JP2020125455A - Colored resin composition - Google Patents
Colored resin composition Download PDFInfo
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- JP2020125455A JP2020125455A JP2019219956A JP2019219956A JP2020125455A JP 2020125455 A JP2020125455 A JP 2020125455A JP 2019219956 A JP2019219956 A JP 2019219956A JP 2019219956 A JP2019219956 A JP 2019219956A JP 2020125455 A JP2020125455 A JP 2020125455A
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- JP
- Japan
- Prior art keywords
- group
- formula
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- compound represented
- ion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 229920005989 resin Polymers 0.000 claims abstract description 35
- 239000011347 resin Substances 0.000 claims abstract description 35
- 239000003086 colorant Substances 0.000 claims abstract description 26
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 239000000049 pigment Substances 0.000 claims description 46
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 239000003505 polymerization initiator Substances 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 6
- 239000000126 substance Substances 0.000 abstract description 8
- -1 2-ethylhexyl group Chemical group 0.000 description 99
- 230000015572 biosynthetic process Effects 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 48
- 150000002430 hydrocarbons Chemical group 0.000 description 41
- 239000002904 solvent Substances 0.000 description 41
- 239000000243 solution Substances 0.000 description 37
- 239000007787 solid Substances 0.000 description 35
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 24
- 229910052744 lithium Inorganic materials 0.000 description 24
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 21
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 238000004040 coloring Methods 0.000 description 17
- 239000006185 dispersion Substances 0.000 description 17
- 239000000975 dye Substances 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 150000002500 ions Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000011324 bead Substances 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000002253 acid Chemical group 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000000977 initiatory effect Effects 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- 238000004949 mass spectrometry Methods 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229940085991 phosphate ion Drugs 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229940116333 ethyl lactate Drugs 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 5
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical group NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 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
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 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
- 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 2
- AJTVSSFTXWNIRG-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanesulfonic acid Chemical compound OCC[NH+](CCO)CCS([O-])(=O)=O AJTVSSFTXWNIRG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000001055 blue pigment Substances 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 150000004292 cyclic ethers Chemical group 0.000 description 2
- GUOJYIXWHMJFDM-UHFFFAOYSA-N decan-2-yl prop-2-enoate Chemical compound CCCCCCCCC(C)OC(=O)C=C GUOJYIXWHMJFDM-UHFFFAOYSA-N 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 229940043264 dodecyl sulfate Drugs 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- WRKCIHRWQZQBOL-UHFFFAOYSA-N octyl dihydrogen phosphate Chemical compound CCCCCCCCOP(O)(O)=O WRKCIHRWQZQBOL-UHFFFAOYSA-N 0.000 description 2
- 150000002891 organic anions Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- UUIPAJHTKDSSOK-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)(O)=O UUIPAJHTKDSSOK-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- IEIADDVJUYQKAZ-UHFFFAOYSA-N 1,8-naphthosultone Chemical compound C1=CC(S(=O)(=O)O2)=C3C2=CC=CC3=C1 IEIADDVJUYQKAZ-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- QIRUERQWPNHWRC-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(CC=2C=C3OCOC3=CC=2)=N1 QIRUERQWPNHWRC-UHFFFAOYSA-N 0.000 description 1
- GWCJNVUIVCCXER-UHFFFAOYSA-N 2-(1-phenylprop-2-enoxymethyl)oxirane Chemical compound C=1C=CC=CC=1C(C=C)OCC1CO1 GWCJNVUIVCCXER-UHFFFAOYSA-N 0.000 description 1
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- 239000004611 light stabiliser Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- FEDFHMISXKDOJI-UHFFFAOYSA-M lithium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FEDFHMISXKDOJI-UHFFFAOYSA-M 0.000 description 1
- VDVLPSWVDYJFRW-UHFFFAOYSA-N lithium;bis(fluorosulfonyl)azanide Chemical compound [Li+].FS(=O)(=O)[N-]S(F)(=O)=O VDVLPSWVDYJFRW-UHFFFAOYSA-N 0.000 description 1
- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001053 orange pigment Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- AVFBYUADVDVJQL-UHFFFAOYSA-N phosphoric acid;trioxotungsten;hydrate Chemical compound O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O AVFBYUADVDVJQL-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- RJPWSGDBEHVWPP-UHFFFAOYSA-N potassium bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound [K+].FC(F)(F)S(=O)(=O)[C-](S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F RJPWSGDBEHVWPP-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- QENAFDOIABJELJ-UHFFFAOYSA-J sodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate;iron(3+);hydrate Chemical compound O.[Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QENAFDOIABJELJ-UHFFFAOYSA-J 0.000 description 1
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
- KQHKITXZJDOIOD-UHFFFAOYSA-M sodium;3-sulfobenzoate Chemical compound [Na+].OS(=O)(=O)C1=CC=CC(C([O-])=O)=C1 KQHKITXZJDOIOD-UHFFFAOYSA-M 0.000 description 1
- IXBPPZBJIFNGJJ-UHFFFAOYSA-N sodium;cyanoiminomethylideneazanide Chemical compound [Na+].N#C[N-]C#N IXBPPZBJIFNGJJ-UHFFFAOYSA-N 0.000 description 1
- XCWOYCJVVPIRIS-UHFFFAOYSA-M sodium;isoquinoline-5-sulfonate Chemical compound [Na+].N1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 XCWOYCJVVPIRIS-UHFFFAOYSA-M 0.000 description 1
- MKAWPVONNWUREJ-UHFFFAOYSA-M sodium;methyl(3-trihydroxysilylpropoxy)phosphinate Chemical compound [Na+].CP([O-])(=O)OCCC[Si](O)(O)O MKAWPVONNWUREJ-UHFFFAOYSA-M 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-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
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Landscapes
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Abstract
Description
本発明は着色樹脂組成物に関するものである。 The present invention relates to a colored resin composition.
液晶表示装置、エレクトロルミネッセンス表示装置及びプラズマディスプレイ等の表示装置やCCDやCMOSセンサなどの固体撮像素子に使用されるカラーフィルタは、着色硬化性樹脂組成物から製造される。このような着色硬化性樹脂組成物としては、着色剤として、式(A−X)で表される化合物を含む組成物が知られている(特許文献1)。
従来から知られる式(A−X)で表される化合物を含む組成物では、形成されるカラーフィルタは耐薬品性の点で満足いくものではなかった。
そこで本発明は、耐薬品性に優れるカラーフィルタを得るのに有用な着色樹脂組成物を提供する。
In the composition containing the compound represented by the formula (AX) known in the related art, the color filter formed was not satisfactory in terms of chemical resistance.
Therefore, the present invention provides a colored resin composition useful for obtaining a color filter having excellent chemical resistance.
本発明は、以下の通りである。
[1] 着色剤及び樹脂を含み、着色剤が式(I)で表される化合物を含む着色樹脂組成物。
[式(I)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ独立に、水素原
子、ヒドロキシ基、ニトロ基、シアノ基、ハロゲン原子、カルボキシ基、スルホ基、スルファモイル基、メタロセニル基、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アミノ基、カルボキシ基、スルホ基、ホスホノ基、スルファモイル基、イソシアナト基、複素環で置換されていてもよく、
R11、R12、R13、R14、R15及びR16は、それぞれ独立に、水素原子、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、複素環又は極性基で置換されていてもよく、
R11、R12、R13、R14、R15及びR16のうちの1つ以上が、置換基として極性基を有する基であり、
nは、1〜3の整数を表し、
Aq-は、q価の陰イオンを表し、
qは1〜3の整数を表し、
pは式(I)で表される化合物の電荷を中性に保つ係数を表す。
群I:−O−、−S−、−CO−、−COO−、−OCO−、−COS−、−OCS−、−SO2−、−SO3−、−NH−、−CONH−、−NHCO−、−SO2NH−、−NHSO2−又は−N=CH−]
[2] さらに、重合性化合物及び重合開始剤を含む[1]に記載の着色樹脂組成物。
[3] 着色剤が、さらに顔料(但し、式(I)で表される化合物を除く。)を含む[1]又は[2]に記載の着色樹脂組成物。
[4] [1]〜[3]のいずれかに記載の着色樹脂組成物から形成されるカラーフィルタ。
[5] [4]に記載のカラーフィルタを含む表示装置。
なお本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組合せて使用することができる。
The present invention is as follows.
[1] A colored resin composition containing a colorant and a resin, and the colorant containing a compound represented by the formula (I).
[In the formula (I),
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, One or more of a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group is a divalent group selected from the following group I. Represents a substituted group, provided that when two or more methylene groups are replaced by a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle. ,
R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently one or two of a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group. One or more represents a group substituted with a divalent group selected from the following group I, provided that two or more methylene groups are replaced with a divalent group selected from the following group I: Groups are not next to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a heterocycle or a polar group,
At least one of R 11 , R 12 , R 13 , R 14 , R 15 and R 16 is a group having a polar group as a substituent,
n represents an integer of 1 to 3,
A q- represents a q-valent anion,
q represents an integer of 1 to 3,
p represents a coefficient for keeping the charge of the compound represented by the formula (I) neutral.
Group I: -O -, - S - , - CO -, - COO -, - OCO -, - COS -, - OCS -, - SO 2 -, - SO 3 -, - NH -, - CONH -, - NHCO -, - SO 2 NH - , - NHSO 2 - or -N = CH-]
[2] The colored resin composition according to [1], which further contains a polymerizable compound and a polymerization initiator.
[3] The colored resin composition according to [1] or [2], wherein the colorant further contains a pigment (excluding the compound represented by the formula (I)).
[4] A color filter formed from the colored resin composition according to any one of [1] to [3].
[5] A display device including the color filter according to [4].
In the present specification, the compounds exemplified as each component can be used alone or in combination of two or more kinds unless otherwise specified.
本発明の着色樹脂組成物によれば、耐薬品性に優れるカラーフィルタが得られる。 According to the colored resin composition of the present invention, a color filter having excellent chemical resistance can be obtained.
<着色樹脂組成物>
本発明の着色樹脂組成物は、着色剤(以下、「着色剤(A)」という場合がある。)、及び樹脂(以下、「樹脂(B)」という場合がある。)を含み、着色剤(A)が、式(I)で表される化合物(以下、「化合物(I)」という場合がある。)を含む。
本発明の着色樹脂組成物は、さらに重合性化合物(以下、「重合性化合物(C)」という場合がある。)、及び重合開始剤(以下、「重合開始剤(D)」という場合がある。)を含むことが好ましい。
本発明の着色樹脂組成物は、さらに重合開始助剤(D1)、溶剤(E)、レベリング剤(F)を含んでいてもよい。
<Colored resin composition>
The colored resin composition of the present invention contains a colorant (hereinafter sometimes referred to as “colorant (A)”) and a resin (hereinafter sometimes referred to as “resin (B)”), and the colorant (A) includes a compound represented by the formula (I) (hereinafter sometimes referred to as “compound (I)”).
The colored resin composition of the present invention may further include a polymerizable compound (hereinafter sometimes referred to as “polymerizable compound (C)”) and a polymerization initiator (hereinafter sometimes referred to as “polymerization initiator (D)”). .) are preferably included.
The colored resin composition of the present invention may further contain a polymerization initiation aid (D1), a solvent (E), and a leveling agent (F).
<着色剤(A)>
本発明の着色樹脂組成物は、着色剤(A)として、化合物(I)を含む。
<Colorant (A)>
The colored resin composition of the present invention contains the compound (I) as the colorant (A).
<化合物(I)>
以下、式(I)を用いて本発明について詳述するが、化合物(I)には、式(I)の共鳴構造が含まれ、さらに式(I)又はその共鳴構造式中の各基を炭素−炭素単結合又は炭素−窒素単結合の結合軸周りに回転させて得られる化合物も含まれることとする。
<Compound (I)>
Hereinafter, the present invention will be described in detail with reference to the formula (I). The compound (I) includes the resonance structure of the formula (I), and further includes formula (I) or each group in the resonance structure formula. A compound obtained by rotating around a bond axis of a carbon-carbon single bond or a carbon-nitrogen single bond is also included.
[式(I)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ独立に、水素原子、ヒドロキシ基、ニトロ基、シアノ基、ハロゲン原子、カルボキシ基、スルホ基、スルファモイル基、メタロセニル基、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アミノ基、カルボキシ基、スルホ基、ホスホノ基、スルファモイル基、イソシアナト基、複素環で置換されていてもよく、
R11、R12、R13、R14、R15及びR16は、それぞれ独立に、水素原子、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、複素環又は極性基で置換されていてもよく、
R11、R12、R13、R14、R15及びR16のうちの1つ以上が、置換基として極性基を有する基であり、
nは、1〜3の整数を表し、
Aq-は、q価の陰イオンを表し、
qは1〜3の整数を表し、
pは式(I)で表される化合物の電荷を中性に保つ係数を表す。
群I:−O−、−S−、−CO−、−COO−、−OCO−、−COS−、−OCS−、−SO2−、−SO3−、−NH−、−CONH−、−NHCO−、−SO2NH−、−NHSO2−又は−N=CH−]
[In the formula (I),
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, One or more of a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group is a divalent group selected from the following group I. Represents a substituted group, provided that when two or more methylene groups are replaced by a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle. ,
R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently one or two of a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group. One or more represents a group substituted with a divalent group selected from the following group I, provided that two or more methylene groups are replaced with a divalent group selected from the following group I: Groups are not next to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a heterocycle or a polar group,
At least one of R 11 , R 12 , R 13 , R 14 , R 15 and R 16 is a group having a polar group as a substituent,
n represents an integer of 1 to 3,
A q- represents a q-valent anion,
q represents an integer of 1 to 3,
p represents a coefficient for keeping the charge of the compound represented by the formula (I) neutral.
