CN113056524A - Coloring composition - Google Patents
Coloring composition Download PDFInfo
- Publication number
- CN113056524A CN113056524A CN201980074259.1A CN201980074259A CN113056524A CN 113056524 A CN113056524 A CN 113056524A CN 201980074259 A CN201980074259 A CN 201980074259A CN 113056524 A CN113056524 A CN 113056524A
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- meth
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- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 238000004040 coloring Methods 0.000 title claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 229
- 239000003086 colorant Substances 0.000 claims abstract description 97
- 239000011347 resin Substances 0.000 claims abstract description 41
- 229920005989 resin Polymers 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 239000002904 solvent Substances 0.000 claims description 60
- 239000011342 resin composition Substances 0.000 claims description 52
- 239000003505 polymerization initiator Substances 0.000 claims description 22
- 125000002723 alicyclic group Chemical group 0.000 claims description 20
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- -1 pentane-1, 5-diyl group Chemical group 0.000 description 341
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 56
- 239000000460 chlorine Substances 0.000 description 54
- 239000000178 monomer Substances 0.000 description 52
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
- 239000000243 solution Substances 0.000 description 36
- 150000002430 hydrocarbons Chemical group 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 20
- 239000010408 film Substances 0.000 description 19
- 239000000975 dye Substances 0.000 description 18
- 239000000049 pigment Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- 239000002270 dispersing agent Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 15
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 239000003963 antioxidant agent Substances 0.000 description 12
- 230000003078 antioxidant effect Effects 0.000 description 12
- 235000006708 antioxidants Nutrition 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 6
- 238000000206 photolithography Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 5
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 239000004471 Glycine Substances 0.000 description 4
- AGPKZVBTJJNPAG-UHFFFAOYSA-N Isoleucine Chemical compound CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000004292 cyclic ethers Chemical group 0.000 description 4
- 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 4
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 3
- VFBJXXJYHWLXRM-UHFFFAOYSA-N 2-[2-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]ethylsulfanyl]ethyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCSCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 VFBJXXJYHWLXRM-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- LOCXTTRLSIDGPS-UHFFFAOYSA-N [[1-oxo-1-(4-phenylsulfanylphenyl)octan-2-ylidene]amino] benzoate Chemical compound C=1C=C(SC=2C=CC=CC=2)C=CC=1C(=O)C(CCCCCC)=NOC(=O)C1=CC=CC=C1 LOCXTTRLSIDGPS-UHFFFAOYSA-N 0.000 description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000004528 spin coating Methods 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- ZBOLYDUBEGGDKS-UHFFFAOYSA-N 1,6,7,12-tetrachloroperylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=C(Cl)C=C(C(O)=O)C2=C(C(O)=O)C=C(Cl)C=1C1=C(Cl)C=C(C(O)=O)C2=C1C3=C(Cl)C=C2C(=O)O ZBOLYDUBEGGDKS-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- SWTNRXKFJNGFRF-UHFFFAOYSA-N 14-aminotetradecanoic acid Chemical compound NCCCCCCCCCCCCCC(O)=O SWTNRXKFJNGFRF-UHFFFAOYSA-N 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AXMCIYLNKNGNOT-UHFFFAOYSA-M sodium;3-[[4-[(4-dimethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)-[4-[ethyl-[(3-sulfonatophenyl)methyl]amino]phenyl]methyl]-n-ethylanilino]methyl]benzenesulfonate Chemical compound [Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](C)C)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 AXMCIYLNKNGNOT-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- BZBMBZJUNPMEBD-UHFFFAOYSA-N tert-butyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC(C)(C)C)CC1C=C2 BZBMBZJUNPMEBD-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 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 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- WNQPPENQFWLADQ-UHFFFAOYSA-J tetrasodium;4-hydroxy-5-[[4-[[4-[(8-hydroxy-3,6-disulfonatonaphthalen-1-yl)diazenyl]-2-methoxy-5-methylphenyl]carbamoylamino]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC(O)=C2C(N=NC3=C(C)C=C(C(=C3)OC)NC(=O)NC3=CC(C)=C(N=NC=4C5=C(O)C=C(C=C5C=C(C=4)S([O-])(=O)=O)S([O-])(=O)=O)C=C3OC)=CC(S([O-])(=O)=O)=CC2=C1 WNQPPENQFWLADQ-UHFFFAOYSA-J 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- VRVDFJOCCWSFLI-UHFFFAOYSA-K trisodium 3-[[4-[(6-anilino-1-hydroxy-3-sulfonatonaphthalen-2-yl)diazenyl]-5-methoxy-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].[Na+].COc1cc(N=Nc2cc(c3cccc(c3c2)S([O-])(=O)=O)S([O-])(=O)=O)c(C)cc1N=Nc1c(O)c2ccc(Nc3ccccc3)cc2cc1S([O-])(=O)=O VRVDFJOCCWSFLI-UHFFFAOYSA-K 0.000 description 1
- WTPOYMNMKZIOGO-UHFFFAOYSA-K trisodium;2,5-dichloro-4-[4-[[5-[[4-chloro-6-(4-sulfonatoanilino)-1,3,5-triazin-2-yl]amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC(N=1)=NC(Cl)=NC=1NC1=CC=C(S([O-])(=O)=O)C=C1 WTPOYMNMKZIOGO-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- JXUKQCUPTNLTCS-UHFFFAOYSA-N vat green 1 Chemical compound C1=CC=C[C]2C(=O)C(C3=C45)=CC=C4C(C4=C67)=CC=C7C(=O)[C]7C=CC=CC7=C6C=C(OC)C4=C5C(OC)=CC3=C21 JXUKQCUPTNLTCS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940042596 viscoat Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 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
- C09B57/08—Naphthalimide dyes; Phthalimide dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
- C08K5/3465—Six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- 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
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with 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
-
- 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
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention aims to provide a coloring composition with excellent heat resistance. The present invention relates to a coloring composition comprising a colorant and a resin, wherein the colorant contains a compound represented by the following formula (I) and a compound represented by the following formula (II).
Description
Technical Field
The present invention relates to a colored composition, and further relates to a colored curable resin composition, a color filter, and a display device.
Background
In the field of agricultural films, a fluorescent film having a resin layer containing Lumogen (registered trademark) F orange 240, which is a trade name of perylene compounds, is known (patent document 1).
Documents of the prior art
Patent document
Patent document 1: japanese laid-open patent publication No. 10-235776
Disclosure of Invention
In the field of coloring agents, improvement of heat resistance is required.
The purpose of the present invention is to provide a coloring composition having excellent heat resistance. Another object of the present invention is to provide a colored composition having high transmittance at a wavelength of 630nm and excellent heat resistance.
The invention provides the following colored composition, colored curable resin composition, color filter and display device.
[1] A coloring composition comprising a coloring agent and a resin, wherein the coloring agent contains a compound represented by the following formula (I) and a compound represented by the following formula (II).
[ in the formula (II),
R1and R2Each independently represents a 2-valent hydrocarbon group having 1 to 20 carbon atoms.
R3~R10Each independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.]
[2]According to [1]The coloring composition, wherein R is1And R2Is a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.
[3]According to [1]The coloring composition, wherein R is1And R2Each independently is an alkanediyl group having 1 to 20 carbon atoms.
[4]According to [1]The coloring composition, wherein R is1And R2Each independently is a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.
[5] A colored curable resin composition comprising a compound represented by the following formula (I), a compound represented by the following formula (II), a resin, a polymerizable compound, a polymerization initiator and a solvent.
[ in the formula (II),
R1and R2Each independently represents a 2-valent hydrocarbon group having 1 to 20 carbon atoms.
R3~R10Each independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.]
[6] A color filter comprising the colored curable resin composition according to [5 ].
[7] A display device comprising the color filter according to [6 ].
According to the present invention, a colored composition having excellent heat resistance can be provided.
Detailed Description
(1) Coloring composition
The coloring composition of the present invention comprises a colorant (hereinafter, also referred to as a colorant (a)) and a resin (hereinafter, also referred to as a resin (B)).
The colorant (a) contains a compound represented by formula (I) (hereinafter, also referred to as compound (I)) and a compound represented by formula (II) (hereinafter, also referred to as compound (II)).
The colorant (a) may contain a colorant other than the compounds (I) and (II) (hereinafter, also referred to as a colorant (a 1)).
The colorant (a) may contain 1 or 2 or more colorants (a 1).
The coloring composition of the present invention may contain a solvent (hereinafter, also referred to as solvent (E)).
The compound (I) and the compound (II) may be dispersed in the solvent (E).
< Compound (I) >)
As the compound (I), a commercially available compound can be used. A typical example of a commercially available compound (I) is Lumogen (registered trademark) F orange 240 (manufactured by BASF).
The compound (I) can be produced by a known general production method, for example, by reacting 3,4,9, 10-perylenetetracarboxylic dianhydride with 2, 6-diisopropylaniline.
< Compound (II) >
R1And R2The 2-valent hydrocarbon group has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms. Examples of the 2-valent hydrocarbon group include a 2-valent chain aliphatic hydrocarbon group, a 2-valent alicyclic hydrocarbon group, and a 2-valent aromatic hydrocarbon group.
R1And R2The 2-valent chained aliphatic hydrocarbon group represented may be saturated or unsaturated. Among them, a 2-valent saturated chain aliphatic hydrocarbon group (hereinafter, also referred to as an alkanediyl group) is preferable. The alkanediyl group may be linear or branchedIs branched.
As R1And R2Examples of the linear alkanediyl group include a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, a hexane-1, 6-diyl group, a heptane-1, 7-diyl group, an octane-1, 8-diyl group, a nonane-1, 9-diyl group, a silane-1, 10-diyl group, an undecane-1, 11-diyl group, a dodecane-1, 12-diyl group, a tridecane-1, 13-diyl group, a tetradecane-1, 14-diyl group, a pentadecane-1, 15-diyl group, a hexadecane-1, 16-diyl group, a heptadecane-1, 17-diyl group, an octadecane-1, 18-diyl group, a nonadecane-1, 19-diyl group and a eicosane-1, 20-diyl group. Among them, preferred is an alkanediyl group having 1 to 10 carbon atoms, more preferred is an alkanediyl group having 1 to 4 carbon atoms, and still more preferred is a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, or a pentane-1, 5-diyl group.
As R1And R2Examples of the branched alkanediyl group include a 1-methylpropane-1, 3-diyl group, a 2-methylpropane-1, 2-diyl group, a 1-methylbutane-1, 4-diyl group, a 2, 2-dimethylpropane-1, 3-diyl group, a 2-ethylpropane-1, 3-diyl group, a 2-methylpentane-1, 5-diyl group, a 3-methylpentane-1, 5-diyl group, and a 2, 3-dimethylpentane-1, 4-diyl group. Among these, a branched alkanediyl group having 4 to 10 carbon atoms is preferable, a branched alkanediyl group having 4 to 6 carbon atoms is more preferable, and a branched alkanediyl group having 4 to 6 carbon atoms is even more preferable.
