KR20180110497A - A black colored photosensitive resin composition and display device produced using the same - Google Patents
A black colored photosensitive resin composition and display device produced using the same Download PDFInfo
- Publication number
- KR20180110497A KR20180110497A KR1020170040127A KR20170040127A KR20180110497A KR 20180110497 A KR20180110497 A KR 20180110497A KR 1020170040127 A KR1020170040127 A KR 1020170040127A KR 20170040127 A KR20170040127 A KR 20170040127A KR 20180110497 A KR20180110497 A KR 20180110497A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- substituted
- interrupted
- phenyl
- unsubstituted
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000003999 initiator Substances 0.000 claims abstract description 35
- 239000000126 substance Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 229910052760 oxygen Inorganic materials 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- -1 diphenylamino Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 32
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 239000011230 binding agent Substances 0.000 claims description 23
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 239000003086 colorant Substances 0.000 claims description 14
- 239000000049 pigment Substances 0.000 claims description 14
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 239000002096 quantum dot Substances 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000000975 dye Substances 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 238000007334 copolymerization reaction Methods 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012860 organic pigment Substances 0.000 claims description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 2
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 5
- 238000005137 deposition process Methods 0.000 abstract description 5
- 238000004090 dissolution Methods 0.000 abstract description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000006229 carbon black Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 230000007261 regionalization Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010943 off-gassing Methods 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- LQANLNZCIDSHKI-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl prop-2-enoate Chemical compound C=CC(=O)OCC1(C)COC1 LQANLNZCIDSHKI-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229930016911 cinnamic acid Natural products 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010292 electrical insulation Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
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- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
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Classifications
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- 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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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Abstract
Description
본 발명은 흑색 감광성 수지 조성물 및 이를 이용하여 제조된 표시 장치에 관한 것이다.The present invention relates to a black photosensitive resin composition and a display device manufactured using the same.
평판 표시 장치(Flat Panel Display Device) 중에 하나인 유기 발광 표시 장치는 자체 발광형이기 때문에 액정 표시 장치(Liquid Crystal Display Device)에 비해 시야각, 콘트라스트(Contrast) 등이 우수하며, 백라이트가 필요하지 않기 때문에 경량박형이 가능하고, 소비전력 측면에서도 유리하다. 또한 직류 저전압 구동이 가능하며, 응답속도가 빠르며, 구성하는 소자 모두가 고체이기 때문에 외부 충격에 강하고 사용 온도 범위도 넓을 뿐만 아니라 제조 비용 측면에서도 저렴하다는 장점이 있다.Since the organic light emitting display device, which is one of the flat panel display devices, is self-emitting type, it has better viewing angle and contrast than a liquid crystal display device and does not require a backlight It is lightweight and thin, and is also advantageous in terms of power consumption. In addition, it can be driven by low-voltage direct current, has a fast response speed, and all the constituent elements are solid, which is strong against external impact, has a wide temperature range, and is also inexpensive in terms of manufacturing cost.
특히, 유기 발광 표시 장치의 제조 공정은 액정 표시 장치나 PDP(Plasma Display Panel)와는 달리 증착/식각(Deposition/Etching) 공정의 반복 및 인캡슐레이션(Encapsulation) 공정으로 이루어지기 때문에 공정이 매우 단순하다는 장점이 있다. In particular, unlike a liquid crystal display device or a plasma display panel (PDP), a manufacturing process of an organic light emitting display device is performed by repeating a deposition / etching process and encapsulating process, There are advantages.
이러한 유기 발광 표시 장치는 각 픽셀간 경계를 구분지어 주면서 이들을 절연시키는 화소정의막(PDL, Pixel Defined Layer)층과 상기 화소정의막의 하부에 평탄하게 형성되면서 절연 특성을 갖는 평탄화층을 포함한다. 이때, 상기 화소정의막층은 포토리소그래피 공정을 통해 정밀하게 패터닝된다.The organic light emitting diode display includes a pixel defining layer (PDL) layer that isolates the pixels and isolates the pixels from each other, and a planarization layer that is formed under the pixel defining layer and has insulation characteristics. At this time, the pixel defining film layer is precisely patterned through a photolithography process.