Group I: -O -, - S - , - CO -, - COO -, - OCO -, - COS -, - OCS -, - SO 2 -, - SO 3 -, - NH -, - CONH -, - NHCO -, - SO 2 NH - , - NHSO 2 - or -N = CH-]
R1〜R16で表される炭素数1〜30の炭化水素基としては、炭素数1〜30の脂肪族炭化水素基又は炭素数6〜30の芳香族炭化水素基等が例示される。 Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R 1 to R 16 include an aliphatic hydrocarbon group having 1 to 30 carbon atoms and an aromatic hydrocarbon group having 6 to 30 carbon atoms.
炭素数1〜30の脂肪族炭化水素基は、飽和及び不飽和の何れであってもよく、直鎖状、分岐鎖状及び環状の何れであってもよい。 The aliphatic hydrocarbon group having 1 to 30 carbon atoms may be saturated or unsaturated, and may be linear, branched or cyclic.
炭素数1〜30の直鎖状又は分岐鎖状の脂肪族炭化水素基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ビニル基、1−プロペニル基、2−プロペニル基(アリル基)等の直鎖状脂肪族炭化水素基;イソプロピル基、イソブチル基、イソペンチル基、ネオペンチル基、2−エチルヘキシル基等の分岐鎖状脂肪族炭化水素基等が挙げられる。直鎖状又は分岐鎖状の脂肪族炭化水素基の炭素数は、好ましくは1〜15であり、より好ましくは1〜10であり、さらに好ましくは1〜8である。
環状の脂肪族炭化水素基は、単環でも多環でもよい。該環状の脂肪族炭化水素基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が挙げられる。環状の脂肪族炭化水素基の炭素数は、好ましくは3〜18であり、より好ましくは3〜15であり、さらに好ましくは4〜15である。
Examples of the linear or branched aliphatic hydrocarbon group having 1 to 30 carbon atoms include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1 -A straight-chain aliphatic hydrocarbon group such as a propenyl group and a 2-propenyl group (allyl group); a branched chain aliphatic hydrocarbon group such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group, and a 2-ethylhexyl group Is mentioned. The linear or branched aliphatic hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 8 carbon atoms.
The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group. The cyclic aliphatic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 15 carbon atoms, and still more preferably 4 to 15 carbon atoms.
炭素数6〜30の芳香族炭化水素基としては、フェニル基、ナフチル基、フェナントリル基、アントリル基等が挙げられる。芳香族炭化水素基の炭素数は、好ましくは6〜20であり、より好ましくは6〜18であり、さらに好ましくは6〜15である。 Examples of the aromatic hydrocarbon group having 6 to 30 carbon atoms include phenyl group, naphthyl group, phenanthryl group and anthryl group. The carbon number of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, and further preferably 6 to 15.
炭素数1〜30の炭化水素基は、炭素数の上限が30以下である限り、上記に挙げた脂肪族炭化水素基、及び芳香族炭化水素基を2つ以上組み合わせた基であってもよい。このような基としては、例えば、キシリル基、トリメチルフェニル基、ジプロピルフェニル基、ジ(2,2−ジメチルプロピル)フェニル基、ベンジル基、フェネチル基、4−フェニルブチル基等が挙げられる。脂肪族炭化水素基、及び芳香族炭化水素基を2つ以上組み合わせた基の炭素数は、好ましくは7〜25であり、より好ましくは8〜20であり、さらに好ましくは8〜15である。 The hydrocarbon group having 1 to 30 carbon atoms may be a group obtained by combining two or more of the aliphatic hydrocarbon group and the aromatic hydrocarbon group mentioned above as long as the upper limit of the carbon number is 30 or less. .. Examples of such a group include a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a benzyl group, a phenethyl group, and a 4-phenylbutyl group. The number of carbon atoms of the group in which two or more aliphatic hydrocarbon groups and aromatic hydrocarbon groups are combined is preferably 7 to 25, more preferably 8 to 20, and further preferably 8 to 15.
R1〜R16で表される炭化水素基中のメチレン基の1つが下記群Iから選ばれる2価の基で置き換えられた基としては、以下のものが例示される。
群I:−O−、−S−、−CO−、−COO−、−OCO−、−COS−、−OCS−、−SO2−、−SO3−、−NH−、−CONH−、−NHCO−、−SO2NH−、−NHSO2−又は−N=CH−
Examples of the group in which one of the methylene groups in the hydrocarbon group represented by R 1 to R 16 is replaced with a divalent group selected from Group I below include the following.
Group I: -O -, - S - , - CO -, - COO -, - OCO -, - COS -, - OCS -, - SO 2 -, - SO 3 -, - NH -, - CONH -, - NHCO -, - SO 2 NH - , - NHSO 2 - or -N = CH-
炭化水素基中のメチレン基の1つが−O−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -O- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−S−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -S- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−CO−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -CO- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−COO−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -COO- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−OCO−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -OCO- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−COS−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -COS- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−OCS−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -OCS- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−SO2−で置き換えられた基としては、例えば、
以下のものが挙げられる(*は結合手を表す)。
Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced by —SO 2 — include, for example,
The following are mentioned (* represents a bond).
炭化水素基中のメチレン基の1つが−SO3−で置き換えられた基としては、例えば、
以下のものが挙げられる(*は結合手を表す)。
Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced by —SO 3 — include, for example,
The following are mentioned (* represents a bond).
炭化水素基中のメチレン基の1つが−NH−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -NH- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−CONH−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -CONH- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−NHCO−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with -NHCO- include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−SO2NH−で置き換えられた基としては、例え
ば、以下のものが挙げられる(*は結合手を表す)。
Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with —SO 2 NH— include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−NHSO2−で置き換えられた基としては、例え
ば、以下のものが挙げられる(*は結合手を表す)。
Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced with —NHSO 2 — include the following (* represents a bond).
炭化水素基中のメチレン基の1つが−N=CH−で置き換えられた基としては、例えば、以下のものが挙げられる(*は結合手を表す)。 Examples of the group in which one of the methylene groups in the hydrocarbon group is replaced by -N=CH- include the following (* represents a bond).
R1〜R16で表される炭化水素基中のメチレン基の2つ以上が、前記群Iから選ばれる2価の基で置き換えられた基としては、前記2価の基が隣り合わなければ、該2価の基は前記群Iのいずれであってもよく、前記炭化水素基中のメチレン基の1つが群Iから選ばれる2価の基で置き換えられた基を適宜組み合わせた基等が挙げられる。 As a group in which two or more of the methylene groups in the hydrocarbon group represented by R 1 to R 16 are replaced with a divalent group selected from Group I, the divalent groups must be adjacent to each other. The divalent group may be any of the above-mentioned group I, and a group in which one of the methylene groups in the hydrocarbon group is replaced with a divalent group selected from the group I is appropriately combined. Can be mentioned.
R11〜R16で表される炭化水素基中のメチレン基の1つ又は2つ以上が、前記群Iから選ばれる2価の基で置き換えられた基としては極性基を形成しないことが好ましい。 As a group in which one or more of the methylene groups in the hydrocarbon group represented by R 11 to R 16 are replaced with a divalent group selected from Group I, it is preferable that a polar group is not formed. ..
R1〜R10で表されるハロゲン原子としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子等が挙げられ、塩素原子が好ましい。 Examples of the halogen atom represented by R 1 to R 10 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom is preferable.
R1〜R10で表されるメタロセニル基としては、フェロセニル基、ニッケロセニル基、コバルトニル基、フェロセンアルキル基、フェロセンアルコキシ基等が挙げられる。 Examples of the metallocenyl group represented by R 1 to R 10 include a ferrocenyl group, a nickelocenyl group, a cobaltnyl group, a ferrocene alkyl group, and a ferrocene alkoxy group.
R1〜R10で表される炭化水素基に含まれる水素原子が置換されていてもよいハロゲン原子としては、R1〜R10で表されるハロゲン原子と同じものが挙げられる。 Examples of the halogen atom which may be substituted for the hydrogen atom contained in the hydrocarbon group represented by R 1 to R 10 include the same halogen atom represented by R 1 to R 10 .
R1〜R16で表される炭化水素基に含まれる水素原子が置換されていてもよい複素環の炭素数は、好ましくは1〜20である。前記複素環としては、窒素原子、酸素原子、及び硫黄原子から選ばれる少なくとも1個の原子を含む複素環等が挙げられ、具体的には、アゼチジン、ピロール、ベンゾオキサゾール、チアゾール、オキセタン、フラン、チエタン、チオフェン等が挙げられる。 The number of carbon atoms of the heterocycle in which the hydrogen atom contained in the hydrocarbon group represented by R 1 to R 16 may be substituted is preferably 1 to 20. Examples of the heterocycle include a heterocycle containing at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom, and specifically, azetidine, pyrrole, benzoxazole, thiazole, oxetane, furan, and the like. Examples include thietane and thiophene.
R1〜R10としては、水素原子、又はハロゲン原子が好ましく、R1〜R10のうち1〜6つがハロゲン原子であり、それ以外が水素原子であることがより好ましく、R1〜R10のうち1〜4つがハロゲン原子であり、それ以外が水素原子であることがさらに好ましく、R1〜R10のうち2つがハロゲン原子であり、それ以外が水素原子であることがよりさらに好ましい。 As R 1 to R 10 , a hydrogen atom or a halogen atom is preferable, 1 to 6 of R 1 to R 10 are halogen atoms, and the others are more preferably hydrogen atoms, and R 1 to R 10 are preferable. It is more preferable that 1 to 4 of them are halogen atoms and the others are hydrogen atoms, and it is even more preferable that 2 of R 1 to R 10 are halogen atoms and the others are hydrogen atoms.
R1〜R10のうち2つがハロゲン原子である場合、該2つのハロゲン原子は、R7〜R10のうちのいずれか2つであることが好ましく、R7及びR9がハロゲン原子であることがより好ましい。 When two of R 1 to R 10 are halogen atoms, the two halogen atoms are preferably any two of R 7 to R 10 , and R 7 and R 9 are halogen atoms. Is more preferable.
R11〜R16で表される炭化水素基に含まれる水素原子が置換されていてもよい極性基とは、炭素原子及び水素原子以外のヘテロ原子を少なくとも1つ以上含有する官能基をいう。ヘテロ原子としては、例えば、酸素原子、硫黄原子、リン原子、窒素原子、ハロゲン原子が挙げられる。前記極性基としては、具体的には、ヒドロキシ基、カルボキシ基、エポキシ基、アミド基(N−メチルアミド基、N−イソプロピルアミド基、N−シクロプロピルアミド基、N−フェニルアミド基等の炭素数1〜12の炭化水素基でN−置換されたアミド基も含む)、ニトリル基、アミノ基、イミド基、イソシアナト基、チオール基、アルコキシ基、スルホ基、ホスホノ基、ニトロ基、アルコキシカルボニル基、アセチル基等のアシル基、ハロゲン原子等が挙げられ、カルボキシ基、アミド基、スルホ基、ホスホノ基等の酸基が好ましく、カルボキシ基又はアミド基がより好ましく、カルボキシ基がさらに好ましい。 The polar group optionally substituted with a hydrogen atom contained in the hydrocarbon group represented by R 11 to R 16 refers to a functional group containing at least one hetero atom other than a carbon atom and a hydrogen atom. Examples of the hetero atom include an oxygen atom, a sulfur atom, a phosphorus atom, a nitrogen atom and a halogen atom. Specific examples of the polar group include carbon numbers such as a hydroxy group, a carboxy group, an epoxy group, an amide group (N-methylamide group, N-isopropylamide group, N-cyclopropylamide group, N-phenylamide group, etc. 1 to 12 also includes N-substituted amide group), nitrile group, amino group, imide group, isocyanato group, thiol group, alkoxy group, sulfo group, phosphono group, nitro group, alkoxycarbonyl group, Examples thereof include an acyl group such as an acetyl group and a halogen atom, and an acid group such as a carboxy group, an amide group, a sulfo group and a phosphono group is preferable, a carboxy group or an amide group is more preferable, and a carboxy group is still more preferable.
炭化水素基に含まれる水素原子が極性基に置換された、置換基として極性基を有する基としては、例えば、極性基がカルボキシ基である下記式(po−1)〜式(po−6)で表される基、極性基がアミド基である下記式(po−7)〜式(po−10)で表される基が挙げられる。式中、*は結合手を表す。 Examples of the group having a polar group as a substituent in which a hydrogen atom contained in a hydrocarbon group is substituted with a polar group include, for example, the following formulas (po-1) to (po-6) in which the polar group is a carboxy group. And a group represented by the following formula (po-7) to formula (po-10) in which the polar group is an amide group. In the formula, * represents a bond.
R11〜R16のうち少なくとも1つは、R11〜R16で表される炭化水素基に含まれる水素原子が極性基に置換された、置換基として極性基を有する基である。R11〜R16のうち少なくとも1つが置換基として極性基を有する基であれば、耐薬品性に優れるカラーフィルタを形成できる。 At least one of R 11 to R 16 are hydrogen atoms contained in the hydrocarbon group represented by R 11 to R 16 is substituted with a polar group, a group having a polar group as a substituent. When at least one of R 11 to R 16 is a group having a polar group as a substituent, a color filter having excellent chemical resistance can be formed.