As R1And R2Examples of the 2-valent unsaturated chain aliphatic hydrocarbon group include ethylene-1, 2-diyl, prop-1-ene-1, 3-diyl, but-2-ene-1, 4-diyl and pent-3-ene-1, 4-diyl.
As R1And R2The 2-valent alicyclic hydrocarbon group may be saturated or unsaturated. Among these, a 2-valent saturated alicyclic hydrocarbon group (hereinafter, also referred to as cycloalkanediyl group) is preferable. The cycloalkanediyl group may be monocyclic or polycyclic. Examples of the monocyclic cycloalkanediyl group include cyclopropane-1, 2-diyl group and a ringCycloalkanediyl groups such as butane-1, 3-diyl, cyclopentane-1, 3-diyl, cyclohexane-1, 4-diyl and cyclooctane-1, 5-diyl. Examples of the polycyclic cycloalkanediyl group include norbornane-1, 4-diyl group, norbornane-2, 5-diyl group, adamantane-1, 5-diyl group, and adamantane-2, 6-diyl group. Among them, cyclohexane-1, 4-diyl is preferable.
As R1And R2Examples of the 2-valent unsaturated alicyclic hydrocarbon group include cyclohex-2-ene-1, 4-diyl group and the like.
R1And R2The 2-valent aromatic hydrocarbon group (hereinafter, also referred to as an arene diyl group) may be monocyclic or polycyclic.
Examples of the monocyclic arenediyl group include a benzenediyl group, an alkylphenediyl group, and a dialkylbenzenediyl group. Specific examples thereof include benzene-1, 2-diyl, benzene-1, 3-diyl, benzene-1, 4-diyl, 2-methylbenzene-1, 4-diyl, 3-methylbenzene-1, 4-diyl, 2-methylbenzene-1, 5-diyl, 3-methylbenzene-1, 5-diyl, 4-methylbenzene-1, 5-diyl, 2-ethylbenzene-1, 4-diyl, 3, 5-dimethylbenzene-1, 4-diyl, 3, 5-diethylbenzene-1, 4-diyl, 3-methyl-5-ethylbenzene-1, 4-diyl and 2-methyl-6-ethylbenzene-1, 4-diyl.
Examples of the polycyclic aromatic hydrocarbon diyl group include a naphthalene-1, 5-diyl group, a naphthalene-1, 6-diyl group, a naphthalene-1, 7-diyl group, and a naphthalene-1, 8-diyl group. In addition, R1And R2The 2-valent aromatic hydrocarbon group may be a group in which 2 or more aromatic hydrocarbon groups are bonded, and [1, 1' -biphenyl group]-4, 4' -diyl and the like.
R1And R2The aromatic hydrocarbon diyl group is preferably a monocyclic aromatic hydrocarbon diyl group, and more preferably a benzene-1, 4-diyl group, a 3, 5-dimethylbenzene-1, 4-diyl group, a 2-methylbenzene-1, 4-diyl group, a 2-ethylbenzene-1, 4-diyl group and a 3-ethyl-5-methylbenzene-1, 4-diyl group.
R1And R2Each independently preferably selected from an alkanediyl group having 1 to 20 carbon atoms and a ring having 3 to 20 carbon atomsThe alkanediyl group and the arenediyl group having 6 to 20 carbon atoms are more preferably selected from the group consisting of an alkanediyl group having 1 to 10 carbon atoms, a cycloalkanediyl group having 3 to 10 carbon atoms and an arenediyl group having 6 to 10 carbon atoms, still more preferably selected from the group consisting of an alkanediyl group having 1 to 6 carbon atoms, a monocyclic cycloalkanediyl group having 5 to 7 carbon atoms, a benzenediyl group, an alkylphenyl group and a dialkylbenzenediyl group, and yet more preferably selected from the group consisting of a methylene group, an ethylene group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, a 4-methylpentane-1, 2-diyl group, a cyclohexane-1, 4-diyl group, a benzene-1, 4-diyl group and a 3, 5-dimethylbenzene-1, 4-diyl group.
R1And R2Each of the hydrocarbon groups may be independently a group obtained by combining 2 or more hydrocarbon groups, and for example, a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, or a group obtained by combining an aromatic hydrocarbon group and at least 1 of the chain hydrocarbon group and the alicyclic hydrocarbon group may be used. The total number of carbon atoms of the groups obtained by combining these groups is 20 or less.
R1And R2May be of the same kind or of different kinds, preferably of the same kind.
As R1And R2Specific examples of (A) include groups represented by the following formulae. And indicates the bonding site.
As R1And R2Preferred groups are each independently a group represented by the formulae (A-1) to (A-8), (A-14), (B-1) to (B-3), (B-16) to (B-19) or (C-3). From the viewpoint of production, the above-mentioned groups are preferable.
As R3~R10Examples of the halogen atom include a fluorine atom, a chlorine atom and a bromine atomAnd iodine atom, etc. Among them, fluorine atom and chlorine atom are preferable.
As R3~R10Examples of the hydrocarbon group having 1 to 40 carbon atoms include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, or may be linear or cyclic.
As R3~R10Examples 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, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl, tritriacontyl, tetratriacontyl, pentadecanyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, and forty-alkyl groups; 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, 2-pentenyl, and the like. 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. Among them, a linear or branched alkyl group having 1 to 8 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable.
As R3~R10Examples of the saturated or unsaturated alicyclic hydrocarbon group include cyclopropyl, 1-methylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, and 3-methylCycloalkyl groups such as a cyclohexyl group, a 4-methylcyclohexyl group, a1, 2-dimethylcyclohexyl group, a1, 3-dimethylcyclohexyl group, a1, 4-dimethylcyclohexyl group, a 2, 3-dimethylcyclohexyl group, a 2, 4-dimethylcyclohexyl group, a 2, 5-dimethylcyclohexyl group, a 2, 6-dimethylcyclohexyl group, a 3, 4-dimethylcyclohexyl group, a 3, 5-dimethylcyclohexyl group, a 2, 2-dimethylcyclohexyl group, a 3, 3-dimethylcyclohexyl group, a4, 4-dimethylcyclohexyl group, a cyclooctyl group, a 2,4, 6-trimethylcyclohexyl group, a 2,2,6, 6-tetramethylcyclohexyl group, a 3,3,5, 5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylcyclohexyl group; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptene, cyclooctene, and the like; norbornyl, adamantyl, bicyclo [2.2.2]Octyl, 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, further preferably 4 to 20, particularly preferably 4 to 15, further preferably 5 to 15, and particularly preferably 5 to 10. Among them, most preferred is cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
As R3~R10The aromatic hydrocarbon group may include a phenyl group, an o-tolyl group, a m-tolyl group, a p-tolyl group, a 2-ethylphenyl group, a 3-ethylphenyl group, a 4-ethylphenyl 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 3, 5-di (tert-butyl) phenyl group, 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, And aromatic hydrocarbon groups such as 1-naphthyl, 2-naphthyl, 5,6,7, 8-tetrahydro-1-naphthyl, 5,6,7, 8-tetrahydro-2-naphthyl, fluorenyl, phenanthryl, anthracyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, and pyrenyl. 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.
R3~R10The hydrocarbon group represented may be a group obtained by combining 2 or more of the above-mentioned hydrocarbon groups, for example, an aromatic hydrocarbon group and at least 1 of a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include an aralkyl group such as a benzyl group, a phenethyl group, and a 1-methyl-1-phenylethyl group; an arylalkenyl group such as a phenylvinyl group (phenylvinyl group); 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.
R3~R10The hydrocarbon group represented may be a group obtained by combining 2 or more of the above-mentioned hydrocarbon groups, for example, a group obtained by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof 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, an adamantylmethyl group, and the like.
The number of carbon atoms of a group obtained by combining 2 or more hydrocarbon groups is preferably 4 to 30, more preferably 4 to 20, still more preferably 4 to 15, and still more preferably 6 to 15.
As R3~R10Examples of the substituent which may be contained in the hydrocarbon group having 1 to 40 carbon atoms include a halogen atom, a formyl group, a carboxyl group, a formyloxy group, a hydroxyl group, a thiol group, a sulfo group, a sulfamoyl group, a pentafluorosulfanyl group, a carbamoyl group, an amino group, a nitro group, a cyano group and-COR12、-COOR12、-OCOR12、-OR12、-SR12、-SOR12、-SO2R12、-SO2NHR12、-SO2NR12R13、-CONHR12、-CONR12R13、-NHR12、-NR12R13、-NHCOR12、-NR13COR12And the like.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. Among them, fluorine atom and chlorine atom are preferable.
R12And R13Each independently represents an alkyl group, a phenyl group or a naphthyl group.
R12And R13The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 10, and still more preferably 1 to 5.
Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group.
as-COR12Examples thereof include acetyl, propionyl, butyryl, 2-dimethylpropionyl, pentanoyl, hexanoyl, 2-ethylhexanoyl, heptanoyl, octanoyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, heneicosanoyl and benzoyl.
as-COOR12Examples thereof include methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, pentoxycarbonyl, hexyloxycarbonyl, (2-ethyl) hexyloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl, dodecyloxycarbonyl, phenoxycarbonyl and eicosyloxycarbonyl.
as-OCOR12Examples thereof include acetoxy, propionyloxy, butyryloxy, 2-dimethylpropionyloxy, valeryloxy, hexanoyloxy, (2-ethyl) hexanoyloxy, heptanoyloxy, octanoyloxy, nonanoyloxy, decanoyloxy, undecanoyloxy, dodecanoyloxy, heneicosanoyloxy, benzoyloxy, vinylcarbonyloxy, 2-propenylcarbonyloxy and the like.
as-OR12Examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, phenoxy and naphthyloxy.
