KR20200136169A - Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same - Google Patents
Compound, colorant composition comprising same, photosensitive resin composition, photosensitive material, color filter, display device comprising same Download PDFInfo
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- KR20200136169A KR20200136169A KR1020190061869A KR20190061869A KR20200136169A KR 20200136169 A KR20200136169 A KR 20200136169A KR 1020190061869 A KR1020190061869 A KR 1020190061869A KR 20190061869 A KR20190061869 A KR 20190061869A KR 20200136169 A KR20200136169 A KR 20200136169A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 113
- 239000011342 resin composition Substances 0.000 title claims abstract description 47
- 239000000463 material Substances 0.000 title claims abstract description 38
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 239000003086 colorant Substances 0.000 title claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000011230 binding agent Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims description 11
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- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002560 nitrile group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 5
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 3
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- 238000002360 preparation method Methods 0.000 description 35
- -1 9,9-dimethylfluorenyl Chemical group 0.000 description 34
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- 230000000052 comparative effect Effects 0.000 description 14
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- 238000010438 heat treatment Methods 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 229940126062 Compound A Drugs 0.000 description 4
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
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- 125000002947 alkylene group Chemical group 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
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- MALZYBOXBVXCSN-UHFFFAOYSA-N 11h-pyrido[3,2-a]carbazole Chemical group C1=CC2=NC=CC=C2C2=C1C1=CC=CC=C1N2 MALZYBOXBVXCSN-UHFFFAOYSA-N 0.000 description 2
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- 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
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
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- 238000003912 environmental pollution Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SYGAXBISYRORDR-UHFFFAOYSA-N ethyl 2-(hydroxymethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CO SYGAXBISYRORDR-UHFFFAOYSA-N 0.000 description 1
- GOPRFQYEQXSXNS-UHFFFAOYSA-N ethyl 2-[4-[4,6-bis(trichloromethyl)-1,3,5-triazin-2-yl]phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OCC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 GOPRFQYEQXSXNS-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000001046 green dye Substances 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 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 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229920001427 mPEG Polymers 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- RFUCOAQWQVDBEU-UHFFFAOYSA-N methyl 2-(hydroxymethyl)prop-2-enoate Chemical compound COC(=O)C(=C)CO RFUCOAQWQVDBEU-UHFFFAOYSA-N 0.000 description 1
- DBQGARDMYOMOOS-UHFFFAOYSA-N methyl 4-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N(C)C)C=C1 DBQGARDMYOMOOS-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- ALIATVYMFGMEJC-UHFFFAOYSA-N phenyl-[2,4,6-tris(methylamino)phenyl]methanone Chemical compound CNC1=CC(NC)=CC(NC)=C1C(=O)C1=CC=CC=C1 ALIATVYMFGMEJC-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000012985 polymerization agent Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- YKENVNAJIQUGKU-UHFFFAOYSA-N tetraazaporphin Chemical compound C=1C(C=N2)=NC2=NC(NN2)=NC2=CC(C=C2)=NC2=CC2=NC=1C=C2 YKENVNAJIQUGKU-UHFFFAOYSA-N 0.000 description 1
- KPNZYDNOFDZXNR-UHFFFAOYSA-N tetratert-butyl 4-benzoylcyclohexa-3,5-diene-1,1,2,2-tetracarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)(C(=O)OOC(C)(C)C)C=CC(C(=O)C=2C=CC=CC=2)=C1 KPNZYDNOFDZXNR-UHFFFAOYSA-N 0.000 description 1
- 239000003017 thermal stabilizer Substances 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
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- QEDNBHNWMHJNAB-UHFFFAOYSA-N tris(8-methylnonyl) phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OCCCCCCCC(C)C QEDNBHNWMHJNAB-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
Description
본 명세서는 화합물, 이를 포함하는 색재 조성물, 감광성 수지 조성물에 관한 것이다. 또한, 본 명세서는 상기 감광성 수지 조성물을 이용하여 제조된 감광재, 컬러필터 및 이를 포함하는 디스플레이 장치에 관한 것이다.The present specification relates to a compound, a color material composition including the same, and a photosensitive resin composition. In addition, the present specification relates to a photosensitive material manufactured by using the photosensitive resin composition, a color filter, and a display device including the same.
최근 컬러필터에 있어서 고휘도, 고명암비를 특징으로 하는 성능이 요구되고 있다. 또한, 디스플레이 장치 개발의 주 목적 중 하나는 색순도 향상을 통한 표시소자 성능의 차별화 및 제조 공정상의 생산성 향상에 있다. Recently, a color filter is required to have high luminance and high contrast ratio. In addition, one of the main objectives of the development of a display device is to differentiate display device performance through improved color purity and to improve productivity in a manufacturing process.
기존에 컬러필터의 색재로 사용되는 안료 타입은 입자 분산 상태로 컬러 포토레지스트에 존재하기 때문에, 안료 입자 크기와 분포 조절에 따른 휘도 및 명암비 조절에 어려움이 있었다. 안료 입자의 경우 컬러 필터 내에서 응집되어 용해 및 분산성이 떨어지며 응집(aggregation)되어 있는 큰 입자들로 인하여 빛의 다중 산란(multiple scattering)이 일어난다. 이러한 편광된 빛의 산란은 명암비를 저하시키는 주 요인으로 지목되고 있다. 안료의 초미립화 및 분산 안정화를 통해 휘도 및 명암비 향상을 위한 노력이 계속되고 있으나, 고색순도 표시장치용 색좌표를 구현하기 위한 색재 선정에 있어 자유도가 제한된다. 또한, 이미 개발된 색재료 특히 안료를 이용한 안료분산법은 이를 이용한 컬러필터의 색순도, 휘도 및 명암비를 향상시키는데 한계에 도달했다.Conventionally, since the pigment type used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, they are aggregated in a color filter, so that dissolution and dispersibility are inferior, and multiple scattering of light occurs due to large aggregated particles. The scattering of polarized light has been pointed out as the main factor that lowers the contrast ratio. Efforts have been made to improve brightness and contrast ratio through ultra-fine pigmentation and dispersion stabilization, but the degree of freedom is limited in selecting a color material for realizing color coordinates for high-color purity display devices. In addition, the already developed color material, particularly the pigment dispersion method using a pigment, has reached its limit in improving the color purity, brightness, and contrast ratio of a color filter using the same.
이에 따라서, 색순도를 높여 색재현, 휘도 및 명암비를 향상시킬 수 있는 신규 색재 개발이 요구되고 있다.Accordingly, there is a need to develop a new color material capable of improving color reproduction, brightness, and contrast ratio by increasing color purity.
본 명세서는 화합물, 이를 포함하는 색재 조성물, 감광성 수지 조성물, 이를 이용하여 제조된 감광재, 컬러필터 및 이를 포함하는 디스플레이 장치를 제공하고자 한다. The present specification is to provide a compound, a color material composition containing the same, a photosensitive resin composition, a photosensitive material manufactured using the same, a color filter, and a display device including the same.
본 명세서의 일 실시상태는, 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에 있어서,In Formula 1,
Y는 직접결합; 또는 CQ1Q2이고,Y is a direct bond; Or CQ1Q2,
R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R13 and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다.R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태는 상기 화합물을 포함하는 색재 조성물을 제공한다. An exemplary embodiment of the present specification provides a colorant composition comprising the compound.
본 명세서의 일 실시상태는, 상기 색재 조성물; 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 포함하는 감광성 수지 조성물을 제공한다.An exemplary embodiment of the present specification, the coloring material composition; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.
본 명세서의 일 실시상태는, 상기 감광성 수지 조성물을 포함하는 감광재를 제공한다.An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.
본 명세서의 일 실시상태는, 상기 감광재를 포함하는 컬러필터를 제공한다.An exemplary embodiment of the present specification provides a color filter including the photosensitive material.
본 명세서의 일 실시상태는, 상기 컬러필터를 포함하는 디스플레이 장치를 제공한다.An exemplary embodiment of the present specification provides a display device including the color filter.
본 명세서에 따른 화학식 1로 표시되는 화합물은 컬러필터의 색재 조성물 재료로 사용될 수 있다. 종래에 알려진 퀴노프탈론(quinophthalone)계 염료 화합물에 비해 장파장 흡수가 가능하고, 내열성이 향상되어 열에 의한 열화가 적고, 색순도가 향상된 컬러필터를 제작하는 것이 가능하다.The compound represented by Formula 1 according to the present specification may be used as a material for a color material composition of a color filter. Compared to the conventionally known quinophthalone-based dye compound, it is possible to absorb long wavelengths and improve heat resistance, so that deterioration due to heat is less and color purity is improved.
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서에 있어서, 어떤 부재가 다른 부재 “상에” 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present specification, when a member is positioned “on” another member, this includes not only a case where a member is in contact with another member, but also a case where another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다. An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
상기 화학식 1에 있어서,In Formula 1,
Y는 직접결합; 또는 CQ1Q2이고,Y is a direct bond; Or CQ1Q2,
R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R13 and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다.R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
상기 화학식 1의 화합물은 컬러필터의 색재 조성물 재료로 사용될 수 있다. 기존 퀴노프탈론(quinophthalone)계 화합물의 퀴놀린 골격 대신에 전자 밀도가 증가한 전자주개 역할의 피리도 카바졸 골격을 도입하고, 전자 받개 역할을 하는 인덴다이온이 연결된 형태로 일반적인 퀴노프탈론계 안료에 비해 장파장 흡수가 가능하다. OLED 패널의 경우 색재현성을 높이기 위해 순도가 높은 녹색(Green)의 파장이 필요하다. 이를 위해 녹색(Green)의 단파장 영역인 460nm~470nm의 흡수를 향상시킬 필요가 있다. 기존의 퀴노프탈론계 색재는 430nm~460nm의 흡수를 보이며, 460nm~470nm의 흡수는 부족한 수준이다. 본 발명을 통해 이를 만족할 수 있는 화합물 제조가 가능하다. 또한, 피리도 카바졸 골격과 2번에 치환된 인덴다이온의 입체장애가 증가하여 인덴다이온의 회전을 방해함으로 스펙트럼의 반치폭을 감소시키는 효과를 가질 수 있다. 이로 인해 프탈로시아닌계 녹색 염료와 함께 사용할 경우, 단파장영역의 흡수 및 스펙트럼 기울기가 향상되어 녹색의 색순도가 향상된다.The compound of Formula 1 may be used as a colorant composition material for a color filter. Instead of the quinoline skeleton of the existing quinophthalone-based compound, a pyridocarbazole skeleton that acts as an electron donor with increased electron density is introduced, and indendione, which acts as an electron acceptor, is connected to a general quinophthalone pigment. In comparison, long wavelength absorption is possible. In the case of OLED panels, a green wavelength with high purity is required to increase color reproducibility. For this, it is necessary to improve the absorption of 460nm to 470nm, which is a short wavelength region of green. Existing quinophthalone colorants show absorption of 430nm~460nm, and absorption of 460nm~470nm is insufficient. Through the present invention, it is possible to prepare a compound that can satisfy this. In addition, the steric hindrance of the pyrido carbazole skeleton and the indendione substituted at No. 2 increases, thereby hindering the rotation of the indendione, thereby reducing the half width of the spectrum. For this reason, when used together with a phthalocyanine-based green dye, absorption and spectral slope in a short wavelength region are improved, thereby improving the color purity of green.
