KR101661733B1 - Dye compounds and resin composition for color filter comprising the same - Google Patents
Dye compounds and resin composition for color filter comprising the same Download PDFInfo
- Publication number
- KR101661733B1 KR101661733B1 KR1020140086913A KR20140086913A KR101661733B1 KR 101661733 B1 KR101661733 B1 KR 101661733B1 KR 1020140086913 A KR1020140086913 A KR 1020140086913A KR 20140086913 A KR20140086913 A KR 20140086913A KR 101661733 B1 KR101661733 B1 KR 101661733B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- carbon atoms
- substituted
- formula
- dye compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 239000011342 resin composition Substances 0.000 title claims abstract description 22
- 239000000126 substance Substances 0.000 claims abstract description 8
- 239000000975 dye Substances 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000003086 colorant Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 16
- -1 bistrifluoromethanesulfonimide anion Chemical class 0.000 claims description 15
- 239000000049 pigment Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 239000001055 blue pigment Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000012719 thermal polymerization Methods 0.000 claims description 2
- 239000001018 xanthene dye Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 6
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002904 solvent Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000001003 triarylmethane dye Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- XGPOMXSYOKFBHS-UHFFFAOYSA-M sodium;trifluoromethanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(F)(F)F XGPOMXSYOKFBHS-UHFFFAOYSA-M 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)C(OCCN(C)C1=CC[C@@](C(c(cc2)ccc2N(C)c2ccccc2)=C(C=C2)C=CC2=CC(C)*C2C=CC=CC2)C(C)=C1)=O Chemical compound CC(C)C(OCCN(C)C1=CC[C@@](C(c(cc2)ccc2N(C)c2ccccc2)=C(C=C2)C=CC2=CC(C)*C2C=CC=CC2)C(C)=C1)=O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- IZZVHOPLTANRPW-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)ethyl acetate Chemical compound CC(C)OCCOCCOC(C)=O IZZVHOPLTANRPW-UHFFFAOYSA-N 0.000 description 1
- GWQAFGZJIHVLGX-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethyl acetate Chemical compound CCCOCCOCCOC(C)=O GWQAFGZJIHVLGX-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NVSCAPMJFRYMFK-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl acetate Chemical compound CCOCCOCCOCCOC(C)=O NVSCAPMJFRYMFK-UHFFFAOYSA-N 0.000 description 1
- SDHQGBWMLCBNSM-UHFFFAOYSA-N 2-[2-(2-methoxyethoxy)ethoxy]ethyl acetate Chemical compound COCCOCCOCCOC(C)=O SDHQGBWMLCBNSM-UHFFFAOYSA-N 0.000 description 1
- WZDMGBHDHARVNN-UHFFFAOYSA-N 2-[2-(2-propan-2-yloxyethoxy)ethoxy]ethyl acetate Chemical compound CC(C)OCCOCCOCCOC(C)=O WZDMGBHDHARVNN-UHFFFAOYSA-N 0.000 description 1
- ONPJEOPZOXVCDK-UHFFFAOYSA-N 2-[2-(2-propoxyethoxy)ethoxy]ethyl acetate Chemical compound CCCOCCOCCOCCOC(C)=O ONPJEOPZOXVCDK-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 1
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 description 1
- NMSZFQAFWHFSPE-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxycarbonyl)but-3-enoic acid Chemical compound OC(=O)CC(=C)C(=O)OCC1CO1 NMSZFQAFWHFSPE-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- RHVBCJVWPMFXDC-ZIRCCNIJSA-N CCC(C/C=C(\C=C1)/C=C/C1=C(/c(cc1)ccc1N(C)c1ccccc1)\c(c(C)c1)ccc1N(C)CCOC(C(C)=C)=O)c1ccccc1 Chemical compound CCC(C/C=C(\C=C1)/C=C/C1=C(/c(cc1)ccc1N(C)c1ccccc1)\c(c(C)c1)ccc1N(C)CCOC(C(C)=C)=O)c1ccccc1 RHVBCJVWPMFXDC-ZIRCCNIJSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- MLHOXUWWKVQEJB-UHFFFAOYSA-N Propyleneglycol diacetate Chemical compound CC(=O)OC(C)COC(C)=O MLHOXUWWKVQEJB-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 1
- 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 1
- 230000032900 absorption of visible light Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- SZOJKESAWDFSND-UHFFFAOYSA-N acetic acid;2-methyl-2-[(2-methylpropan-2-yl)oxy]propane Chemical compound CC(O)=O.CC(C)(C)OC(C)(C)C SZOJKESAWDFSND-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920003090 carboxymethyl hydroxyethyl cellulose Polymers 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001326 naphthylalkyl group Chemical group 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-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
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Power Engineering (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Nonlinear Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Electromagnetism (AREA)
- Crystallography & Structural Chemistry (AREA)
- Mathematical Physics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Computer Hardware Design (AREA)
- Optical Filters (AREA)
Abstract
본 발명은 컬러필터용 염료 화합물에 관한 것으로서, 하기 [화학식 1] 에 따른 염료 화합물인 것을 특징으로 하며, 본 발명에 따른 염료 화합물을 포함하는 수지 조성물은 프로필렌글리콜 메틸에테르 아세테이트(PGMEA) 등의 유기 용제에 대한 우수한 용해성, 높은 내열성, 특히 우수한 내광성을 특성으로 가지고 있어, 이를 이용하여 우수한 컬러필터의 제조가 가능하다.
[화학식 1]
The present invention relates to a dye compound for a color filter, characterized in that it is a dye compound according to the following formula (1), and the resin composition comprising the dye compound according to the present invention is an organic compound such as propylene glycol methyl ether acetate Excellent solubility in solvents, high heat resistance, and particularly excellent light resistance, and it is possible to manufacture excellent color filters by using them.
[Chemical Formula 1]
Description
본 발명은 컬러필터용 염료 화합물에 관한 것으로서, 더욱 상세하게는 유기용매에 대한 용해도가 높고, 내열성과 내광성이 우수한 것을 특징으로 하는 트리아릴메탄계 염료 화합물과 이를 이용한 컬러필터용 수지 조성물에 관한 것이다.More particularly, the present invention relates to a triarylmethane dye compound having high solubility in an organic solvent and excellent heat resistance and light fastness, and a resin composition for a color filter using the dye compound. .
염료 화합물은 화합물의 색 흡수 내지 투과하는 성질에 의해 여러 가지 분야에 응용이 되고 있다. 특히, 섬유 착색제 등으로 활용되는 섬유 산업 분야, 디스플레이 소재 분야, 잉크젯 잉크 조성물, 필기구 색제, 특수하게는 세포나 조직 등의 염색에 사용되는 생화학 분야까지 널리 사용되고 있다.Dye compounds have been applied to various fields due to their color absorption or transmission properties. In particular, it is widely used in the fields of textile industry used as a fiber coloring agent, display materials, inkjet ink composition, writing instrument coloring agent, and especially in biochemistry used for dyeing cells and tissues.