As a-SR12Examples thereof include methylsulfanyl and ethylsulfanylAnd (c) a group such as propyl sulfanyl, butyl sulfanyl, t-butyl sulfanyl, pentyl sulfanyl, hexyl sulfanyl, (2-ethyl) hexyl sulfanyl, heptyl sulfanyl, octyl sulfanyl, nonyl sulfanyl, decyl sulfanyl, undecyl sulfanyl, dodecyl sulfanyl, eicosyl sulfanyl, phenyl sulfanyl, and o-tolyl sulfanyl.
as-SOR12Examples thereof include methylsulfinyl, ethylsulfinyl, propylsulfinyl, butylsulfinyl, pentylsulfinyl, phenylsulfinyl and naphthylsulfinyl groups.
as-SO2R12Examples thereof include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, phenylsulfonyl, naphthylsulfonyl and the like.
as-SO2NHR12Examples thereof include 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 and N-phenylsulfamoyl.
as-SO2NR12R13Examples thereof include 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-di (1-ethylpropyl) sulfamoyl, N-dihexylsulfamoyl, N-di (2-ethyl) hexylsulfamoylAminosulfonyl, N-diheptylsulfamoyl, N-octylmethylsulfamoyl, N-dioctylsulfamoyl, N-dinonylsulfamoyl, N-decylmethylsulfamoyl, N-undecylmethylsulfamoyl, N-dodecylmethylsulfamoyl, N-eicosylmethylsulfamoyl, N-phenylmethylsulfamoyl, N-diphenylsulfamoyl and the like.
as-CONHR12Examples thereof include 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 and N-phenylcarbamoyl.
as-CONR12R13Examples thereof include an N, N-dimethylcarbamoyl group, an N, N-ethylmethylcarbamoyl group, an N, N-diethylcarbamoyl group, an N, N-propylmethylcarbamoyl group, an N, N-dipropylcarbamoyl group, an N, N-isopropylmethylcarbamoyl group, an N, N-diisopropylcarbamoyl group, an N, N-tert-butylmethylcarbamoyl group, an N, N-diisobutylcarbamoyl group, an N, N-di-sec-butylcarbamoyl group, an N, N-di-tert-butylcarbamoyl group, an N, N-butylmethylcarbamoyl group, an N, N-dibutylcarbamoyl group, an N, N-butyloctylcarbamoyl group, an N, N-dipentylcarbamoyl group, an N, N-di (1-ethylpropyl) carbamoyl group, an N, N-dihexylcarbamoyl group, an N, N-di (2-ethyl) hexylcarbamoyl group, N, N-diheptylcarbamoyl, N-octylmethylcarbamoyl, N-dioctylcarbamoyl, N-dinonylcarbamoyl, N-decylmethylcarbamoyl, N-undecylmethylcarbamoyl, N-dodecylmethylcarbamoyl, N,n-eicosylmethyl carbamoyl, N-phenylmethyl carbamoyl, N-diphenylcarbamoyl and the like.
as-NHR12Examples thereof include 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 and N-phenylamino.
as-NR12R13Examples thereof include 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-dinonylamino group, N-decylmethylamino group, N-undecylmethylamino group, N-dodecylmethylamino group, N, N-eicosylmethyl amino, N-phenylmethyl amino, N-diphenylamino and the like.
as-NHCOR12Examples thereof include acetylamino, propionylamino, butyrylamino, 2-dimethylpropionylamino, pentanoylamino, hexanoylamino, (2-ethyl) hexanoylamino, heptanoylamino, octanoylamino, nonanoylamino, decanoylamino, undecanoylamino, dodecanoylamino, heneicosanoylamino, benzoylamino and the like.
as-NR13COR12Examples thereof include N-methyl-N-acetylamino and the like.
R3~R10Containing a hydrocarbon group having 1 to 40 carbon atoms and not constituting a ring-CH2May be substituted by-O-, -CO-, -S (O)2-、-NRx1-. wherein-CH2-not by substitution, -COOH and-S (O)2OH。Rx1Represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Examples of the alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and an isopentyl group.
As R3~R10Examples thereof include groups represented by the following formulae. Denotes the bonding site.
As R3~R10Preferred groups are hydrogen atom, halogen atom, hydroxyl group, nitro group, cyano group, -CH3And groups represented by the formulae (D-1) to (D-18), (E-1) to (E-27), (F-1) to (F-18) and (G-1) to (G-27). The halogen atom is preferably a chlorine atom or a bromine atom. When these atoms are contained as halogen atoms, the colored pattern or colored coating film formed from the colored curable resin composition exhibits excellent heat resistance, and the transmittance at a wavelength of 630nm tends to be high. From a manufacturing point of view, R3~R10Preferably a hydrogen atom.
Specific examples of the compound (II) include the compounds shown in tables 1 to 3 below.
[ Table 1]
R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | |
II-1 | (A-1) | (A-1) | H | H | H | H | H | H | H | H |
II-2 | (A-2) | (A-2) | H | H | H | H | H | H | H | H |
II-3 | (A-3) | (A-3) | H | H | H | H | H | H | H | H |
II-4 | (A-5) | (A-5) | H | H | H | H | H | H | H | H |
II-5 | (A-8) | (A-8) | H | H | H | H | H | H | H | H |
II-6 | (A-14) | (^-14) | H | H | H | H | H | H | H | H |
II-7 | (B-3) | (B-3) | H | H | H | H | H | H | H | H |
II-8 | (B-18) | (B-18) | H | H | H | H | H | H | H | H |
II-9 | (C-3) | (C-3) | H | H | H | H | H | H | H | H |
II-10 | (A-1) | (A-1) | H | (E-9) | H | H | H | (E-9) | H | H |
II-11 | (A-2) | (A-2) | H | (E-9) | H | H | H | (E-9) | H | H |
II-12 | (A-3) | (A-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-13 | (A-5) | (A-5) | H | (E-9) | H | H | H | (E-9) | H | H |
II-14 | (A-8) | (A-8) | H | (E-9) | H | H | H | (E-9) | H | H |
II-15 | (A-14) | (A-14) | H | (E-9) | H | H | H | (E-9) | H | H |
II-16 | (B-3) | (B-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-17 | (B-18) | (B-18) | H | (E-9) | H | H | H | (E-9) | H | H |
II-18 | (C-3) | (C-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-19 | (A-1) | (A-1) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-20 | (A-2) | (A-2) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-21 | (A-3) | (A-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-22 | (A-5) | (A-5) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-23 | (A-8) | (A-8) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-24 | (A-14) | (^-14) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-25 | (B-3) | (B-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-26 | (B-18) | (B-18) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-27 | (C-3) | (C-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-28 | (A-1) | (A-1) | H | (F-14) | H | H | H | (F-14) | H | H |
II-29 | (A-2) | (A-2) | H | (F-14) | H | H | H | (F-14) | H | H |
II-30 | (A-3) | (A-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-31 | (A-5) | (A-5) | H | (F-14) | H | H | H | (F-14) | H | H |
II-32 | (A-8) | (A-8) | H | (F-14) | H | H | H | (F-14) | H | H |
II-33 | (A-14) | (^-14) | H | (F-14) | H | H | H | (F-14) | H | H |
II-34 | (B-3) | (B-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-35 | (B-18) | (B-18) | H | (F-14) | H | H | H | (F-14) | H | H |
II-36 | (C-3) | (C-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-37 | (A-1) | (A-1) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-38 | (A-2) | (A-2) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-39 | (A-3) | (A-3) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-40 | (A-5) | (A-5) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-41 | (A-8) | (A-8) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-42 | (A-14) | (^-14) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-43 | (B-3) | (B-3) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-44 | (B-18) | (B-18) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
II-45 | (C-3) | (C-3) | H | (D-14) | (D-14) | H | H | (D-14) | (D-14) | H |
[ Table 2]
R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | |
II-46 | (A-1) | (A-1) | H | (E-9) | H | H | H | (E-9) | H | H |
II-47 | (^-2) | (^-2) | H | (E-9) | H | H | H | (E-9) | H | H |
II-48 | (A-3) | (^-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-49 | (^-5) | (^-5) | H | (E-9) | H | H | H | (E-9) | H | H |
II-50 | (A-8) | (A-8) | H | (E-9) | H | H | H | (E-9) | H | H |
II-51 | (A-14) | (A-14) | H | (E-9) | H | H | H | (E-9) | H | H |
II-52 | (B-3) | (B-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-53 | (B-18) | (B-18) | H | (E-9) | H | H | H | (E-9) | H | H |
II-54 | (C-3) | (C-3) | H | (E-9) | H | H | H | (E-9) | H | H |
II-55 | (A-1) | (A-1) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-56 | (A-2) | (A-2) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-57 | (A-3) | (^-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-58 | (^-5) | (^-5) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-59 | (A-8) | (^-8) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-60 | (A-14) | (A-14) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-61 | (B-3) | (B-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-62 | (B-18) | (B-18) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-63 | (C-3) | (C-3) | H | (E-9) | (E-9) | H | H | (E-9) | (E-9) | H |
II-64 | (A-1) | (A-1) | H | (F-14) | H | H | H | (F-14) | H | H |
II-65 | (A-2) | (^-2) | H | (F-14) | H | H | H | (F-14) | H | H |
II-66 | (A-3) | (A-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-67 | (A-5) | (^-5) | H | (F-14) | H | H | H | (F-14) | H | H |
II-68 | (A-8) | (^-8) | H | (F-14) | H | H | H | (F-14) | H | H |
II-69 | (A-14) | (A-14) | H | (F-14) | H | H | H | (F-14) | H | H |
II-70 | (B-3) | (B-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-71 | (B-18) | (B-18) | H | (F-14) | H | H | H | (F-14) | H | H |
II-72 | (C-3) | (C-3) | H | (F-14) | H | H | H | (F-14) | H | H |
II-73 | (A-1) | (^-1) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-74 | (A-2) | (A-2) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-75 | (A-3) | (A-3) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-76 | (A-5) | (^-5) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-77 | (A-8) | (^-8) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-78 | (A-14) | (A-14) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-79 | (B-3) | (B-3) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-80 | (B-18) | (B-18) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
II-81 | (C-3) | (C-3) | H | (G-23) | (G-23) | H | H | (G-23) | (G-23) | H |
[ Table 3]
R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | |
II-82 | (A-1) | (A-1) | H | Cl | H | H | H | Cl | H | H |
II-83 | (A-2) | (A-2) | H | Cl | H | H | H | Cl | H | H |
II-84 | (A-3) | (A-3) | H | Cl | H | H | H | Cl | H | H |
II-85 | (A-5) | (A-5) | H | Cl | H | H | H | Cl | H | H |
II-86 | (A-8) | (A-8) | H | Cl | H | H | H | Cl | H | H |
II-87 | (A-14) | (A-14) | H | Cl | H | H | H | Cl | H | H |
II-88 | (B-3) | (B-3) | H | Cl | H | H | H | Cl | H | H |
II-89 | (B-18) | (B-18) | H | Cl | H | H | H | Cl | H | H |
II-90 | (C-3) | (C-3) | H | Cl | H | H | H | Cl | H | H |
II-91 | (A-1) | (A-1) | H | Cl | Cl | H | H | Cl | Cl | H |
II-92 | (A-2) | (A-2) | H | Cl | Cl | H | H | Cl | Cl | H |
II-93 | (A-3) | (A-3) | H | Cl | Cl | H | H | Cl | Cl | H |
II-94 | (A-5) | (A-5) | H | Cl | Cl | H | H | Cl | Cl | H |
II-95 | (A-8) | (A-8) | H | Cl | Cl | H | H | Cl | Cl | H |
II-96 | (A-14) | (A-14) | H | Cl | Cl | H | H | Cl | Cl | H |
II-97 | (B-3) | (B-3) | H | Cl | Cl | H | H | Cl | Cl | H |
II-98 | (B-18) | (B-18) | H | Cl | Cl | H | H | Cl | Cl | H |
II-99 | (C-3) | (C-3) | H | Cl | Cl | H | H | Cl | Cl | H |
II-100 | (A-1) | (A-1) | H | Br | H | H | H | Br | H | H |
II-101 | (A-2) | (A-2) | H | Br | H | H | H | Br | H | H |
II-102 | (A-3) | (A-3) | H | Br | H | H | H | Br | H | H |
II-103 | (A-5) | (A-5) | H | Br | H | H | H | Br | H | H |
II-104 | (A-8) | (A-8) | H | Br | H | H | H | Br | H | H |
II-105 | (A-14) | (A-14) | H | Br | H | H | H | Br | H | H |
II-106 | (B-3) | (B-3) | H | Br | H | H | H | Br | H | H |
II-107 | (B-18) | (B-18) | H | Br | H | H | H | Br | H | H |
II-108 | (C-3) | (C-3) | H | Br | H | H | H | Br | H | H |
II-109 | (A-1) | (A-1) | H | Br | Br | H | H | Br | Br | H |
II-110 | (A-2) | (A-2) | H | Br | Br | H | H | Br | Br | H |
II-111 | (A-3) | (A-3) | H | Br | Br | H | H | Br | Br | H |
II-112 | (A-5) | (A-5) | H | Br | Br | H | H | Br | Br | H |
II-113 | (A-8) | (A-8) | H | Br | Br | H | H | Br | Br | H |
II-114 | (A-14) | (A-14) | H | Br | Br | H | H | Br | Br | H |
II-115 | (B-3) | (B-3) | H | Br | Br | H | H | Br | Br | H |
II-116 | (B-18) | (B-18) | H | Br | Br | H | H | Br | Br | H |
II-117 | (C-3) | (C-3) | H | Br | Br | H | H | Br | Br | H |
Among these compounds, the compounds (II-1) to (II-9) and (I-82) to (I-117) are preferable, and the compounds (II-2) to (II-6), (II-8) and (II-91) to (II-108) are more preferable from the viewpoint of heat resistance and light resistance.