R11〜R16としては、炭素数1〜30の炭化水素基が好ましく、炭素数1〜20の炭化水素基がより好ましく、炭化水素基が脂肪族炭化水素基であることがさらに好ましく、炭化水素基が飽和の直鎖状脂肪族炭化水素基であることがさらにより好ましい。該飽和の直鎖状脂肪族炭化水素基の炭素数は、好ましくは1〜15であり、より好ましくは1〜10であり、さらに好ましくは1〜5である。また、R11〜R16が置換基として極性基を有する基である場合には、R11〜R16としては、脂肪族炭化水素基、又は脂肪族炭化水素基及び芳香族炭化水素基を2つ以上組み合わせた基であることが好ましく、R11〜R16が置換基として極性基を有しない基である場合には、R11〜R16としては、脂肪族炭化水素基、又は芳香族炭化水素基であることが好ましい。 As R 11 to R 16 , a hydrocarbon group having 1 to 30 carbon atoms is preferable, a hydrocarbon group having 1 to 20 carbon atoms is more preferable, and a hydrocarbon group is further preferably an aliphatic hydrocarbon group, Even more preferably, the hydrogen group is a saturated straight-chain aliphatic hydrocarbon group. The saturated linear aliphatic hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 5 carbon atoms. When R 11 to R 16 are groups having a polar group as a substituent, R 11 to R 16 may be an aliphatic hydrocarbon group, or an aliphatic hydrocarbon group and an aromatic hydrocarbon group. A combination of two or more groups is preferable, and when R 11 to R 16 are groups having no polar group as a substituent, R 11 to R 16 are an aliphatic hydrocarbon group or an aromatic carbon group. It is preferably a hydrogen group.
またR11〜R16のうち1〜4つが置換基として極性基を有する基であることが好ましく、2〜4つが置換基として極性基を有する基であることがより好ましく、R11〜R16のうち2つが置換基として極性基を有する基であることがさらに好ましい。 Moreover, it is preferable that 1 to 4 of R 11 to R 16 are groups having a polar group as a substituent, more preferably 2 to 4 are groups having a polar group as a substituent, and R 11 to R 16 It is more preferable that two of them are groups having a polar group as a substituent.
nとしては、1〜2が好ましく、1がより好ましい。 As n, 1-2 are preferable and 1 is more preferable.
Aq-で表されるq価の陰イオンは、1〜3価の陰イオンであり、無機陰イオンでもよく、有機陰イオンでもよい。
該無機陰イオンとしては、例えば、水酸化物イオン、ハロゲン化物イオン(フッ化物イオン、塩化物イオン、臭化物イオン、ヨウ化物イオン等)、硝酸イオン、過塩素酸イオン、塩素酸イオン、硫酸イオン、チオシアン酸イオン、リン酸イオン、リンタングステン酸イオン、リンモリブデン酸イオン、リンタングステンモリブデン酸イオン、ヘキサフルオロリン酸イオン、モリブデン酸イオン、タングステン酸イオン、チタン酸イオン、ジルコン酸イオン、ホウ酸イオン、テトラフルオロホウ酸イオン等が挙げられる。
該有機陰イオンとしては、例えば、酢酸イオン、トリフルオロ酢酸イオン、安息香酸イオン、パルミチン酸イオン、酒石酸イオン、エチレンジアミン四酢酸鉄イオン等の有機カルボン酸系陰イオン;メタンスルホン酸イオン、ドデシルスルホン酸イオン、ビニルスルホン酸イオン、ベンゼンスルホン酸イオン、トリフルオロメタンスルホン酸イオン、ノナフルオロブタンスルホン酸イオン、3−(トリヒドロキシシリル)−1−プロパンスルホン酸イオン、トルエンスルホン酸イオン、クロロベンゼンスルホン酸イオン、ペンタフルオロベンゼンスルホン酸イオン、3−カルボキシフェニルスルホン酸、3−ニトロフェニルスルホン酸イオン、ベンゼンジスルホン酸イオン、ジフェニルアミン−4−スルホン酸イオン、2−アミノ−4−メチル−5−クロロベンゼンスルホン酸イオン、2−アミノ−5−ニトロベンゼンスルホン酸イオン、フタロシアニンスルホン酸イオン、パーフルオロ−4−エチルシクロヘキサンスルホン酸イオン、ナフタレンモノスルホン酸イオン、ナフタレンジスルホン酸イオン、ナフタレントリスルホン酸イオン、ナフチルアミンモノスルホン酸イオン、ナフチルアミンジスルホン酸イオン、ナフチルアミントリスルホン酸イオン、8−{[3−(トリメトキシシリル)プロピル]アミノ}ナフタレン−1−スルホン酸イオン、8−{[3−(トリメトキシシリル)プロピル]アミノ}ナフタレン−1,5−ジスルホン酸イオン、イソキノリン−5−スルホン酸イオン、ナフトールモノスルホン酸イオン、ナフトールジスルホン酸イオン、ナフトールトリスルホン酸イオン、N,N−ビス(2−ヒドロキシエチル)−2−アミノエタンスルホン酸イオン等の有機スルホン酸系陰イオン;オクチルリン酸イオン、ドデシルリン酸イオン、オクタデシルリン酸イオン、フェニルリン酸イオン、ノニルフェニルリン酸イオン、2,2’−メチレンビス(4,6−ジ−t−ブチルフェニル)ホスホン酸イオン、3−(トリヒドロキシシリル)プロピルメチルホスホン酸イオン等の有機リン酸系陰イオン;ラウリル硫酸イオン、ラウレス硫酸イオン、ポリオキシエチレンアルキルフェノールスルホン酸イオン、ラウリル硫酸イオン等の有機硫酸系陰イオン;テトラアリールホウ酸イオン、ブチルトリフェニルホウ酸イオン等の有機ホウ酸系陰イオン;トリシアノメチドイオン、トリス(トリフルオロメタンスルホニル)メチドイオン、トリス(パーフルオロエチルスルホニル)メチドイオン等のメチドイオン類;ジシアナミドイオン;トリフルオロメタンスルホンアミドイオン、ベンゼンスルホンアミドイオン等のスルホンアミドイオン類;N,N−ビス(フルオロスルホニル)イミドイオン、ビス(トリフルオロメチルスルホニル)イミドイオン、ビス(ノナフルオロブタンスルホニル)イミドイオン、N,N−ヘキサフルオロ−1,3−ジスルホニルイミドイオン、1,1,2,2,3,3−ヘキサフルオロプロパン−1,3−ジスルホンイミドイオン等のスルホンイミドイオン類;等が挙げられる。
The q-valent anion represented by A q- is a 1-3-valent anion, and may be an inorganic anion or an organic anion.
Examples of the inorganic anion include hydroxide ion, halide ion (fluoride ion, chloride ion, bromide ion, iodide ion, etc.), nitrate ion, perchlorate ion, chlorate ion, sulfate ion, Thiocyanate ion, phosphate ion, phosphotungstate ion, phosphomolybdate ion, phosphotungsten molybdate ion, hexafluorophosphate ion, molybdate ion, tungstate ion, titanate ion, zirconate ion, borate ion, Tetrafluoroborate ion etc. are mentioned.
Examples of the organic anion include an acetate, a trifluoroacetate ion, a benzoate ion, a palmitate ion, a tartaric acid ion, an ethylenediaminetetraacetic acid iron ion, and other organic carboxylic acid anions; methanesulfonate ion, dodecylsulfonate ion. Ion, vinyl sulfonate ion, benzene sulfonate ion, trifluoromethane sulfonate ion, nonafluorobutane sulfonate ion, 3-(trihydroxysilyl)-1-propane sulfonate ion, toluene sulfonate ion, chlorobenzene sulfonate ion, Pentafluorobenzene sulfonate ion, 3-carboxyphenyl sulfonate ion, 3-nitrophenyl sulfonate ion, benzenedisulfonate ion, diphenylamine-4-sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino-5-nitrobenzene sulfonate ion, phthalocyanine sulfonate ion, perfluoro-4-ethylcyclohexane sulfonate ion, naphthalene monosulfonate ion, naphthalene disulfonate ion, naphthalene trisulfonate ion, naphthylamine monosulfonate ion, Naphthylamine disulfonate ion, naphthylamine trisulfonate ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene-1-sulfonate ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene -1,5-disulfonate ion, isoquinoline-5-sulfonate ion, naphthol monosulfonate ion, naphthol disulfonate ion, naphthol trisulfonate ion, N,N-bis(2-hydroxyethyl)-2-aminoethane Organic sulfonate anions such as sulfonate ions; octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2′-methylenebis(4,6-di- Organic phosphate anions such as t-butylphenyl)phosphonate ion and 3-(trihydroxysilyl)propylmethylphosphonate ion; lauryl sulfate ion, laureth sulfate ion, polyoxyethylene alkylphenol sulfonate ion, lauryl sulfate ion and the like Organic sulfate anions; Tetraarylborate ions, butyltriphenylborate ions and other organic borate anions; Tricyanomethide ions, Tris(trifluoromethanes) Rufonyl)methide ion, tris(perfluoroethylsulfonyl)methide ion, and other methide ions; dicyanamide ion; trifluoromethanesulfonamide ion, benzenesulfonamide ion, and other sulfonamide ions; N,N-bis(fluorosulfonyl)imide ion, bis (Trifluoromethylsulfonyl)imide ion, bis(nonafluorobutanesulfonyl)imide ion, N,N-hexafluoro-1,3-disulfonylimide ion, 1,1,2,2,3,3-hexafluoropropane-1 , 3-disulfonimide ion and other sulfonimide ions; and the like.
Aq-で表されるq価の陰イオンとしては、ヘキサフルオロリン酸イオン、タングステン酸イオン、1価の有機カルボン酸系陰イオン、1価又は2価の有機スルホン酸系陰イオン、1価の有機リン酸系陰イオン、1価の有機ホウ酸系陰イオン、1価のメチドイオン類、ジシアナミドイオン、1価のスルホンアミドイオン類、及び1価のスルホンイミドイオン類が好ましく、タングステン酸イオン、1価の有機カルボン酸系陰イオン、1価又は2価の有機スルホン酸系陰イオン、1価の有機リン酸系陰イオン、1価のメチドイオン類、ジシアナミドイオン、及び1価のスルホンイミドイオン類がより好ましく、タングステン酸イオン、1価の有機カルボン酸系陰イオン、1価又は2価の有機スルホン酸系陰イオン、1価の有機リン酸系陰イオン、1価のメチドイオン類、及び1価のスルホンイミドイオン類がさらに好ましく、タングステン酸イオン、1価の有機カルボン酸系陰イオン、1価又は2価の有機スルホン酸系陰イオン、1価の有機リン酸系陰イオン、及び1価のスルホンイミドイオン類がさらにより好ましく、タングステン酸イオン、1価の有機カルボン酸系陰イオン、1価又は2価の有機スルホン酸系陰イオン、及び1価のスルホンイミドイオン類がいっそう好ましく、1価の有機スルホン酸系陰イオン、及び1価のスルホンイミドイオン類がよりいっそう好ましく、3−カルボキシフェニルスルホン酸、及びビス(トリフルオロメチルスルホニル)イミドイオンが特に好ましい。 As the q-valent anion represented by A q- , hexafluorophosphate ion, tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent Preferred are organic phosphate anions, monovalent organic borate anions, monovalent methide ions, dicyanamide ions, monovalent sulfonamide ions, and monovalent sulfonimide ions, and tungstate ion Monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent organic phosphate anion, monovalent methide ions, dicyanamide ion, and monovalent sulfonimide Ions are more preferable, and tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent organic phosphate anion, monovalent methide ions, and Monovalent sulfonimide ions are more preferable, and tungstate ion, monovalent organic carboxylic acid anion, monovalent or divalent organic sulfonic acid anion, monovalent organic phosphate anion, and 1 Even more preferred are monovalent sulfonimide ions, more preferred are tungstate ions, monovalent organic carboxylic acid anions, monovalent or divalent organic sulfonic acid anions, and monovalent sulfonimide ions. Monovalent organic sulfonic acid anions and monovalent sulfonimide ions are even more preferable, and 3-carboxyphenyl sulfonic acid and bis(trifluoromethylsulfonyl)imide ion are particularly preferable.
化合物(I)としては、表1〜4に示す、式(I−1)〜式(I−146)で表される化合物等が挙げられる。
化合物(I)は、好ましくは式(I−25)〜式(I−48)、式(I−73)、式(I−74)、式(I−77)〜式(I−80)、式(I−87)、式(I−88)、式(I−109)〜式(I−127)で表される化合物である。
Examples of the compound (I) include the compounds represented by the formulas (I-1) to (I-146) shown in Tables 1 to 4.
The compound (I) is preferably formula (I-25) to formula (I-48), formula (I-73), formula (I-74), formula (I-77) to formula (I-80), The compounds represented by formula (I-87), formula (I-88), formula (I-109) to formula (I-127).
表1〜4中、Etはエチル基、Prはプロピル基、Phはフェニル基を表し、po−2〜po−4、po−6、po−7、及びpo−9は、それぞれ、上記式(po−2)〜式(po−4)、式(po−6)、式(po−7)、及び式(po−9)で表される基を意味し、an−1〜an−21は、それぞれ下記式(an−1)〜式(an−21)で表される基を表す。 In Tables 1 to 4, Et represents an ethyl group, Pr represents a propyl group, Ph represents a phenyl group, and po-2 to po-4, po-6, po-7, and po-9 are each represented by the above formula ( po-2) to a formula (po-4), a formula (po-6), a formula (po-7), and a formula (po-9) are represented by an-1 to an-21. Represent groups represented by the following formula (an-1) to formula (an-21), respectively.
化合物(I)の合成方法は特に限定されないが、国際公開第2014/196464号に記載の方法を参考に合成することもできる。 The method for synthesizing the compound (I) is not particularly limited, but the compound (I) can also be synthesized with reference to the method described in WO 2014/196464.