대한민국 공개특허 제2015-0072581호는 적어도 하나의 실록산(SiO3/2)이 반복적으로 연결된 폴리실록산을 포함하는 OLED 디스플레이 장치용 감광성 수지 조성물에 관한 것으로서, 상기 감광성 수지 조성물이 OLED 디스플레이 장치의 각 픽셀간 경계를 구분지어 주면서 절연시키는 PDL층과 상기 PDL층의 하부에 평탄하게 평성되면서 절연 특성을 갖는 평탄화층으로 사용될 수 있다는 내용을 개시하고 있다. Korean Patent Laid-Open Publication No. 2015-0072581 relates to a photosensitive resin composition for an OLED display device in which at least one siloxane (SiO 3/2 ) is repeatedly connected to a polysiloxane, wherein the photosensitive resin composition is applied between each pixel of the OLED display device Discloses that the PDL layer can be used as a planarization layer having insulation characteristics while being flatly flattened under the PDL layer.
그러나, 상기 감광성 수지 조성물은 투명한 조성물이기 때문에 외광이 밝을 경우 콘트라스트가 좋지 않으며, 유기 발광 소자의 음극면은 반사율이 우수한 금속으로 되어 있기 때문에 외부에서 유기 발광 소자 내부로 들어오는 빛이 유기 발광 소자의 음극면에 반사되어 발광층에서 나오는 빛과 섞이는 문제점이 존재한다.However, since the photosensitive resin composition is a transparent composition, the contrast is not good when the external light is bright, and since the cathode surface of the organic light emitting element is made of a metal having excellent reflectance, light entering the organic light emitting element from the outside is emitted to the cathode There is a problem that the light is reflected by the surface and mixed with light emitted from the light emitting layer.
상기와 같은 문제를 해결하기 위하여 현재 대부분의 유기발광소자는 투명기판 하부에 원편광판(Circular polarizer)을 형성함으로써 음극에 의한 외부 입사광의 반사를 줄였다. 즉, 상기 원편광판에 의해 외부의 빛이 입사될 때, 절반이 차단되고, 나머지 반은 음극에 반사되어 나올 때 차단됨으로써, 외광에 의한 콘트라스트 저하를 억제할 수 있다.In order to solve the above problems, most of the organic light emitting devices currently have a circular polarizer formed under the transparent substrate, thereby reducing the reflection of external incident light by the cathode. That is, when external light is incident by the circularly polarizing plate, half is cut off, and the other half is blocked when it is reflected on the cathode, thereby suppressing a decrease in contrast due to external light.
그러나 상술한 종래의 투명기판 위에 원편광판을 붙인 유기발광소자는 음극에 의한 외부 입사광의 반사를 크게 줄여줌과 동시에 유기 발광층으로부터 외부로 발산되는 빛까지도 차단하기 때문에, 콘트라스트는 향상되지만 휘도는 50%이상 감소하는 문제점과 고비용이 야기되는 문제점이 있었다. However, since the organic light emitting device having the circular polarizer on the above-mentioned conventional transparent substrate greatly reduces the reflection of the external incident light by the cathode and also blocks the light emitted to the outside from the organic light emitting layer, the contrast is improved, There is a problem in that the cost is reduced.
따라서, 상기 문제점을 해결하기 위해, 외부 입사광을 흡수하여, 콘트라스트를 향상시키는 블랙 화소정의막을 형성할 수 있다. 블랙 화소정의막(Pixel Defined Layer)은 포토리소그래피 공정을 통해 정밀하게 패터닝되며, 유기발광소자 픽셀을 제작하는 고압 증착 공정 중에 소자 구동에 치명적인 아웃가스 성분이 용출되지 않아야 하는 신뢰성이 요구된다. Therefore, in order to solve the above problems, it is possible to form a black pixel defining layer that absorbs external incident light and improves the contrast. The black pixel definition layer is precisely patterned through a photolithography process, and reliability is required such that an outgas component that is lethal to device driving is not eluted during a high-pressure deposition process for manufacturing an organic light-emitting device pixel.