A preferred embodiment of the compound (II) in the present invention includes a compound represented by the following formula (IIa) (hereinafter, also referred to as compound (IIa)).
[ in the formula (IIa),
R1aand R2aEach independently represents an alkanediyl group having 1 to 20 carbon atoms.
R3a~R10aEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.]
As R1aAnd R2aExamples of the alkanediyl group represented by the formula (II)1And R2Examples of the alkanediyl group in the above description are the same.
R3a~R10aIs defined with R in formula (II)3~R10The same definition is applied.
Specific examples of the compound (IIa) include the compounds (II-1) to (II-6), (II-10) to (II-15), (II-19) to (II-24), (II-28) to (II-33), (II-37) to (II-42), (II-46) to (II-51), (II-55) to (II-60), (II-64) to (II-69), (II-73) to (II-78), (I-82) to (I-87), (I-91) to (I-96), (I-100) to (I-105), and (I-109) to (I-114) shown in tables 1 to 3.
Another preferred embodiment of the compound (II) in the present invention includes a compound represented by the following formula (IIb) (hereinafter, also referred to as compound (IIb)).
[ in the formula (IIb),
R1band R2bEach independently represents a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.
R3b~R10bEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.]
As R1bAnd R2bExamples of the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (II)1And R2In the description above, the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.
R3b~R10bIs defined with R in formula (II)3~R10The same definition is applied.
Specific examples of the compound (IIb) include the compounds (II-9), (II-18), (II-27), (II-36), (II-45), (II-54), (II-63), (II-72), (II-81), (I-90), (I-99), (I-108), and (I-117) shown in tables 1 to 3.
Another preferred embodiment of the compound (II) in the present invention includes a compound represented by the following formula (IIc) (hereinafter, also referred to as compound (IIc)).
[ in the formula (IIc),
R1cand R2cEach independently represents a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.
R3c~R10cEach independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.]
As R1cAnd R2cExamples of the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (II)1And R2In the description above, the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.
R3c~R10cIs defined with R in formula (II)3~R10The same definition is applied.
Specific examples of the compound (IIc) include the compounds (II-7), (II-8), (II-16), (II-17), (II-25), (II-26), (II-34), (II-35), (II-43), (II-44), (II-52), (II-53), (II-61), (II-62), (II-70), (II-71), (II-79), (II-80), (I-88), (I-89), (I-97), (I-98), (I-106), (I-107), (I-115), and (I-116) shown in tables 1 to 3.
The compound (II) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1) in a solvent.
[ in the formula, R3~R10As defined above.]
[ wherein R represents a C1-20 2-valent hydrocarbon group. ]
Examples of the compound represented by the formula (pt1) include 3,4,9, 10-perylenetetracarboxylic dianhydride and the like.
Examples of the C1-20 2-valent hydrocarbon group represented by R in the formula (ca1) are the same as those for R in the above-mentioned compound (II)1And R2The 2-valent hydrocarbon group having 1 to 20 carbon atoms in the description above is exemplified in the same manner.
Examples of the compound represented by the formula (ca1) include 2-glycine, 2-aminopropionic acid, 2-amino-3-methylbutyric acid, 2-amino-4-methylpentanoic acid, 2-amino-3-methylpentanoic acid, 4-aminobenzoic acid, and 2-amino-3-phenylpropionic acid.
The amount of the compound represented by the formula (ca1) used is usually 1 to 10 moles, preferably 1 to 8 moles, more preferably 1 to 6 moles, and still more preferably 1 to 4 moles, based on 1 mole of the compound represented by the formula (pt 1).
Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as dichloromethane, chloroform, and 1, 2-dichlorobenzene; amide solvents such as N, N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide.
The amount of the solvent used is usually 1 to 1000 parts by mass per 1 part by mass of the compound represented by the formula (pt 1).
The reaction temperature is usually from-100 ℃ to 300 ℃, preferably from-90 ℃ to 200 ℃, more preferably from-10 ℃ to 150 ℃.
After the reaction is completed, the method for removing the compound (II) is not particularly limited, and the compound (II) can be removed by various known methods. For example, the compound (II) can be removed by distilling off the solvent. After the solvent is distilled off, the obtained residue may be further purified by column chromatography, recrystallization, or the like. After the reaction is completed, the compound (II) can be removed by filtration. After filtration, the obtained residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound (II) can be analyzed by a known analytical method and conditions thereof. Such an analysis method is not particularly limited, and includes an X-ray crystal structure analysis method, a mass spectrometry (LC), an NMR analysis method, an elemental analysis method, and the like. The X-ray crystal structure analysis method can be performed, for example, according to Chemistry of Materials, 2012, volume 24, p.4647-4652.
The compound (IIa) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1a) (hereinafter, also referred to as compound (ca1a)) in a solvent.
[ in the formula, RaRepresents an alkanediyl group having 1 to 20 carbon atoms.]
As RaExamples of the alkanediyl group having 1 to 20 carbon atoms represented by the formula (II)1And R2Examples of the alkanediyl group having 1 to 20 carbon atoms in the description of (1) are the same as those given above.
Specific examples of the compound (ca1a) include 2-glycine (glycine), 3-aminopropionic acid, 4-aminobutyric acid, 5-aminopentanoic acid, 6-aminocaproic acid, 7-aminoheptanoic acid, 8-aminocaprylic acid, 9-aminononanoic acid, 10-aminodecanoic acid, 11-aminoundecanoic acid, 12-aminododecanoic acid, 13-aminotridecanoic acid, 14-aminotetradecanoic acid, 15-aminopentadecanoic acid, 16-aminocaproic acid, 17-aminoheptadecanoic acid, 18-aminooctadecanoic acid, 19-aminononadecanoic acid, 20-aminoeicosanoic acid, 2-aminopropionic acid, 2-amino-3-methylbutyric acid, 2-amino-4-methylpentanoic acid, 2-amino-3-methylpentanoic acid, and the like.
The compound (IIb) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1b) (hereinafter, also referred to as a compound (ca1b)) in a solvent.
[ in the formula, RbRepresents a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.]
As RbExamples of the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (II)1And R2In the description above, the 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.
Specific examples of the compound (ca1b) include 3-aminocyclopentane-1-carboxylic acid and 3-aminocyclopentane-1-carboxylic acid.
The compound (IIc) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a compound represented by the following formula (ca1c) in a solvent.
[ in the formula, RcRepresents a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.]
As RcExamples of the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms represented by the formula (II)1And R2In the description above, the 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms is exemplified in the same manner.
Specific examples of the compound (ca1c) include 4-aminobenzoic acid and 2- (4-aminophenyl) benzoic acid.
< colorant (A) >)
The content of the compound (I) in the colorant (a) may be, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 5% by mass or more, particularly preferably 10% by mass or more, further preferably 20% by mass or more, further preferably 50% by mass or more, relative to the total amount of the colorant (a), and on the other hand, the content of the compound (I) in the colorant (a) may be usually less than 100% by mass, for example, 99% by mass or less, relative to the total amount of the colorant (a).
The content of the compound (II) in the colorant (a) may be, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 5% by mass or more, particularly preferably 10% by mass or more, and further preferably 20% by mass or more, relative to the total amount of the colorant (a), and on the other hand, the content of the compound (II) in the colorant (a) may be usually less than 100% by mass, for example, 99% by mass or less, relative to the total amount of the colorant (a).
The mass ratio of the compound (I) to the compound (II) in the colorant (A) may be, for example, 1:99 to 99:1, preferably 20:80 to 80:20, more preferably 30:70 to 70:30, and still more preferably 40:60 to 60: 40. When the mass ratio of the compound (I) to the compound (II) in the colorant (a) is in the above range, the dispersibility of the compound (I) in the coloring composition is improved, and the heat resistance tends to be easily improved.
The content of the colorant (a) in the coloring composition may be, for example, 0.1 to 99.9% by mass, preferably 0.5 to 99% by mass, more preferably 1 to 90% by mass, still more preferably 5 to 80% by mass, particularly preferably 10 to 70% by mass, still more preferably 15 to 60% by mass, still more preferably 20 to 50% by mass, particularly preferably 25 to 45% by mass, and very preferably 30 to 40% by mass, based on the total amount of solid components in the coloring composition.
In the present specification, the "total amount of solid components in the coloring composition" refers to the total amount of components excluding all solvent components from the coloring composition. The total amount of solid components and the contents of the respective components relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.
< colorant (A1) >)
The colorant (a1) may be a dye or a pigment. As The dye, known dyes can be used, and for example, known dyes described in The color index (published by The Society of Dyers and Colourists) and dyeing guidelines (chromo). Further, depending on the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinonimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, and the like can be given. These dyes may be used alone or in combination of 2 or more.
Specific examples thereof include the following color index (c.i.) numbered dyes.