상기 화학식 1로 표시되는 화합물의 치환기들의 예시는 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents of the compound represented by Formula 1 are described below, but are not limited thereto.
본 명세서에 있어서, 는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification, Means a site bonded to another substituent or a bonding portion.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 에스테르기; -COOH; 알킬기; 시클로알킬기; 알케닐기; 시클로알케닐기; 아릴기; 헤테로아릴기; 아크릴로일기; 아크릴레이트기; 에테르기; N, O, S 또는 P 원자 중 1개 이상을 포함하는 헤테로 고리기 및 음이온성기를 포함하는 군에서 선택된 1개 이상의 치환기로 치환되었거나 또는 어떠한 치환기도 갖지 않는 것을 의미한다. In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Ester group; -COOH; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heteroaryl group; Acryloyl group; Acrylate group; Ether group; It means that it is substituted with one or more substituents selected from the group containing a heterocyclic group and an anionic group including one or more of N, O, S, or P atoms, or does not have any substituents.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 인접한 기는 결합하여 “고리”를 형성한다는 것에서 상기 고리란, 방향족 또는 지방족 고리를 의미한다. 구체적으로, 상기 고리는 방향족 고리일 수 있으며, 아릴기 또는 헤테로아릴기일 수 있다. 상기 아릴기 및 헤테로아릴기는 후술하는 설명이 적용될 수 있다.In the present specification, the ring means an aromatic or aliphatic ring in that adjacent groups are bonded to form a “ring”. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The aryl group and the heteroaryl group may be described below.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 상기 에스테르기는 -COOR100으로 표시될 수 있고, 상기 R100은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 30의 아릴기로 치환될 수 있다. 구체적으로, 하기 구조식의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the ester group may be represented by -COOR 100 , and R 100 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or it may be a substituted or unsubstituted aryl group. In the ester group, oxygen of the ester group may be substituted with a C 1 to C 25 linear, branched or cyclic chain alkyl group or a C 6 to C 30 aryl group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 이소부틸기, tert-부틸기, n-펜틸기, n-헥실기, n-헵틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-oxy And the like, but are not limited to these.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 2 내지 10이다. 알케닐기의 구체적인 예로는 스틸베닐기(stylbenyl), 스티레닐기(styrenyl)기 등의 아릴기가 치환된 알케닐기가 바람직하나 이들에 한정되지 않는다. In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group are preferably an alkenyl group substituted with an aryl group such as a stylbenyl group and a styrenyl group, but are not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 1 내지 30일 수 있으며, 구체적으로는 1 내지 20일 수 있고, 더욱 구체적으로는 1 내지 10일 수 있다.In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.
본 명세서에 있어서, 시클로알케닐기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 시클로알케닐기의 예로는 시클로펜테닐렌기, 시클로헥세닐렌기가 바람직하나, 이들에 한정되지 않는다. In the present specification, the cycloalkenyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group are preferably a cyclopentenylene group and a cyclohexenylene group, but are not limited thereto.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 인데닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우, , 등의 스피로플루오레닐기, (9,9-디메틸플루오레닐기), 및 (9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted, , Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
본 명세서에 있어서, 상기 헤테로고리기는 이종원자로 O, N 또는 S를 포함하는 헤테고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 30, 구체적으로는 탄소수 2 내지 20이다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 트리아진기, 아크리딜기, 피리다진기, 퀴놀리닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨란기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited to these.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 명세서에 있어서, 아크릴로일기는 광중합성 불포화기를 의미하며, 예컨대, (메타)아크릴로일기를 들 수 있으나 이에 한정되는 것은 아니다. In the present specification, the acryloyl group refers to a photopolymerizable unsaturated group, for example, a (meth)acryloyl group, but is not limited thereto.
본 명세서에 있어서, 아크릴레이트기는 광중합성 불포화기를 의미하며, 예컨대 (메타)아크릴레이트기를 들 수 있으나 이에 한정되는 것은 아니다. In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, such as a (meth)acrylate group, but is not limited thereto.
본 명세서에 있어서, '(메타)아크릴로일'이란, 아크릴로일 및 메타아크릴로일로 이루어지는 군으로부터 선택되는 적어도 1종을 나타낸다. '(메타)아크릴레이트' 의 표기도 마찬가지의 의미를 갖는다.In the present specification, "(meth)acryloyl" refers to at least one selected from the group consisting of acryloyl and methacryloyl. The notation of'(meth)acrylate' has the same meaning.
본 명세서에서 알킬렌기는 알칸(alkane)에 결합위치가 두 개 있는 것을 의미한다. 상기 알킬렌기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알킬렌기의 탄소수는 특별히 한정되지 않으나, 예컨대 탄소수 1 내지 30, 구체적으로는 1 내지 20, 더욱 구체적으로는 1 내지 10이다.In the present specification, the alkylene group means that the alkane has two bonding sites. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 1 to 30, specifically 1 to 20, and more specifically 1 to 10 carbon atoms.
본 명세서에 있어서, 헤테로알킬렌기는 이종원자로 O, N 또는 S를 포함하는 알칸(alkane)에 결합위치가 두 개 있는 것을 의미한다. 상기 헤테로알킬렌기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 헤테로알킬렌기의 탄소수는 특별히 한정되지 않으나, 예컨대 탄소수 2 내지 30, 구체적으로는 탄소수 2 내지 20, 더욱 구체적으로는 탄소수 2 내지 10이다.In the present specification, the heteroalkylene group means that there are two bonding positions in an alkane containing O, N or S as a hetero atom. The heteroalkylene group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.
본 명세서의 일 실시상태에 있어서, Y는 직접결합; 또는 CQ1Q2이다. In an exemplary embodiment of the present specification, Y is a direct bond; Or CQ1Q2.
본 명세서의 일 실시상태에 있어서, Y는 직접결합이다. In an exemplary embodiment of the present specification, Y is a direct bond.
본 명세서의 일 실시상태에 있어서, Y는 CQ1Q2이다. In an exemplary embodiment of the present specification, Y is CQ1Q2.
본 명세서의 일 실시상태에 있어서, R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In an exemplary embodiment of the present specification, R1 to R13, and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 30의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 30의 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 방향족 고리를 형성한다.In an exemplary embodiment of the present specification, R1 to R13, and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 30 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic ring.
본 명세서의 일 실시상태에 있어서, R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 20의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 방향족 고리를 형성한다.In an exemplary embodiment of the present specification, R1 to R13, and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic ring.
본 명세서의 일 실시상태에 있어서, R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 3 내지 10의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 10의 알콕시기; 치환 또는 비치환된 탄소수 6 내지 12의 아릴옥시기; 치환 또는 비치환된 탄소수 1 내지 10의 알케닐기; 치환 또는 비치환된 탄소수 6 내지 12의 아릴기; 또는 치환 또는 비치환된 탄소수 3 내지 20의 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 방향족 고리를 형성한다.In an exemplary embodiment of the present specification, R1 to R13, and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted C1-C10 alkyl group; 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 substituted or unsubstituted aryloxy group having 6 to 12 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 3 to 20 carbon atoms, or adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic ring.
본 명세서의 일 실시상태에 있어서, R1 내지 R13는 서로 같거나 상이하고 각각 독립적으로, 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In the exemplary embodiment of the present specification, R1 to R13 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 할로겐기; 또는 치환 또는 비치환된 아릴기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Halogen group; Or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 할로겐기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Halogen group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 할로겐기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Halogen group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 할로겐기; 또는 치환 또는 비치환된 탄소수 6 내지 12의 아릴기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Halogen group; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 불소; 염소; 또는 치환 또는 비치환된 페닐기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Fluorine; Goat; Or a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 있어서, R1 내지 R4는 서로 같거나 상이하고 각각 독립적으로, 수소; 불소; 염소; 또는 페닐기이다. In the exemplary embodiment of the present specification, R1 to R4 are the same as or different from each other, and each independently, hydrogen; Fluorine; Goat; Or a phenyl group.
본 명세서의 일 실시상태에 있어서, R5 내지 R8은 수소이다.In an exemplary embodiment of the present specification, R5 to R8 are hydrogen.
본 명세서의 일 실시상태에 있어서, R9 내지 R12는 서로 같거나 상이하고 각각 독립적으로 수소; 할로겐기; 니트로기; 또는 -C(=O)OR이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 방향족 고리를 형성한다. In the exemplary embodiment of the present specification, R9 to R12 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitro group; Or -C(=O)OR, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic ring.
본 명세서의 일 실시상태에 있어서, R9 내지 R12는 서로 같거나 상이하고 각각 독립적으로 수소; 염소; 니트로기; 또는 -C(=O)OR이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 벤젠고리를 형성한다. In the exemplary embodiment of the present specification, R9 to R12 are the same as or different from each other, and each independently hydrogen; Goat; Nitro group; Or -C(=O)OR, or adjacent groups combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, R9 내지 R12는 서로 같거나 상이하고 각각 독립적으로 수소; 염소; 니트로기; 또는 -C(=O)OR이거나, 인접하는 기는 서로 결합하여 벤젠고리를 형성한다.In the exemplary embodiment of the present specification, R9 to R12 are the same as or different from each other, and each independently hydrogen; Goat; Nitro group; Or -C(=O)OR, or adjacent groups combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 있어서, R10 및 R11은 서로 결합하여 치환 또는 비치환된 벤젠고리를 형성한다. In an exemplary embodiment of the present specification, R10 and R11 combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, R10 및 R11은 서로 결합하여 벤젠고리를 형성한다. In an exemplary embodiment of the present specification, R10 and R11 are bonded to each other to form a benzene ring.
본 명세서의 일 실시상태에 있어서, R9 및 R10은 서로 결합하여 치환 또는 비치환된 벤젠고리를 형성한다. In an exemplary embodiment of the present specification, R9 and R10 are bonded to each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, R9 및 R10은 서로 결합하여 벤젠고리를 형성한다. In an exemplary embodiment of the present specification, R9 and R10 are bonded to each other to form a benzene ring.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이다.In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted C1-C30 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 3 내지 20의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C20 cycloalkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 치환 또는 비치환된 탄소수 3 내지 10의 시클로알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 12의 아릴기이다.In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 프로필기; 치환 또는 비치환된 펜틸기; 치환 또는 비치환된 시클로헥실기; 또는 치환 또는 비치환된 페닐기이다. In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted pentyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 에틸기; 치환 또는 비치환된 n-프로필기; 치환 또는 비치환된 네오펜틸기; 치환 또는 비치환된 시클로헥실기; 또는 치환 또는 비치환된 페닐기이다. In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted neopentyl group; A substituted or unsubstituted cyclohexyl group; Or a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 있어서, R13은 수소; 에틸기; n-프로필기; 네오펜틸기; 시클로헥실기; 또는 페닐기이다. In an exemplary embodiment of the present specification, R13 is hydrogen; Ethyl group; n-propyl group; Neopentyl group; Cyclohexyl group; Or a phenyl group.
본 명세서의 일 실시상태에 있어서, Q1은 R9와 서로 결합하여 치환 또는 비치환된 벤젠고리를 형성한다. In the exemplary embodiment of the present specification, Q1 is bonded to each other with R9 to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, Q1은 R9와 서로 결합하여 벤젠고리를 형성한다. In an exemplary embodiment of the present specification, Q1 is bonded to each other with R9 to form a benzene ring.