이러한 염료 화합물 중에서 트리아릴메탄계 화합물에 해당하고, 널리 사용되고 있는 하기 Victoria Blue BO 화합물의 경우, 색특성이 우수하나, 유기용매에 대한 용해도 및 내열성이 떨어지고 특히 내광성이 좋지 않아 그 활용분야가 섬유산업, 잉크젯 잉크 및 필기구 색제에 한정되어 사용되고 있는 실정이다.Among these dye compounds, the Victoria Blue BO compound, which is a widely used triarylmethane compound and is widely used, has excellent color characteristics, but has poor solubility and heat resistance to an organic solvent and is not particularly excellent in light resistance. , Inkjet ink, and writing instrument coloring agent.
[Victoria Blue BO][Victoria Blue BO]
일반적으로 트리아릴메탄계 염료의 광에 의한 분해 메카니즘은 하기 참고문헌(Dyes and Pigments 3(1982) 49~58)에 아래와 같이 잘 나타나 있다.In general, the light-induced decomposition mechanism of triarylmethane-based dyes is well described in the following reference (Dyes and Pigments 3 (1982) 49-58).
앞에서 언급한 Victoria Blue BO 화합물이 갖는 상기 한계점을 개선하기 위하여, Victoria Blue BO의 음이온을 알킬 술폰산 음이온, 방향족 술폰산 음이온, 옥살레이트, 알킬카르복시산 음이온 등으로 치환하여 물성을 개선하려는 여러 시도들이 진행되어져 왔다. 이와 같은 염치환으로 용해도 및 내열성의 많은 개선은 이루어져 왔으나, 내광성은 개선이 크게 이루어지지 않았다.In order to improve the above-mentioned limitation of the above-mentioned Victoria Blue BO compound, various attempts have been made to improve the physical properties by replacing the anion of Victoria Blue BO by an alkylsulfonic acid anion, an aromatic sulfonic acid anion, oxalate, an alkylcarboxylic acid anion or the like . Although many improvements in solubility and heat resistance have been made with such a salt solution, the improvement in light resistance has not been largely improved.
따라서, 본 발명이 해결하고자 하는 과제는 상기의 문제점을 해결하기 위한 것으로서, 유기용매에 대한 용해도 개선 및 우수한 내열성을 확보하고, 특히 취약한 내광성을 개선하여 컬러필터에 사용이 가능한 신규한 트리아릴메탄 염료 화합물을 제공하는 것이다.Accordingly, it is an object of the present invention to provide a novel triarylmethane dye capable of improving solubility in an organic solvent and having excellent heat resistance, Compound. ≪ / RTI >
또한, 본 발명은 상기 신규한 트리아릴메탄 염료 화합물을 착색제로 포함하는 컬러필터용 수지 조성물 및 이를 이용한 컬러필터를 제공하고자 한다.The present invention also provides a resin composition for a color filter comprising the novel triarylmethane dye compound as a colorant and a color filter using the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 1]로 표시되는 트리아릴메탄 염료 화합물을 제공한다.In order to solve the above problems, the present invention provides a triarylmethane dye compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 [화학식 1]의 구체적인 구조 및 치환기에 대한 설명은 후술한다.
The specific structure and substituent of the above formula (1) will be described later.
또한, 본 발명은 상기 과제를 해결하기 위하여, 착색제, 반응성 불포화 화합물, 중합 개시제, 유기용제 및 첨가제를 포함하는 컬러필터용 수지 조성물을 제공하고, 상기 착색제는 상기 [화학식 1]에 따른 염료 화합물을 포함하는 것을 특징으로 하는 컬러필터용 수지 조성물을 제공한다.The present invention also provides a resin composition for a color filter comprising a colorant, a reactive unsaturated compound, a polymerization initiator, an organic solvent and an additive, wherein the colorant comprises a dye compound according to the above formula (1) The present invention also provides a resin composition for a color filter.
또한, 상기 착색제는 컬러필터의 색좌표 및 색보정 등을 고려하여 염료 또는 안료로 이루어진 군에서 선택된 어느 하나 이상을 더 포함할 수 있다.In addition, the colorant may further include at least one selected from the group consisting of a dye and a pigment in consideration of the color coordinate and color correction of the color filter.
또한, 상기 착색제는 수지 조성물 총 중량에 대하여 0.01 중량% 내지 50 중량%일 수 있다.In addition, the colorant may be 0.01% by weight to 50% by weight based on the total weight of the resin composition.
또한, 상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머, 광경화성 단량체나 올리고머 및 이들의 조합으로 이루어지는 군에서 선택된 어느 하나 이상일 수 있다.The reactive unsaturated compound may be at least one selected from the group consisting of thermosetting monomers and oligomers, photocurable monomers and oligomers, and combinations thereof.
또한, 상기 중합 개시제는 열중합 개시제, 광중합 개시제 및 이들의 조합으로 이루어지는 군에서 선택된 어느 하나 이상일 수 있다.The polymerization initiator may be any one selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof.
본 발명에 따른 염료 화합물은 프로필렌글리콜 모노메틸 에테르 아세테이트(PGMEA)에 대한 우수한 용해성, 내열성 및 내광성을 가진다. 따라서 이를 컬러필터 수지 조성물의 착색제로 사용할 경우, 안료를 사용한 경우보다 용해도가 높고, 안료 분산안정성을 위해 추가되는 첨가제의 사용량을 줄일 수 있어, 착색력을 극대화시킬 수 있는 장점이 있으며, 이로 인해 고색재현이 가능한 장점이 있다.The dye compound according to the present invention has excellent solubility, heat resistance and light resistance to propylene glycol monomethyl ether acetate (PGMEA). Therefore, when it is used as a coloring agent for a color filter resin composition, the solubility is higher than that of a pigment, and the amount of additives to be added for stabilizing the dispersion of pigments can be reduced, thereby having an advantage of maximizing coloring power. This has the advantage.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
염료를 컬러필터에 착색제로 적용하기 위해서는 유기 용제에 대한 우수한 용해도와 고내열성 및 고내광성을 필요로 한다. 최근에 컬러필터의 착색제로서, 투과율이 높은 염료에 대한 개발이 이루어지고 있으나, 현재까지 유기 용제에 대한 우수한 용해도와 고내열성 및 고내광성을 모두 만족하는 염료들은 드문 실정이다.In order to apply a dye as a coloring agent to a color filter, excellent solubility in an organic solvent, high heat resistance and high light resistance are required. Recently, dyes having high transmittance have been developed as coloring agents for color filters. However, dyes satisfying excellent solubility, high heat resistance and high light resistance to organic solvents are rarely present.
본 발명의 발명자들은 여러 가지 실험을 진행하여 용해도, 내열성, 내광성이 우수한 트리아릴메탄 염료를 합성하였으며, 이를 컬러필터 수지 조성물의 착색제로 적용이 가능함을 확인하였다.The inventors of the present invention have conducted various experiments and have synthesized triarylmethane dyes excellent in solubility, heat resistance and light resistance, and confirmed that the triarylmethane dyes can be applied as coloring agents for color filter resin compositions.
본 발명에 따른 염료 화합물은 하기 [화학식 1]로 표시되는 염료 화합물인 것을 특징으로 한다.The dye compound according to the present invention is characterized by being a dye compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 [화학식 1]에서,In the above formula (1)
X-는 플루오르화알킬술폰산 음이온 또는 비스트리플루오르메탄술폰이미드 음이온일 수 있다.X - may be a fluorinated alkylsulfonic acid anion or a bistrifluoromethanesulfonimide anion.