C.i. solvent yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189;
c.i. solvent red 24, 45, 49, 90, 91111, 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. solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99;
c.i. solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
c.i. solvent blue 4,5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
c.i. solvent dyes such as c.i. solvent green 1,3, 4,5, 7, 28, 29, 32, 33, 34, 35,
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. acid red 1,4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
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. acid violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
c.i. acid blue 1,3,5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90:1, 91, 92, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 243, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 267, 296, 278, 285, 340, 285, 340;
c.i. acid dyes such as c.i. acid green 1,3,5, 6,7,8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and the like,
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. direct red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;
c.i. direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
c.i. direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
c.i. direct blue 1,2,3,6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 256, 236, 229, 237, 242, 244, 245, 247, 238, 248, 250, 257, 275, 260, 251, 293, 268, 274, 251, 268;
c.i. direct dyes such as c.i. direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82,
c.i. disperse yellow 51, 54, 76;
c.i. disperse violet 26, 27;
c.i. disperse dyes such as c.i. disperse blue 1,14, 56, 60, etc.,
c.i. basic red 1, 10;
c.i. basic blue 1,3,5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;
c.i. basic violet 2;
c.i. basic red 9;
c.i. alkaline green 1; and the like, the basic dye is added,
c.i. reactive yellow 2, 76, 116;
c.i. reactive orange 16;
C.I. reactive dyes such as C.I. reactive red 36,
c.i. media yellow 5, 8,10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
c.i. medium red 1,2,3, 4,9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
c.i. intermediate orange 3,4,5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
c.i. media violet 1, 1:1, 2,3,4, 5,6,7,8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
c.i. medium blue 1,2,3, 7,8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84;
c.i. mordant dyes such as c.i. mordant green 1,3, 4,5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53,
c.i. vat dyes such as c.i. vat green 1, and the like.
Further, Lumogen (registered trademark) F yellow 083 (manufactured by BASF), Lumogen (registered trademark) F yellow 170 (manufactured by BASF), and Lumogen (registered trademark) F red 305 (manufactured by BASF) may be mentioned.
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 yellow pigments such as 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, 231 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, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273 and the like;
c.i. pigment blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc.;
c.i. pigment violet 1,19, 23, 29, 32, 36, 38 and the like violet pigment;
green pigments such as c.i. pigment green 7, 36, 58, 59, 62, 63;
c.i. brown pigments such as pigment brown 23, 25;
c.i. pigment black 1,7, 31, 32 and the like.
The colorant (a1) may be subjected to, if necessary, rosin treatment, surface treatment using a derivative or the like into which an acidic group or a basic group has been introduced, grafting treatment on the surface of the colorant (a1) by a polymer compound or the like, microparticulation treatment by a sulfuric acid microparticulation method or the like, cleaning treatment by an organic solvent, water or the like for removing impurities, removal treatment by an ion exchange method or the like for removing ionic impurities, or the like. The particle diameter of the colorant (a1) is preferably substantially uniform.
When the colorant (a) further contains the colorant (a1), the lower limit of the content of the total amount of the compound (I) and the compound (II) in the colorant (a) is usually 1% by mass or more, preferably 2% by mass or more, more preferably 10% by mass or more, further preferably 25% by mass or more, and particularly preferably 50% by mass or more, relative to the total amount of the colorant (a). On the other hand, the upper limit of the content of the total amount of the compound (I) and the compound (II) in the colorant (a) is usually 100% by mass or less with respect to the total amount of the colorant (a).
When the colorant (a) further contains a colorant (a1), the content of the colorant (a) in the coloring composition is usually 0.1 to 99% by mass, for example, 0.1 to 90% by mass, preferably 0.5 to 80% by mass, more preferably 0.7 to 70% by mass, and particularly preferably 1 to 60% by mass, based on the total amount of solid components in the coloring composition.
When the coloring composition contains the solvent (E), a coloring composition can be prepared by preparing a coloring agent-containing solution containing the coloring agent (a) and the solvent (E) in advance and then using the coloring agent-containing solution. When the colorant (a) is insoluble in the solvent (E), a solution containing the colorant can be prepared by dispersing and mixing the colorant (a) in the solvent (E). The solution containing the colorant may contain a part or all of the solvent (E) contained in the coloring composition.
The content of the solid content in the colorant-containing solution is preferably 0.01 to 99.99% by mass, more preferably 0.1 to 99.9% by mass, even more preferably 0.1 to 99% by mass, even more preferably 1 to 90% by mass, even more preferably 1 to 60% by mass, even more preferably 3 to 50% by mass, particularly preferably 3 to 30% by mass, and extremely preferably 5 to 30% by mass, based on the total amount of the colorant-containing solution.
The content of the colorant (a) in the colorant-containing solution is usually less than 100% by mass, preferably 0.0001 to 99.9999% by mass, more preferably 0.01 to 99% by mass, still more preferably 0.1 to 99% by mass, particularly preferably 1 to 99% by mass, and still more preferably 2 to 99% by mass, of the total amount of solid components in the colorant-containing solution.
In the present specification, the "total amount of solid components in the colorant-containing solution" refers to the total amount of components other than the solvent (E) in the colorant-containing solution. The total amount of solid components and the contents of the respective components relative to the total amount can be measured by a known analytical method such as liquid chromatography or gas chromatography.
The colorant (a) can be dispersed by a dispersing agent to obtain a state in which the colorant (a) is uniformly dispersed in a solution containing the colorant. The colorant (a) may be dispersed alone or in combination of two or more.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamide, 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 industry Co., Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by AJIAOSU Fine chemical Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and the like.
When a dispersant is used for the preparation of the colorant-containing solution, the amount of the dispersant (solid content) used is usually 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, still more preferably 200 parts by mass or less, still more preferably 5 to 150 parts by mass, and particularly preferably 5 to 110 parts by mass, per 100 parts by mass of the colorant (a). When the amount of the dispersant used is within the above range, a more uniformly dispersed solution containing the colorant tends to be obtained.
< 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 (hereinafter, sometimes referred to as "monomer (a)") selected from 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 having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (B)") and another structural unit.
Examples of the other structural units include structural units derived from a monomer copolymerizable with the monomer (a) (which is different from the monomer (a) and the monomer (b) and may be referred to as "monomer (c)" hereinafter), structural units having an ethylenically unsaturated bond, and the like.
Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, 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-cyclohexene dicarboxylic acid;
carboxyl group-containing bicyclic unsaturated compounds such as 5-norbornene-2, 3-dicarboxylic acid methyl ester, 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 excluding fumaric acid and methylfumaric 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 them, 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 alkali solution.
The monomer (b) is a polymerizable compound having 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. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
Examples of the monomer (b) include a monomer having an oxirane group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 2)"), a monomer having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter, sometimes referred to as "monomer (b 3)"), and the like.
Examples of the monomer (b1) include a monomer having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b 1-1)") and a monomer having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter, sometimes referred to as "monomer (b 1-2)").
As the monomer (b 1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable.
Specific examples of the monomer (b 1-1) include glycidyl (meth) acrylate, β -methylglycidyl (meth) acrylate, β -ethylglycidyl (meth) acrylate, glycidyl vinyl ether, vinylbenzyl glycidyl ether, α -methylvinylbenzyl glycidyl ether, 2, 3-bis (glycidoxymethyl) styrene, 2, 4-bis (glycidoxymethyl) styrene, 2, 5-bis (glycidoxymethyl) styrene, 2, 6-bis (glycidoxymethyl) styrene, 2,3, 4-tris (glycidoxymethyl) styrene, 2,3, 5-tris (glycidoxymethyl) styrene, 2,3, 6-tris (glycidoxymethyl) styrene, 3,4, 5-tris (glycidoxymethyl) styrene and 2,4, 6-tris (glycidoxymethyl) styrene, and the like.
Examples of the monomer (b 1-2) 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.)), compounds represented by the formula (BI), and compounds represented by the formula (BII).
[ formula (BI) and formula (BII) wherein RaAnd RbEach independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxyl group.
XaAnd XbEach independently represents a single bond, [ R ]c-、*-Rc-O-、*-Rc-S-or Rc-NH-。
RcRepresents an alkanediyl group having 1 to 6 carbon atoms.
Denotes the bonding site to O. ]
Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.
Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxyl group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.
As RaAnd RbPreferred examples thereof include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferred examples thereof include a hydrogen atom and a methyl group.
Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1, 2-diyl group, a propane-1, 3-diyl group, a butane-1, 4-diyl group, a pentane-1, 5-diyl group, and a hexane-1, 6-diyl group.
As XaAnd XbPreferred examples thereof include a single bond, methylene, ethylene and-CH2-O-and-CH2CH2More preferably, the group-O-includes a single bond and-CH2CH2-O- (. indicates a bonding site to O.).
Examples of the compound represented by formula (BI) include compounds represented by any one of formulae (BI-1) to (BI-15). Among them, preferred are compounds represented by formula (BI-1), formula (BI-3), formula (BI-5), formula (BI-7), formula (BI-9) and formulae (BI-11) to (BI-15), and more preferred are compounds represented by formula (BI-1), formula (BI-7), formula (BI-9) and formula (BI-15).
Examples of the compound represented by formula (BII) include compounds represented by any one of formulae (BII-1) to (BII-15), among which compounds represented by formulae (BII-1), (BII-3), formula (BII-5), formula (BII-7), formula (BII-9), and formulae (BII-11) to (BII-15) are preferable, and compounds represented by formulae (BII-1), (BII-7), formula (BII-9), and formula (BII-15) are more preferable.
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.
As the monomer (b2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable.
Examples of the monomer (b2) include 3-methyl-3-methacryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-ethyl-3-methacryloxymethyloxetane, 3-ethyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxyethyloxetane, 3-methyl-3-acryloxyethyloxetane, 3-ethyl-3-methacryloxyethyloxetane, and 3-ethyl-3-acryloxyethyloxetane.
As the monomer (b3), a monomer having a tetrahydrofuranyl group and a (meth) acryloyloxy group is more preferable.
Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V #150, manufactured by Osaka Organischen chemical industries, Ltd.), tetrahydrofurfuryl methacrylate, and the like.
The monomer (b) is preferably the monomer (b1) in view of enabling the obtained color filter to have higher reliability such as heat resistance, chemical resistance and the like. Further, the monomer (b 1-2) is more preferable in terms of excellent storage stability of the coloring composition.
Examples of the monomer (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, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, and 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, dicyclopentyloxyethyl (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 [ 2.1] hept-2-ene, 5, 6-bis (2.1) hept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxyhept-2-ene, 5-hydroxybicyclo [2.2.1] hept-2-ene, 5-2.1 ] hept-2, Bicyclic unsaturated compounds such as 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 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-maleimidocaproate, 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.
Among them, styrene, vinyltoluene, and tricyclo [5.2.1.0 ] meth (acrylic acid) 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 andbenzyl (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 a group reactive with the groups of the monomer (a) and the monomer (b) and an ethylenically unsaturated bond to a polymer having a structural unit derived from the monomer (a) and the monomer (b).
Examples of such a structural unit include a structural unit obtained by adding glycidyl (meth) acrylate to a (meth) acrylic acid unit, a structural unit obtained by adding 2-hydroxyethyl (meth) acrylate to a maleic anhydride unit, and a structural unit obtained by adding (meth) acrylic acid to a glycidyl (meth) acrylate unit. When these structural units have a hydroxyl group, a structural unit to which a carboxylic anhydride is further added may be mentioned as a structural unit having an ethylenically unsaturated bond.
The polymer having a structural unit derived from the monomer (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, the solvent and the like are not particularly limited, and those 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 the solution after the reaction, may be used as it is, may be used as a concentrated or diluted solution, or may be used as it is taken out as a solid (powder) 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) may 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 3, 4-epoxycyclohexylmethyl (meth) acrylate/(meth) acrylic acid copolymer, and 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 ester copolymer, 3, 4-epoxytricyclo [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 the monomer (a) and a structural unit derived from the monomer (B).