본 명세서의 일 실시상태에 있어서, Q2은 R9와 서로 결합하여 치환 또는 비치환된 벤젠고리를 형성한다.In the exemplary embodiment of the present specification, Q2 is bonded to each other with R9 to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, Q2은 R9와 서로 결합하여 벤젠고리를 형성한다. In the exemplary embodiment of the present specification, Q2 is bonded to each other with R9 to form a benzene ring.
본 명세서의 일 실시상태에 있어서, R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다.In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 있어서, R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기이다.In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 20의 알킬기이다.In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알킬기이다.In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.
본 명세서의 일 실시상태에 있어서, R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 에틸기이다. In the exemplary embodiment of the present specification, R and R'are the same as or different from each other, and each independently a substituted or unsubstituted ethyl group.
본 명세서의 일 실시상태에 있어서, R 및 R'는 에틸기이다. In an exemplary embodiment of the present specification, R and R'are ethyl groups.
본 명세서의 일 실시상태에 있어서 R은 에틸기이다. In an exemplary embodiment of the present specification, R is an ethyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 또는 1-2로 표시된다. In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1 or 1-2.
[화학식 1-1][Formula 1-1]
[화학식 1-2][Formula 1-2]
상기 화학식 1-1 및 1-2에 있어서,In Formulas 1-1 and 1-2,
R1 내지 R13, Q1 및 Q2의 정의는 상기 화학식 1과 동일하다.The definitions of R1 to R13, Q1 and Q2 are the same as in Formula 1.
본 명세서의 일 실시상태에 있어서, R1 내지 R12는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; -C(=O)OR; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성한다. In the exemplary embodiment of the present specification, R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; -C(=O)OR; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, R13은 수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 또는 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, R13 is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 고리는 치환 또는 비치환된 벤젠 고리이다. In the exemplary embodiment of the present specification, the ring is a substituted or unsubstituted benzene ring.
본 명세서의 또 하나의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 중 어느 하나로 표시될 수 있으나, 반드시 이에 한정되는 것은 아니다.According to another exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following formulas, but is not limited thereto.
본 명세서의 일 실시상태는 상기 화합물을 포함하는 색재 조성물을 제공한다. An exemplary embodiment of the present specification provides a colorant composition comprising the compound.
본 명세서의 일 실시상태에 있어서, 상기 색재 조성물은 프탈로시아닌계 화합물을 더 포함한다. In one embodiment of the present specification, the colorant composition further includes a phthalocyanine-based compound.
상기 프탈로시아닌계 화합물은 하기 화학식 P-1 또는 P-2로 표시될 수 있다. The phthalocyanine-based compound may be represented by the following Formula P-1 or P-2.
[화학식 P-1][Chemical Formula P-1]
[화학식 P-2][Formula P-2]
상기 화학식 P-1 및 P-2에 있어서, R1 내지 R16은 서로 같거나 동일하고 각각 독립적으로 수소; 할로겐기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 인접하는 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,In Formulas P-1 and P-2, R1 to R16 are the same as or identical to each other, and each independently hydrogen; Halogen group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
A1 및 A2는 서로 같거나 동일하고 각각 독립적으로 수소; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 -OA3이고,A1 and A2 are the same as or identical to each other, and each independently hydrogen; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or -OA3,
상기 A3는 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다. A3 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
상기 화학식 P-1 및 P-2에 있어서, R1 및 R2는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있다. In Formulas P-1 and P-2, R1 and R2 may be bonded to each other to form a substituted or unsubstituted ring.
상기 프탈로시아닌계 화합물과 상기 화학식 1로 표시되는 화합물의 함유량은 상기 프탈로시아닌계 화합물 100 중량부에 대해, 상기 화학식 1로 표시되는 화합물 5 내지 800 중량부의 범위가 바람직하다. The content of the phthalocyanine compound and the compound represented by Formula 1 is preferably in the range of 5 to 800 parts by weight of the compound represented by Formula 1 with respect to 100 parts by weight of the phthalocyanine compound.
상기 화학식 1로 표시되는 화합물이 상기 중량부 범위를 만족하는 경우, 상기 화학식 1로 표시되는 화합물이 휘도 향상의 효과를 발휘 할 수 있고, 내열성 및 내광성이 양호한 감광성 수지 조성물 제조가 가능하다. When the compound represented by Formula 1 satisfies the range by weight, the compound represented by Formula 1 may exhibit an effect of improving luminance, and a photosensitive resin composition having good heat resistance and light resistance may be prepared.
또 다른 일 실시상태에 있어서, 상기 색재 조성물은 상기 화학식 1의 화합물 이외에 염료 및 안료 중 적어도 1종을 더 포함할 수 있다. 예컨대, 상기 색재 조성물은 상기 화학식 1의 화합물만을 포함할 수도 있으나, 상기 화학식 1의 화합물과 1종 이상의 염료를 포함하거나, 상기 화학식 1의 화합물과 1종 이상의 안료를 포함하거나, 상기 화학식 1의 화합물, 1종 이상의 염료 및 1종 이상의 안료를 포함할 수도 있다. In another exemplary embodiment, the colorant composition may further include at least one of a dye and a pigment in addition to the compound of Formula 1 above. For example, the color material composition may include only the compound of Formula 1, but includes the compound of Formula 1 and at least one dye, the compound of Formula 1 and at least one pigment, or the compound of Formula 1 , One or more dyes and one or more pigments may be included.
본 명세서의 일 실시상태에 있어서, 상기 염료 및 안료는 금속-복합체(metal-complex)계열 화합물; 아조(azo)계열 화합물; 금속아조(metal azo)계열 화합물; 퀴노프탈론(quinophthalone)계열 화합물; 아이소인돌린(isoindoine)계열 화합물; 메틴(Methine)계열 화합물; 금속프탈로시아닌(metal phthalocyanine)계열 화합물; 포피린(porphyrin)계열 화합물; 금속포피린(metal porphyrin)계열 화합물; 테트라아자포피린(tetra aza porphyrin)계열 화합물; 금속테트라아자포피린(metal tetra aza porphyrin)계열 화합물; 시아닌(Cyanine)계열 화합물; 크산텐(Xanthene)계열 화합물; 금속디피로메텐(metal dipyrromethane)계열 화합물; 보론디피로메텐(boron dipyrromethane)계열 화합물; 금속디피로메텐(metal dipyrromethane)계열 화합물; 안트라퀴논(anthraquinone)계열 화합물; 디케토피롤로피롤(diketopyrrolopyrrole)계열 화합물; 트리아릴메탄(triarylmethane)계열 화합물; 및 퍼릴렌(perylene)계열 화합물로 이루어진 군에서 1종 이상 선택된다. In the exemplary embodiment of the present specification, the dye and the pigment are metal-complex (metal-complex)-based compounds; Azo-based compounds; Metal azo-based compounds; Quinophthalone-based compounds; Isoindoine-based compounds; Methine-based compounds; Metal phthalocyanine-based compounds; Porphyrin-based compounds; Metal porphyrin-based compounds; Tetra aza porphyrin-based compounds; Metal tetra aza porphyrin series compounds; Cyanine-based compounds; Xanthene-based compounds; Metal dipyrromethane series compounds; Boron dipyrromethane series compounds; Metal dipyrromethane series compounds; Anthraquinone-based compounds; Diketopyrrolopyrrole-based compounds; Triarylmethane series compounds; And one or more is selected from the group consisting of perylene-based compounds.
본 명세서의 일 실시상태에 있어서, 상기 색재 조성물은 상기 화합물을 포함하는 분산액일 수 있다.In an exemplary embodiment of the present specification, the colorant composition may be a dispersion containing the compound.
구체적으로, 상기 색재 조성물은 상기 화합물; 분산제; 바인더 수지; 용매; 및 지르코니아 비드를 포함하는 조성물의 분산액일 수 있다. Specifically, the color material composition is the compound; Dispersant; Binder resin; menstruum; And it may be a dispersion of a composition comprising zirconia beads.
본 명세서의 일 실시상태는 상기 색재 조성물; 바인더 수지; 다관능성 모노머; 광개시제; 및 용매를 포함하는 감광성 수지 조성물을 제공한다.An exemplary embodiment of the present specification is the color material composition; Binder resin; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.
상기 바인더 수지는 수지 조성물로 제조된 막의 강도, 현상성 등의 물성을 나타낼 수 있다면, 특별히 한정하지 않는다. The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of a resin composition.
상기 바인더 수지는 기계적 강도를 부여하는 다관능성 모노머와 알칼리 용해성을 부여하는 모노머의 공중합 수지를 이용할 수 있으며, 당 기술분야에서 일반적으로 사용하는 바인더를 더 포함할 수 있다. The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.
상기 막의 기계적 강도를 부여하는 다관능성 모노머는 불포화 카르복시산 에스테류; 방향족 비닐류; 불포화 에테르류; 불포화 이미드류; 및 산 무수물 중 어느 하나 이상일 수 있다. Polyfunctional monomers that impart mechanical strength of the film include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.
상기 불포화 카르복시산 에스테르류의 구체적인 예로는, 벤질(메타)아크릴레이트, 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 디메틸아미노에틸(메타)아크릴레이트, 이소부틸(메타)아크릴레이트, t-부틸(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 에틸헥실(메타)아크릴레이트, 2-페녹시에틸(메타)아크릴레이트, 테트라히드로퍼프릴(메타)아크릴레이트, 히드록시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시-3-클로로프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메타)아크릴레이트, 글리세롤(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 에톡시디에틸렌글리콜 (메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시트리프로필렌글리콜(메타)아크릴레이트, 폴리(에틸렌 글리콜) 메틸에테르(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메타)아크릴레이트, 글리시딜(메타)아크릴레이트, 테트라플루오로프로필(메타)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필 (메타)아크릴레이트, 옥타플루오로펜틸(메타)아크릴레이트, 헵타데카플루오로데실(메타)아크릴레이트, 트리브로모페닐(메타)아크릴레이트, 메틸 α-히드록시메틸 아크릴레이트, 에틸 α-히드록시메틸 아크릴레이트, 프로필 α-히드록시메틸 아크릴레이트 및 부틸 α-히드록시메틸 아크릴레이트로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated carboxylic acid esters are benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofurpril (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, acyloctyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) )Acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) Acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate, but only these It is not limited.
상기 방향족 비닐류의 구체적인 예로는, 스티렌, α-메틸스티렌, (o,m,p)-비닐 톨루엔, (o,m,p)-메톡시 스티렌, 및 (o,m,p)-클로로 스티렌으로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro styrene. It may be selected from the group consisting of, but is not limited thereto.
상기 불포화 에테르류의 구체적인 예로는, 비닐 메틸 에테르, 비닐 에틸 에테르, 및 알릴 글리시딜 에테르로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.
상기 불포화 이미드류의 구체적인 예로는, N-페닐 말레이미드, N-(4-클로로페닐) 말레이미드, N-(4-히드록시페닐) 말레이미드, 및 N-시클로헥실 말레이미드로 이루어진 그룹으로부터 선택될 수 있으나, 이들에만 한정되는 것은 아니다.Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.