化合物(I)の含有量は、樹脂(B)100質量部に対して、0.05〜100質量部であることが好ましく、0.1〜80質量部であることがより好ましく、0.5〜50質量部であることがさらに好ましく、0.5〜30質量部であることがよりさらに好ましい。 The content of the compound (I) is preferably 0.05 to 100 parts by mass, more preferably 0.1 to 80 parts by mass, and 0.5 to 100 parts by mass of the resin (B). To 50 parts by mass is more preferable, and 0.5 to 30 parts by mass is even more preferable.
化合物(I)の含有率は、着色剤(A)の総量中、1質量%以上であることが好ましく、5質量%以上であることがより好ましい。 The content of the compound (I) is preferably 1% by mass or more and more preferably 5% by mass or more in the total amount of the colorant (A).
着色剤(A)は、化合物(I)以外に、化合物(I)とは異なる着色剤を含んでいてもよく、該化合物(I)とは異なる着色剤は、染料(以下、染料(A1)という場合がある。)、及び顔料(以下、顔料(A2)という場合がある。)のいずれでもよく、化合物(I)とは異なる着色剤は、これら染料(A1)及び顔料(A2)の一方又は両方を含んでいてもよい。 The colorant (A) may contain a colorant different from the compound (I) in addition to the compound (I), and the colorant different from the compound (I) is a dye (hereinafter, dye (A1)). Or a pigment (hereinafter, sometimes referred to as a pigment (A2)), and the colorant different from the compound (I) is one of the dye (A1) and the pigment (A2). Or both may be included.
染料(A1)は、化合物(I)を包含しない限り、特に限定されず公知の染料を使用することができ、例えば、溶剤染料、酸性染料、直接染料、媒染染料等が挙げられる。染料としては、例えば、カラーインデックス(The Society of Dyers and Colourists出版)でピグメント以外で色相を有するものに分類されている化合物や、染色ノート(色染社)に記載されている公知の染料が挙げられる。また、化学構造によれば、アゾ染料、シアニン染料、トリフェニルメタン染料、キサンテン染料、フタロシアニン染料、アントラキノン染料、ナフトキノン染料、キノンイミン染料、メチン染料、アゾメチン染料、スクアリリウム染料、アクリジン染料、スチリル染料、クマリン染料、キノリン染料及びニトロ染料等が挙げられる。これらのうち、有機溶剤可溶性染料が好ましい。 The dye (A1) is not particularly limited as long as it does not include the compound (I), and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes and mordant dyes. Examples of the dye include compounds that are classified into those having a hue other than pigment by the Color Index (published by The Society of Dyers and Colourists), and known dyes described in Dyeing Note (Color Dye Co.). To be Further, according to the chemical structure, azo dye, cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye, acridine dye, styryl dye, coumarin. Examples thereof include dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferred.
顔料(A2)としては、特に限定されず公知の顔料を使用することができ、例えば、カラーインデックス(The Society of Dyers and Colourists出版)でピグメントに分類されている顔料が挙げられる。
顔料としては、例えば、C.I.ピグメントイエロー1、3、12、13、14、15、16、17、20、24、31、53、83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、185、194、214等の黄色顔料;
C.I.ピグメントオレンジ13、31、36、38、40、42、43、51、55、59、61、64、65、71、73等のオレンジ色顔料;
C.I.ピグメントレッド9、97、105、122、123、144、149、166、168、176、177、180、192、202、209、215、216、224、242、254、255、264、265、269、291等の赤色顔料;
C.I.ピグメントブルー15、15:3、15:4、15:6、60等の青色顔料;
C.I.ピグメントバイオレット1、19、23、29、32、36、38等のバイオレット色顔料;
C.I.ピグメントグリーン7、36、58等の緑色顔料;
C.I.ピグメントブラウン23、25等のブラウン色顔料;
C.I.ピグメントブラック1、7などの黒色顔料等が挙げられる。
The pigment (A2) is not particularly limited, and known pigments can be used, and examples thereof include pigments classified as pigments by the color index (published by The Society of Dyers and Colorists).
Examples of the pigment include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and the like orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, Red pigments such as 291;
C. I. Pigment Blue 15, 15:3, 15:4, 15:6, 60 and other blue pigments;
C. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments;
C. I. Pigment Green 7, 36, 58 and other green pigments;
C. I. Pigment Brown 23, 25 and other brown pigments;
C. I. Pigment Black 1, 7 and the like black pigments and the like.
顔料(A2)としては、C.I.ピグメントイエロー185等の黄色顔料;C.I.ピグメントレッド177、202、264、269、291等の赤色顔料;C.I.ピグメントブルー15:6等の青色顔料が好ましい。 Examples of the pigment (A2) include C.I. I. Pigment Yellow 185 and other yellow pigments; C.I. I. Pigment Red 177, 202, 264, 269, 291 and the like; C.I. I. Pigment Blue 15:6 and other blue pigments are preferred.
顔料は、粒径が均一であることが好ましく、顔料分散剤を含有させて分散処理を行うことで、顔料が溶液中で均一に分散した状態の顔料分散液を得ることができる。 The pigment preferably has a uniform particle size, and by performing a dispersion treatment by adding a pigment dispersant, a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution can be obtained.
前記の顔料分散剤としては、例えば、カチオン系、アニオン系、ノニオン系、両性、ポリエステル系、ポリアミン系、アクリル系等の界面活性剤等が挙げられる。
顔料分散剤を用いる場合、その使用量は、顔料(A2)の総量に対して、好ましくは1質量%以上100質量%以下であり、より好ましくは5質量%以上50質量%以下である。顔料分散剤の使用量が前記の範囲にあると、均一な分散状態の顔料分散液が得られる傾向がある。
Examples of the above-mentioned pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic, and other surfactants.
When a pigment dispersant is used, its amount is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 50% by mass or less, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is in the above range, a pigment dispersion liquid in a uniform dispersed state tends to be obtained.
着色剤(A)の含有率は、着色樹脂組成物の固形分の総量に対して、好ましくは0.5〜60質量%であり、より好ましくは1〜50質量%であり、さらに好ましくは3〜45質量%である。ここで、本明細書における「固形分の総量」とは、着色樹脂組成物の総量から溶剤の含有量を除いた量のことをいう。固形分の総量及びこれに対する各成分の含有量は、例えば、液体クロマトグラフィー又はガスクロマトグラフィーなどの公知の分析手段で測定することができる。 The content of the colorant (A) is preferably 0.5 to 60% by mass, more preferably 1 to 50% by mass, and further preferably 3 with respect to the total solid content of the colored resin composition. Is 45% by mass. Here, the “total amount of solids” in the present specification refers to the amount obtained by removing the content of the solvent from the total amount of the colored resin composition. The total amount of solid content and the content of each component relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.
<樹脂(B)>
樹脂(B)は、特に限定されないが、アルカリ可溶性樹脂であることが好ましく、不飽和カルボン酸及び不飽和カルボン酸無水物からなる群から選ばれる少なくとも1種(a)(以下、「(a)」という場合がある。)に由来する構造単位を有する樹脂がより好ましい。樹脂(B)は、さらに、炭素数2〜4の環状エーテル構造とエチレン性不飽和結合とを有する単量体(b)(以下、「(b)」という場合がある。)に由来する構造単位、(a)と共重合可能な単量体(c)(ただし、(a)及び(b)とは異なる。)(以下、「(c)」という場合がある。)に由来する構造単位、並びに、側鎖にエチレン性不飽和結合を有する構造単位からなる群から選ばれる少なくとも1種の構造単位を有することが好ましい。
<Resin (B)>
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and at least one kind (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, “(a) The resin having a structural unit derived from (4) may be more preferable. The resin (B) further has a structure derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter, may be referred to as “(b)”). A structural unit derived from a unit, a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as “(c)”). , And at least one structural unit selected from the group consisting of structural units having an ethylenically unsaturated bond in the side chain.
(a)としては、具体的には、例えば、アクリル酸、メタクリル酸、無水マレイン酸、イタコン酸無水物、3,4,5,6−テトラヒドロフタル酸無水物、こはく酸モノ〔2−(メタ)アクリロイルオキシエチル〕等が挙げられ、好ましくは、アクリル酸、メタクリル酸、無水マレイン酸である。 Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, succinic acid mono[2-(meth Acryloyloxyethyl] and the like, and preferably acrylic acid, methacrylic acid, maleic anhydride.
(b)は、炭素数2〜4の環状エーテル構造(例えば、オキシラン環、オキセタン環及びテトラヒドロフラン環からなる群から選ばれる少なくとも1種)と(メタ)アクリロイルオキシ基とを有する単量体が好ましい。
尚、本明細書において、「(メタ)アクリル酸」とは、アクリル酸及びメタクリル酸よりなる群から選ばれる少なくとも1種を表す。「(メタ)アクリロイル」及び「(メタ)アクリレート」等の表記も、同様の意味を有する。
(b)としては、例えば、グリシジル(メタ)アクリレート、ビニルベンジルグリシジルエーテル、3,4−エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート、3−エチル−3−(メタ)アクリロイルオキシメチルオキセタン、テトラヒドロフルフリル(メタ)アクリレート等が挙げられ、好ましくは、グリシジル(メタ)アクリレート、3,4−エポキシトリシクロ[5.2.1.02,6]デシル(メタ)アクリレート、3−エチル−3−(メタ)アクリロイルオキシメチルオキセタンである。
(B) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth)acryloyloxy group. ..
In addition, in this specification, "(meth)acrylic acid" represents at least one selected from the group consisting of acrylic acid and methacrylic acid. The expressions such as “(meth)acryloyl” and “(meth)acrylate” have the same meaning.
Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate, and 3-ethyl-3-. Examples thereof include (meth)acryloyloxymethyloxetane and tetrahydrofurfuryl (meth)acrylate, and preferably glycidyl (meth)acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl( (Meth)acrylate and 3-ethyl-3-(meth)acryloyloxymethyloxetane.
(c)としては、例えば、メチル(メタ)アクリレート、ブチル(メタ)アクリレートシクロヘキシル(メタ)アクリレート、2−メチルシクロヘキシル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−8−イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−9−イル(メタ)アクリレート、ベンジル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−ベンジルマレイミド、スチレン、ビニルトルエン等が挙げられ、好ましくは、スチレン、ビニルトルエン、2−ヒドロキシエチル(メタ)アクリレート、N−フェニルマレイミド、N−シクロヘキシルマレイミド、N−ベンジルマレイミド、トリシクロ[5.2.1.02,6]デカン−8−イル(メタ)アクリレート、トリシクロ[5.2.1.02,6]デカン−9−イル(メタ)アクリレート等が好ましい。 Examples of (c) include methyl(meth)acrylate, butyl(meth)acrylate cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8. -Yl(meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-9-yl(meth)acrylate, benzyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, N-phenylmaleimide, Examples thereof include N-cyclohexylmaleimide, N-benzylmaleimide, styrene and vinyltoluene, and preferably styrene, vinyltoluene, 2-hydroxyethyl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide and N-benzylmaleimide. , Tricyclo[5.2.1.0 2,6 ]decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 ]decan-9-yl(meth)acrylate and the like are preferable.
側鎖にエチレン性不飽和結合を有する構造単位を有する樹脂は、(a)と(c)との共重合体に(b)を付加させるか、(b)と(c)との共重合体に(a)を付加させることにより製造することができる。該樹脂は、(b)と(c)との共重合体に(a)を付加させさらにカルボン酸無水物を反応させた樹脂であってもよい。 The resin having a structural unit having an ethylenically unsaturated bond in the side chain is obtained by adding (b) to the copolymer of (a) and (c) or the copolymer of (b) and (c). Can be produced by adding (a) to. The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting it with a carboxylic acid anhydride.
樹脂(B)のポリスチレン換算の重量平均分子量は、好ましくは3,000〜100,000であり、より好ましくは5,000〜50,000であり、さらに好ましくは5,000〜30,000である。
樹脂(B)の分散度[重量平均分子量(Mw)/数平均分子量(Mn)]は、好ましくは1.1〜6であり、より好ましくは1.2〜4である。
The polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and further preferably 5,000 to 30,000. ..
The dispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
樹脂(B)の酸価は、固形分換算で、好ましくは20〜170mg−KOH/gであり、より好ましくは30〜150mg−KOH/g、さらに好ましくは40〜135mg−KOH/gである。ここで酸価は樹脂(B)1gを中和するために必要な水酸化カリウムの量(mg)として測定される値であり、例えば水酸化カリウム水溶液を用いて滴定することにより求めることができる。 The acid value of the resin (B) in terms of solid content is preferably 20 to 170 mg-KOH/g, more preferably 30 to 150 mg-KOH/g, and further preferably 40 to 135 mg-KOH/g. Here, the acid value is a value measured as an amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be determined by, for example, titration with an aqueous potassium hydroxide solution. ..
樹脂(B)の含有率は、着色樹脂組成物の固形分の総量に対しては、好ましくは10〜90質量%であり、より好ましくは20〜80質量%であり、さらに好ましくは25〜70質量%である。 The content of the resin (B) is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and further preferably 25 to 70, based on the total solid content of the colored resin composition. It is% by mass.
<重合性化合物(C)>
重合性化合物(C)は、重合開始剤(D)から発生した活性ラジカル及び/又は酸によって重合しうる化合物であり、例えば、重合性のエチレン性不飽和結合を有する化合物等が挙げられ、好ましくは(メタ)アクリル酸エステル化合物である。
<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and/or an acid generated from the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenic unsaturated bond, and the like. Is a (meth)acrylic acid ester compound.
中でも、重合性化合物(C)は、エチレン性不飽和結合を3つ以上有する重合性化合物であることが好ましい。このような重合性化合物としては、例えば、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールトリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート等が挙げられる。 Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa( Examples thereof include (meth)acrylate.