R1, R2, R8 및 R9는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기, 치환 또는 비치환 탄소수 7 내지 20 아랄킬기, 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소기, 또는 하기 [구조식 1] 및 [구조식 2] 중에서 선택되며, 상기 R1, R2, R8 및 R9 중에서 적어도 1개 이상은 하기 [구조식 1] 또는 [구조식 2]이다.R 1 , R 2 , R 8 And R < 9 > are the same or different from each other and each independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or a group selected from the following Structural Formulas 1 and 2, wherein R 1 , R 2 , R 8 And R 9 Is at least one of [structural formula 1] or [structural formula 2].
[구조식 1] [구조식 2][Structural formula 1] [Structural formula 2]
상기 [구조식 1] 내지 [구조식 2]에서,In the above Structural Formulas 1 to 2,
R10은 치환 또는 비치환 탄소수 1 내지 10의 알킬렌기이며, R11은 수소 또는 메틸이고, R12 및 R13은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환 탄소수 1 내지 4의 알킬렌기이다.R 10 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, R 11 is hydrogen or methyl, R 12 And R < 13 > are the same or different and each independently represents a substituted or unsubstituted alkylene group having 1 to 4 carbon atoms.
R3, R4, R5, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환 탄소수 1 내지 10의 알킬기, 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기, 치환 또는 비치환 탄소수 1 내지 10의 알콕시기, 치환 비치환 탄소수 3 내지 10의 씨클로알콕시기, 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소기 및 할로겐 중에서 선택된다.R 3 , R 4 , R 5 , R 6 And R 7 are the same or different from each other and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, A cycloalkoxy group having 3 to 10 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, and halogen.
a, b, c는 각각 0 내지 4의 정수이고, d, e는 0 내지 5의 정수이며, 상기 a, b, c, d, 및 e가 2 이상인 경우, 복수의 R3, R4, R5, R6 및 R7은 각각 서로 동일하거나 상이할 수 있다.
a, b, c is an integer from 0 to 4, respectively, d, e is an integer from 0 to 5, wherein a, b, c, d, and when e is 2 or more, a plurality of R 3, R 4, R 5 , R 6 And R < 7 > may be the same or different from each other.
상기 R1 , R2 , R8 및 R9는 보다 구체적으로 치환 또는 비치환 탄소수 1 내지 10의 알킬기로서, 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, i-프로필기, i-부틸기, i-펜틸기, t-부틸기, 2-에틸헥실기와 또한, 이들에 추가적으로 치환되어 있는 알킬기 등일 수 있다. 또한 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기로서, 씨클로프로필, 씨클로부틸기, 씨클로펜틸기, 씨클로헥실기, 씨클로헵틸기, 씨클로옥틸기, 씨클로데실기와 또한 이들에 추가적으로 치환되어 있는 씨클로알킬기 등일 수 있다. 또한, 치환 또는 비치환 탄소수 7 내지 20의 아랄킬기로는 벤질기, 나프틸알킬기와 또한, 이들에 추가적으로 치환되어 있는 아랄킬기 등일 수 있다. 또한, 치환 또는 비치환 탄소수 6 내지 10의 방향족 탄화수소기로는 페닐기, 나프틸기와 또한, 이들에 추가적으로 치환되어 있는 방향족 탄화수소기 등일 수 있다.The above R 1 , R 2 , R 8 And R 9 is more specifically a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms which is an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, Butyl group, an i-pentyl group, a t-butyl group, a 2-ethylhexyl group, and an alkyl group additionally substituted thereto. As the substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group and a cycloalkyl group And so on. Examples of the substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms may include a benzyl group, a naphthylalkyl group, and an aralkyl group additionally substituted thereon. The substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms may be a phenyl group, a naphthyl group, and an aromatic hydrocarbon group additionally substituted thereto.
상기 [구조식 1]에서 R10은 보다 구체적으로 메틸렌기, 에틸렌기, 프로필렌기, 부틸렌기, 펜틸렌기, 헥실렌기와 이들에 추가적으로 치환되어 있는 알킬렌기 등일 수 있다.In the above structural formula 1, R 10 may more specifically be a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, an alkylene group additionally substituted thereto, or the like.
상기 [구조식 2]에서 R12 및 R13은 각각 메틸렌기, 에틸렌기, 프로필렌기, 부틸렌기와 또한, 이들에 추가적으로 치환되어 있는 알킬렌기 등일 수 있다.In the above formula 2, R 12 And R 13 may each be a methylene group, an ethylene group, a propylene group, a butylene group, and an alkylene group additionally substituted thereto.
상기 R3, R4, R5, R6 및 R7은 보다 구체적으로 치환 또는 비치환 탄소수 1 내지 10의 알킬기로서 메틸기, 에틸기, 프로필기, 부틸기, 펜틸기, 헥실기, 헵틸기, 옥틸기, 노닐기, 데실기, i-프로필기, i-부틸기, i-펜틸기, t-부틸기, 2-에틸헥실기와 또한, 이들에 추가적으로 치환되어 있는 알킬기 등일 수 있다. 또한 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기로서, 씨클로프로필, 씨클로부틸기, 씨클로펜틸기, 씨클로헥실기, 씨클로헵틸기, 씨클로옥틸기, 씨클로데실기와 또한 이들에 추가적으로 치환되어 있는 씨클로알킬기 등일 수 있다. 또한, 치환 또는 비치환 탄소수 1 내지 10의 알콕시기로는, 메톡시, 에톡시, 프로폭시, 부톡시, 펜톡시, 헥실옥시, 헵틸옥시, 노닐옥시, 데실옥시, i-프로폭시, i-부톡시, i-펜톡시, t-부톡시, 2-에틸헥실옥시와 또한, 이들에 추가적으로 치환되어 있는 알콕시기 등일 수 있다. 또한 치환 또는 비치환 탄소수 3 내지 10의 씨클로알콕시기로서, 씨클로프로필옥시, 씨클로부틸옥시, 씨클로펜틸옥시, 씨클로헥실옥시, 씨클로헵틸옥시, 씨클로옥틸옥시, 씨클로데실옥시기와 또한 이들에 추가적으로 치환되어 있는 씨클로알콕시기 등일 수 있다.
R 3 , R 4 , R 5 , R 6 And R 7 are more specifically a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms which may have a substituent selected from the group consisting of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, , an i-butyl group, an i-pentyl group, a t-butyl group, a 2-ethylhexyl group and an alkyl group additionally substituted thereto. As the substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group and a cycloalkyl group And so on. Examples of the substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexyloxy, heptyloxy, nonyloxy, decyloxy, i- -Butoxy, i-pentoxy, t-butoxy, 2-ethylhexyloxy and also alkoxy groups additionally substituted on these groups. Further, examples of the substituted or unsubstituted cycloalkoxy group having 3 to 10 carbon atoms include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy, cyclooctyloxy, And the like.
본 발명의 [화학식 1]에 따른 염료 화합물은 구체적으로 하기 [1] 내지 [16]의 화합물로 표시될 수 있고, 다만 이에 의해서 본 발명에 따른 [화학식 1]의 범위가 제한되는 것은 아니다.The dye compound according to Formula 1 of the present invention can be specifically represented by the following [1] to [16], but the scope of Formula 1 according to the present invention is not limited thereto.