상기 산 무수물로는 무수 말레인산, 무수 메틸 말레인산, 테트라하이드로 프탈산 무수물 등이 있으나, 이들에만 한정되는 것은 아니다.Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.
상기 알칼리 용해성을 부여하는 모노머는 산기를 포함한다면 특별히 한정되지 않으며, 예를 들면, (메타)아크릴산, 크로톤산, 이타콘산, 말레인산, 푸마르산, 모노메틸 말레인산, 5-노보넨-2-카복실산, 모노-2-((메타)아크릴로일옥시)에틸 프탈레이트, 모노-2-((메타)아크릴로일옥시)에틸 숙시네이트, ω-카르복시 폴리카프로락톤 모노(메타)아크릴레이트로 이루어지는 군으로부터 선택되는 1 종 이상을 사용하는 것이 바람직하나, 이들에만 한정되는 것은 아니다.The monomer imparting alkali solubility is not particularly limited as long as it includes an acid group, and examples include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ω-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more, but is not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 바인더 수지의 산가는 50 내지 130 KOH mg/g이고, 중량 평균 분자량은 1,000 g/mol 내지 50,000 g/mol이다. According to an exemplary embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg/g, and the weight average molecular weight is 1,000 g/mol to 50,000 g/mol.
상기 바인더 수지의 산가는 0.1N 농도의 수산화칼륨(KOH) 메탄올 용액으로 적정하여 측정할 수 있다. The acid value of the binder resin can be measured by titration with a 0.1N concentration of potassium hydroxide (KOH) methanol solution.
상기 다관능성 모노머는 광에 의해 포토레지스트상을 형성하는 역할을 하는 모노머로서, 구체적으로는 프로필렌글리콜 메타크릴레이트, 디펜타에리쓰리톨 헥사아크릴레이트, 디펜타에리쓰리톨 아크릴레이트, 네오펜틸글리콜 디아크릴레이트, 6-헥산디올 디아크릴레이트, 1,6-헥산디올 아크릴레이트 테트라에틸렌글리콜 메타크릴레이트, 비스페녹시 에틸알콜 디아크릴레이트, 트리스히드록시에틸이소시아누레이트 트리메타크릴레이트, 트리메틸프로판 트리메타크릴레이트, 디페닐펜타에리쓰톨리톨 헥사아크릴레이트, 펜타에리 쓰리톨 트리메타 크릴레이트, 펜타에리쓰리톨 테트라메타크릴레이트 및 디펜타에리쓰리톨 헥사메타 크릴레이트로 이루어진 그룹 중에서 선택되는 1종 또는 2종 이상의 혼합물일 수 있다.The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di. Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl Selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate. It may be one or a mixture of two or more.
상기 광개시제는 빛에 의해 라디칼을 발생시켜 가교를 촉발하는 개시제이면, 특별히 한정되지 않으나, 예를 들면, 아세토페논계 화합물, 비이미다졸계 화합물, 트리아진계 화합물, 및 옥심계 화합물로 이루어진 군으로부터 선택되는 1종 이상일 수 있다. The photoinitiator is not particularly limited as long as it is an initiator that generates a radical by light to trigger crosslinking, but is, for example, selected from the group consisting of an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more.
상기 아세토페논계 화합물은 2-히드록시-2-메틸-1-페닐프로판-1-온, 1-(4-이소프로필페닐)-2-히드록시-2-메틸프로판-1-온, 4-(2-히드록시에톡시)-페닐-(2-히드록시-2-프로필)케톤, 1-히드록시시클로헥실페닐케톤, 벤조인메틸 에테르, 벤조인에틸 에테르, 벤조인이소부틸 에테르, 벤조인부틸 에테르, 2,2-디메톡시-2-페닐아세토페논, 2-메틸-(4-메틸티오)페닐-2-몰폴리노-1-프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온, 2-(4-브로모-벤질-2-디메틸아미노-1-(4-몰폴리노페닐)-부탄-1-온 또는 2-메틸-1-[4-(메틸티오)페닐]-2-몰폴리노프로판-1-온 등이 있으며, 이에 한정되지 않는다. The acetophenone compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like, but is not limited thereto.
상기 비이미다졸계 화합물로는 2,2-비스(2-클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4',5,5'-테트라키스(3,4,5-트리메톡시페닐)-1,2'-비이미다졸, 2,2'-비스(2,3-디클로로페닐)-4,4',5,5'-테트라페닐 비이미다졸, 2,2'-비스(o-클로로페닐)-4,4,5,5'-테트라페닐-1,2'-비이미다졸 등이 있으며, 이에 한정되지 않는다. The biimidazole-based compound is 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , Is not limited thereto.
상기 트리아진계 화합물은 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 1,1,1,3,3,3-헥사플로로이소프로필-3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오네이트, 에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 2-에폭시에틸-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 시클로헥실-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 벤질-2-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}아세테이트, 3-{클로로-4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피오닉산, 3-{4-[2,4-비스(트리클로로메틸)-s-트리아진-6-일]페닐티오}프로피온아미드, 2,4-비스(트리클로로메틸)-6-p-메톡시스티릴-s-트리아진, 2,4-비스(트리클로로메틸)-6-(1-p-디메틸아미노페닐)-1,3,-부타디에닐-s-트리아진, 2-트리클로로메틸-4-아미노-6-p-메톡시스티릴-s-트리아진 등이 있으며, 이에 한정되지 않는다. The triazine compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -Bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionamide, 2,4-bis(trichloro Methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s -Triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.
상기 옥심계 화합물은 1,2-옥타디온-1-(4-페닐치오)페닐,-2-(o-벤조일옥심)(시바가이기사, 시지아이124), 에타논-1-(9-에틸)-6-(2-메틸벤조일-3-일)-,1-(O-아세틸옥심)(씨지아이242), N-1919(아데카사) 등이 있으며, 이에 한정되지 않는다. The oxime compound is 1,2-octadione-1-(4-phenylthio)phenyl,-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii124), ethanol-1-(9-ethyl) )-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime)(CGI242), N-1919(Adeca), and the like, but are not limited thereto.
상기 용매는 아세톤, 메틸 에틸 케톤, 메틸 이소부틸 케톤, 메틸셀로솔브, 에틸셀로솔브, 테트라히드로퓨란, 1,4-디옥산, 에틸렌글리콜 디메틸 에테르, 에틸렌글리콜 디에틸 에테르, 프로필렌글리콜 디메틸 에테르, 프로필렌글리콜 디에틸 에테르, 디에틸렌글리콜 디메틸에테르, 디에틸렌글리콜 디에틸에테르, 디에틸렌글리콜 메틸 에틸 에테르, 클로로포름, 염화메틸렌, 1,2-디클로로에탄, 1,1,1-트리클로로에탄, 1,1,2-트리클로로에탄, 1,1,2-트리클로로에텐, 헥산, 헵탄, 옥탄, 시클로헥산, 벤젠, 톨루엔, 크실렌, 메탄올, 에탄올, 이소프로판올, 프로판올, 부탄올, t-부탄올, 2-에톡시 프로판올, 2-메톡시 프로판올, 3-메톡시 부탄올, 시클로헥사논, 시클로펜타논, 프로필렌글리콜 메틸 에테르 아세테이트, 프로펠렌글리콜 에틸 에테르 아세테이트, 3-메톡시부틸 아세테이트, 에틸 3-에톡시프로피오네이트, 에틸 셀로솔브아세테이트, 메틸 셀로솔브아세테이트, 부틸 아세테이트, 프로필렌글리콜 모노메틸에테르 및 디프로필렌글리콜 모노메틸에테르로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다.The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로, 상기 색재 화합물의 함량은 2 중량% 내지 50 중량%이고, 상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이고, 상기 광개시제의 함량은 0.1 중량% 내지 10 중량%이며, 상기 다관능성 모노머의 함량은 0.1 중량% 내지50 중량%이고, 상기 용매의 함량은 50 중량% 내지 500 중량%인 것인 감광성 수지 조성물을 제공한다. According to an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the colorant compound is 2% to 50% by weight, and the content of the binder resin is 1% to 60% by weight And, the content of the photoinitiator is 0.1% to 10% by weight, the content of the polyfunctional monomer is 0.1% to 50% by weight, and the content of the solvent is 50% to 500% by weight Provides.
상기 감광성 수지 조성물이 상기 함량을 만족하는 경우, 착색력이 우수한 컬러필터를 제조할 수 있다. When the photosensitive resin composition satisfies the above content, a color filter having excellent coloring power may be manufactured.
상기 고형분의 총 중량이란, 감광성 수지 조성물에서 용매를 제외한 성분 총 중량의 합을 의미한다. 고형분 및 각 성분의 고형분을 기준으로 한 중량%의 기준은 액체크로마토그래피 또는 가스크로마토그래피 등의 당업계에서 쓰이는 일반적인 분석 수단으로 측정할 수 있다. The total weight of the solid content means the sum of the total weight of components excluding the solvent in the photosensitive resin composition. The basis of the solid content and the weight percent based on the solid content of each component can be measured by a general analysis means used in the art such as liquid chromatography or gas chromatography.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물은 산화방지제를 더 포함할 수 있다.According to an exemplary embodiment of the present specification, the photosensitive resin composition may further include an antioxidant.
본 명세서의 일 실시상태에 따르면, 상기 산화방지제의 함량은 상기 수지 조성물 중 고형분의 총 중량을 기준으로 0.1 중량% 내지 20 중량%이다.According to an exemplary embodiment of the present specification, the content of the antioxidant is 0.1% to 20% by weight based on the total weight of the solid content in the resin composition.
본 명세서의 일 실시상태에 따르면, 상기 감광성 수지 조성물은 광가교증감제, 경화촉진제, 밀착촉진제, 계면활성제, 열중합방지제, 자외선흡수제, 분산제, 접착조제 및 레벨링제로 이루어진 군으로부터 선택되는 1 또는 2 이상의 첨가제를 추가로 포함한다.According to an exemplary embodiment of the present specification, the photosensitive resin composition is 1 or 2 selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, an anti-thermal polymerization agent, an ultraviolet absorber, a dispersant, an adhesion aid, and a leveling agent. It further contains the above additives.
본 명세서의 일 실시상태에 따르면, 상기 첨가제의 함량은 상기 감광성 수지 조성물 중 고형분의 총 중량을 기준으로 0.1 중량% 내지 20 중량%이다.According to an exemplary embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the photosensitive resin composition.