重合性化合物(C)の重量平均分子量は、好ましくは150以上2,900以下、より好ましくは250以上1,500以下である。 The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
重合性化合物(C)を含む場合、重合性化合物(C)の含有率は、着色樹脂組成物の固形分の総量に対して、5〜60質量%であることが好ましく、より好ましくは10〜50質量%であり、さらに好ましくは15〜40質量%である。 When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) is preferably 5 to 60% by mass, more preferably 10 to 10% by mass based on the total amount of the solid content of the colored resin composition. It is 50% by mass, more preferably 15 to 40% by mass.
<重合開始剤(D)>
重合開始剤(D)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始しうる化合物であれば特に限定されることなく、公知の重合開始剤を用いることができる。活性ラジカルを発生する重合開始剤としては、例えば、N−ベンゾイルオキシ−1−(4−フェニルスルファニルフェニル)ブタン−1−オン−2−イミン、N−ベンゾイルオキシ−1−(4−フェニルスルファニルフェニル)オクタン−1−オン−2−イミン、N−ベンゾイルオキシ−1−(4−フェニルスルファニルフェニル)−3−シクロペンチルプロパン−1−オン−2−イミン、N−アセチルオキシ−1−(4−フェニルスルファニルフェニル)−3−シクロヘキシルプロパン−1−オン−2−イミン、2−メチル−2−モルホリノ−1−(4−メチルスルファニルフェニル)プロパン−1−オン、2−ジメチルアミノ−1−(4−モルホリノフェニル)−2−ベンジルブタン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、2,4−ビス(トリクロロメチル)−6−ピペロニル−1,3,5−トリアジン、2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド、2,2’−ビス(2−クロロフェニル)−4,4’,5,5’−テトラフェニルビイミダゾール等が挙げられる。
<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids and the like by the action of light or heat and initiating polymerization, and known polymerization initiators can be used. Examples of the polymerization initiator that generates an active radical include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl). ) Octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetyloxy-1-(4-phenyl Sulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4- Morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexylphenylketone, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyl Examples thereof include diphenylphosphine oxide and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole.
重合開始剤は、トリアジン化合物、アシルホスフィンオキサイド化合物、アルキルフェノン化合物、オキシム化合物及びビイミダゾール化合物からなる群から選ばれる少なくとも1種を含む重合開始剤が好ましく、オキシム化合物を含む重合開始剤がより好ましい。 The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of triazine compounds, acylphosphine oxide compounds, alkylphenone compounds, oxime compounds and biimidazole compounds, and more preferably a polymerization initiator containing oxime compounds. ..
重合開始剤(D)を含む場合、重合開始剤(D)の含有量は、樹脂(B)及び重合性化合物(C)の合計量100質量部に対して、好ましくは0.1〜30質量部であり、より好ましくは1〜20質量部である。重合開始剤(D)の含有量が、前記の範囲内にあると、高感度化して露光時間が短縮される傾向があるためカラーフィルタの生産性が向上する。 When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Parts, and more preferably 1 to 20 parts by mass. When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.
<重合開始助剤(D1)>
重合開始助剤(D1)は、重合開始剤によって重合が開始された重合性化合物の重合を促進するために用いられる化合物、もしくは増感剤である。重合開始助剤(D1)を含む場合、通常、重合開始剤(D)と組み合わせて用いられる。
重合開始助剤(D1)としては、4,4’−ビス(ジメチルアミノ)ベンゾフェノン(通称ミヒラーズケトン)、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、9,10−ジメトキシアントラセン、2,4−ジエチルチオキサントン、N−フェニルグリシン等が挙げられる。
<Polymerization initiation aid (D1)>
The polymerization initiation aid (D1) is a compound or a sensitizer used for promoting the polymerization of the polymerizable compound whose polymerization is initiated by the polymerization initiator. When the polymerization initiator auxiliary agent (D1) is contained, it is usually used in combination with the polymerization initiator (D).
As the polymerization initiation aid (D1), 4,4′-bis(dimethylamino)benzophenone (commonly called Michler's ketone), 4,4′-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone , N-phenylglycine and the like.
これらの重合開始助剤(D1)を用いる場合、その含有量は、樹脂(B)及び重合性化合物(C)の合計量100質量部に対して、好ましくは0.1〜30質量部、より好ましくは1〜20質量部である。重合開始助剤(D1)の量がこの範囲内にあると、さらに高感度で着色パターンを形成することができ、カラーフィルタの生産性が向上する傾向にある。 When using these polymerization initiation aids (D1), the content thereof is preferably 0.1 to 30 parts by mass, and more preferably 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is preferably 1 to 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.
<溶剤(E)>
溶剤(E)は、特に限定されず、当該分野で通常使用される溶剤を用いることができる。例えば、エステル溶剤(分子内に−COO−を含み、−O−を含まない溶剤)、エーテル溶剤(分子内に−O−を含み、−COO−を含まない溶剤)、エーテルエステル溶剤(分子内に−COO−と−O−とを含む溶剤)、ケトン溶剤(分子内に−CO−を含み、−COO−を含まない溶剤)、アルコール溶剤(分子内にOHを含み、−O−、−CO−及び−COO−を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等が挙げられる。
<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule, not containing -COO-), ether ester solvent (intramolecular) A solvent containing -COO- and -O-), a ketone solvent (a solvent containing -CO- in the molecule and not containing -COO-), an alcohol solvent (containing OH in the molecule, -O-,- CO- and -COO--free solvents), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.
溶剤としては、
乳酸エチル、乳酸ブチル、2−ヒドロキシイソブタン酸メチル、酢酸n−ブチル、酪酸エチル、酪酸ブチル、ピルビン酸エチル、アセト酢酸メチル、シクロヘキサノールアセテート及びγ−ブチロラクトン等のエステル溶剤(分子内に−COO−を含み、−O−を含まない溶剤);
エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、3−メトキシ−1−ブタノール、ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル等のエーテル溶剤(分子内に−O−を含み、−COO−を含まない溶剤);
3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−メトキシブチルアセテート、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート等のエーテルエステル溶剤(分子内に−COO−と−O−とを含む溶剤);
4−ヒドロキシ−4−メチル−2−ペンタノン(ジアセトンアルコール)、ヘプタノン、4−メチル−2−ペンタノン、シクロヘキサノン等のケトン溶剤(分子内に−CO−を含み、−COO−を含まない溶剤);
ブタノール、シクロヘキサノール、プロピレングリコール等のアルコール溶剤(分子内にOHを含み、−O−、−CO−及び−COO−を含まない溶剤);
N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド及びN−メチルピロリドン等のアミド溶剤;等が挙げられる。
溶剤としては、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテル、4−ヒドロキシ−4−メチル−2−ペンタノン(ジアセトンアルコール)、乳酸エチル及び3−エトキシプロピオン酸エチルがより好ましい。
As a solvent,
Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and γ-butyrolactone (within the molecule -COO- And a solvent not containing -O-);
Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether (solvent containing -O- in the molecule, not containing -COO- );
Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate (within the molecule -COO- And a solvent containing -O-);
Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone and cyclohexanone (solvents containing -CO- in the molecule but not -COO-) ;
Alcohol solvents such as butanol, cyclohexanol, propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-);
Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone; and the like.
As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate and ethyl 3-ethoxypropionate are more preferable.
溶剤(E)を含む場合、溶剤(E)の含有率は、本発明の着色樹脂組成物の総量に対して、好ましくは60〜95質量%であり、より好ましくは65〜92質量%である。言い換えると、着色樹脂組成物の固形分の総量は、好ましくは5〜40質量%、より好ましくは8〜35質量%である。溶剤(E)の含有量が前記の範囲内にあると、塗布時の平坦性が良好になり、またカラーフィルタを形成した際に色濃度が不足しないために表示特性が良好となる傾向がある。 When the solvent (E) is included, the content of the solvent (E) is preferably 60 to 95% by mass, more preferably 65 to 92% by mass, based on the total amount of the colored resin composition of the present invention. .. In other words, the total solid content of the colored resin composition is preferably 5 to 40% by mass, more preferably 8 to 35% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of application becomes good, and the display characteristics tend to become good because the color density is not insufficient when the color filter is formed. ..
<レベリング剤(F)>
レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。
<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a fluorine-containing silicone-based surfactant. These may have a polymerizable group in the side chain.
シリコーン系界面活性剤としては、分子内にシロキサン結合を有する界面活性剤等が挙げられる。具体的には、トーレシリコーンDC3PA、同SH7PA、同DC11PA、同SH21PA、同SH28PA、同SH29PA、同SH30PA、同SH8400(商品名:東レ・ダウコーニング(株)製);KP321、KP322、KP323、KP324、KP326、KP340、KP341(信越化学工業(株)製);TSF400、TSF401、TSF410、TSF4300、TSF4440、TSF4445、TSF4446、TSF4452及びTSF4460(モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製)等が挙げられる。 Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.); KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.); TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC) and the like. ..
前記のフッ素系界面活性剤としては、分子内にフルオロカーボン鎖を有する界面活性剤等が挙げられる。具体的には、フロラード(登録商標)FC430、同FC431(住友スリーエム(株)製)、メガファック(登録商標)F142D、同F171、同F172、同F173、同F177、同F183、同F554、同R30、同RS−718−K(DIC(株)製)、エフトップ(登録商標)EF301、同EF303、同EF351、同EF352(三菱マテリアル電子化成(株)製)、サーフロン(登録商標)S381、同S382、同SC101、同SC105(旭硝子(株)製)及びE5844((株)ダイキンファインケミカル研究所製)等が挙げられる。 Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F543. R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).
前記のフッ素原子を有するシリコーン系界面活性剤としては、分子内にシロキサン結合及びフルオロカーボン鎖を有する界面活性剤等が挙げられる。具体的には、メガファック(登録商標)R08、同BL20、同F475、同F477及び同F443(DIC(株)製)等が挙げられる。 Examples of the silicone-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafac (registered trademark) R08, BL20, F475, F477 and F443 (manufactured by DIC Corporation).
レベリング剤(F)を含む場合、レベリング剤(F)の含有量は、着色樹脂組成物の総量に対して、好ましくは0.001〜0.2質量%であり、より好ましくは0.002〜0.1質量%である。尚、この含有量に、顔料分散剤の含有量は含まれない。レベリング剤(F)の含有量が前記の範囲内にあると、カラーフィルタの平坦性を良好にすることができる。 When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.001 to 0.2% by mass, more preferably 0.002 to 0.2% by mass based on the total amount of the colored resin composition. It is 0.1% by mass. The content of the pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.
<その他の成分>
本発明の着色樹脂組成物は、必要に応じて、充填剤、高分子化合物、密着促進剤、酸化防止剤、光安定剤、連鎖移動剤等、当該技術分野で公知の添加剤を含んでもよい。
<Other ingredients>
The colored resin composition of the present invention may optionally contain additives known in the art, such as a filler, a polymer compound, an adhesion promoter, an antioxidant, a light stabilizer and a chain transfer agent. ..
<着色樹脂組成物の製造方法>
本発明の着色樹脂組成物は、着色剤(A)及び樹脂(B)、並びに必要に応じて用いられる重合性化合物(C)、重合開始剤(D)、重合開始助剤(D1)、溶剤(E)、レベリング剤(F)及びその他の成分を混合することにより調製できる。
<Method for producing colored resin composition>
The colored resin composition of the present invention comprises a colorant (A) and a resin (B), and optionally a polymerizable compound (C), a polymerization initiator (D), a polymerization initiation aid (D1), a solvent. It can be prepared by mixing (E), the leveling agent (F) and other components.
<カラーフィルタの製造方法>
本発明の着色樹脂組成物から着色パターンを製造する方法としては、フォトリソグラフ法、インクジェット法、印刷法等が挙げられる。中でも、フォトリソグラフ法が好ましい。
<Method of manufacturing color filter>
Examples of the method for producing a colored pattern from the colored resin composition of the present invention include a photolithographic method, an inkjet method, a printing method and the like. Among them, the photolithographic method is preferable.
着色樹脂組成物が、着色剤及び樹脂を含み、着色剤が化合物(I)を含むことにより、耐薬品性に優れたカラーフィルタを作製することができる。該カラーフィルタは、表示装置(例えば、液晶表示装置、有機EL装置、電子ペーパー等)及び固体撮像素子に用いられるカラーフィルタとして有用である。 When the colored resin composition contains a colorant and a resin, and the colorant contains the compound (I), a color filter having excellent chemical resistance can be produced. 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, etc.) and a solid-state image sensor.
以下、実施例を挙げて本発明をより詳細に説明するが、本発明はこれらの実施例によって限定されるものではない。例中、含有量ないし使用量を表す%および部は、特に断らないかぎり質量基準である。 Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples. In the examples,% and parts representing the content or the amount used are based on mass unless otherwise specified.