The resin (B) may be used in combination of 2 or more, and in this case, the resin (B) preferably contains at least one member selected from the group consisting of 3, 4-epoxytricyclo [5.2.1.0 ] s of (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 1000 to 100000, more preferably 1000 to 50000, still more preferably 1000 to 30000, and particularly preferably 3000 to 30000.
The molecular weight distribution [ weight average molecular weight (Mw)/number average molecular weight (Mn) ] of the resin (B) is preferably 1 to 6, more preferably 1.001 to 4, and still more preferably 1.01 to 4.
The acid value (solid content equivalent value) of the resin (B) is preferably from 10 mg-KOH/g to 300 mg-KOH/g, more preferably from 20 mg-KOH/g to 250 mg-KOH/g, still more preferably from 20 mg-KOH/g to 200 mg-KOH/g, particularly preferably from 20 mg-KOH/g to 170 mg-KOH/g, still more preferably from 30 mg-KOH/g to 170 mg-KOH/g, particularly preferably from 60 mg-KOH/g to 150 mg-KOH/g, and very preferably from 65 mg-KOH/g to 135 mg-KOH/g. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of the resin (B), and can be determined, for example, by titration with an aqueous solution of potassium hydroxide.
The content of the resin (B) in the coloring composition may be, for example, 0.1 to 99.9% by mass, preferably 0.5 to 99% by mass, more preferably 1 to 95% by mass, still more preferably 2 to 90% by mass, particularly preferably 3 to 80% by mass, still more preferably 5 to 70% by mass, still more preferably 7 to 60% by mass, particularly preferably 10 to 50% by mass, and very preferably 10 to 30% by mass, based on the total amount of solid components in the coloring composition.
When the coloring composition of the present invention is prepared by using a solution containing a colorant after preparing the solution containing a colorant in advance, the solution containing a colorant may contain a part or all, preferably a part, of the resin (B) described later contained in the coloring composition in advance. By containing the resin (B) in advance, the dispersion stability of the solution containing the colorant can be further improved.
The content of the resin (B) in the colorant-containing solution may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 1 to 500 parts by mass, particularly preferably 5 to 200 parts by mass, and still more preferably 10 to 100 parts by mass, per 100 parts by mass of the colorant (a).
< embodiment 1 >
The coloring composition of embodiment 1 includes a colorant (a) and a resin (B), and the colorant (a) contains a compound represented by formula (I) and a compound represented by formula (IIa).
[ in the formula (IIa), R1a~R10aThe definitions of (a) are the same as those described above.]
The exemplary and preferred ranges of the respective contents of the compound (I) and the compound (IIa) in the colorant (a) are the same as those of the respective contents of the compound (I) and the compound (II) in the colorant (a) described above.
< embodiment 2 >
The coloring composition of embodiment 2 includes a colorant (a) and a resin (B), and the colorant (a) contains a compound represented by formula (I) and a compound represented by formula (IIb).
[ formula (IIb) wherein R1b~R10bThe definitions of (a) are the same as those described above.]
Examples and preferred ranges of the respective contents of the compound (I) and the compound (IIb) in the colorant (a) are the same as those of the respective contents of the compound (I) and the compound (II) in the colorant (a) described above.
< embodiment 3 >
The coloring composition of embodiment 3 includes a colorant (a) and a resin (B), and the colorant (a) contains a compound (IIc).
[ formula (IIc) wherein R1c~R10cThe definitions of (a) are the same as those described above.]
Examples and preferred ranges of the respective contents of the compound (I) and the compound (IIc) in the colorant (a) are the same as those of the respective contents of the compound (I) and the compound (II) in the colorant (a) described above.
(2) Colored curable resin composition
The colored curable resin composition contains a compound (I), a compound (II), a resin (B) (hereinafter, these are also collectively referred to as a colorant (a)), a polymerizable compound (hereinafter, sometimes referred to as a polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as a polymerization initiator (D)).
The colored curable resin composition may further contain 1 kind selected from a leveling agent (hereinafter, sometimes referred to as a leveling agent (F)), an antioxidant (hereinafter, sometimes referred to as an antioxidant (G)), and a solvent (E).
The content of the solid content in the colored composition contained in the colored curable resin composition is not particularly limited since it is appropriately adjusted according to the chromaticity, brightness, film thickness, and the like required for curing the colored curable resin composition, and may be, for example, 1 to 99% by mass, preferably 1 to 90% by mass, more preferably 2 to 80% by mass, further preferably 3 to 70% by mass, particularly preferably 4 to 60% by mass, further preferably 5 to 50% by mass, particularly preferably 6 to 45% by mass, and extremely preferably 7 to 40% by mass, based on the total amount of the solid content in the colored curable resin composition.
The content of the colorant (a) in the colored curable resin composition is not particularly limited since it is appropriately adjusted according to the chromaticity, brightness, film thickness, and the like required for curing the colored curable resin composition, and may be, for example, 0.1 to 99% by mass, preferably 1 to 90% by mass, more preferably 2 to 80% by mass, further preferably 3 to 70% by mass, particularly preferably 4 to 60% by mass, further preferably 5 to 50% by mass, particularly preferably 8 to 40% by mass, and very preferably 10 to 30% by mass of the total amount of solid components in the colored curable resin composition.
In the present specification, the "total amount of solid components in the colored curable resin composition" refers to the total amount of components excluding the solvent (E) from the colored curable resin composition. The total amount of the solid components and the contents of the respective components relative to the total amount can be measured by a known analysis method such as liquid chromatography or gas chromatography. The content of the solid content in the colored curable resin composition may be, for example, 0.01% by mass or more and less than 100% by mass, preferably 0.1% by mass to 99.9% by mass, more preferably 0.1% by mass to 99% by mass, particularly preferably 1% by mass to 60% by mass, further preferably 3% by mass to 50% by mass, further preferably 3% by mass to 30% by mass, and particularly preferably 5% by mass to 30% by mass, based on the total amount of the colored curable resin composition.
The colored pattern and the colored coating film, which will be described later, formed from the colored curable resin composition of the present invention are excellent in heat resistance and tend to have a high transmittance at a wavelength of 630nm, and it is preferable that the transmittance at a wavelength of 630nm be higher than that of a colored pattern and a colored coating film formed from a colored curable resin composition containing the compound (I) alone. The transmittance at a wavelength of 630nm of a colored pattern or a colored coating film to be described later formed from the colored curable resin composition of the present invention may be, for example, 90% or more, preferably 95% or more, and more preferably 97% or more. The transmittance at a wavelength of 630nm can be measured, for example, by using a color measuring machine (OSP-SP-200; manufactured by OLYMPUS).
< polymerizable Compound (C) >)
The polymerizable compound (C) is a compound which can be polymerized 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 nonylphenylcarbinol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, 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) acrylate Esters 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 50 to 4000, more preferably 50 to 3500, still more preferably 50 to 3000, particularly preferably 150 to 2900, and particularly preferably 250 to 1500.
The content of the polymerizable compound (C) in the colored curable resin composition may be, for example, 1 to 99% by mass, preferably 2 to 90% by mass, more preferably 3 to 80% by mass, still more preferably 4 to 70% by mass, particularly preferably 5 to 60% by mass, still more preferably 6 to 50% by mass, and particularly preferably 7 to 40% by mass, based on the total amount of solid components.
< polymerization initiator (D) >)
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical, an acid, or the like under the action of light or heat to initiate polymerization, and a known polymerization initiator can be used.
Examples of the polymerization initiator (D) include an O-acyloxime compound, an alkylphenone compound, a bisimidazole compound, a triazine compound, and an acylphosphine oxide compound.
Examples of the O-acyloxime compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- (4-phenylsulfanylphenyl) -3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-1- [ 9-ethyl-6- { 2-methyl-4- (3, 3-dimethyl-2, 4-dioxopentylmethyloxy) benzoyl } -9H-carbazol-3-yl ] ethane-1-imine, N-acetoxy-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, etc. Further, as the O-acyloxime compound, commercially available products such as Irgacure OXE01, OXE02 (both of which are manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) can be used. Among them, as the O-acyloxime compound, at least 1 selected from the group consisting of N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine is preferable, and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine is more preferable.
Examples of the alkylphenone compound include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, and 2- (dimethylamino) -2- [ (4-methylphenyl) methyl ] -1- [ 4- (4-morpholino) phenyl ] butan-1-one. As the alkylphenone compound, commercially available products such as Irgacure 369, 907 and 379 (all of which are manufactured by BASF) 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 (see, for example, japanese patent publication No. 48-38403, japanese patent publication No. 62-174204, etc.), and 4, 4', and biimidazole compounds in which the phenyl group at the 5, 5' -position is substituted with a carbonylalkoxy group (see, for example, Japanese patent 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 ] -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, and the like.
Examples of the acylphosphine oxide compound include 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and the like. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.
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 compounds, and the like.
These are preferably used in combination with a polymerization initiation aid (D1) (particularly an amine) described later.
The polymerization initiator (D) is preferably a polymerization initiator containing at least 1 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) may be, for example, 0.01 to 40% by mass, and preferably 0.1 to 35% by mass, based on the total amount of all the resins (B) and the polymerizable compound (C) contained in the colored curable resin composition.
< polymerization initiation assistant (D1) >)
The polymerization initiation aid (D1) is a compound or sensitizer for promoting polymerization of a polymerizable compound whose polymerization is initiated by a polymerization initiator. When the polymerization initiator (D1) is contained, it is usually 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 (commonly known as michelson), 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 phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylsulfanylacetic acid, N-naphthylglycine, and naphthyloxyacetic acid.
When the polymerization initiator aid (D1) is used, the content thereof may be, for example, 0.01 to 40% by mass, preferably 0.1 to 30% by mass, based on the total amount of the resin (B) and the polymerizable compound (C).
< 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-COO-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-, a solvent), 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-di-nAlkane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, methyl anisole, and the like.
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, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, ethylene glycol monoethyl ether acetate, and the like, Diethylene glycol monobutyl ether acetate and 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 usually 99.99% by mass or less, preferably 0.1% by mass to 99.9% by mass, more preferably 1% by mass to 99.9% by mass, even more preferably 10% by mass to 99% by mass, particularly preferably 40% by mass to 99% by mass, even more preferably 50% by mass to 90% by mass, particularly preferably 60% by mass to 95% by mass, and very preferably 70% by mass to 90% by mass, based on the total amount of the colored curable resin composition.
The colored curable resin composition of the present invention can be prepared by dispersing all or a part of the compound (I) and the compound (II) in all or a part of the solvent (E) to prepare a colorant-containing solution, and then using the colorant-containing solution.
The content of the solid content in the colorant-containing solution may be, for example, 0.01 to 99.99% by mass, preferably 0.1 to 99.9% by mass, more preferably 0.1 to 99% by mass, still more preferably 1 to 90% by mass, still more preferably 1 to 60% by mass, yet more preferably 3 to 50% by mass, particularly preferably 3 to 30% by mass, and extremely preferably 5 to 30% by mass, based on the total amount of the colorant-containing solution.