본 발명에 따른 컬러필터용 수지 조성물은 착색제로 상기 본 발명에 따른 [화학식 1]로 표시되는 염료 화합물을 사용하고, 바인더 수지, 반응성 불포화 화합물, 중합 개시제, 유기용제 및 첨가제를 포함할 수 있다.The resin composition for a color filter according to the present invention may contain a binder resin, a reactive unsaturated compound, a polymerization initiator, an organic solvent and an additive, using a dye compound represented by the formula (1) according to the present invention as a colorant.
또한, 상기 착색제는 컬러필터의 색좌표 및 색보정 등을 고려하여 본 발명에 따른 [화학식 1]의 염료 화합물과 함께 선택적으로 1종 이상의 염료 화합물 또는 안료 화합물을 더 포함할 수 있다.The colorant may further include at least one dye compound or pigment compound together with the dye compound of formula (I) according to the present invention in consideration of the color coordinate and color correction of the color filter.
상기 염료 화합물로는 크산텐염료, 시아닌 염료, 아자포피린 염료 등이 있으며, 상기 안료 화합물로는 청색안료, 또는 보라색 안료에 해당하는 것이면 특별한 제한 없이 사용될 수 있는 것이지만, 바람직하게는 컬러 인덱스(The Society of Dyers and Colourists출판)에서 피그먼트로 분류되어 있는 화합물을 들 수 있다. 구체적인 예로는 C.I. 청색안료(Color Index Pigment Blue) 1, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60 등을 들 수 있으며, C.I. 보라색안료(Color Index Pigment Violet) 23등을 들 수 있다.Examples of the dye compounds include xanthene dyes, cyanine dyes, and azapphyrin dyes. The pigment compounds may be blue pigments or purple pigments, and may be used without any particular limitation. of Dyers and Colourists). < / RTI > Specific examples include C.I. 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60 and the like can be mentioned as color pigments (Color Index Pigment Blue). And Color Index Pigment Violet 23 and the like.
또한, 상기 착색제는 컬러필터용 수지 조성물 총중량에 대하여 0.01 중량% 내지 50 중량%로 포함할 수 있다.
The colorant may be contained in an amount of 0.01 to 50% by weight based on the total weight of the resin composition for a color filter.
상기 바인더 수지는 결착력을 나타낼 수 있는 수지이면 특별히 제한되지 않으며, 특히 공지되어 있는 필름형성 수지일 수 있다.The binder resin is not particularly limited as long as it is a resin capable of exhibiting binding force, and may be a known film-forming resin.
예를 들어, 셀룰로오스 수지, 특히 카르복시메틸히드록시에틸 셀룰로오스 및 히드록시에틸 셀룰로오스, 아크릴산 수지, 알키드 수지, 멜라민 수지, 에폭시 수지, 폴리비닐 알코올, 폴리비닐 피롤리돈, 폴리아미드, 폴리아미드-이민, 폴리이미드 등의 바인더이다. 더욱 바람직하게는 광중합성 불포화 결합을 갖는 수지가 포함되며, 예를 들어, 아크릴산 수지일 수 있다. 특히, 중합성 단량체의 단독중합체 및 공중합체, 예를 들어 메틸메타아크릴레이트, 에틸메타아크릴레이트, 프로필메타아크릴레이트, 부틸메타아크릴레이트, 스티렌 및 스티렌 유도체, 메타아크릴산, 이타콘산, 말레산, 말레 무수물, 모노알킬 말레에이트과 같은 카르복시기를 함유한 중합성 단량체, 및 메타아크릴산, 스티렌 및 스티렌 유도체와 같은 중합성 단량체들 간의 공중합체가 유용하며, 또한 옥시란 고리와 에틸렌계 불포화 화합물을 각각 함유하는 화합물, 예를 들어, 글리시딜(메트)아크릴레이트, 아크릴로일 글리시딜 에테르 및 모노알킬글리시딜 이타코네이트 등과 카르복실-함유 중합 화합물의 반응 생성물, 또한 히드록실기와 에틸렌계 불포화 화합물(불포화 알코올)을 각각 함유하는 화합물 예를 들어, 알릴 알코올, 2-부텐-4-올, 올레일 알코올, 2-히드록시에틸 (메트)아크릴레이트, N-메틸올아크릴아미드 등과 카르복시기-함유 중합 화합물의 반응 생성물이 있으며, 이러한 바인더는 이소시아네이트기가 없는 불포화 화합물을 함유할 수도 있다.For example, cellulose resins such as carboxymethylhydroxyethylcellulose and hydroxyethylcellulose, acrylic acid resin, alkyd resin, melamine resin, epoxy resin, polyvinyl alcohol, polyvinylpyrrolidone, polyamide, polyamide- Polyimide and the like. More preferably, a resin having a photopolymerizable unsaturated bond is included, and for example, it may be an acrylic acid resin. In particular, homopolymers and copolymers of polymerizable monomers such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, styrene and styrene derivatives, methacrylic acid, itaconic acid, maleic acid, A copolymer of a polymerizable monomer containing a carboxyl group such as an anhydride and a monoalkyl maleate and a polymerizable monomer such as a methacrylic acid, a styrene and a styrene derivative is useful, and a compound containing an oxirane ring and an ethylenically unsaturated compound , For example, a reaction product of a carboxyl-containing polymer compound with glycidyl (meth) acrylate, acryloyl glycidyl ether, monoalkyl glycidyl itaconate, etc., and a reaction product of a hydroxyl group and an ethylenically unsaturated compound (Unsaturated alcohols), for example, allyl alcohol, 2-buten-4-ol, oleyl Alcohol, 2-hydroxyethyl (meth) acrylate, N- methylol acrylamide as the carboxyl group-containing, and the reaction product of a polymerizable compound, the binder may also contain an unsaturated compound with no isocyanate group.
상기 바인더의 불포화도의 당량(불포화 화합물 당 바인더의 분자량)은 적당한 광중합성뿐만 아니라 필름 경도를 제공하기 위해 일반적으로 200 내지 3,000이고, 특히 230 내지 1,000 범위일 수 있다. 필름 노광 후 충분한 알칼리 현상성을 제공하기 위해 산가는 일반적으로 20 내지 300이며, 특히 40 내지 200일 수 있다. 바인더의 평균분자량은 1,500 내지 200,000 특히 10,000 내지 50,000 g/mol이 바람직하다.
The equivalent of the unsaturation of the binder (molecular weight of the binder per unsaturated compound) may generally range from 200 to 3,000, in particular from 230 to 1,000, in order to provide adequate photopolymerization as well as film hardness. In order to provide sufficient alkali developability after film exposure, the acid number may generally be from 20 to 300, in particular from 40 to 200. The average molecular weight of the binder is preferably 1,500 to 200,000, particularly 10,000 to 50,000 g / mol.
상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머, 광경화성 단량체나 올리고머 및 이들의 조합으로 이루어진 군에서 선택되는 것일 수 있고, 바람직하게는 상기 광경화성 단량체일 수 있으며, 분자 내에 하나 이상의 반응성 이중결합 및 추가 반응성기를 함유할 수 있다.The reactive unsaturated compound may be selected from the group consisting of a thermosetting monomer or an oligomer, a photo-curable monomer or oligomer, and a combination thereof. Preferably, the reactive unsaturated compound may be the photo-curable monomer. The reactive unsaturated compound may have one or more reactive double bond Group.