〔合成例1〕
還流冷却器、滴下ロート及び撹拌機を備えたフラスコ内に窒素を適量流し窒素雰囲気に置換し、エチルラクテート141部、プロピレングリコールモノメチルエーテルアセテート178部を入れ、撹拌しながら85℃まで加熱した。次いで、アクリル酸38部、3,4−エポキシトリシクロ[5.2.1.02,6]デカ−8−イルアクリレート及び3,4−エポキシトリシクロ[5.2.1.02,6]デカ−9−イルアクリレートの混合物(含有率は1:1)25部、シクロヘキシルマレイミド137部、2−ヒドロキシエチルメタクリレート50部、プロピレングリコールモノメチルエーテルアセテート338部の混合溶液を5時間かけて滴下した。一方、2,2−アゾビスイソブチロニトリル5部をプロピレングリコールモノメチルエーテルアセテート88部に溶解した混合溶液を6時間かけて滴下した。滴下終了後、4時間同温度で保持した後、室温まで冷却して、固形分25.6%の共重合体(樹脂(B−1))溶液を得た。生成した共重合体の重量平均分子量Mwは8000、分散度2.1、固形分換算の酸価は111mg−KOH/gであった。樹脂(B−1)は下記構造単位を有する。
[Synthesis Example 1]
An appropriate amount of nitrogen was flown into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]deca-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2, 6 ] A mixed solution of 25 parts of a mixture of deca-9-yl acrylate (content ratio is 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate and 338 parts of propylene glycol monomethyl ether acetate is added dropwise over 5 hours. did. On the other hand, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropping was completed, the temperature was maintained at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution having a solid content of 25.6%. The produced copolymer had a weight average molecular weight Mw of 8000, a polydispersity of 2.1, and an acid value in terms of solid content of 111 mg-KOH/g. The resin (B-1) has the following structural unit.
〔合成例2〕
還流冷却器、滴下ロート及び撹拌機を備えたフラスコ内に窒素を適量流して窒素雰囲気とし、プロピレングリコールモノメチルエーテルアセテート280部を入れ、撹拌しながら80℃まで加熱した。次いで、該フラスコ内に、アクリル酸38部、3,4−エポキシトリシクロ[5.2.1.02,6]デカン−8−イルアクリレート及び3,4−エポキシトリシクロ[5.2.1.02,6]デカン−9−イルアクリレートの混合物(含有率は1:1)289部をプロピレングリコールモノメチルエーテルアセテート125部に溶解した溶液を滴下ポンプを用いて約5時間かけて滴下した。一方、重合開始剤2,2−アゾビス(2,4−ジメチルバレロニトリル)33部をプロピレングリコールモノメチルエーテルアセテート235部に溶解した溶液を別の滴下ポンプを用いて約6時間かけてフラスコ内に滴下した。滴下終了後、4時間同温度で保持した後、室温まで冷却して、固形分35.1%の共重合体(樹脂(B−2))溶液を得た。生成した共重合体の重量平均分子量Mwは9200、分散度2.08、固形分換算の酸価は77mg−KOH/gであった。樹脂(B−2)は下記構造単位を有する。
[Synthesis example 2]
An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to create a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80° C. with stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2. A solution of 289 parts of a mixture of 1.02,6 ] decan-9-yl acrylate (content ratio: 1:1) dissolved in 125 parts of propylene glycol monomethyl ether acetate was added dropwise over about 5 hours using a dropping pump. .. On the other hand, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile), a polymerization initiator, dissolved in 235 parts of propylene glycol monomethyl ether acetate was dropped into the flask over about 6 hours using another dropping pump. did. After the dropping was completed, the temperature was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-2)) solution having a solid content of 35.1%. The produced copolymer had a weight average molecular weight Mw of 9,200, a dispersity of 2.08, and an acid value in terms of solid content of 77 mg-KOH/g. The resin (B-2) has the following structural unit.
樹脂のポリスチレン換算の重量平均分子量(Mw)及び数平均分子量(Mn)の測定は、GPC法により以下の条件で行った。
装置 ;HLC−8120GPC(東ソー(株)製)
カラム ;TSK−GELG2000HXL
カラム温度 ;40℃
溶媒 ;THF
流速 ;1.0mL/min
被検液固形分濃度;0.001〜0.01質量%
注入量 ;50μL
検出器 ;RI
校正用標準物質 ;TSK STANDARD POLYSTYRENE
F−40、F−4、F−288、A−2500、A−500
(東ソー(株)製)
上記で得られたポリスチレン換算の重量平均分子量及び数平均分子量の比(Mw/Mn)を分散度とした。
The polystyrene equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Device: HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature: 40°C
Solvent; THF
Flow rate: 1.0 mL/min
Test liquid solid content concentration: 0.001-0.01 mass%
Injection volume: 50 μL
Detector ;RI
Calibration standard; TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Manufactured by Tosoh Corporation)
The polystyrene equivalent weight average molecular weight and number average molecular weight ratio (Mw/Mn) obtained above was taken as the dispersity.
〔合成例3〕
N,N−ジエチルアミノ−3−フェノール4部、下記式(B−1)で表される化合物0.5部、及びトリフルオロスルホン酸7.4部を混合し、100℃で3時間撹拌して反応液を得た。反応液を室温まで冷却後、反応液に水50部を加え、クロロホルム及び酢酸エチルで抽出し、それぞれの有機層を水洗した。水洗した各有機層を合わせて溶媒溜去した。残渣にp−クロラニル0.9部、アセトニトリル50部を加え、室温で12時間撹拌した。反応液を溶媒溜去後、クロロホルム50部を加え、析出した固体をろ別した。ろ液を濃縮後、濃縮したろ液に4%水酸化ナトリウム水溶液50部を加え室温で12時間撹拌した。2N塩酸で反応液をpH4まで中和し、析出した固体をろ取した。得られた固体を酢酸エチル−ヘキサン(3:1)混合溶液で3時間分散洗浄し、乾燥後、濃塩酸5部に溶解させ、溶解液を得た。得られた溶解液をフィルタろ過し、ろ液を20%食塩水にて晶析し、25%水酸化ナトリウム水溶液でpHが4になるまで中和した。析出固体をろ取し、60℃減圧オーブンにて乾燥し、式(A−Y)で表される化合物を0.21部(収率24%)得た。
[Synthesis Example 3]
4 parts of N,N-diethylamino-3-phenol, 0.5 parts of a compound represented by the following formula (B-1), and 7.4 parts of trifluorosulfonic acid were mixed and stirred at 100° C. for 3 hours. A reaction solution was obtained. After the reaction solution was cooled to room temperature, 50 parts of water was added to the reaction solution, extracted with chloroform and ethyl acetate, and each organic layer was washed with water. The organic layers washed with water were combined and the solvent was distilled off. 0.9 part of p-chloranil and 50 parts of acetonitrile were added to the residue, and the mixture was stirred at room temperature for 12 hours. After distilling off the solvent from the reaction solution, 50 parts of chloroform was added, and the precipitated solid was separated by filtration. After concentrating the filtrate, 50 parts of a 4% aqueous sodium hydroxide solution was added to the concentrated filtrate and the mixture was stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was collected by filtration. The obtained solid was dispersed and washed with a mixed solution of ethyl acetate-hexane (3:1) for 3 hours, dried and then dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The obtained solution was filtered with a filter, the filtrate was crystallized with 20% saline, and neutralized with a 25% aqueous sodium hydroxide solution until the pH reached 4. The precipitated solid was collected by filtration and dried in a vacuum oven at 60° C. to obtain 0.21 part (yield 24%) of the compound represented by the formula (AY).
式(A−Y)で表される化合物0.77部と、ビス(トリフルオロメタンスルホニル)リチウム0.5部、及びN,N−ジメチルスルホキシド12.3部を混合し、50℃で3時間撹拌し、反応液を得た。得られた反応液を20%食塩水40部に滴下し、析出した固体をろ取した。固体をクロロホルムに溶解させ、有機層を水で洗浄したのち硫酸ナトリウムを加えて乾燥後溶媒留去し、60℃減圧オーブンにて乾燥し、式(A−2)で表される化合物を0.73部(収率76%)得た。得られた化合物の質量分析結果は、m/z=654[M]+であった。なお、質量分析は、LCはAgilent製1200型を、MASSはAgilent製LC/MSD6130型を用いて測定した(以下の質量分析でも同様である)。 0.77 parts of the compound represented by the formula (AY), 0.5 part of bis(trifluoromethanesulfonyl)lithium, and 12.3 parts of N,N-dimethylsulfoxide are mixed and stirred at 50° C. for 3 hours. Then, a reaction solution was obtained. The resulting reaction solution was added dropwise to 40 parts of 20% saline, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform, the organic layer was washed with water, sodium sulfate was added and dried, the solvent was distilled off, and the residue was dried in a vacuum oven at 60° C. to give the compound represented by the formula (A-2) at 0. 73 parts (yield 76%) was obtained. The mass spectrometry result of the obtained compound was m/z=654 [M] + . In the mass spectrometry, LC was measured using Agilent model 1200 and MASS was measured using Agilent model LC/MSD6130 (the same applies to the following mass spectrometry).
〔合成例4〕
式(A−2)で表される化合物3部、4−アミノ安息香酸エチル5部、1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミド塩酸塩6部、4−ジメチルアミノピリジン0.5部、(+)−10−カンファースルホン酸0.4部、及びジメチルスルホキシド156部を混合し、室温で3時間撹拌した。反応物を飽和食塩水に晶析し、析出固体をろ取し、100部の水で3回水洗した。60℃減圧オーブンにて乾燥し、式(A−6)で表される化合物を1.6部(収率34%)得た。得られた化合物の質量分析結果は、m/z=892[M]+であった。
[Synthesis Example 4]
3 parts of the compound represented by the formula (A-2), 5 parts of ethyl 4-aminobenzoate, 6 parts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 4-dimethylaminopyridine 0.5. Parts, 0.4 parts of (+)-10-camphorsulfonic acid, and 156 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 3 hours. The reaction product was crystallized in saturated saline, and the precipitated solid was collected by filtration and washed with 100 parts of water three times. It was dried in a vacuum oven at 60° C. to obtain 1.6 parts (yield 34%) of the compound represented by the formula (A-6). The mass analysis result of the obtained compound was m/z=892 [M] + .
〔合成例5〕
4−アミノ安息香酸エチルをアニリンに変更した以外は合成例4と同様にして、式(A−7)で表される化合物を2.0部(収率42%)得た。得られた化合物の質量分析結果は、m/z=804[M]+であった。
[Synthesis example 5]
2.0 parts (yield 42%) of the compound represented by the formula (A-7) was obtained in the same manner as in Synthesis Example 4 except that ethyl 4-aminobenzoate was changed to aniline. The mass spectrometry result of the obtained compound was m/z=804 [M] + .
〔合成例6〕
3−ヒドロキシジフェニルアミン0.6部、上記式(B−1)で表される化合物0.6部、及びトリフルオロメタンスルホン酸8.8部を混合し、100℃で4時間撹拌して反応液を得た。反応液を室温まで冷却後、反応液に50部の水を加え、クロロホルム及び酢酸エチルで抽出し、それぞれの有機層を水洗した。水洗した各有機層を合わせて溶媒溜去した。残渣にp−クロラニル0.6部、アセトニトリル11部を加え、室温で10時間撹拌した。反応液を溶媒溜去後、クロロホルム30部を加え、析出した固体をろ別した。ろ液を濃縮後、濃縮したろ液に4%水酸化ナトリウム水溶液20部を加え室温で12時間撹拌した。2N塩酸で反応液をpH4まで中和し、析出した固体をろ取した。得られた固体を酢酸エチル−ヘキサン(3:1)混合溶液で5時間分散洗浄し、乾燥後、濃塩酸5部に溶解させ、溶解液を得た。得られた溶解液をフィルタろ過し、ろ液を20%食塩水にて晶析し、25%水酸化ナトリウム水溶液でpHが4になるまで中和した。析出固体をろ取し、ヨウ化エチル7.6部、炭酸カリウム4.1部、及びN−メチル−2−ピロリドン5部を混合し、75℃で17時間撹拌した。反応液を室温まで冷却後、反応液に2N塩酸70部を加え、クロロホルムで抽出し有機層を水洗し、溶媒溜去した。60℃減圧オーブンにて乾燥し、式(B−2)で表される化合物を0.2部(収率15%)得た。得られた化合物の質量分析結果は、m/z=750[M]+であった。
続いて、式(B−2)で表される化合物0.2部、ビス(トリフルオロメタンスルホニル)リチウム0.1部、及びN,N−ジメチルスルホキシド2.7部を混合し、50℃で5時間撹拌し、反応液を得た。得られた反応液を20%食塩水40部に滴下し、析出した固体をろ取した。固体をクロロホルムに溶解させ、有機層を水で洗浄したのち硫酸ナトリウムを加えて乾燥後溶媒溜去し、60℃減圧オーブンにて乾燥し、式(A−8)で表される化合物を0.2部(収率90%)を得た。
[Synthesis example 6]
0.6 part of 3-hydroxydiphenylamine, 0.6 part of the compound represented by the above formula (B-1), and 8.8 parts of trifluoromethanesulfonic acid were mixed and stirred at 100° C. for 4 hours to obtain a reaction liquid. Obtained. After cooling the reaction solution to room temperature, 50 parts of water was added to the reaction solution, extracted with chloroform and ethyl acetate, and each organic layer was washed with water. The organic layers washed with water were combined and the solvent was distilled off. 0.6 part of p-chloranil and 11 parts of acetonitrile were added to the residue, and the mixture was stirred at room temperature for 10 hours. After distilling off the solvent from the reaction solution, 30 parts of chloroform was added, and the precipitated solid was separated by filtration. After concentrating the filtrate, 20 parts of a 4% aqueous sodium hydroxide solution was added to the concentrated filtrate, and the mixture was stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was collected by filtration. The obtained solid was dispersed and washed in a mixed solution of ethyl acetate-hexane (3:1) for 5 hours, dried and then dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The obtained solution was filtered with a filter, the filtrate was crystallized with 20% saline, and neutralized with a 25% aqueous sodium hydroxide solution until the pH reached 4. The precipitated solid was collected by filtration, mixed with 7.6 parts of ethyl iodide, 4.1 parts of potassium carbonate, and 5 parts of N-methyl-2-pyrrolidone, and stirred at 75°C for 17 hours. After cooling the reaction solution to room temperature, 70 parts of 2N hydrochloric acid was added to the reaction solution, extracted with chloroform, the organic layer was washed with water, and the solvent was distilled off. It was dried in a vacuum oven at 60° C. to obtain 0.2 part (yield 15%) of the compound represented by the formula (B-2). The mass spectrometry result of the obtained compound was m/z=750 [M] + .