상기 광가교증감제는 벤조페논, 4,4-비스(디메틸아미노)벤조페논, 4,4-비스(디에틸아미노)벤조페논, 2,4,6-트리메틸아미노벤조페논, 메틸-o-벤조일벤조에이트, 3,3-디메틸-4-메톡시벤조페논, 3,3,4,4-테트라(t-부틸퍼옥시카보닐)벤조페논 등의 벤조페논계 화합물; 9-플로레논, 2-크로로-9-프로레논, 2-메틸-9-플로레논 등의 플로레논계 화합물; 티옥산톤, 2,4-디에틸 티옥산톤, 2-클로로 티옥산톤, 1-클로로-4-프로필옥시 티옥산톤, 이소프로필티옥산톤, 디이소프로필티옥산톤 등의 티옥산톤계 화합물; 크산톤, 2-메틸크산톤 등의 크산톤계 화합물; 안트라퀴논, 2-메틸 안트라퀴논, 2-에틸 안트라퀴논, t-부틸 안트라퀴논, 2,6-디클로로-9,10- 안트라퀴논 등의 안트라퀴논계 화합물; 9-페닐아크리딘, 1,7-비스(9-아크리디닐)헵탄, 1,5-비스(9-아크리디닐펜탄), 1,3-비스(9-아크리디닐)프로판 등의 아크리딘계 화합물; 벤질, 1,7,7-트리메틸-비시클로[2,2,1]헵탄-2,3-디온, 9,10-펜안트렌퀴논 등의 디카보닐 화합물; 2,4,6-트리메틸벤조일 디페닐포스핀 옥사이드, 비스(2,6-디메톡시벤조일)-2,4,4-트리메틸펜틸 포스핀 옥사이드 등의 포스핀 옥사이드계 화합물; 메틸-4-(디메틸아미노)벤조에이트, 에틸-4-(디메틸아미노)벤조에이트, 2-n-부톡시에틸-4-(디메틸아미노)벤조에이트 등의 벤조에이트계 화합물; 2,5-비스(4-디에틸아미노벤잘)시클로펜타논, 2,6-비스(4-디에틸아미노벤잘)시클로헥사논, 2,6-비스(4-디에틸아미노벤잘)-4-메틸-시클로펜타논 등의 아미노 시너지스트; 3,3-카본닐비닐-7-(디에틸아미노)쿠마린, 3-(2-벤조티아졸일)-7-(디에틸아미노)쿠마린, 3-벤조일-7-(디에틸아미노)쿠마린, 3-벤조일-7-메톡시-쿠마린, 10,10-카르보닐비스[1,1,7,7-테트라메틸-2,3,6,7-테트라히드로-1H,5H,11H-C1]-벤조피라노[6,7,8-ij]-퀴놀리진-11-온 등의 쿠마린계 화합물; 4-디에틸아미노 칼콘, 4-아지드벤잘아세토페논 등의 칼콘 화합물; 2-벤조일메틸렌, 3-메틸-b-나프토티아졸린;으로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. Acridine compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.
상기 경화촉진제로는 경화 및 기계적 강도를 높이기 사용되며, 구체적으로 2-머캅토벤조이미다졸, 2-머캅토벤조티아졸, 2-머캅토벤조옥사졸, 2,5-디머캅토-1,3,4-티아디아졸, 2-머캅토-4,6-디메틸아미노피리딘, 펜타에리쓰리톨-테트라키스(3-머캅토프로피오네이트), 펜타에리쓰리톨-트리스(3-머캅토프로피오네이트), 펜타에리쓰리톨-테트라키스(2-머캅토아세테이트), 펜타에리쓰리톨-트리스(2-머캅토아세테이트), 트리메틸올프로판-트리스(2-머캅토아세테이트), 및 트리메틸올프로판-트리스(3-머캅토프로피오네이트)로 이루어진 군으로부터 선택되는 1종 이상을 사용할 수 있다.The curing accelerator is used to increase curing and mechanical strength, and specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropio) Nate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane- At least one selected from the group consisting of tris (3-mercaptopropionate) may be used.
본 명세서에서 사용되는 밀착촉진제로는 메타아크릴로일옥시 프로필트리메톡시 실란, 메타아크릴로일옥시 프로필디메톡시 실란, 메타아크릴로일옥시 프로필트리에톡시 실란, 메타아크릴로일옥시 프로필디메톡시실란 등의 메타 아크릴로일 실란 커플링제 중 1종 이상을 선택하여 사용할 수 있고, 알킬 트리메톡시 실란으로서 옥틸트리메톡시 실란, 도데실트리메톡시 실란, 옥타데실트리메톡시 실란 등에서 1종 이상을 선택하여 사용할 수 있다.The adhesion promoter used in this specification is methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents such as may be selected and used, and as an alkyl trimethoxy silane, one or more types of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can choose and use it.
상기 계면활성제는 실리콘계 계면활성제 또는 불소계 계면활성제이며, 구체적으로 실리콘계 계면활성제는 BYK-Chemie 사의 BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390 등을 사용할 수 있으며, 불소계 계면활성제로는 DIC(DaiNippon Ink & Chemicals) 사의 F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442 등을 사용할 수 있으나, 이에만 한정되는 것은 아니다.The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used, and as a fluorine-based surfactant, DIC (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like may be used, but are not limited thereto.
상기 산화 방지제로는 힌더드 페놀계(Hindered phenol) 산화 방지제, 아민계 산화 방지제, 티오계 산화 방지제 및 포스핀계 산화 방지제로 이루어지는 군으로부터 선택되는 1종 이상일 수 있으나, 이에만 한정되는 것은 아니다. The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.
상기 산화 방지제의 구체적인 예로는, 인산, 트리메틸포스페이트 또는 트리에틸포스페이트와 같은 인산계 열안정제; 2,6-디-t-부틸-p-크레졸, 옥타데실-3-(4-하이드록시-3,5-디-t-부틸페닐)프로피오네이트, 테트라비스[메틸렌-3-(3,5-디-t-부틸-4-하이드록시페닐)프로피오네이트]메탄, 1,3,5-트리메틸-2,4,6-트리스(3,5-디-t-부틸-4-하이드록시벤질)벤젠, 3,5-디-t-부틸-4-하이드록시벤질포스파이트 디에틸에스테르, 2,2-티오비스(4-메틸-6-t-부틸페놀), 2,6-g,t-부틸페놀 4,4'-부틸리덴-비스(3-메틸-6-t-부틸페놀), 4,4'-티오비스(3-메틸-6-t-부틸페놀) 또는 비스[3,3-비스-(4'-히드록시-3'-터트-부틸페닐)부탄산]글리콜 에스테르 (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol ester)와 같은 힌더드 페놀(Hindered phenol)계 1차 산화방지제; 페닐-α-나프틸아민, 페닐-β-나프틸아민, N,N'-디페닐-p-페닐렌디아민 또는 N,N'-디-β-나프틸-p-페닐렌디아민과 같은 아민계 2차 산화방지제; 디라우릴디설파이드, 디라우릴티오프로피오네이트, 디스테아릴티오프로피오네이트, 머캡토벤조티아졸 또는 테트라메틸티우람디설파이드 테트라비스[메틸렌-3-(라우릴티오)프로피오네이트]메탄 등의 Thio계 2차 산화방지제; 또는 트리페닐 포스파이트, 트리스(노닐페닐)포스파이트, 트리이소데실포스파이트, 비스(2,4-디부틸페닐) 펜타에리쓰리톨 디포스파이트(Bis (2,4-ditbutylphenyl)Pentaerythritol Diphosphite 또는 (1,1'-비페닐)-4,4'-디일비스포스포노산 테트라키스 [2,4-비스(1,1-디메틸에틸)페닐]에스테르((1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester)와 같은 포스파이트계 2차 산화방지제를 들 수 있다.Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethylphosphate, or triethylphosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy Benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethylester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol Hindered phenol-based primary antioxidants such as ester); Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine Secondary antioxidants; Thio such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane Secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1 ,1'-biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester ((1,1'-Biphenyl)-4,4 And phosphite-based secondary antioxidants such as'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester).
상기 자외선 흡수제로는 2-(3-t-부틸-5-메틸-2-히드록시페닐)-5-클로로-벤조트리아졸, 알콕시 벤조페논 등을 사용할 수 있으나, 이에 한정되지 않고, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다. As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.
상기 열중합방지제로는 예컨대 p-아니솔, 히드로퀴논, 피로카테콜(pyrocatechol), t-부틸카테콜(t-butyl catechol), N-니트로소페닐히드록시아민 암모늄염, N-니트로소페닐히드록시아민 알루미늄염, p-메톡시페놀, 디-t-부틸-p-크레졸, 피로가롤, 벤조퀴논, 4,4-티오비스(3-메틸-6-t-부틸페놀), 2,2-메틸렌비스(4-메틸-6-t-부틸페놀), 2-머캅토이미다졸 및 페노티아진(phenothiazine)으로 이루어진 군으로부터 선택된 1 종 이상을 포함할 수 있으나, 이들로만 한정되는 것은 아니며 당 기술분야에 일반적으로 알려져 있는 것들을 포함할 수 있다.Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy. Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology It may include those generally known in the field.
상기 분산제는 미리 안료를 표면 처리하는 형태로 안료에 내부 첨가시키는 방법, 또는 안료에 외부 첨가시키는 방법으로 사용할 수 있다. 상기 분산제로는 화합물형, 비이온성, 음이온성 또는 양이온성 분산제를 사용할 수 있으며, 불소계, 에스테르계, 양이온계, 음이온계, 비이온계, 양쪽성 계면활성제 등을 들 수 있다. 이들은 각각 또는 2종 이상을 조합하여 사용될 수 있다. The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. Compound type, nonionic, anionic or cationic dispersants can be used as the dispersant, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants and the like can be used. These may be used individually or in combination of two or more.
구체적으로 상기 분산제는 폴리알킬렌글리콜 및 이의 에스테르, 폴리옥시알킬렌 다가 알코올, 에스테르알킬렌옥사이드 부가물, 알코올알킬렌옥사이드 부가물, 설폰산 에스테르, 설폰산염, 카르복실산에스테르, 카르복실산염, 알킬아미드알킬렌옥사이드 부가물 및 알킬아민으로 이루어진 그룹으로부터 선택된 1종 이상이 있으나, 이에 한정되는 것은 아니다.Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylate, There may be at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.
상기 레벨링제로는 폴리머성이거나 비폴리머성일 수 있다. 폴리머성의 레벨링제의 구체적인 예로는 폴리에틸렌이민, 폴리아미드아민, 아민과 에폭사이드의 반응 생성물을 예로 들 수 있고, 비폴리머성의 레벨링제의 구체적인 예로는 비-폴리머 황-함유 및 비-폴리머 질소-함유 화합물을 포함하지만, 이에 한정되지는 않으며, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다.The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but is not limited thereto, all those generally used in the art may be used.
상기 접착조제로는 예컨대 KBM-503일 수 있으나, 이에 한정되지는 않으며, 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다. The adhesive agent may be KBM-503, for example, but is not limited thereto, and all those generally used in the art may be used.
본 명세서의 일 실시상태는 상기 감광성 수지 조성물을 포함하는 감광재를 제공한다. An exemplary embodiment of the present specification provides a photosensitive material including the photosensitive resin composition.
상기 감광성 수지 조성물을 포함하는 감광재는, 본 명세서의 감광성 수지 조성물을 기재 위에 적절한 방법으로 도포 및 경화하여 박막 또는 패턴형태의 감광재를 형성하는 것을 의미할 수 있다. The photosensitive material including the photosensitive resin composition may mean forming a photosensitive material in the form of a thin film or pattern by applying and curing the photosensitive resin composition of the present specification on a substrate by an appropriate method.
상기 도포 방법으로는 특별히 제한되지는 않지만 스프레이 법, 롤 코팅법, 스핀 코팅법 등을 사용할 수 있으며, 일반적으로 스핀 코팅법을 널리 사용한다. 또한, 도포막을 형성한 후 경우에 따라서 감압 하에 잔류 용매를 일부 제거할 수 있다.The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.