이와 관련하여 유용한 광경화성 단량체는 특히 반응성 용매 또는 반응성 희석제, 예를 들어 모노-, 디-, 트리- 및 다관능성 아크릴레이트 및 메타크릴레이트, 비닐 에테르, 그리시딜 에테르 등이다. 추가 반응성기에는 아릴, 히드록실, 포스페이트, 우레탄, 2차아민, N-알콕시메틸기 등이 포함된다.Useful photocurable monomers in this context are, in particular, reactive solvents or reactive diluents, for example mono-, di-, tri- and multifunctional acrylates and methacrylates, vinyl ethers, glycidyl ethers and the like. Additional reactive groups include aryl, hydroxyl, phosphate, urethane, secondary amines, N-alkoxymethyl groups and the like.
이런 종류의 단량체들은 당업계에 공지되어 있으며, 예를 들어 문헌 [Roempp, Lexikon, Lacke und Druckfarben, Dr. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 491/492]에 언급되어 있다. 단량체의 선택은 특히 사용되는 조사의 종류 및 강도, 광개시제에 의한 목적 반응 및 필름 특성에 좌우된다. 이들 광경화성 단량체는 단독으로 또는 단량체의 조합으로 사용하는 것도 가능하다.
Monomers of this type are known in the art and are described, for example, in Roempp, Lexikon, Lacke und Druckfarben, et al. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 491/492. The choice of monomers will depend, inter alia, on the type and intensity of the irradiation used, the desired reaction by the photoinitiator and the film properties. These photocurable monomers may be used alone or in combination of monomers.
상기 중합 개시제는 열경화 개시제, 광경화 개시제 또는 이들의 조합일 수 있으며, 바람직하게는 광경화 개시제일 수 있고, 이러한 광경화 개시제는 가시광선 또는 자외선의 흡수결과, 예를 들어 상기 단량체 및/또는 바인더의 중합 반응을 유도할 수 있는 반응 중간체를 형성하는 화합물이다. 광개시제 또는 당업계에 공지되어 있으며, 예를 들어 문헌 [Roempp, Lexikon, Lacke und Druckfarben, Dr. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 445/446]으로부터 알 수 있다.
The polymerization initiator may be a thermosetting initiator, a photo-curing initiator, or a combination thereof, and may preferably be a photo-curing initiator. Such a photo-curing initiator may be, for example, the result of absorption of visible light or ultraviolet light, To form a reaction intermediate capable of inducing polymerization of the binder. Photoinitiators or are known in the art, see for example Roempp, Lexikon, Lacke und Druckfarben, et al. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 445/446.
상기의 유기 용제는 예를 들어, 케톤, 알킬렌 글리콜 에테르, 알코올 및 방향족 화합물이다. 케톤 군에는 아세톤, 메틸 에틸 케톤, 시클로헥사논 등이 있고, 알킬렌 글리콜 에테르 군에는 메틸셀로솔브(에틸렌 글리콜 모노메틸 에테르), 부틸셀로솔브(에틸렌 글리콜 모노부틸 에테르), 메틸솔로솔브 아세테이트, 에틸셀로솔브 아세테이트, 부틸셀로솔브 아세테이트, 에틸렌 글리콜 모노프로필 에테르, 에틸렌 글리콜 모노헥실 에테르, 에틸렌 글리콜 디메틸 에테르, 디에틸렌 글리콜 에틸 에테르, 프로필렌 글리콜 모노메틸 에테르, 프로필렌 글리콜 모노에틸 에테르, 프로필렌 글리콜 모노프로필 에테르, 프로필렌 글리콜 모노부틸 에테르, 프로필렌 글리콜 모노메틸 에테르 아세테이트, 디에틸렌 글리콜 메틸 에테르 아세테이트, 디에틸렌 글리콜 에틸 에테르 아세테이트, 디에틸렌 글리콜 프로필 에테르 아세테이트, 디에틸렌 글리콜 이소프로필 에테르 아세테이트, 디에틸렌 글리콜 부틸 에테르 아세테이트, 디에틸렌 글리콜 t-부틸 에테르 아세테이트, 트리에틸렌 글리콜 메틸 에테르 아세테이트, 트리에틸렌 글리콜 에틸 에테르 아세테이트, 트리에틸렌 글리콜 프로필 에테르 아세테이트, 트리에틸렌 글리콜 이소프로필 에테르 아세테이트, 트리에틸렌 글리콜, 트리에틸렌 글리콜 부틸 에테르 아세테이트, 트리에틸렌 글리콜 t-부틸 에테르 아세테이트 등이 있고, 알코올 군에는 메틸 알코올, 에틸 알코올, 이소프로필 알코올, n-부틸 알코올, 3-메틸-3-메톡시 부탄올 등이 있고, 방향족 용매 군에는 벤젠, 톨루엔, 크실렌, N-메틸-2-피롤리돈, 에틸 N-히드록시메틸피롤리돈-2 아세테이트 등이 있다. 추가의 다른 용매로는 1,2-프로판디올 디아세테이트, 3-메틸-3-메틸-3메톡시부틸 아세테이트, 에틸 아세테이트, 테트라하이드로푸란 등이 있다. 이 용매들은 단독으로 또는 혼합물로 사용할 수 있다.
Such organic solvents are, for example, ketones, alkylene glycol ethers, alcohols and aromatic compounds. Examples of the ketone group include acetone, methyl ethyl ketone, and cyclohexanone, and the alkylene glycol ether group includes methyl cellosolve (ethylene glycol monomethyl ether), butyl cellosolve (ethylene glycol monobutyl ether), methylol solos acetate , Ethyl cellosolve acetate, butyl cellosolve acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol Monopropyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate, diethylene glycol propyl ether acetate, diethylene glycol isopropyl Ether acetate, diethylene glycol butyl ether acetate, diethylene glycol t-butyl ether acetate, triethylene glycol methyl ether acetate, triethylene glycol ethyl ether acetate, triethylene glycol propyl ether acetate, triethylene glycol isopropyl ether acetate, triethylene glycol Methyl alcohol, isopropyl alcohol, n-butyl alcohol, 3-methyl-3-methoxybutanol and the like may be used. Examples of the alcohol include methyl alcohol, ethyl alcohol, isopropyl alcohol, Examples of the aromatic solvent group include benzene, toluene, xylene, N-methyl-2-pyrrolidone and ethyl N-hydroxymethylpyrrolidone-2 acetate. Additional solvents include 1,2-propanediol diacetate, 3-methyl-3-methyl-3-methoxybutyl acetate, ethyl acetate, tetrahydrofuran and the like. These solvents may be used alone or as a mixture.
상기의 추가 첨가제는 각각의 목적에 부합하는 것이라면 제한 없이 사용될 수 있을 것이다. 바람직한 예로 표면질감을 향상시키기 위해서, 지방산, 지방아민, 알코올류, Bean oil, 왁스, 로진, 레진류, 벤조트리아졸 유도체 등이 사용될 수 있다. 더욱 바람직하게는 상기 지방산으로는 Stearic acid 또는 Behenic acid 등이 사용될 수 있고, 지방 아민으로는 Stearylamine 등이 사용될 수 있다.