그러나 종래의 액정 표시 장치(Liquid Crystal Display Deivce)에서 사용되는 BM(Black Matrix)용 감광성 수지 조성물의 경우에는 유기 발광 소자 픽셀을 제작하는 고압 증착 공정 중에 유기 발광 소자 구동에 치명적인 아웃가스 성분이 용출되어 휘도 저하 및 심한 경우 유기 발광 소자가 구동이 불가능한 문제점이 존재한다.However, in the case of a photosensitive resin composition for BM (Black Matrix) used in a conventional liquid crystal display device, an outgas component that is liable to drive an organic light emitting element is eluted during a high pressure deposition process for manufacturing organic light emitting device pixels There is a problem that the luminance is lowered and the organic light emitting device can not be driven in severe cases.
그러므로, 유기 발광 표시 장치를 제조하는 데 있어서 고압 증착 과정 중에 유기 발광 소자 구동에 치명적인 아웃가스 성분의 용출을 최소화하며, 우수한 콘트라스트 및 휘도를 가지는 유기 발광 표시 장치를 제조할 수 있는 감광성 수지 조성물에 대한 연구가 요구되고 있다.Therefore, it is an object of the present invention to provide a photosensitive resin composition capable of producing an organic light emitting display having excellent contrast and brightness while minimizing dissolution of an outgas component, which is critical for driving an organic light emitting element during a high pressure deposition process, Research is required.
본 발명은 유기 발광 표시 장치를 제조하는 데 있어서 고압 증착 과정 중에 유기 발광 소자 구동에 치명적인 아웃가스 성분의 용출을 감소시키며, 외부 입사광을 흡수하여 콘트라스트 및 휘도를 향상시킬 수 있는 흑색 감광성 수지 조성물을 제공하는 것을 목적으로 한다.Disclosed is a black photosensitive resin composition capable of reducing dissolution of an outgas component that is critical to the driving of an organic light emitting device during a high pressure deposition process and improving contrast and brightness by absorbing external incident light .
또한, 상기 흑색 감광성 수지 조성물을 이용한 화소정의막을 포함하는 표시 장치를 제공하는 것을 목적으로 한다. Another object of the present invention is to provide a display device including a pixel defining layer using the black photosensitive resin composition.
상기 목적을 달성하기 위한 본 발명에 따른 흑색 감광성 수지 조성물은 광중합 개시제가 하기 화학식 1의 화합물로 이루어진 군으로부터 선택되는 1종 이상을 포함하는 것을 특징으로 한다.In order to achieve the above object, the black photosensitive resin composition according to the present invention is characterized in that the photopolymerization initiator comprises at least one selected from the group consisting of compounds represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
또한, 본 발명은 전술한 흑색 감광성 수지 조성물의 경화물을 포함하는 화소정의막을 포함하는 표시 장치를 제공한다.The present invention also provides a display device comprising a pixel defining layer comprising a cured product of the above-mentioned black photosensitive resin composition.
본 발명의 흑색 감광성 수지 조성물은 유기발광소자 또는 양자점발광소자의화소정의막을 형성하는 데 사용될 수 있으며, 유기발광소자 또는 양자점발광소자를 포함하는 표시 장치를 제조하는 데 있어서 고압 증착 과정 중에 유기발광소자 또는 양자점발광소자 구동에 치명적인 아웃가스 성분의 용출을 감소시킬 수 있는 이점이 있다. The black photosensitive resin composition of the present invention can be used to form a pixel defining layer of an organic light emitting device or a quantum dot light emitting device, and in manufacturing a display device including an organic light emitting device or a quantum dot light emitting device, Or the dissolution of the outgas component, which is critical for driving the quantum dot light emitting element, can be reduced.
그러므로, 본 발명의 흑색 감광성 수지 조성물을 이용하여 제조된 화소정의막을 포함하는 유기발광소자, 양자점발광소자, 및 상기 유기발광소자 또는 양자점발광소자를 포함하는 표시 장치는 휘도, 구동성 및 내구성 등에서 우수한 이점이 있다.Therefore, an organic light-emitting device, a quantum dot light-emitting device, and a display device including the organic light-emitting device or the quantum dot light-emitting device including the pixel defining film manufactured using the black photosensitive resin composition of the present invention are excellent in brightness, There is an advantage.
이하, 본 발명에 대하여 더욱 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에서 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.When a member is referred to as being " on "another member in the present invention, this includes not only when a member is in contact with another member but also when another member exists between the two members.