본 명세서에 따른 감광성 수지 조성물을 경화시키기 위한 광원으로는, 예컨대 파장이 250 nm 내지 450 ㎚의 광을 발산하는 수은 증기 아크(arc), 탄소 아크, Xe 아크 등이 있으나 반드시 이에 국한되지는 않는다.Light sources for curing the photosensitive resin composition according to the present specification include, for example, a mercury vapor arc, a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.
본 명세서에 따른 감광성 수지 조성물은 박막 트랜지트터 액정 표시장치(TFT LCD) 컬러필터 제조용 안료분산형 감광재, 박막 트랜지트터 액정 표시장치(TFT LCD) 또는 유기 발광 다이오드의 블랙 매트릭스 형성용 감광재, 오버코트층 형성용 감광재, 컬럼 스페이서 감광재, 광경화형 도료, 광경화성 잉크, 광경화성 접착제, 인쇄판, 인쇄배선반용 감광재, 플라즈마 디스플레이 패널(PDP)용 감광재 등에 사용할 수 있으며, 그 용도에 제한을 특별히 두지는 않는다.The photosensitive resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode. , Photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.
본 명세서의 일 실시상태에 따르면, 상기 감광재를 포함하는 컬러필터를 제공한다.According to an exemplary embodiment of the present specification, a color filter including the photosensitive material is provided.
상기 컬러필터는 상기 화학식 1로 표시되는 화합물을 포함하는 색재 조성물을 포함하는 감광성 수지 조성물을 이용하여, 제조될 수 있다. 상기 감광성 수지 조성물을 기판상에 도포하여 코팅막을 형성하고, 상기 코팅막을 노광, 현상 및 경화를 함으로써 컬러필터를 형성할 수 있다.The color filter may be manufactured by using a photosensitive resin composition including a color material composition containing the compound represented by Formula 1 above. A color filter may be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.
본 명세서의 일 실시상태에 따른 감광성 수지 조성물은 내열성이 우수하여, 열처리에 의한 색의 변화가 적어, 컬러 필터의 제조시 경화 과정에 의해서도 색재현율이 높고, 휘도 및 명암비가 높은 컬러필터를 제공할 수 있다. The photosensitive resin composition according to an exemplary embodiment of the present specification has excellent heat resistance and has little change in color due to heat treatment, so that it is possible to provide a color filter having high color reproduction rate and high luminance and contrast ratio even by the curing process when manufacturing a color filter. I can.
상기 기판은 유리판, 실리콘 웨이퍼 및 폴리에테르설폰(Polyethersulfone, PES), 폴리카보네이트(Polycarbonate, PC) 등의 플라스틱 기재의 판 등일 수 있으며, 그 종류가 특별히 제한되는 것은 아니다. The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited.
상기 컬러필터는 적색 패턴, 녹색 패턴, 청색 패턴, 블랙 매트릭스를 포함할 수 있다. The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
또 하나의 실시상태에 따르면, 상기 컬러필터는 오버코트층를 더 포함할 수 있다. According to another exemplary embodiment, the color filter may further include an overcoat layer.
상기 컬러필터의 컬러픽셀 사이에는 콘트라스트를 향상시킬 목적으로 블랙 매트릭스라고 불리는 격자상의 흑색패턴을 배치할 수 있다. 블랙 매트릭스의 재료로서 크롬을 사용할 수 있다. 이 경우, 크롬을 유리기판 전체에 증착시키고 에칭 처리에 의해 패턴을 형성하는 방식을 이용할 수 있다. 그러나, 공정상의 고비용, 크롬의 고반사율, 크롬 폐액에 의한 환경오염을 고려하여, 미세가공이 가능한 안료분산법에 의한 레진 블랙 매트릭스를 사용할 수 있다. A grid-like black pattern called a black matrix may be disposed between the color pixels of the color filter for the purpose of improving contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching treatment may be used. However, in consideration of the high process cost, high reflectance of chromium, and environmental pollution due to chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing may be used.
본 명세서의 일 실시상태에 따른 블랙 매트릭스는 색재로서 블랙안료 또는 블랙 염료를 사용할 수 있다. 예컨대, 카본블랙을 단독으로 사용하거나, 카본블랙과 착색안료를 혼합하여 사용할 수 있으며, 이때 차광성이 부족한 착색안료를 혼합하기 때문에 상대적으로 색재의 양이 증가하더라도 막의 강도 또는 기판에 대한 밀착성이 저하되지 않는 장점이 있다. The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material increases. There is an advantage that does not work.
본 명세서의 일 실시상태는 컬러필터를 포함하는 디스플레이 장치를 제공한다. An exemplary embodiment of the present specification provides a display device including a color filter.
상기 디스플레이 장치는 플라즈마 디스플레이 패널(Plasma Display Panel, PDP), 발광 다이오드(Light Emitting Diode, LED), 유기 발광 소자(Organic Light Emitting Diode, OLED), 액정 표시 장치(Liquid Crystal Display, LCD), 박막 트랜지스터 액정 표시 장치(Thin FIlm Transistor- Liquid Crystal Display, LCD-TFT) 및 음극선관(Cathode Ray Tube, CRT) 중 어느 하나일 수 있다.The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be any one of a liquid crystal display (Thin Film Transistor- Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 기술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.
<실시예><Example>
화합물 1의 제조Preparation of compound 1
화합물 1-1의 제조Preparation of compound 1-1
2-methylquinolin-8-amine (10 g, 63.2 mmol)과 1-bromo-2-chlorobenzene (12.1 g, 63.2 mmol)을 톨루엔 100mL에 투입하여 녹이고, 포타슘포스페이트 (40 g, 189 mmol)를 첨가하여 가온하였다. 비스(트리 터셔리-부틸포스핀)팔라듐(0.32g, 1mol%)을 투입하여 3시간 환류 교반시켰다. 반응이 완결되면 톨루엔을 환류하에 제거하고, 상온으로 온도를 낮춘 후 클로로포름 200mL을 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 에틸아세테이트와 헥산을 이용하여 실리카 컬럼크로마토그래피를 통해 정제하여 고체 화합물인 화학식 1-1(12.4 g, 수율 73%)을 제조하였다.2-methylquinolin-8-amine (10 g, 63.2 mmol) and 1-bromo-2-chlorobenzene (12.1 g, 63.2 mmol) were dissolved in 100 mL of toluene, and potassium phosphate (40 g, 189 mmol) was added to warm. I did. Bis (tri tertiary-butylphosphine) palladium (0.32 g, 1 mol%) was added and stirred under reflux for 3 hours. When the reaction was completed, toluene was removed under reflux, and after lowering the temperature to room temperature, 200 mL of chloroform was added to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through silica column chromatography using ethyl acetate and hexane to prepare a solid compound, Formula 1-1 (12.4 g, yield 73%).
화합물 1-2의 제조Preparation of compound 1-2
화합물 1-1(10 g, 37.2 mmol)을 N,N-dimethylforamide에 녹이고, 0℃에서 소듐하이드라이드(1.6 g, 40.9 mmol)를 천천히 투입하여 30분 교반하였다. 반응물에 iodoethane(6.4 g, 40.9 mmol)을 투입하여 3시간 실온에서 교반하였다. 반응이 완결 되면 물을 첨가하여 석출된 고체를 여과하였다. 여과한 고체를 클로로포름에 녹여 물로 세척한 후 무수황산마그네슘을 넣고 여과하여 여액을 감압 증류하였다. 농축한 화합물을 에틸아세테이트와 헥산을 이용하여 실리카 컬럼크로마토그래피를 통해 정제하여 고체 화합물인 화학식 1-2(8.94 g, 수율 81%)를 제조하였다. Compound 1-1 (10 g, 37.2 mmol) was dissolved in N,N-dimethylforamide, sodium hydride (1.6 g, 40.9 mmol) was slowly added at 0°C, followed by stirring for 30 minutes. Iodoethane (6.4 g, 40.9 mmol) was added to the reaction and stirred at room temperature for 3 hours. When the reaction was completed, water was added to filter the precipitated solid. The filtered solid was dissolved in chloroform, washed with water, anhydrous magnesium sulfate was added, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through silica column chromatography using ethyl acetate and hexane to prepare a solid compound, Formula 1-2 (8.94 g, yield 81%).
화합물 1-3의 제조Preparation of compound 1-3
화합물 1-2(10 g, 33.7 mmol)를 다이에틸아세트아마이드(DMAc) 100mL에 녹인 후 포타슘포스페이트(21.5 g, 101 mmol)를 투입하여 가온하여 환류시켰다. 디벤질리덴아세톤팔라듐 (0.58 g, 1.0 mmol)과 트리시클로헥실포스핀 (0.57 g, 2.0 mmol)을 첨가하고 6시간 환류 교반시켰다. 반응이 완결되면 반응물을 실온으로 식히고, 물1.0L에 반응물을 투입하여 교반 후 생성된 고체를 여과하였다. 여과한 고체를 클로로포름에 완전히 녹인 후 물로 씻어주고, 분리한 유기층을 무수황산마그네슘으로 처리하여 여과 후, 여액을 감압농축 하였다. 농축한 화합물을 에틸아세테이트와 헥산을 이용하여 실리카 컬럼크로마토그래피를 통해 정제하여 고체 화합물인 화학식 1-3(5.9 g, 수율 68%)을 제조하였다.Compound 1-2 (10 g, 33.7 mmol) was dissolved in diethylacetamide (DMAc) 100 mL, and potassium phosphate (21.5 g, 101 mmol) was added thereto, followed by heating to reflux. Dibenzylideneacetonepalladium (0.58 g, 1.0 mmol) and tricyclohexylphosphine (0.57 g, 2.0 mmol) were added, followed by reflux stirring for 6 hours. Upon completion of the reaction, the reaction product was cooled to room temperature, the reaction product was added to 1.0 L of water, stirred, and the resulting solid was filtered. The filtered solid was completely dissolved in chloroform, washed with water, and the separated organic layer was treated with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrated compound was purified through silica column chromatography using ethyl acetate and hexane to prepare a solid compound, Formula 1-3 (5.9 g, yield 68%).