Such additional additives may be used without limitation as long as they meet the respective purposes. As a preferable example, fatty acids, fatty amines, alcohols, bean oil, wax, rosin, resins, benzotriazole derivatives and the like can be used for improving the surface texture. More preferably, stearic acid or behenic acid may be used as the fatty acid, and stearylamine may be used as the fatty amine.
이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않고, 본 발명의 범주 및 기술사상 범위 내에서 다양한 변경 및 수정이 가능함은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.
Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. It will be clear to those who have knowledge.
<실시예><Examples>
1. 합성예의 합성1. Synthesis of Synthetic Example
(1) [화학식 Ⅰ] 화합물의 합성(1) Synthesis of Compound of Formula (I)
하기 [반응식 1]에 따라 [화학식 Ⅰ]로 표시되는 화합물을 합성하였다.A compound represented by the formula (I) was synthesized according to the following Reaction Scheme 1.
[반응식 1][Reaction Scheme 1]
[화학식 a] [화학식 h] [화학식 Ⅰ][Chemical Formula a] [Chemical Formula h] [Chemical Formula I]
[화학식 a] 80.00 mmol을 Toluene 320 mL를 첨가하고 교반하였다. 그 후, 옥시염화인 480.00 mmol을 추가하고 15 분간 교반하였다. [화학식 h] 80 mmol을 추가한 후, 환류시켰다. 반응종료 후, 상온 냉각을 진행하고 물 300 mL를 추가한 후, 교반하였다. 층분리 후, 감압농축을 진행하고 얻어진 화합물을 컬럼크로마토그래피로 정제하여 [화학식 I] 화합물 55.71 mmol을 얻었으며, LC/MS를 이용하여 분자량을 확인하였다.
80.00 mmol of [Formula a] was added with 320 mL of Toluene and stirred. Then, 480.00 mmol of phosphorus oxychloride was added and stirred for 15 minutes. 80 mmol of [Formula h] was added, and the mixture was refluxed. After completion of the reaction, cooling at room temperature was continued, 300 mL of water was added, and the mixture was stirred. After layer separation, concentration under reduced pressure was carried out, and the obtained compound was purified by column chromatography to obtain 55.71 mmol of the compound of the formula (I), and the molecular weight was confirmed by LC / MS.
(2) [화학식 Ⅱ] 내지 [화학식 VIII]화합물의 합성(2) Synthesis of compounds of the formulas (II) to (VIII)
하기 [표 1]과같이 벤조페논 유도체와 아닐린유도체를 선정하였으며, 하기 [표 2]와 같이 반응물을 선정하여 [화학식 I]의 합성과 동일한 방법으로 합성을 진행하여 [화학식 II] 내지 [화학식 VIII]를 얻었다. 합성한 [화학식 II] 내지 [화학식 VIII]은 LC/MS를 이용하여 분자량을 확인하였다.Benzophenone derivatives and aniline derivatives were selected as shown in the following Table 1 and the synthesis was carried out in the same manner as in the synthesis of the compound of the formula (I) by selecting reactants as shown in the following [Table 2] ]. The synthesized [Formula II] to [Formula VIII] were confirmed by LC / MS.
[표 1][Table 1]
[표 2][Table 2]
(3) 합성예 1의 합성(3) Synthesis of Synthesis Example 1
[화학식 I] [합성예 1][Synthesis Example 1]
[화학식 I] 화합물 20.00 mmol을 디클로로메탄 100 g에 넣은 후, 교반하여 용해하고, 트리플루오르메탄술폰산 나트륨 24.00 mmol을 20% 수용액으로 첨가하여 1시간 교반하여 염을 치환하였다. 층분리 후, 유기층을 물로 세척하고 감압농축한 후, 정제하여 합성예 1 화합물 14.68 mmol을 얻었다.
20.00 mmol of the compound of formula (I) was dissolved in 100 g of dichloromethane and dissolved with stirring. 24.00 mmol of sodium trifluoromethanesulfonate was added thereto as a 20% aqueous solution and stirred for 1 hour to replace the salt. After layer separation, the organic layer was washed with water, concentrated under reduced pressure, and purified to obtain 14.68 mmol of the compound of Synthesis Example 1.
(4) 합성예 2 내지 16의 합성(4) Synthesis of Synthesis Examples 2 to 16
합성예 1과 동일한 방법으로 합성을 진행하였다 다만 하기 [표 3]과 같이 [화학식 I] 내지 [화학식 VIII]중에서 반응물로 선정하고, 염화합물로 트리플루오르메탄술폰산 나트륨(A) 또는 리튬 비스트리플루오르메탄술폰이미드(B), 리튬 노나플루오르술포네이트(C) 중에서 선택하여 합성예 2 내지 합성예 16을 합성하였다.Synthesis was carried out in the same manner as in Synthesis Example 1 except that the reaction product was selected from the compounds represented by the formulas (I) to (VIII) as shown in the following Table 3 and sodium trifluoromethanesulfonate (A) or lithium bistrifluoride (B), and lithium nonafluorosulfonate (C) were synthesized.
[표 3][Table 3]
(5) 비교예 2 내지 3의 합성(5) Synthesis of Comparative Examples 2 to 3
합성예 1과 동일한 방법으로 합성을 진행하였다. 다만 하기 반응물로 Victoria Blue BO(비교예 1)선정하고, 염화합물로 트리플루오르메탄술폰산 나트륨(A)를 선택하여 비교예 2 화합물을 합성하였고, 또한 염화합물로 리튬 비스트리플루오르메탄술폰이미드(B)를 선택하여 비교예 3을 합성하였다.Synthesis was carried out in the same manner as in Synthesis Example 1. Except that Victoria Blue BO (Comparative Example 1) was selected as the following reactant, and the sodium trifluoromethanesulfonate (A) was selected as the salt compound, and the compound of Comparative Example 2 was also synthesized. Lithium bistrifluoromethane sulfonimide B) was selected to synthesize Comparative Example 3.
[비교예 1] [비교예 2] [비교예 3]
[Comparative Example 1] [Comparative Example 2] [Comparative Example 3]
2. 용해도 평가2. Solubility assessment
합성예 1 내지 16과 비교예 1 내지 3을 PGMEA에 용해하여 각각의 용해도를 확인하였고, 그 결과를 하기 [표 4]에 나타내었다.Synthesis Examples 1 to 16 and Comparative Examples 1 to 3 were dissolved in PGMEA to confirm their respective solubilities, and the results are shown in Table 4 below.
[표 4][Table 4]
상기 [표 4]에서 합성예 1 내지 16과 비교예 1 내지 3의 결과로 용해도는 음이온에 따라 큰 차이를 보이는 것으로 확인되었다. 염을 치환하지 않은 비교예 1의 경우, 용해도가 <1%이하로 매우 낮음을 알 수 있으며, 다른 결과들을 통해 클로라이드, 플루오르화알킬술폰산 음이온, 비스트리플루오르메탄술폰이미드 음이온 순으로 용해도가 증가함을 알 수 있다. 특히 비스트리플루오르메탄술폰이미드 음이온의 경우일 경우, 용해도가 >10%이상으로 매우 우수한 것을 알 수 있다.