The total content of the compound (I) and the compound (II) in the colorant-containing solution may be, for example, 0.0001% by mass or more, preferably 0.01% by mass or more, more preferably 1% by mass or more, further preferably 5% by mass or more, further preferably 10% by mass or more, further preferably 20% by mass or more, and particularly preferably 30% by mass or more, of the total amount of solid components in the coloring dispersion liquid. On the other hand, the upper limit of the total content of the compound (I) and the compound (II) in the colorant-containing solution is usually less than 100% by mass, for example, may be 99% by mass or less, based on the total amount of solid components in the colorant-containing solution.
When the colorant-containing solution is prepared by dispersing all or a part of the compound (I) and the compound (II) in all or a part of the solvent (E), the dispersion stability of the colorant-containing solution can be further improved by previously containing all or a part of the resin (B). The content of the resin (B) in the colorant-containing solution may be, for example, 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, still more preferably 1 to 500 parts by mass, particularly preferably 5 to 200 parts by mass, and still more preferably 10 to 100 parts by mass, based on 100 parts by mass of the total of the compound (I) and the compound (II).
The compound (I) and the compound (II) may be subjected to, if necessary, rosin treatment, surface treatment using a derivative or the like into which an acidic group or a basic group has been introduced, grafting treatment of the surfaces of the compound (I) and the compound (II) with a polymer compound or the like, micronization treatment with a sulfuric acid micronization method or the like, cleaning treatment with an organic solvent, water or the like for removing impurities, removal treatment with an ion exchange method or the like for removing ionic impurities, or the like. The particle diameters of the compound (I) and the compound (II) are preferably substantially uniform.
The compound (I) and the compound (II) can be dispersed by a dispersing treatment with a dispersant to obtain a state in which the compound (I) and the compound (II) are uniformly dispersed in the coloring dispersion liquid. The compound (I) and the compound (II) may be dispersed separately or in combination. When the colorant (a) contains the compound (I), the compound (II), and the dispersant, the dispersibility of the compound (I) tends to be improved.
The dispersant may be any of cationic, anionic, nonionic and amphoteric surfactants. Specifically, there may be mentioned polyester, polyamide, 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 industry Co., Ltd.), FLOWLEN (manufactured by Kyoho chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by AJIAOSU Fine chemical Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and the like.
When the dispersant is used, the amount of the dispersant (solid content) used is 10000 parts by mass or less, preferably 5000 parts by mass or less, more preferably 1000 parts by mass or less, further preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less, further preferably 100 parts by mass or less, further preferably 5 to 100 parts by mass, and particularly preferably 5 to 50 parts by mass, based on 100 parts by mass of the total of the compound (I) and the compound (II). When the amount of the dispersant used is within the above range, a colored dispersion liquid in a more uniform dispersion state tends to be obtained.
The colored curable resin composition of the present invention may further contain a leveling agent (F) and an antioxidant (G).
< leveling agent (F) >
Examples of the leveling agent (F) include a silicone surfactant, a fluorine surfactant, and a silicone surfactant having a fluorine atom. These 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 corporation), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by shin-Etsu chemical industry Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by MONTMEIVE PERFURIACE MATLS. MATPANI contract Co., Ltd.) may 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 Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC (Co., Ltd.), F-top (registered trademark) EF301, F-top EF303, F-top EF351, F-top EF352 (manufactured by Mitsubishi electro chemical Co., Ltd.), Surflon (registered trademark) S381, Surflon S382, Surflon SC101, Surflon SC105 (manufactured by Asahi Nitron (Co., Ltd.), and E5844 (manufactured by King Kogyo chemical Co., Ltd.).
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 (manufactured by DIC Co., Ltd.).
When the leveling agent (F) is contained, the content thereof is usually 0.0005 to 5% by mass, preferably 0.001 to 1% by mass, more preferably 0.001 to 0.5% by mass, still more preferably 0.002 to 0.2% by mass, and particularly preferably 0.005 to 0.1% by mass, based on the total amount of the colored curable resin composition. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
< antioxidant (G) >
From the viewpoint of improving the heat resistance of the colorant, the antioxidant (G) is preferably used alone or in combination of 2 or more. 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 above-mentioned phenolic antioxidants include Irganox 1010(Irganox 1010: pentaerythritol tetrakis [ 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF), Irganox 1076(Irganox 1076: octadecyl-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate, manufactured by BASF), Irganox 1330(Irganox 1330:3,3 ', 5,5 ' -hexa-t-butyl-a, a ' - (mesitylene-2, 4, 6-triyl) tri-p-cresol, manufactured by BASF), Irganox 3114(Irganox 3114:1,3, 5-tris (3, 5-di-t-butyl-4-hydroxybenzyl) -1, 3, 5-triazine-2, 4,6(1H, 3H, 5H) -trione, manufactured by BASF), Irganox 3790(Irganox 3790:1,3, 5-tri-t-butyl-4-hydroxybenzyl) -1, 3, 5-triazine-2, 4,6(1H, 5H) -trione, manufactured by BASF), 3, 5-triazine-2, 4,6(1H, 3H, 5H) -trione, manufactured by BASF), Irganox 1035(Irganox 1035: thiodiethylene bis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], manufactured by BASF), Irganox1135 (Irganox1135: phenylalanic acid, 3, 5-bis (1, 1-dimethylethyl) -4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF), Irganox 1520L (Irganox 1520L:4, 6-bis (octylthiomethyl) -o-cresol, manufactured by BASF), Irganox 3125(Irganox 3125, manufactured by BASF), Irganox 565(Irganox 565:2, 4-bis (n-octylthio) -6- (4-hydroxy 3 ', 5' -di-tert-butylanilino) -1, 3, 5-triazine, manufactured by BASF), ADK B80 (ADK B80: ADK 3-bis (ADK 3-5-hydroxy propionyloxy) -1, 3, 5-bis (ADB 3-5-hydroxy-phenyl-5-methyl-o-phenyl-5, 1-dimethylethyl) -2, 4,8, 10-tetraoxaspiro (5,5) undecane (manufactured by ADEKA), Sumilizer BHT (Sumilizer BHT, manufactured by Sumitomo chemical Co., Ltd.), Sumilizer GA-80 (Sumilizer GA-80, manufactured by Sumitomo chemical Co., Ltd.), Sumilizer GS (Sumilizer GS, manufactured by Sumitomo chemical Co., Ltd.), Cyanox 1790 (manufactured by Sitech)) and vitamin E (manufactured by Eisai).
Examples of the phosphorus-based antioxidant include Irgafos 168(Irgafos 168: tris (2, 4-di-t-butylphenyl) phosphite, manufactured by BASF), Irgafos 12(Irgafos 12: tris [ 2- [ [2,4,8, 10-tetra-t-butylbenzo [ d, f ] [1,3,2] dioxaphosphin-6-yl ] oxy ] ethyl ] amine, manufactured by BASF), Irgafos 38(Irgafos 38: bis (2, 4-bis (1, 1-dimethylethyl) -6-methylphenyl) ethyl phosphite, manufactured by BASF), ADK STAB 329K (manufactured by ADEKA), ADK STAB PEP36 (manufactured by ADEKA), ADSTAB PEP-8 ((manufactured by ADEKA), Sandstab P-EPQ (manufactured by Clariant), Weston618 (GE, manufactured by Weston618, manufactured by Wemilstin), Wemilstin 626 (manufactured by Westin G619, manufactured by Westin 626, manufactured by Westin GK-6-hydroxy propoxy 3- (GP-3, manufactured by Westin) (manufactured by Westin) and U.3- (3-butyl) propoxy G, manufactured by BASF) -2, 4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1.3.2] dioxaphosphepin) (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 colored curable resin 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-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-thioalkylpropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, N-glycidyloxy-3-epoxysilane, and the like, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane and N-phenyl-3-aminopropyltriethoxysilane, etc.
< method for producing colored curable resin composition >
The colored curable resin composition can be prepared, for example, by mixing the colorant (a), the resin (B), the solvent (E), and the leveling agent (F), and further mixing the mixture with the polymerizable compound (C), the polymerization initiator (D), the polymerization initiation aid (D1), and other components when the pattern is formed by photolithography.
The pigment is preferably mixed with a part or all of the solvent (E) in advance, and dispersed by a bead mill until the average particle diameter of the pigment becomes about 0.2 μm or less. In this case, a part or all of the pigment dispersant and the resin (B) may be blended as necessary. The remaining components are mixed in the thus obtained pigment dispersion liquid so as to have a predetermined concentration, whereby the target colored curable resin composition can be prepared.
The dyes may be dissolved in a part or all of the solvent (E) separately in advance to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.
The mixed colored curable resin composition is preferably filtered through a filter having a pore size of about 0.1 to 10 μm.
(3) Color filter
The color filter can be formed from the colored curable resin composition of the present invention. Examples of a method for forming a colored pattern include a photolithography method, an ink jet method, a printing method, and the like. Among them, photolithography is preferable. The photolithography method is a method in which 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, a colored coating film which is a cured product of the colored curable resin composition layer can be formed without using a photomask and/or without performing development at the time of exposure. The colored pattern and the colored coating film formed in this way are the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited, and can be suitably adjusted according to the purpose, application, 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 in which a thin film of aluminum, silver/copper/palladium alloy, or the like is formed on the substrate, or the like is 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 conventional apparatus and conditions. For example, the following can be used.
First, a substrate is coated with the colored curable resin composition, and is dried by heating (prebaking) and/or drying under reduced pressure to remove volatile components such as a solvent and dry the composition, thereby obtaining a smooth colored curable resin composition layer.
Examples of the coating method include a spin coating method, a slit coating method, and a slit/spin coating method.
The temperature for heating and drying is preferably 30 to 120 ℃, more preferably 50 to 110 ℃. The heating time is preferably 10 seconds to 60 minutes, and more preferably 30 seconds to 30 minutes.
When the drying is carried out under reduced pressure, the drying is preferably carried out under a pressure of 50 to 150Pa and at a temperature of 20 to 25 ℃.
The film thickness of the colored curable resin composition is not particularly limited, and may be appropriately selected according to the film thickness of the target color filter.
Next, the colored curable resin composition layer is exposed to light through a photomask for forming a target colored pattern. In order to uniformly irradiate parallel light rays to the entire exposure surface and perform precise alignment of the photomask and 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 light source used for exposure is preferably a light source that generates light having a wavelength of 250 to 450 nm. For example, light less than 350nm may be cut off using a filter that cuts off the wavelength region, or light near 436nm, near 408nm, or near 365nm may be selectively extracted using a band-pass filter that extracts these wavelength regions. Specifically, mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like can be given.
The exposed colored curable composition layer is brought into contact with a developer to develop the layer, thereby forming a colored pattern on the substrate. The unexposed portion of the colored curable composition layer is dissolved in a developing solution and removed by development.