화합물 1의 제조Preparation of compound 1
화합물 1-3(10 g, 38.4 mmol)과 1,3-Isobenzofurandione(6.3 g, 42.3 mmol)을 methylbenzoate 50 mL, 벤조산 9.4 g에 투입하여 150℃ 로 가온하였다. 3시간 교반 후 실온으로 냉각하고, 에탄올 20mL을 투입하여 석출된 고체를 여과한다. 여과한 고체를 에틸아세테이트와 에탄올 1/1 용액으로 슬러리 정제하여 목적 화합물인 1(7.9 g, 수율 72%)을 제조하였다. MS:[M+H]+=391Compound 1-3 (10 g, 38.4 mmol) and 1,3-Isobenzofurandione (6.3 g, 42.3 mmol) were added to 50 mL of methylbenzoate and 9.4 g of benzoic acid, followed by heating to 150°C. After stirring for 3 hours, the mixture was cooled to room temperature, and 20 mL of ethanol was added to filter the precipitated solid. The filtered solid was slurry-purified with a 1/1 solution of ethyl acetate and ethanol to prepare the target compound 1 (7.9 g, yield 72%). MS:[M+H] + =391
화합물 2의 제조Preparation of compound 2
화합물 2-1의 제조Preparation of compound 2-1
화합물 1-1(10 g, 37.2 mmol)과 iodobenzene (8.4 g, 40.9 mmol)을 톨루엔 100mL에 투입하여 녹이고, 소듐 터트-부톡사이드(7.2 g, 74.4 mmol)를 첨가하여 가온하였다. 환류 상태에서 비스(트리 터셔리-부틸포스핀)팔라듐(0.19 g, 1mol%)을 투입하여 6시간 교반 시켰다. 반응이 완결되면 톨루엔을 환류하에 제거하고, 상온으로 온도를 낮춘 후 클로로포름 200mL을 투입하여 녹이고, 물로 2회 세척 후에 유기층을 분리하여, 무수황산마그네슘을 넣고 교반한 후 여과하여 여액을 감압 증류하였다. 농축한 화합물을 에틸아세테이트와 헥산을 이용하여 실리카 컬럼크로마토그래피를 통해 정제하여 고체 화합물인 화학식 2-1(6.7 g, 수율 72%)을 제조하였다.Compound 1-1 (10 g, 37.2 mmol) and iodobenzene (8.4 g, 40.9 mmol) were added to 100 mL of toluene to dissolve, and sodium tert-butoxide (7.2 g, 74.4 mmol) was added to warm. At reflux, bis(tri-tertiary-butylphosphine)palladium (0.19 g, 1 mol%) was added and stirred for 6 hours. When the reaction was completed, toluene was removed under reflux, and after lowering the temperature to room temperature, 200 mL of chloroform was added to dissolve it, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through silica column chromatography using ethyl acetate and hexane to prepare a solid compound, Formula 2-1 (6.7 g, yield 72%).
화합물 2-2의 제조Preparation of compound 2-2
화합물 1-2 대신 화합물 2-1(10 g, 29 mmol)을 사용하여 화합물 1-3의 제조예와 동일하게 실험하여 목적화합물 2-2(4.5 g, 75%)를 제조하였다.Compound 2-1 (10 g, 29 mmol) was used instead of compound 1-2 to prepare the target compound 2-2 (4.5 g, 75%) in the same manner as in Preparation Example of compound 1-3.
화합물 2의 제조Preparation of compound 2
화합물 1-3과 1,3-Isobenzofurandione 대신 화합물 2-2(10 g, 38.4 mmol)와 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (10.2 g, 35.7 mmol)을 사용하여 화합물 1의 제조예와 동일하게 실험하여 목적화합물 2(14.2 g, 76%)를 제조하였다. MS:[M+H]+=577Compound 1 using compound 2-2 (10 g, 38.4 mmol) and 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (10.2 g, 35.7 mmol) instead of compound 1-3 and 1,3-Isobenzofurandione Subject compound 2 (14.2 g, 76%) was prepared by the same experiment as in Preparation Example of. MS:[M+H] + =577
화합물 3의 제조Preparation of compound 3
화합물 3-1의 제조Preparation of compound 3-1
화합물 8-bromo-2-methylquinoline (10 g, 45 mmol)과 (4-fluoro-2-nitrophenyl)boronic acid (8.3 g, 45 mmol)을 테트라하이드로퓨란 120 ml에 분산시킨 후, 2M 탄산칼륨수용액(aq. K2CO3)(68 ml, 135 mmol)을 첨가하고 테트라키스트리페닐포스피노팔라듐(0.5 g, 1 mol%)을 넣은 후 6시간 동안 교반 환류하였다. 상온으로 온도를 낮추고 물층을 분리하고, 유기층을 다시 물로 1회 더 세척하여 유기층을 분리하였다. 모아진 유기층에 무수황산마그네슘을 투입하여 슬러리 후 여과하여 감압 농축하였다. 농축한 화합물을 에틸아세테이트와 헥산을 이용하여 실리카 컬럼크로마토그래피를 통해 정제하여 고체 화합물인 화학식 3-1(10.4 g, 82%)을 제조하였다.Compound 8-bromo-2-methylquinoline (10 g, 45 mmol) and (4-fluoro-2-nitrophenyl) boronic acid (8.3 g, 45 mmol) were dispersed in 120 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution ( aq.K 2 CO 3 )(68 ml, 135 mmol) was added and tetrakistriphenylphosphinopalladium (0.5 g, 1 mol%) was added, followed by stirring and refluxing for 6 hours. The temperature was lowered to room temperature, the water layer was separated, and the organic layer was washed once more with water to separate the organic layer. Anhydrous magnesium sulfate was added to the collected organic layer, the slurry was filtered, and concentrated under reduced pressure. The concentrated compound was purified through silica column chromatography using ethyl acetate and hexane to prepare a solid compound, Formula 3-1 (10.4 g, 82%).
화합물 3-2의 제조Preparation of compound 3-2
화합물 3-1(10 g, 35 mmol)에 트리에틸포스파이트(P(OEt)3)(6.5 g, 39 mmol)를 투입하고 가온하여 교반시켰다. 반응이 완결되면 남아있는 트리에틸포스파이트를 진공으로 증류하여 제거하고, 혼합물을 실온으로 냉각하였 다. 헥산과 에틸아세테이트를 첨가하여 석출된 고체를 여과하고, 여과된 고체를 헥산으로 씻어주었다. 고체를 다시 클로로포름에 녹이고, 물로 2회 세척하여 분리하고, 유기층에 무수황산마그네슘을 넣어 슬러리 후 여과하여 감압 농축하였다. 농축한 화합물을 에탄올과 에틸아세테이트로 재결정하여 목적화합물 3-2(6.5 g, 수율 73%)를 얻었다.Triethylphosphite (P(OEt) 3 ) (6.5 g, 39 mmol) was added to compound 3-1 (10 g, 35 mmol), heated and stirred. When the reaction was complete, the remaining triethylphosphite was distilled off by vacuum, and the mixture was cooled to room temperature. Hexane and ethyl acetate were added to filter the precipitated solid, and the filtered solid was washed with hexane. The solid was again dissolved in chloroform, washed twice with water, separated, and anhydrous magnesium sulfate was added to the organic layer, followed by filtration and concentration under reduced pressure. The concentrated compound was recrystallized from ethanol and ethyl acetate to obtain the target compound 3-2 (6.5 g, yield 73%).
화합물 3-3의 제조Preparation of compound 3-3
화합물 1-1 대신 화합물 3-2(10 g, 40 mmol)를 사용하여 화합물 2-1의 제조예와 동일하게 실험하여 목적화합물 3-3(9.9 g, 76%)을 제조하였다.Compound 3-2 (10 g, 40 mmol) was used instead of compound 1-1 to prepare the target compound 3-3 (9.9 g, 76%) in the same manner as in Preparation Example of compound 2-1.
화합물 3의 제조Preparation of compound 3
화합물 1-3 대신 화합물 3-3(10 g, 30.6 mmol)을 사용하여 화합물 1의 제조예와 동일하게 실험하여 목적화합물 3(5.2 g, 75%)을 제조하였다. MS:[M+H]+=457The target compound 3 (5.2 g, 75%) was prepared in the same manner as in Preparation Example 1 by using compound 3-3 (10 g, 30.6 mmol) instead of compound 1-3. MS:[M+H] + =457
화합물 4의 제조Preparation of compound 4
화합물 4-1의 제조Preparation of compound 4-1
화합물 8-bromo-2-methylquinoline (10 g, 45 mmol)과 (2-nitrophenyl)boronic acid (8.3 g, 50 mmol)을 사용하여 화합물 3-1의 제조예와 동일하게 실험하여 목적화합물 4-1(9.8 g, 82%)을 제조하였다.Target compound 4-1 by the same experiment as the preparation example of compound 3-1 using compound 8-bromo-2-methylquinoline (10 g, 45 mmol) and (2-nitrophenyl)boronic acid (8.3 g, 50 mmol) (9.8 g, 82%) was prepared.
화합물 4-2의 제조Preparation of compound 4-2
화합물 3-1 대신 화합물 4-1(10 g, 38 mmol)을 사용하여 화합물 3-2의 제조예와 동일하게 실험하여 목적화합물 4-2(4.6 g, 72%)를 제조하였다.Compound 4-1 (10 g, 38 mmol) was used instead of compound 3-1 to prepare the target compound 4-2 (4.6 g, 72%) in the same manner as in Preparation Example of compound 3-2.
화합물 4-3의 제조Preparation of compound 4-3
화합물 1-1 대신 화합물 4-2(10 g, 43 mmol)를 사용하여 화합물 2-1의 제조예와 동일하게 실험하여 목적화합물 4-3(9.7 g, 73%)을 제조하였다.Compound 4-2 (10 g, 43 mmol) was used instead of compound 1-1 to prepare the target compound 4-3 (9.7 g, 73%) in the same manner as in Preparation Example of compound 2-1.
화합물 4의 제조Preparation of compound 4
화합물 1-3과 1,3-Isobenzofurandione 대신 화합물 4-3(10 g, 32.4 mmol)과 5-nitroisobenzofuran-1,3-dione(6.9 g, 36 mmol)을 사용하여 화합물 1의 제조예와 동일하게 실험하여 목적화합물 4(12.7 g, 81%)을 제조하였다. MS:[M+H]+=484In the same manner as in Preparation Example of Compound 1, using Compound 4-3 (10 g, 32.4 mmol) and 5-nitroisobenzofuran-1,3-dione (6.9 g, 36 mmol) instead of Compound 1-3 and 1,3-Isobenzofurandione By experiment, the target compound 4 (12.7 g, 81%) was prepared. MS:[M+H] + =484
<비교예><Comparative Example>
비교 화합물 A의 제조Preparation of Comparative Compound A
2-methylquinolin-8-amine (10 g, 63.2 mmol)과 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (40 g, 139 mmol)을 사용하여 화합물 1의 제조예와 동일하게 실험하여 비교 화합물 A(32 g, 73%)를 제조하였다. MS:[M+H]+=694Using 2-methylquinolin-8-amine (10 g, 63.2 mmol) and 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (40 g, 139 mmol) in the same manner as in Preparation Example Comparative compound A (32 g, 73%) was prepared. MS:[M+H] + =694
<실험예><Experimental Example>
<분산액 제조><Dispersion solution preparation>
최종 분산액 총 100 중량부를 기준으로 상기 화합물 및 비교예 화합물을 7 중량부 포함하고, 분산제 LPN-22102 (BYK사) 및 바인더 수지를 각각 8.75 중량부, 14.25 중량부 포함하며, 용매 프로필렌글리콜 모노메틸에테르 아세테이트 28.00 중량부, 지르코니아 비드 200 중량부를 포함하는 조성물을 제작하였다. 상기 조성물을 paint shaker에서 분쇄(milling) 과정을 거친 후, 42 중량부의 프로필렌글리콜 모노메틸에테르 아세테이트로 희석(dilution)하고, 6㎛의 필터를 사용하여 비드(beads)를 여과(filter)하는 과정을 통해 최종 분산액을 제조하였다. Based on a total of 100 parts by weight of the final dispersion, 7 parts by weight of the compound and the comparative example compound are included, 8.75 parts by weight and 14.25 parts by weight of a dispersant LPN-22102 (BYK) and a binder resin are included, respectively, and the solvent propylene glycol monomethyl ether A composition comprising 28.00 parts by weight of acetate and 200 parts by weight of zirconia beads was prepared. After the composition is milled in a paint shaker, it is diluted with 42 parts by weight of propylene glycol monomethyl ether acetate, and the beads are filtered using a 6 μm filter. The final dispersion was prepared.