As a result of Synthesis Examples 1 to 16 and Comparative Examples 1 to 3 in Table 4, it was confirmed that the solubility showed a large difference depending on the anion. In the case of Comparative Example 1 in which the salt was not substituted, it was found that the solubility was as low as <1%, and the solubility was increased in the order of chloride, fluorinated alkylsulfonic acid anion and bistrifluoromethanesulfonimide anion . In particular, in the case of the bistrifluoromethanesulfonimide anion, the solubility is excellent, i.e., > 10%.
3. 수지 조성물의 제조3. Preparation of Resin Composition
내열성 및 내광성 평가를 위해 아래와 같이 실시예 1 내지 16의 수지 조성물과 비교예 4 내지 6의 수지 조성물을 제조하였다.For the evaluation of heat resistance and light resistance, the resin compositions of Examples 1 to 16 and Comparative Examples 4 to 6 were prepared as follows.
(1) 실시예 1 수지 조성물의 제조(1) Example 1 Production of resin composition
다음과 같은 조성으로 수지 조성물을 제조하였다.A resin composition was prepared in the following composition.
(a) 바인더수지 : 벤질메타아크릴레이트/메타아크릴산(60 : 40 질량비)의 공중합체(Mw=20000) 2.7 g(a) Binder resin: 2.7 g of a copolymer (Mw = 20000) of benzylmethacrylate / methacrylic acid (60: 40 mass ratio)
(b) 아크릴 모노머 : 디펜타에리트리톨 헥사아크릴레이트 10 g(b) Acrylic monomer: 10 g of dipentaerythritol hexaacrylate
(c) 염료 화합물 : 합성예 1 2.3 g(c) Dye compound: Synthesis Example 1 2.3 g
(d) 광중합 개시제 : BASF사의 Irgacure OXE-02 2 g(d) Photopolymerization initiator: 2 g of Irgacure OXE-02 manufactured by BASF
(e) 용제 : 프로필렌글리콜 모노메틸에테르 아세테이트 83 g
(e) Solvent: Propylene glycol monomethyl ether acetate 83 g
(2) 실시예 2 내지 16 및 비교예 4 내지 6 수지 조성물의 제조(2) Examples 2 to 16 and Comparative Examples 4 to 6 Preparation of resin composition
상기 실시예 1과 동일한 조성과 동일하게 수지 조성물을 제조하였으며, 다만 염료 화합물을 합성예 1 대신 하기 [표 5]와 같이 화합물을 바꾸어 수지 조성물을 제조하였다.A resin composition was prepared in the same manner as in Example 1 except that the dye compound was changed to the compound shown in Table 5 instead of the compound of Synthesis Example 1 to prepare a resin composition.
[표 5][Table 5]
4. 물성평가4. Property evaluation
(1) 내열성 측정(1) Heat resistance measurement
내열성 측정을 위해 10 ㎝ × 10 ㎝의 유리기판 위에 상기 실시예 및 비교예에서 제조한 수지 조성물을 각각 2 ㎛ 두께로 스핀 코팅하여 90 ℃의 핫플레이트에서 3 분 동안 프리베이크(pre-bake)를 수행한 후, 상온에서 1 분 동안 냉각하였다. 이를 노광기를 이용하여 100 mJ/㎠의 노광량(365 ㎚ 기준)으로 노광하였다.For the measurement of the heat resistance, the resin compositions prepared in the above Examples and Comparative Examples were each spin-coated on a glass substrate of 10 cm x 10 cm in thickness of 2 mu m and pre-baked on a hot plate at 90 DEG C for 3 minutes And then cooled at room temperature for 1 minute. This was exposed using an exposure machine at an exposure amount of 100 mJ / cm 2 (based on 365 nm).
이후, 230 ℃의 컨벡션 오븐(convection oven)에서 20 분 동안 포스트베이크(postbake)를 수행한 후, 분광광도계인 Otsuka electronic사의 MCPD3700을 사용하여 색 특성을 확인하고, 230 ℃ 컨벡션 오븐에서 1시간 추가로 열처리를 진행한 후, 다시 색 특성을 확인하여 ΔEab*값을 구하여 하기 [표 6]에 나타내었다.
After post-baking for 20 minutes in a convection oven at 230 ° C, the color characteristics were confirmed using a spectrophotometer, MCPD3700 from Otsuka electronic Co., Ltd., and an additional one hour at 230 ° C in a convection oven After the heat treatment, the color characteristic was confirmed again and the value of [Delta] Eab * was obtained, and it is shown in Table 6 below.
(2) 내광성 측정(2) Light resistance measurement
내열성 측정과 동일한 방법으로 스핀코팅, 노광, 포스트베이크를 진행 한 후, 분광광도계인 Otsuka electronic사의 MCPD3700을 사용하여 색 특성을 확인하고, Q-sun Xenon Chamber에서 1.34W/㎡/nm (at 420 nm)의 조도로 8시간 조사한 후, 다시 색 특성을 확인하여 ΔEab*값을 구하여 하기 [표 6]에 나타내었다.After the spin coating, exposure and post-baking were carried out in the same manner as in the heat resistance measurement, the color characteristics were confirmed using a spectrophotometer, MCPD3700 manufactured by Otsuka electronic Co., Ltd., and 1.34 W / m 2 / ) For 8 hours, and the color characteristic was confirmed again, and the value of [Delta] Eab * was obtained, and the results are shown in Table 6 below.
[표 6][Table 6]
상기 [표 6]에서 비교예 4 내지 6에서 클로라이드, 플루오르화알킬술폰산, 비스트리플루오르메탄술폰이미드 순으로 내열성이 향상되는 것을 알 수 있으며, 또한 실시예 1 내지 실시예 16과 비교예 4 내지 6의 결과에서 실시예의 내열성, 내광성이 비교예에 비해 우수한 것을 알 수 있다.In Table 6, it can be seen that the heat resistance is improved in the order of chloride, fluorinated alkylsulfonic acid, and bistrifluoromethanesulfonimide in Comparative Examples 4 to 6, and in Examples 1 to 16 and Comparative Examples 4 to 6, 6 shows that the heat resistance and the light resistance of the examples are superior to those of the comparative examples.