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 concentration of the basic compound in the aqueous solution may be, for example, 0.01 to 10% by mass. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spraying method, and the like. Further, the substrate can be inclined at an arbitrary angle during development.
The developed substrate is preferably washed with water.
Further preferably, the obtained colored pattern is subjected to post-baking.
(4) Display device
The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, or the like) and a solid-state imaging element, and particularly as a color filter used in an organic EL device.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to the following examples, and it goes without saying that the present invention can be carried out with appropriate modifications within a range that can be adapted to the gist described above and below, and these are included in the technical scope of the present invention. In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass".
In the following synthesis examples, the structure of the compound was confirmed by MASS spectrometry (LC; model 1200 by Agilent, MASS; model LC/MSD6130 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.
HLC-8120 GPC (manufactured by Tosoh corporation)
The column is TSK-GELG 2000HXL
Column temperature 40 deg.C
Solvent tetrahydrofuran
Flow rate 1.0 mL/min
The solid content concentration of the analysis sample is 0.001-0.01 mass%
Sample size 50 μ L
Detector RI
Calibration standard materials 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) to the number average molecular weight (Mn) in terms of polystyrene obtained above was defined as the degree of dispersion.
Synthesis example 1
8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industry Co., Ltd.), 3.8 parts of glycine (manufactured by Tokyo chemical industry Co., Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industry Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industry Co., Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 7 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the orange-red precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried at 60 ℃ under reduced pressure to obtain 9.1 parts (yield: 88%) of a compound represented by formula (II-1) (also referred to as compound II-1).
< identification of Compound II-1 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-505
Accurate mass 506
Synthesis example 2
8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industries, Ltd.), 6.0 parts of 5-aminopentanoic acid (manufactured by Tokyo chemical industries, Ltd.), 1.3 parts of zinc acetate (manufactured by Kanto chemical industries, Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industries, Ltd.) were added thereto and stirred at 150 ℃ for 14 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the orange-red precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 8.8 parts (yield: 77%) of a compound represented by formula (II-4) (also referred to as compound II-4).
< identification of Compound II-4 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-589
Accurate mass 590
Synthesis example 3
8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Tokyo chemical industry Co., Ltd.), 8.4 parts of 4-amino-3, 5-dimethylbenzoic acid (synthesized according to the method described in European Journal of medicinal Chemistry2014, 78.236), 1.3 parts of zinc acetate (manufactured by Kanto chemical Co., Ltd.) and 314 parts of imidazole (manufactured by Tokyo chemical industry Co., Ltd.) were added thereto, and the mixture was stirred at 150 ℃ for 22 hours. While the resulting mixture was kept at 20 ℃ or lower, 267 parts of previously prepared 37% hydrochloric acid (manufactured by Kanto chemical Co., Ltd.) and 1300 parts of water were added to the mixture, whereby an orange-red precipitate was produced. The mixture containing the orange-red precipitate was filtered, and the filtered residue was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60 ℃ to obtain 13 parts (yield: 90%) of a compound represented by formula (II-8) (also referred to as compound II-8).
< identification of Compound II-8 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-685
Accurate mass 686
Synthesis example 4
The same procedures as in synthesis example 1 were repeated except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.4 parts of 1,6,7, 12-tetrachloro-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by ComBi Blocks), thereby obtaining 2.9 parts of a compound represented by formula (II-91) (also referred to as compound II-91) (yield: 70%).
< identification of Compound II-91 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-641
Accurate mass 642
Synthesis example 5
The same procedures as in synthesis example 2 were repeated except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.4 parts of 1,6,7, 12-tetrachloro-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by ComBi Blocks), thereby obtaining 3.7 parts (yield: 79%) of a compound represented by formula (II-94) (also referred to as compound II-94).
< identification of Compound II-94 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-725
Accurate mass 726
Synthesis example 6
The same procedures as in synthesis example 1 were repeated except that 8.0 parts of 3,4,9, 10-perylenetetracarboxylic dianhydride in synthesis example 1 was changed to 3.5 parts of 1, 7-dibromo-3, 4,9, 10-perylenetetracarboxylic dianhydride (manufactured by Aldrich), thereby obtaining 2.7 parts (yield: 65%) of the compound represented by formula (II-100) (also referred to as compound II-100).
< identification of Compound II-100 >
(Mass analysis) ionization mode ESI-M/z [ M-H ]]-661
Accurate mass 662
Synthesis example 7
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 changed to a nitrogen atmosphere, and 280 parts of propylene glycol monomethyl ether acetate was charged and 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 (containing 1:1 ratio in terms of molar ratio) and 125 parts of propylene glycol monomethyl ether acetate. On the other hand, 2-azo was added dropwise over 6 hoursA solution of 33 parts of bis (2, 4-dimethylvaleronitrile) in 235 parts of propylene glycol monomethyl ether acetate. After completion of the dropwise addition, the mixture was held at 80 ℃ for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution containing 35.1% of a solid content and having a viscosity of 125 mPas as measured with a type B viscometer (23 ℃). The weight-average molecular weight Mw of the resulting copolymer was 9.2X 103The dispersion degree was 2.08, and the acid value in terms of solid content was 77 mg-KOH/g. The resin B1 has the following structural units.
< example 1 >
(1) Preparation of coloring composition
The ingredients were mixed in the following proportions and the colorant was dispersed using a bead mill. Thereafter, the beads were removed by filtration to obtain coloring composition 1.
Next, the respective components were mixed at the following ratio to obtain a colored curable resin composition 1.
(2) Production of colored coating film
The colored curable resin composition is applied onto a 5cm square glass substrate (EAGLE XG; manufactured by CORNING) by spin coating so that the post-baking film thickness is 1.7 to 2 μm, and then pre-baked at 100 ℃ for 3 minutes to form a colored curable resin composition layer. After cooling, the colored curable resin composition formed on the substrate was exposed to an exposure apparatus (TME-150 RSK; manufactured by TOPCON Ltd.) in an air atmosphereThe mixture layer has a thickness of 80mJ/cm2The exposure amount (365nm basis) of (A) was irradiated with light. After the light irradiation, the resultant was postbaked at 230 ℃ for 30 minutes in an oven to obtain a colored coating film.
(3) Heat resistance test
The absorbance of the obtained colored coating film was calculated using a color measuring machine (OSP-SP-200; manufactured by OLYMPUS). The colored coating film after the measurement was heated at 230 ℃ for 120 minutes in an oven under an air atmosphere, and then the absorbance was calculated using a color measuring machine. The absorbance retention was determined from the change in absorbance at the maximum absorption wavelength of the colored curable composition film before and after the heat resistance test.
< example 2 >
A colored curable resin composition 2 was obtained in the same manner as in example 1 except that the compound (II-4) was used in place of the compound (II-1). The results are shown in Table 4.
< example 3 >
A colored curable resin composition 3 was obtained in the same manner as in example 1 except that the compound (II-8) was used instead of the compound (II-1). The results are shown in Table 4.
< example 4 >
A colored curable resin composition 4 was obtained in the same manner as in example 1, except that the amount of compound (I) was changed to 40 parts and the amount of compound (II-8) was changed to 60 parts. The results are shown in Table 4.
< example 5 >
A colored curable resin composition 5 was obtained in the same manner as in example 1, except that the amount of compound (I) was changed to 60 parts and the amount of compound (II-8) was changed to 40 parts. The results are shown in Table 4.
< example 6 >
A colored curable resin composition 6 was obtained in the same manner as in example 1, except that the compound (II-91) was used instead of the compound (II-1). The results are shown in Table 4.
< example 7 >
A colored curable resin composition 7 was obtained in the same manner as in example 1 except that the compound (II-94) was used in place of the compound (II-1). The results are shown in Table 4.
< example 8 >
A colored curable resin composition 8 was obtained in the same manner as in example 1, except that the compound (II-100) was used in place of the compound (II-1). The results are shown in Table 4.
< comparative example 1 >
A colored curable resin composition 9 was obtained in the same manner as in example 1, except that a colorant was prepared without using the compound (II-1). The results are shown in Table 4.
[ Table 4]
Claims (7)
1. A coloring composition comprising a coloring agent and a resin, wherein the coloring agent comprises a compound represented by the following formula (I) and a compound represented by the following formula (II),
in the formula (II), the compound is shown in the specification,
R1and R2Each independently represents a 2-valent hydrocarbon group having 1 to 20 carbon atoms,
R3~R10each independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.
2. The coloring composition according to claim 1, wherein R is1And R2Is a 2-valent aromatic hydrocarbon group having 1 to 20 carbon atoms.
3. The coloring composition according to claim 1, wherein R is1And R2Each independently is an alkanediyl group having 1 to 20 carbon atoms.
4. The coloring composition according to claim 1, wherein R is1And R2Each independently is a 2-valent alicyclic hydrocarbon group having 1 to 20 carbon atoms.
5. A colored curable resin composition comprising a compound represented by the following formula (I), a compound represented by the following formula (II), a resin, a polymerizable compound, a polymerization initiator and a solvent,
in the formula (II), the compound is shown in the specification,
R1and R2Each independently represents a 2-valent hydrocarbon group having 1 to 20 carbon atoms,
R3~R10each independently represents a hydrogen atom, a nitro group, a halogen atom, or a hydrocarbon group having 1 to 40 carbon atoms and having a substituent.
6. A color filter comprising the colored curable resin composition according to claim 5.
7. A display device containing the color filter according to claim 6.
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JP2000297224A (en) * | 1999-01-26 | 2000-10-24 | Clariant Gmbh | Pigment preparation containing 2 or more kinds of perylene compounds |
JP2006335995A (en) * | 2005-06-06 | 2006-12-14 | Hitachi Maxell Ltd | Electrically-conductive ink for inkjet, electrically-conductive pattern, and electrically-conductive material |
JP2016124971A (en) * | 2014-12-26 | 2016-07-11 | 住友化学株式会社 | Compound |
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ATE60071T1 (en) * | 1987-03-13 | 1991-02-15 | Ciba Geigy Ag | PERYLENETETRACARBONIC ACID DIIMIDES WITH LONG-CHAIN RAILS CONTAINING CARBONYL GROUPS. |
DE3926564A1 (en) * | 1989-08-11 | 1991-02-14 | Hoechst Ag | NEW PIGMENT PREPARATIONS BASED ON PERYLENE COMPOUNDS |
JP4174842B2 (en) * | 1996-12-16 | 2008-11-05 | 富士ゼロックス株式会社 | Photo-semiconductor electrode, photoelectric conversion device, and photoelectric conversion method |
JP3877243B2 (en) | 1997-02-26 | 2007-02-07 | 住友化学株式会社 | Fluorescent film |
US6166210A (en) * | 1997-12-15 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Perylene imide monocarboxylic acids |
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JP2000297224A (en) * | 1999-01-26 | 2000-10-24 | Clariant Gmbh | Pigment preparation containing 2 or more kinds of perylene compounds |
JP2006335995A (en) * | 2005-06-06 | 2006-12-14 | Hitachi Maxell Ltd | Electrically-conductive ink for inkjet, electrically-conductive pattern, and electrically-conductive material |
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