Subsequently, 0.2 part of the compound represented by the formula (B-2), 0.1 part of bis(trifluoromethanesulfonyl)lithium, and 2.7 parts of N,N-dimethylsulfoxide are mixed, and the mixture is mixed at 50° C. for 5 minutes. After stirring for a time, a reaction solution was obtained. The resulting reaction solution was added dropwise to 40 parts of 20% saline, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform, the organic layer was washed with water, sodium sulfate was added and dried, the solvent was distilled off, and the residue was dried in a vacuum oven at 60° C. to give the compound represented by the formula (A-8) at 0. Two parts (yield 90%) were obtained.
〔合成例7〕
3,5−ジクロロアニリン15.0部、4−ブロモ酪酸エチル19.9部、N,N−ジイソプロピルエチルアミン35.9部、及びN,N−ジメチルホルムアミド52.5部を混合し、120℃で2時間加熱撹拌した。続けて、反応溶液にヨウ化エチル28.9部を加え、70℃で24時間加熱撹拌した。室温まで冷却後、反応物を酢酸エチルで抽出した後、抽出した反応物を水洗した。有機層を溶媒溜去し、残渣をシリカゲルカラムクロマトグラフィ(展開溶媒:酢酸エチル:ヘキサン=1:5)で精製した。さらに、0℃下で得られた化合物に塩化ホスホリル28.4部、及びN,N−ジメチルホルムアミド52.5部を混合し60℃で6時間加熱撹拌した。反応物を4%水酸化ナトリウム水溶液に晶析し、析出固体をろ取し、100部のメタノールで洗浄した。60℃減圧オーブンにて乾燥し、式(B−3)で表される化合物を5.0部(収率16%)得た。得られた化合物の質量分析結果は、m/z=333[M+H]+であった。
[Synthesis example 7]
3,5-Dichloroaniline 15.0 parts, ethyl 4-bromobutyrate 19.9 parts, N,N-diisopropylethylamine 35.9 parts, and N,N-dimethylformamide 52.5 parts were mixed, and at 120°C. The mixture was heated and stirred for 2 hours. Subsequently, 28.9 parts of ethyl iodide was added to the reaction solution, and the mixture was heated and stirred at 70° C. for 24 hours. After cooling to room temperature, the reaction product was extracted with ethyl acetate, and then the extracted reaction product was washed with water. The solvent was distilled off from the organic layer, and the residue was purified by silica gel column chromatography (developing solvent:ethyl acetate:hexane=1:5). Furthermore, 28.4 parts of phosphoryl chloride and 52.5 parts of N,N-dimethylformamide were mixed with the compound obtained at 0° C., and the mixture was heated with stirring at 60° C. for 6 hours. The reaction product was crystallized in a 4% aqueous sodium hydroxide solution, and the precipitated solid was collected by filtration and washed with 100 parts of methanol. It was dried in a vacuum oven at 60° C. to obtain 5.0 parts (yield 16%) of the compound represented by the formula (B-3). The mass spectrometry result of the obtained compound was m/z=333 [M+H] + .
式(B−1)で表される化合物を式(B−3)で表される化合物に、3−ヒドロキシジフェニルアミンをN,N−ジエチルアミノフェノールに変更した以外は合成例6と同様にして、式(B−4)で表される化合物を1.3部(収率31%)得た。得られた化合物の質量分析結果は、m/z=596[M]+であった。 The compound represented by the formula (B-1) was replaced by the compound represented by the formula (B-3), and 3-hydroxydiphenylamine was replaced by N,N-diethylaminophenol. 1.3 parts (yield 31%) of the compound represented by (B-4) was obtained. The mass spectrometry result of the obtained compound was m/z=596 [M] + .
続いて、式(B−2)で表される化合物を式(B−4)で表される化合物に変更した以外は合成例6と同様にして、式(A−9)で表される化合物を0.4部(収率64%)得た。 Subsequently, a compound represented by the formula (A-9) in the same manner as in Synthesis Example 6 except that the compound represented by the formula (B-2) is changed to the compound represented by the formula (B-4). 0.4 part (yield 64%) was obtained.
〔合成例8〕
ビス(トリフルオロメタンスルホニル)リチウムを3−スルホ安息香酸モノナトリウムに変更した以外は合成例7と同様にして、式(A−10)で表される化合物を0.3部(収率45%)得た。
[Synthesis Example 8]
0.3 parts of the compound represented by the formula (A-10) (yield 45%) was obtained in the same manner as in Synthesis Example 7 except that bis(trifluoromethanesulfonyl)lithium was changed to monosodium 3-sulfobenzoate. Obtained.
〔合成例9〕
ビス(トリフルオロメタンスルホニル)リチウムをリチウムビス(フルオロスルホニル)イミドに変更した以外は合成例3と同様にして、式(A−11)で表される化合物を0.88部(収率91%)得た。
[Synthesis Example 9]
0.88 parts of the compound represented by the formula (A-11) (yield 91%) in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to lithium bis(fluorosulfonyl)imide. Obtained.
〔合成例10〕
ビス(トリフルオロメタンスルホニル)リチウムをトリフルオロメタンスルホン酸リチウムに変更した以外は合成例3と同様にして、式(A−12)で表される化合物を0.77部(収率71%)得た。
[Synthesis Example 10]
0.77 parts (yield 71%) of the compound represented by formula (A-12) was obtained in the same manner as in Synthesis Example 3 except that lithium trifluoromethanesulfonate was used instead of bis(trifluoromethanesulfonyl)lithium. ..
〔合成例11〕
ビス(トリフルオロメタンスルホニル)リチウムをノナフルオロ−1−ブタンスルホン酸リチウムに変更した以外は合成例3と同様にして、式(A−13)で表される化合物を0.5部(収率72%)得た。
[Synthesis Example 11]
0.5 part of the compound represented by the formula (A-13) (yield 72%) was obtained in the same manner as in Synthesis Example 3 except that lithium bis(trifluoromethanesulfonyl)lithium was changed to lithium nonafluoro-1-butanesulfonate. )Obtained.
〔合成例12〕
ビス(トリフルオロメタンスルホニル)リチウムをテトラフェニルホウ酸ナトリウムに変更した以外は合成例3と同様にして、式(A−14)で表される化合物を0.93部(収率83%)得た。
[Synthesis Example 12]
0.93 parts (yield 83%) of a compound represented by the formula (A-14) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to sodium tetraphenylborate. ..
〔合成例13〕
ビス(トリフルオロメタンスルホニル)リチウムをナトリウムジシアナミドに変更した以外は合成例3と同様にして、式(A−15)で表されるキサンテン化合物を0.78部(収率93%)得た。
[Synthesis Example 13]
0.78 parts (yield 93%) of a xanthene compound represented by the formula (A-15) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to sodium dicyanamide.
〔合成例14〕
ビス(トリフルオロメタンスルホニル)リチウムをヘキサフルオロリン酸リチウムに変更した以外は合成例3と同様にして、式(A−16)で表される化合物を0.58部(収率63%)得た。
[Synthesis Example 14]
0.58 parts (yield 63%) of a compound represented by the formula (A-16) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to lithium hexafluorophosphate. ..
〔合成例15〕
ビス(トリフルオロメタンスルホニル)リチウムを3−ニトロベンゼンスルホン酸ナトリウムに変更した以外は合成例3と同様にして、式(A−17)で表される化合物を0.74部(収率75%)得た。
[Synthesis Example 15]
0.74 parts (yield 75%) of a compound represented by the formula (A-17) was obtained in the same manner as in Synthesis Example 3 except that sodium bis(trifluoromethanesulfonyl)lithium was changed to sodium 3-nitrobenzenesulfonate. It was
〔合成例16〕
ビス(トリフルオロメタンスルホニル)リチウムをイソキノリン−5−スルホン酸ナトリウムに変更した以外は合成例3と同様にして、式(A−18)で表される化合物を0.65部(収率63%)得た。
[Synthesis Example 16]
0.65 parts of the compound represented by the formula (A-18) (yield 63%) in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to sodium isoquinoline-5-sulfonate. Obtained.
〔合成例17〕
ビス(トリフルオロメタンスルホニル)リチウムをトリフルオロメタンスルホンアミドに変更した以外は合成例3と同様にして、式(A−19)で表される化合物を0.74部(収率75%)得た。
[Synthesis Example 17]
0.74 parts (yield 75%) of the compound represented by the formula (A-19) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to trifluoromethanesulfonamide.
〔合成例18〕
ビス(トリフルオロメタンスルホニル)リチウムをN,N−ビス(2−ヒドロキシエチル)−2−アミノエタンスルホン酸に変更した以外は合成例3と同様にして、式(A−20)で表される化合物を0.87部(収率87%)得た。
[Synthesis Example 18]
A compound represented by the formula (A-20) in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid. 0.87 part (yield 87%) was obtained.
〔合成例19〕
ビス(トリフルオロメタンスルホニル)リチウムをエチレンジアミン四酢酸モノナトリウム鉄(III)水和物に変更した以外は合成例3と同様にして、式(A−21)で表される化合物を0.65部(収率60%)得た。
[Synthesis Example 19]
0.65 parts of the compound represented by the formula (A-21) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to ethylenediaminetetraacetic acid monosodium iron(III) hydrate. Yield 60%) was obtained.
〔合成例20〕
ビス(トリフルオロメタンスルホニル)リチウムをビニルスルホン酸ナトリウムに変更した以外は合成例3と同様にして、式(A−22)で表される化合物を0.65部(収率74%)得た。
[Synthesis Example 20]
0.65 parts (yield 74%) of the compound represented by the formula (A-22) was obtained in the same manner as in Synthesis Example 3 except that sodium bis(trifluoromethanesulfonyl)lithium was changed to vinyl sulfonate.
〔合成例21〕
ビス(トリフルオロメタンスルホニル)リチウムを3−(トリヒドロキシシリル)プロピルメチルホスホネートモノナトリウム塩溶液に変更した以外は合成例3と同様にして、式(A−23)で表される化合物を0.47部(収率46%)得た。
[Synthesis Example 21]
0.47% of the compound represented by the formula (A-23) was prepared in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to 3-(trihydroxysilyl)propylmethylphosphonate monosodium salt solution. Part (yield 46%) was obtained.
〔合成例22〕
ビス(トリフルオロメタンスルホニル)リチウムを3−(トリヒドロキシシリル)プロパン−1−スルホン酸に変更した以外は合成例3と同様にして、式(A−24)で表されるキサンテン化合物を0.32部(収率36%)得た。
[Synthesis Example 22]
0.32% of the xanthene compound represented by the formula (A-24) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to 3-(trihydroxysilyl)propane-1-sulfonic acid. Parts (yield 36%) were obtained.
〔合成例23〕
1,8−ナフトスルトン0.2部、3−アミノプロピルトリエトキシシラン0.2部、及びジメチルスルホキシド8.5部を混合し、室温で3時間撹拌した後、式(B−5)で表される化合物を得た。その後、ビス(トリフルオロメタンスルホニル)リチウムを式(B−5)で表される化合物に変更した以外は合成例3と同様にして、式(A−25)で表される化合物を0.78部(収率93%)得た。
[Synthesis Example 23]
After mixing 0.2 part of 1,8-naphtho sultone, 0.2 part of 3-aminopropyltriethoxysilane and 8.5 part of dimethylsulfoxide and stirring at room temperature for 3 hours, the compound represented by the formula (B-5) was used. A compound was obtained. Then, 0.78 parts of the compound represented by the formula (A-25) was prepared in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to the compound represented by the formula (B-5). (Yield 93%) was obtained.
〔合成例24〕
1,8−ナフトスルトンを1,8−ナフトスルトン−4−スルホン酸ナトリウムに変更した以外は合成例23と同様にして、式(A−26)で表される化合物を0.5部(収率44%)得た。
[Synthesis Example 24]
0.5 part of the compound represented by the formula (A-26) (yield 44 %)Obtained.
〔合成例25〕
ビス(トリフルオロメタンスルホニル)リチウムをホスホタングステン酸水和物に変更した以外は合成例3と同様にして、式(A−27)で表される化合物を0.5部(収率72%)得た。
[Synthesis Example 25]
0.5 parts (yield 72%) of a compound represented by the formula (A-27) was obtained in the same manner as in Synthesis Example 3 except that bis(trifluoromethanesulfonyl)lithium was changed to phosphotungstic acid hydrate. It was
〔合成例26〕
ビス(トリフルオロメタンスルホニル)リチウムを1,1,2,2,3,3−ヘキサフルオロプロパン−1,3−ジスルホンイミドリチウムに変更した以外は合成例3と同様にして、式(A−28)で表されるキサンテン化合物を0.69部(収率63%)得た。
[Synthesis example 26]
Lithium bis(trifluoromethanesulfonyl)lithium was changed to 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide lithium in the same manner as in Synthesis Example 3 except that the formula (A-28) 0.69 parts (yield 63%) of a xanthene compound represented by
〔合成例27〕
ビス(トリフルオロメタンスルホニル)リチウムをカリウムトリス(トリフルオロメタンスルホニル)メタニドに変更した以外は合成例3と同様にして、式(A−29)で表される化合物を0.63部(収率58%)得た。
[Synthesis Example 27]
0.63 parts of the compound represented by the formula (A-29) (yield 58%) was obtained in the same manner as in Synthesis Example 3 except that potassium tris(trifluoromethanesulfonyl)methanide was used instead of bis(trifluoromethanesulfonyl)lithium. )Obtained.