Claims (9)
[화학식 1]
상기 [화학식 1]에서,
X-는 플루오르화알킬술폰산 음이온 또는 비스트리플루오르메탄술폰이미드 음이온이고,
R1, R2, R8 및 R9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기, 치환 또는 비치환 탄소수 7 내지 20 아랄킬기, 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소기 및 하기 [구조식 1] 중에서 선택되고,
[구조식 1]
상기 [구조식 1]에서,
R10은 치환 또는 비치환 탄소수 1 내지 10의 알킬렌기이며,
R11은 메틸이고,
R8 및 R9는 서로 상이하고, 상기 R8 및 R9 중에서 어느 하나는 상기 [구조식 1]이며,
R3, R4, R5, R6 및 R7은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환 탄소수 1 내지 10의 알킬기, 치환 또는 비치환 탄소수 3 내지 10의 씨클로알킬기, 치환 또는 비치환 탄소수 1 내지 10의 알콕시기, 치환 비치환 탄소수 3 내지 10의 씨클로알콕시기, 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소기 및 할로겐 중에서 선택되며,
a, b 및 c는 각각 0 내지 4의 정수이고, d, e는 0 내지 5의 정수이며, 상기 a, b, c, d, 및 e가 2 이상인 경우, 복수의 R3, R4, R5, R6 및 R7은 각각 서로 동일하거나 상이하다.A dye compound represented by the following Chemical Formula 1:
[Chemical Formula 1]
In the above formula (1)
X - is a fluorinated alkylsulfonic acid anion or a bistrifluoromethanesulfonimide anion,
R 1 , R 2 , R 8 and R 9 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, 7 to 20 aralkyl groups, substituted or unsubstituted aromatic hydrocarbon groups having 6 to 10 carbon atoms, and [Structural Formula 1]
[Structural formula 1]
In the above formula 1,
R 10 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms,
R < 11 > is methyl,
R 8 and R 9 are different from each other, and any one of R 8 and R 9 is the above-mentioned [formula 1]
R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, An alkoxy group having 1 to 10 ring carbon atoms, a substituted or unsubstituted cycloalkyloxy group having 3 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms and halogen,
a, b and c are integers of 0 to 4, d and e are integers of 0 to 5, and when a, b, c, d and e are 2 or more, a plurality of R 3 , R 4 , R 5 , R 6 and R 7 are the same or different from each other.
상기 [화학식 1]로 표시되는 염료 화합물은 하기 [1] 내지 [6], [9] 내지 12], [15] 및 [16]으로 표시되는 화합물 중에서 선택되는 것을 특징으로 하는 염료 화합물:
The method according to claim 1,
The dye compound represented by Formula 1 is selected from the compounds represented by the following [1] to [6], [9] to 12], [15]
상기 착색제는 제1항에 따른 염료 화합물을 포함하는 것을 특징으로 하는 컬러필터용 수지 조성물.coloring agent; Binder resin; Reactive unsaturated compounds; A polymerization initiator; Organic solvent; And an additive,
The resin composition for a color filter according to claim 1, wherein the coloring agent comprises the dye compound according to claim 1.
상기 착색제는 크산텐 염료, 시아닌 염료 및 아자포피린 염료 중에서 선택되는 하나 이상의 염료를 더 포함하는 것을 특징으로 하는 컬러필터용 수지 조성물.The method of claim 3,
Wherein the colorant further comprises at least one dye selected from xanthene dyes, cyanine dyes and azapphyrin dyes.
상기 수지 조성물은 청색 안료 또는 보라색 안료를 더 포함하는 것을 특징으로 하는 컬러필터용 수지 조성물.The method of claim 3,
Wherein the resin composition further comprises a blue pigment or a violet pigment.
상기 착색제는 수지 조성물 총 중량에 대하여 0.01 중량% 내지 50 중량%인 것을 특징으로 하는 컬러필터용 수지 조성물.The method of claim 3,
Wherein the colorant is 0.01% by weight to 50% by weight based on the total weight of the resin composition.
상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머, 광경화성 단량체나 올리고머 및 이들의 조합으로 이루어지는 군에서 선택된 어느 하나 이상인 것을 특징으로 하는 컬러필터용 수지 조성물. The method of claim 3,
Wherein the reactive unsaturated compound is at least one selected from the group consisting of thermosetting monomers and oligomers, photocurable monomers and oligomers, and combinations thereof.
상기 중합 개시제는 열중합 개시제, 광중합 개시제 및 이들의 조합으로 이루어지는 군에서 선택된 어느 하나 이상인 것을 특징으로 하는 컬러필터용 수지 조성물.The method of claim 3,
Wherein the polymerization initiator is at least one selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020140086913A KR101661733B1 (en) | 2014-07-10 | 2014-07-10 | Dye compounds and resin composition for color filter comprising the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020140086913A KR101661733B1 (en) | 2014-07-10 | 2014-07-10 | Dye compounds and resin composition for color filter comprising the same |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20160007023A KR20160007023A (en) | 2016-01-20 |
KR101661733B1 true KR101661733B1 (en) | 2016-10-04 |
Family
ID=55307763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020140086913A KR101661733B1 (en) | 2014-07-10 | 2014-07-10 | Dye compounds and resin composition for color filter comprising the same |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR101661733B1 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR102149969B1 (en) * | 2017-09-26 | 2020-08-31 | 삼성에스디아이 주식회사 | Compound, photosensitive resin composition comprising the same and color filter |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101361680B1 (en) | 2012-03-30 | 2014-02-12 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
KR101380942B1 (en) * | 2012-05-23 | 2014-04-01 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI546574B (en) * | 2011-06-01 | 2016-08-21 | Jsr股份有限公司 | Coloring composition, color filter and display element |
JP5743801B2 (en) * | 2011-08-15 | 2015-07-01 | 富士フイルム株式会社 | Colored composition, colored radiation-sensitive composition, polymer production method, pattern formation method, color filter, production method thereof, and solid-state imaging device |
-
2014
- 2014-07-10 KR KR1020140086913A patent/KR101661733B1/en active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101361680B1 (en) | 2012-03-30 | 2014-02-12 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
KR101380942B1 (en) * | 2012-05-23 | 2014-04-01 | (주)경인양행 | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same |
Also Published As
Publication number | Publication date |
---|---|
KR20160007023A (en) | 2016-01-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101361679B1 (en) | Xanthene dye compounds, colored resin composition comprising the same for color filter and color filter using the same | |
KR101380942B1 (en) | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same | |
KR101361680B1 (en) | Triarylmethane dye compounds, colored resin composition comprising the same for color filter and color filter using the same | |
KR101467995B1 (en) | Triarylmethane dye polymer compound, colored resin composition comprising the same for color filter and color filter using the same | |
CN102645844B (en) | Colored curable resin composition | |
JP6113916B2 (en) | Blue dye compound, blue resin composition for color filter containing the same, and color filter using the same | |
KR20190079541A (en) | Colored resin composition, colored filter and display device | |
JP6695971B2 (en) | Xanthene-based polymer compound, resin composition for color filter containing the same, and color filter using the same | |
KR20150092918A (en) | Polymer dye compounds, resin composition comprising the same for color filter and color filter using the same | |
KR20150005139A (en) | Blue dye compounds, colored resin composition comprising the same for color filter and color filter using the same | |
KR101661733B1 (en) | Dye compounds and resin composition for color filter comprising the same | |
KR101662745B1 (en) | Dye compounds and resin composition for color filter comprising the same | |
KR101696182B1 (en) | Resin composition for color filter comprising pyridone azo compounds | |
US7973197B2 (en) | Colorant compound and blue resist composition for use in color filter containing the same | |
KR101662804B1 (en) | Dye compounds and resin composition for color filter comprising the same | |
KR20210071535A (en) | Dye compounds and the use thereof | |
KR101785603B1 (en) | polymer additives and pigment dispersion composition containing the same | |
KR101758073B1 (en) | Resin composition for color filter comprising pyridone azo compounds | |
KR20220057022A (en) | Dye compounds, colored resin composition comprising the same for color filter and color filter using the same | |
KR101637223B1 (en) | Dye compounds and resin composition for color filter comprising the same |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20190918 Year of fee payment: 6 |