감광성 수지 조성물 실시예 1의 제조Preparation of photosensitive resin composition Example 1
감광성 수지 조성물 총 중량을 기준으로 상기 화합물 1의 분산액을 11 중량% 포함하고, TOYO사의 Pigment Green 63 분산 조성물을 22 중량%, 바인더 수지 15.05 중량%, 다관능성 모노머 디펜타에리쓰리톨 헥사아크릴레이트 13.28 중량%, 레벨링제 F-554 0.6 중량%, 접착조제 KBM-503 0.15 중량%, 광개시제 SPI-03 0.72 중량%, 용매 프로필렌글리콜 모노메틸에테르 아세테이트 37.20 중량%를 포함하도록 혼합하여 감광성 수지 조성물 실시예 1을 제조하였다. Based on the total weight of the photosensitive resin composition, 11% by weight of the dispersion of Compound 1 is included, and 22% by weight of the Pigment Green 63 dispersion composition of TOYO, 15.05% by weight of a binder resin, and 13.28 of the polyfunctional monomer dipentaerythritol hexaacrylate. Photosensitive resin composition Example 1 by mixing so as to contain% by weight, 0.6% by weight of leveling agent F-554, 0.15% by weight of adhesive aid KBM-503, 0.72% by weight of photoinitiator SPI-03, and 37.20% by weight of solvent propylene glycol monomethyl ether acetate. Was prepared.
실시예 및 비교예에서 사용된 바인더 수지는 모두 동일한 바인더 수지이며 총 중량을 기준으로 메타아크릴산, 벤질메타아크릴산, 스타이렌의 함량이 각각 29 중량%, 52 중량%, 19 중량%인 공중합체이다.The binder resins used in Examples and Comparative Examples are all the same binder resin, and are copolymers in which the contents of methacrylic acid, benzyl methacrylic acid, and styrene are 29% by weight, 52% by weight, and 19% by weight, respectively, based on the total weight.
감광성 수지 조성물 실시예 2의 제조Preparation of photosensitive resin composition Example 2
감광성 수지 조성물 실시예 1의 화합물 1 대신 화합물 2를 사용한 것을 제외하고, 상기 감광성 수지 조성물 실시예 1과 동일한 방법으로 감광성 수지 조성물 실시예 2를 제조하였다.Photosensitive resin composition Example 2 was prepared in the same manner as in the photosensitive resin composition Example 1, except for using the compound 2 instead of the compound 1 of Example 1.
감광성 수지 조성물 실시예 3의 제조Preparation of photosensitive resin composition Example 3
감광성 수지 조성물 실시예 1의 화합물 1 대신 화합물 3을 사용한 것을 제외하고, 상기 감광성 수지 조성물 실시예 1과 동일한 방법으로 감광성 수지 조성물 실시예 3을 제조하였다.Photosensitive resin composition Example 3 was prepared in the same manner as in the photosensitive resin composition Example 1, except for using the compound 3 instead of the compound 1 of Example 1.
감광성 수지 조성물 실시예 4의 제조Preparation of photosensitive resin composition Example 4
감광성 수지 조성물 실시예 1의 화합물 1 대신 화합물 4를 사용한 것을 제외하고, 상기 감광성 수지 조성물 실시예 1과 동일한 방법으로 감광성 수지 조성물 실시예 4를 제조하였다.Photosensitive resin composition Example 4 was prepared in the same manner as in the photosensitive resin composition Example 1, except for using the compound 4 instead of the compound 1 of Example 1.
감광성 수지 조성물 비교예 1의 제조Preparation of photosensitive resin composition Comparative Example 1
감광성 수지 조성물 실시예 1의 화합물 1 대신 비교 화합물 A를 사용한 것을 제외하고 상기 감광성 수지 조성물 실시예 1과 동일한 방법으로 감광성 수지 조성물 비교예 1을 제조하였다. Photosensitive resin composition Comparative Example 1 was prepared in the same manner as in Example 1 of the photosensitive resin composition except that Comparative Compound A was used instead of Compound 1 of Example 1.
<실험예><Experimental Example>
[컬러필터의 기판 제작][Production of color filter substrate]
실시예 및 비교예에서 제조한 감광성 수지 조성물을 글래스(5 cm X 5 cm)에 스핀코팅을 이용하여 도포한 후 100℃에서 2분간 건조(PreBake)하여 잔류 용매를 제거하였다. 만들어진 기판은 포토마스크 공정을 통하여 패턴을 입힌 후 KOH 알칼리 수용액으로 현상하고 증류수로 세척하였다. The photosensitive resin composition prepared in Examples and Comparative Examples was applied to glass (5 cm X 5 cm) by spin coating and then dried at 100° C. for 2 minutes (PreBake) to remove residual solvent. The resulting substrate was patterned through a photomask process, developed with an aqueous KOH alkali solution, and washed with distilled water.
[흡수 스펙트럼 측정][Absorption spectrum measurement]
실시예에서 제조한 각각의 화합물 및 비교 화합물 A를 톨루엔에 10-5M 농도로 용해시킨 용액을 제조하여 PerkinElmer사의 Lamda365 장비를 이용해 UV 흡수를 측정하였다. 측정을 통해 얻어진 λmax 값을 하기 표 1에 기재하였다. A solution prepared by dissolving each of the compounds prepared in Examples and Comparative Compound A in toluene at a concentration of 10 -5 M was prepared, and UV absorption was measured using PerkinElmer's Lamda365 equipment. The λ max values obtained through the measurement are shown in Table 1 below .
[기판의 휘도 및 내열성 평가방법][Method of evaluating the brightness and heat resistance of the substrate]
최종적으로 만들어진 기판은 230℃ 오븐에서 후열처리(PostBake)로 20분, 추가 열처리 과정으로는 20분(총 40분 열처리)을 거쳤다. 이 때, 추가 열처리과정에 따라 변동되는 컬러 패턴의 흡수 스펙트럼 및 C 광원에서의 color index (x,y,Y, L*,a*,b*)를 측정하였다. 이를 통해 광학적 차이 값인 △Eab 값을 하기 식 1에 따라 계산하였다. 이를 하기 표 2 및 3에 기재하였다. The resulting substrate was subjected to a post-heat treatment (PostBake) of 20 minutes in an oven at 230° C. and an additional heat treatment process of 20 minutes (a total of 40 minutes). At this time, the absorption spectrum of the color pattern varied according to the additional heat treatment process and the color index (x,y,Y, L*,a*,b*) of the C light source were measured. Through this, an optical difference value of ΔEab was calculated according to Equation 1 below. This is shown in Tables 2 and 3 below.
[식 1][Equation 1]
ΔEab(L*, a*, b*) = {(ΔL*)2+(Δa*)2+(Δb*)2}1/2 ΔEab(L*, a*, b*) = {(ΔL*) 2 +(Δa*) 2 +(Δb*) 2 } 1/2
상기 식 1에서, △Eab 후열 처리 이후의 ΔE(L*, a*, b*) 값과 전열 처리 이후의 ΔE(L*, a*, b*)의 차이를 의미하고, L*, a*, b*는 CIE 1976 L*a*b* 색공간에서의 휘도 및 좌표를 3차함수로서 변환한 값을 의미한다. In Equation 1, ΔEab means the difference between the value of ΔE(L*, a*, b*) after heat treatment and ΔE(L*, a*, b*) after heat treatment, L*, a* , b* denotes a value obtained by converting luminance and coordinates in the CIE 1976 L*a*b* color space as a cubic function.
구체적으로 L*는 밝기를 나타내는 수치로 0~100사이 값을 가지며, a*는 적색과 녹색 중 가까운 정도를 나타내며, 양/음수의 값을 가질 수 있다. b*는 황색과 청색 중 가까운 정도를 의미하여 양/음의 값을 가진다. Specifically, L* is a value representing the brightness and has a value between 0 and 100, and a* represents a degree that is close among red and green, and may have a positive/negative value. b* means the nearest degree between yellow and blue, and has a positive/negative value.
△Eab 값이 작다는 것은 추가 열처리에 따른 컬러 패턴의 안정성이 높다는 것을 의미하므로 제조된 감광성 수지 조성물의 내열성이 우수함을 나타낸다.A small ΔEab value means that the stability of the color pattern according to the additional heat treatment is high, indicating that the prepared photosensitive resin composition has excellent heat resistance.
휘도(Y) 값은 후열처리 된 단판의 값을 나타내었다. The luminance (Y) value represents the value of the post-heat-treated veneer.
(10-5M )λ max
( 10 -5 M)
상기 표 1 내지 3에서 확인할 수 있듯이, 비교예 1에 비해 실시예 1 내지 4의 화합물이 장파장 흡수가 가능하며, 이를 포함하는 감광성 조성물의 경우 내열성 및 휘도(Y)가 향상되는 것을 확인할 수 있다. 이로써, 본 명세서의 일 실시상태에 따른 화합물을 이용함으로써 열에 의한 열화가 적고 휘도가 우수한 감광성 수지 조성물과 컬러필터를 제조할 수 있음을 확인하였다.As can be seen in Tables 1 to 3, compared to Comparative Example 1, the compounds of Examples 1 to 4 can absorb longer wavelengths, and in the case of a photosensitive composition including the same, it can be seen that heat resistance and brightness (Y) are improved. Accordingly, it was confirmed that by using the compound according to the exemplary embodiment of the present specification, a photosensitive resin composition and a color filter having less heat deterioration and excellent luminance can be manufactured.
Claims (13)
[화학식 1]
상기 화학식 1에 있어서,
Y는 직접결합; 또는 CQ1Q2이고,
R1 내지 R13 및 Q1 및 Q2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; -COOH; -C(=O)OR; -OC(=O)R'; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 또는 인접한 기는 서로 결합하여 치환 또는 비치환된 고리를 형성하고,
R 및 R'는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기이다.Compound represented by the following formula (1):
[Formula 1]
In Formula 1,
Y is a direct bond; Or CQ1Q2,
R1 to R13 and Q1 and Q2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; -COOH; -C(=O)OR; -OC(=O)R'; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
R and R'are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.
[화학식 1-1]
[화학식 1-2]
상기 화학식 1-1 및 1-2에 있어서,
R1 내지 R13, Q1 및 Q2의 정의는 상기 화학식 1과 동일하다.The compound of claim 1, wherein the formula 1 is represented by the following formula 1-1 or 1-2:
[Formula 1-1]
[Formula 1-2]
In Formulas 1-1 and 1-2,
The definitions of R1 to R13, Q1 and Q2 are the same as in Formula 1.
.The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following formulas:
.
상기 바인더 수지의 함량은 1 중량% 내지 60 중량%이고,
상기 광개시제의 함량은 0.1 중량% 내지 10 중량%이며,
상기 다관능성 모노머의 함량은 0.1 중량% 내지 50 중량%인 것인 감광성 수지 조성물.The method according to claim 9, based on the total weight of the solid content of the photosensitive resin composition, the content of the color material composition is 2% by weight to 50% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1% to 10% by weight,
The content of the polyfunctional monomer is 0.1% to 50% by weight of the photosensitive resin composition.
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