〔分散液1の作製〕
C.I.ピグメントレッド291(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を3.3部、樹脂(B−2)(固形分換算)を4.0部、プロピレングリコールモノメチルエーテル12.7部を混合し、プロピレングリコールモノメチルエーテルアセテート41.3部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液1を得た。
[Preparation of dispersion 1]
C. I. Pigment Red 291 (pigment) 10.0 parts, dispersing agent (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 3.3 parts, resin (B-2) (solid content conversion) 4 0.0 parts and 12.7 parts of propylene glycol monomethyl ether were mixed, 41.3 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and a paint conditioner (manufactured by LAU) was used. And shaken for 1 hour. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 1.
〔分散液2の作製〕
C.I.ピグメントレッド177(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を4.3部、樹脂(B−2)(固形分換算)を4.0部、プロピレングリコールモノメチルエーテルアセテート59.2部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液2を得た。
[Preparation of dispersion 2]
C. I. Pigment Red 177 (pigment) 10.0 parts, dispersant (BYK, BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 4.3 parts, resin (B-2) (solid content conversion) 4 0.0 parts and 59.2 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 2.
〔分散液3の作製〕
C.I.ピグメントレッド202(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を7.5部、樹脂(B−2)(固形分換算)を3.5部、プロピレングリコールモノメチルエーテル8.5部、プロピレングリコールモノメチルエーテルアセテート202部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液3を得た。
[Preparation of dispersion 3]
C. I. Pigment Red 202 (pigment) 10.0 parts, dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 7.5 parts, resin (B-2) (solid content conversion) 3 0.5 parts, propylene glycol monomethyl ether 8.5 parts, and propylene glycol monomethyl ether acetate 202 parts were mixed, 0.4 μm zirconia beads 600 parts were added, and the mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). .. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 3.
〔分散液4の作製〕
C.I.ピグメントレッド264(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を7.6部、樹脂(B−2)(固形分換算)を3.6部、プロピレングリコールモノメチルエーテル6.7部、プロピレングリコールモノメチルエーテルアセテート55.4部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液4を得た。
[Preparation of dispersion 4]
C. I. Pigment Red 264 (pigment) 10.0 parts, dispersant (BYK, BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 7.6 parts, and resin (B-2) (solid content conversion) 3 6 parts, 6.7 parts of propylene glycol monomethyl ether, and 55.4 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and a paint conditioner (manufactured by LAU) was used for 1 hour. Shaken. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 4.
〔分散液5の作製〕
C.I.ピグメントレッド269(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を5.0部、樹脂(B−2)(固形分換算)を3.0部、プロピレングリコールモノメチルエーテル5.5部、プロピレングリコールモノメチルエーテルアセテート47.7部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液5を得た。
[Preparation of dispersion 5]
C. I. Pigment Red 269 (pigment) 10.0 parts, dispersant (BYK Co. BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 5.0 parts, resin (B-2) (solid content conversion) 3 0.0 part, 5.5 parts of propylene glycol monomethyl ether, and 47.7 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and a paint conditioner (manufactured by LAU) was used for 1 hour. Shaken. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 5.
〔分散液6の作製〕
C.I.ピグメントイエロー185(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を10.8部、樹脂(B−2)(固形分換算)を3.5部、プロピレングリコールモノメチルエーテル4.2部、プロピレングリコールモノメチルエーテルアセテート96.5部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液6を得た。
[Preparation of Dispersion 6]
C. I. Pigment Yellow 185 (pigment) 10.0 parts, dispersant (BYK Co. BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 10.8 parts, resin (B-2) (solid content conversion) 3 0.5 parts, propylene glycol monomethyl ether 4.2 parts, and propylene glycol monomethyl ether acetate 96.5 parts are mixed, 0.4 μm zirconia beads 600 parts are added, and a paint conditioner (manufactured by LAU) is used for 1 hour. Shaken. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 6.
〔分散液7の作製〕
C.I.ピグメントブルー15:6(顔料)を10.0部、分散剤(BYK社製 BYKLPN−6919;プロピレングリコールモノメチルエーテルアセテート60%溶液)を5.8部、樹脂(B−2)(固形分換算)を4.0部、乳酸エチル7.6部、プロピレングリコールモノメチルエーテルアセテート96.5部を混合し、0.4μmのジルコニアビーズ600部を加え、ペイントコンディショナー(LAU社製)を使用して1時間振盪した。その後、ジルコニアビーズをろ過により除去して分散液7を得た。
[Preparation of dispersion 7]
C. I. Pigment Blue 15:6 (pigment) 10.0 parts, dispersant (BYK, BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution) 5.8 parts, resin (B-2) (solid content conversion). Was mixed with 4.0 parts of ethyl lactate and 96.5 parts of propylene glycol monomethyl ether acetate, 600 parts of 0.4 μm zirconia beads were added, and a paint conditioner (manufactured by LAU) was used for 1 hour. Shaken. Then, the zirconia beads were removed by filtration to obtain a dispersion liquid 7.
<実施例1〜36、比較例1、2>
〔着色樹脂組成物の調製〕
表5〜7に示す成分を混合して、各々の着色樹脂組成物を得た。
<Examples 1 to 36, Comparative Examples 1 and 2>
[Preparation of colored resin composition]
The components shown in Tables 5 to 7 were mixed to obtain each colored resin composition.
・色材1:式(A−1)で表される化合物 Color material 1: compound represented by formula (A-1)
・色材2:式(A−2)で表される化合物 Color material 2: compound represented by formula (A-2)
・色材3:式(A−3)で表される化合物 Color material 3: compound represented by formula (A-3)
・色材4:式(A−4)で表される化合物 Color material 4: compound represented by formula (A-4)
・色材5:式(A−X)で表される化合物 Color material 5: compound represented by formula (AX)
・色材6:式(A−6)で表される化合物
・色材7:式(A−7)で表される化合物
・色材8:式(A−8)で表される化合物
・色材9:式(A−9)で表される化合物
・色材10:式(A−10)で表される化合物
・色材11:式(A−11)で表される化合物
・色材12:式(A−12)で表される化合物
・色材13:式(A−13)で表される化合物
・色材14:式(A−14)で表される化合物
・色材15:式(A−15)で表される化合物
・色材16:式(A−16)で表される化合物
・色材17:式(A−17)で表される化合物
・色材18:式(A−18)で表される化合物
・色材19:式(A−19)で表される化合物
・色材20:式(A−20)で表される化合物
・色材21:式(A−21)で表される化合物
・色材22:式(A−22)で表される化合物
・色材23:式(A−23)で表される化合物
・色材24:式(A−24)で表される化合物
・色材25:式(A−25)で表される化合物
・色材26:式(A−26)で表される化合物
・色材27:式(A−27)で表される化合物
・色材28:式(A−28)で表される化合物
・色材29:式(A−29)で表される化合物
Color material 6: Compound represented by formula (A-6) Color material 7: Compound represented by formula (A-7) Color material 8: Compound represented by formula (A-8) Material 9: Compound represented by Formula (A-9)/Coloring Material 10: Compound represented by Formula (A-10)/Coloring Material 11: Compound represented by Formula (A-11)/Coloring Material 12 : Compound represented by Formula (A-12)/Coloring material 13: Compound represented by Formula (A-13)/Coloring material 14: Compound represented by Formula (A-14)/Coloring material 15: Formula Compound represented by (A-15)/Coloring material 16: Compound represented by Formula (A-16)/Coloring material 17: Compound represented by Formula (A-17)/Coloring material 18: Formula (A -18) compound/coloring material 19: compound represented by formula (A-19)/coloring material 20: compound represented by formula (A-20)/coloring material 21: formula (A-21) ) Compound/colorant 22: compound represented by formula (A-22)/colorant 23: compound represented by formula (A-23)/colorant 24: represented by formula (A-24) Compound/Coloring Material 25: Compound Represented by Formula (A-25)/Coloring Material 26: Compound Represented by Formula (A-26)/Coloring Material 27: Represented by Formula (A-27) Compound/coloring material 28: compound represented by formula (A-28)/coloring material 29: compound represented by formula (A-29)
・樹脂(B):樹脂(B−1)(固形分換算)
・重合性化合物(C):ジペンタエリスリトールヘキサアクリレート(KAYARAD(登録商標)DPHA;日本化薬(株)製)
・重合開始剤(D):TR−PBG327(登録商標)(常州強力電子新材料株式会社製;オキシム化合物)
・溶剤(E):溶剤(E−1):乳酸エチル
溶剤(E−2):ジアセトンアルコール
溶剤(E−3):プロピレングリコールモノメチルエーテルアセテート
・レベリング剤(F):ポリエーテル変性シリコーンオイル(固形分換算)(トーレシリコーンSH8400;東レダウコーニング(株)製)
-Resin (B): Resin (B-1) (solid content conversion)
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
-Polymerization initiator (D): TR-PBG327 (registered trademark) (Changzhou Power Electronics Co., Ltd.; oxime compound)
-Solvent (E): Solvent (E-1): Ethyl lactate
Solvent (E-2): diacetone alcohol
Solvent (E-3): Propylene glycol monomethyl ether acetate/leveling agent (F): Polyether-modified silicone oil (solid content conversion) (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)
〔カラーフィルタ(着色塗膜)の作製〕
5cm角のガラス基板(イーグル2000;コーニング社製)上に、着色樹脂組成物をスピンコート法で塗布したのち、100℃で3分間プリベークして着色樹脂組成物層を形成した。放冷後、露光機(TME−150RSK;トプコン(株)製)を用いて、大気雰囲気下、60mJ/cm2の露光量(365nm基準)で光照射した。その後オーブン中、230℃で20分間ポストベークを行い、カラーフィルタを得た。
[Preparation of color filter (colored coating film)]
The colored resin composition was applied on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Incorporated) by a spin coating method, and then prebaked at 100° C. for 3 minutes to form a colored resin composition layer. After cooling, light exposure was performed using an exposure device (TME-150RSK; manufactured by Topcon Corp.) in the air atmosphere at an exposure amount of 60 mJ/cm 2 (365 nm standard). Then, post baking was performed at 230° C. for 20 minutes in an oven to obtain a color filter.
〔耐薬品性試験〕
得られたカラーフィルタを40℃に調温したN−メチルピロリドンに10分間浸漬させた。浸漬前後のカラーフィルタについて、測色機(OSP−SP−200;オリンパス(株)製)を用いて分光を測定し、C光源の特性関数を用いてCIEのXYZ表色系におけるxy色度座標(x、y)と刺激値Yを算出した。該測定値からJIS Z 8730:2009(7.色差の計算方法)に記載される方法で色差△E*abを計算し、結果を表8〜9に示した。△E*abは小さいほど色変化が小さいことを意味する。
[Chemical resistance test]
The obtained color filter was immersed in N-methylpyrrolidone adjusted to 40° C. for 10 minutes. About the color filter before and after the immersion, the spectrum was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corp.), and the xy chromaticity coordinates in the XYZ color system of CIE were measured using the characteristic function of the C light source. (X, y) and the stimulation value Y were calculated. The color difference ΔE*ab was calculated from the measured values by the method described in JIS Z 8730:2009 (7. Calculation method of color difference), and the results are shown in Tables 8 to 9. The smaller ΔE*ab means that the color change is smaller.
Claims (5)
[式(I)中、
R1、R2、R3、R4、R5、R6、R7、R8、R9及びR10は、それぞれ独立に、水素原子、ヒドロキシ基、ニトロ基、シアノ基、ハロゲン原子、カルボキシ基、スルホ基、スルファモイル基、メタロセニル基、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アミノ基、カルボキシ基、スルホ基、ホスホノ基、スルファモイル基、イソシアナト基、複素環で置換されていてもよく、
R11、R12、R13、R14、R15及びR16は、それぞれ独立に、水素原子、炭素数1〜30の炭化水素基、又は前記炭化水素基中のメチレン基の1つ又は2つ以上が下記群Iから選ばれる2価の基で置き換えられた基を表し、ただし、2つ以上のメチレン基が下記群Iから選ばれる2価の基で置き換えられている場合、前記2価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、複素環又は極性基で置換されていてもよく、
R11、R12、R13、R14、R15及びR16のうちの1つ以上が、置換基として極性基を有する基であり、
nは、1〜3の整数を表し、
Aq-は、q価の陰イオンを表し、
qは1〜3の整数を表し、
pは式(I)で表される化合物の電荷を中性に保つ係数を表す。
群I:−O−、−S−、−CO−、−COO−、−OCO−、−COS−、−OCS−、−SO2−、−SO3−、−NH−、−CONH−、−NHCO−、−SO2NH−、−NHSO2−又は−N=CH−] A colored resin composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by the formula (I).
[In the formula (I),
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, One or more of a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group is a divalent group selected from the following group I. Represents a substituted group, provided that when two or more methylene groups are replaced by a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle. ,
R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each independently one or two of a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a methylene group in the hydrocarbon group. One or more represents a group substituted with a divalent group selected from the following group I, provided that two or more methylene groups are replaced with a divalent group selected from the following group I: Groups are not next to each other,
The hydrogen atom contained in the hydrocarbon group may be substituted with a heterocycle or a polar group,
At least one of R 11 , R 12 , R 13 , R 14 , R 15 and R 16 is a group having a polar group as a substituent,
n represents an integer of 1 to 3,
A q- represents a q-valent anion,
q represents an integer of 1 to 3,
p represents a coefficient for keeping the charge of the compound represented by the formula (I) neutral.
Group I: -O -, - S - , - CO -, - COO -, - OCO -, - COS -, - OCS -, - SO 2 -, - SO 3 -, - NH -, - CONH -, - NHCO -, - SO 2 NH - , - NHSO 2 - or -N = CH-]
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