 |
Example 171Z6 | A compound represented by the formula (IFZ6-3) | 2.3 | 3 |
Example 172Z6 | A compound represented by the formula (IFZ6-6) | 2.3 | 3 |
Example 173Z6 | A compound represented by the formula (IFZ6-10) | 2.3 | 3 |
Example 174Z6 | A compound represented by the formula (IFZ6-11) | 2.3 | 3 |
Example 175Z6 | A compound represented by the formula (IFZ6-12) | 2.3 | 3 |
Example 176Z6 | A compound represented by the formula (IFZ6-31) | 2.3 | 3 |
Example 177Z6 | A compound represented by the formula (IJZ6-1) | 2.3 | 3 |
Example 178Z6 | A compound represented by the formula (IJZ6-2) | 2.3 | 3 |
Example 179Z6 | A compound represented by the formula (IJZ6-3) | 2.3 | 3 |
Example 180Z6 | A compound represented by the formula (IJZ6-4) | 2.3 | 3 |
Example 181Z6 | A compound represented by the formula (IJZ6-6) | 2.3 | 3 |
Example 182Z6 | A compound represented by the formula (IJZ6-10) | 2.3 | 3 |
Example 183Z6 | A compound represented by the formula (IJZ6-11) | 2.3 | 3 |
Example 184Z6 | A compound represented by the formula (IJZ6-12) | 2.3 | 3 |
Example 185Z6 | A compound represented by the formula (IJZ6-31) | 2.3 | 3 |
[ Table 11Z6]
TABLE 11Z6
Film thickness (mum) | Phase difference value (nm) | ||
Example 186Z6 | A compound represented by the formula (IFZ6-4) | 2.3 | 3 |
Example 187Z6 | A compound represented by the formula (IFZ6-2) | 2.3 | 3 |
Example 188Z6 | A compound represented by the formula (IFZ6-3) | 2.3 | 3 |
Example 189Z6 | A compound represented by the formula (IFZ6-6) | 2.3 | 3 |
Example 190Z6 | A compound represented by the formula (IFZ6-10) | 2.3 | 3 |
Example 191Z6 | A compound represented by the formula (IFZ6-11) | 2.3 | 3 |
Example 192Z6 | A compound represented by the formula (IFZ6-12) | 2.3 | 3 |
Example 193Z6 | A compound represented by the formula (IFZ6-31) | 2.3 | 3 |
Example 194Z6 | A compound represented by the formula (IJZ6-1) | 2.3 | 3 |
Example 195Z6 | A compound represented by the formula (IJZ6-2) | 2.3 | 3 |
Example 196Z6 | A compound represented by the formula (IJZ6-3) | 2.3 | 3 |
Example 197Z6 | A compound represented by the formula (IJZ6-4) | 2.3 | 3 |
Example 198Z6 | A compound represented by the formula (IJZ6-6) | 2.3 | 3 |
Example 199Z6 | A compound represented by the formula (IJZ6-10) | 2.3 | 3 |
Example 200Z6 | A compound represented by the formula (IJZ6-11) | 2.3 | 3 |
Example 201Z6 | A compound represented by the formula (IJZ6-12) | 2.3 | 3 |
Example 202Z6 | A compound represented by the formula (IJZ6-31) | 2.3 | 3 |
In example Z6, it is understood from the above results that the retardation value of the colored coating film formed from the colored curable composition containing the compound of the present invention is smaller than that of the colored coating film formed from the colored curable composition containing c.i. pigment yellow 185.
Industrial applicability
The coloring composition and the compound of the present invention can be used for forming a color filter having a small phase difference value, and thus can be suitably used for a display device such as a color filter and a liquid crystal display device.
Claims (13)
1. A coloring composition comprising:
an alkali-soluble resin, and
a compound represented by formula (IZ 3);
in the formula (IZ3), R1Z3、R2Z3、R3Z3、R4Z3、R5Z3、R6Z3And R7Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R2Z3and R3Z3、R3Z3And R4Z3And R4Z3And R5Z3May be bonded to each other to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
2. The coloring composition according to claim 1, wherein R1Z3、R6Z3And R7Z3Is a hydrogen atom.
3. The coloring composition according to claim 1 or 2, wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is2Z3And R3Z3、R3Z3And R 4Z3And R4Z3And R5Z3At least one group of them is bonded to form a ring.
4. A coloring composition according to any one of claims 1 to 3, wherein R2Z3、R3Z3、R4Z3And R5Z3At least one of which is nitro or tert-butyl.
5. The coloring composition according to any one of claims 1 to 4, further comprising a solvent.
6. The coloring composition according to any one of claims 1 to 5, further comprising a yellow colorant or a green colorant.
7. A colored curable composition comprising a polymerizable compound and the colored composition according to any one of claims 1 to 6.
8. The colored curable composition according to claim 7, further comprising a polymerization initiator.
9. A color filter comprising the colored composition according to any one of claims 1 to 6 or the colored curable composition according to claim 7 or 8.
10. A liquid crystal display device comprising the color filter of claim 9.
11. A compound represented by the formula (IZ 3-B);
in the formula (IZ3-B), R1Z3、R21Z3、R31Z3、R41Z3、R51Z3、R61Z3And R71Z3Independently of one another, represents a hydrogen atom, -CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent;
R21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3May be bonded to each other to form a ring;
wherein R is21Z3、R31Z3、R41Z3And R51Z3At least one of which is-CO-R102Z3、-COO-R101Z3、-OCO-R102Z3、-COCO-R102Z3、-O-R102Z3、-SO2-R101Z3、-SO2N(R102Z3)2、-CON(R102Z3)2、-N(R102Z3)2、-NHCO-R102Z3、-NHCO-N(R102Z3)2、-NHCOOR102Z3、-OCON(R102Z3)2Halogen atom, cyano group, nitro group, -SO3M、-CO2M is a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent or a heterocyclic group which may have a substituent, or R is21Z3And R31Z3、R31Z3And R41Z3And R41Z3And R51Z3At least one group of them is bonded to form a ring;
R101Z3represents an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
R102Z3represents a hydrogen atom, an optionally substituted hydrocarbon group having 1 to 40 carbon atoms or an optionally substituted heterocyclic group;
m represents a hydrogen atom or an alkali metal atom;
R101Z3、R102Z3and when there are a plurality of M, they may be the same or different; the wavy line indicates the E-body or the Z-body.
12. The compound of claim 11Wherein R is1Z3、R61Z3And R71Z3Is a hydrogen atom.
13. The compound of claim 11 or 12, wherein R21Z3、R31Z3、R41Z3And R51Z3At least one of which is nitro or tert-butyl.
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