본 발명에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.Whenever a part is referred to as "including " an element in the present invention, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
<흑색 감광성 수지 조성물><Black Photosensitive Resin Composition>
본 발명의 한 양태는, 착색제, 결합제 수지, 광중합성 화합물, 광중합 개시제, 및 용제를 포함하며, 상기 광중합 개시제가 하기 화학식 1로 표시되는 화합물로 이루어진 군으로부터 선택되는 1종 이상을 포함하는 것인 흑색 감광성 수지 조성물에 관한 것이다. 바람직하게, 본 발명의 흑색 감광성 수지 조성물은 유기발광소자 또는 양자점발광소자의 화소정의막을 형성하는 데 사용될 수 있다.One embodiment of the present invention is a photopolymerizable composition comprising a colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerization initiator comprises at least one compound selected from the group consisting of compounds represented by the following general formula To a black photosensitive resin composition. Preferably, the black photosensitive resin composition of the present invention can be used to form a pixel defining layer of an organic light emitting element or a quantum dot light emitting element.
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
R1, R2, R3, R4는 서로 독립적으로 수소, C1-C20알킬, OR15, 할로겐, 또는 NO2이거나; R 1 , R 2 , R 3 and R 4 independently of one another are hydrogen, C 1 -C 20 alkyl, OR 15 , halogen, or NO 2 ;
또는 R1 및 R2, R2 및 R3, R3 및 R4는 서로 독립적으로 함께 으로서, 이들이 부착되어 있는 탄소 원자와 함께 6-원 고리를 형성하고;Or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , Together with the carbon atoms to which they are attached form a 6-membered ring;
R11, R12, R13, R14는 서로 독립적으로 수소, 비치환되거나 또는 1개 이상의 할로겐, 페닐, CN, OH, SH, C1-C4-알콕시, (CO)OH에 의해 또는 (CO)O(C1-C4알킬)에 의해 치환된 C1-C20알킬이거나;R 11 , R 12 , R 13 and R 14 are each independently of the other hydrogen, unsubstituted or substituted by one or more halogen, phenyl, CN, OH, SH, C 1 -C 4 -alkoxy, CO) O (C 1 -C 4 alkyl) in the substituted C 1 -C 20 alkyl, or by;
또는 R11, R12, R13, R14는 서로 독립적으로 비치환된 페닐 또는 1개 이상의 C1-C6알킬, 할로겐, CN, OR15에 의해 또는 NR17R18에 의해 치환된 페닐이거나;Or R 11 , R 12 , R 13 and R 14 are independently of each other unsubstituted phenyl or phenyl substituted by one or more C 1 -C 6 alkyl, halogen, CN, OR 15 or NR 17 R 18 ;
또는 R11, R12, R13, R14는 서로 독립적으로 할로겐, CN, OR15, SR16, SOR16, SO2R16 또는 NR17R18이고, 여기서 치환기 OR15, SR16 또는 NR17R18은 임의로 나프틸 고리의 탄소 원자 중 1개와 함께 라디칼 R15, R16, R17 및/또는 R18을 통해 5- 또는 6-원 고리를 형성하고; Or R 11 , R 12 , R 13 and R 14 independently of one another are halogen, CN, OR 15 , SR 16 , SOR 16 , SO 2 R 16 or NR 17 R 18 in which substituents OR 15 , SR 16 or NR 17 R 18 together with one of the carbon atoms of the naphthyl ring optionally form a 5- or 6-membered ring via the radicals R 15 , R 16 , R 17 and / or R 18 ;
R5는, 비치환되거나 또는 1개 이상의 할로겐, R15, COOR15, OR15, SR16, CONR17R18, NR17R18에 의해 치환된 C1-C20알킬이거나;R 5 is C 1 -C 20 alkyl unsubstituted or substituted by one or more halogens, R 15 , COOR 15 , OR 15 , SR 16 , CONR 17 R 18 , NR 17 R 18 ;
또는 R5는 1개 이상의 O, S, SO, SO2, NR23 또는 CO가 개재된 C2-C20알킬이거나,Or R 5 is C 2 -C 20 alkyl interrupted by one or more O, S, SO, SO 2 , NR 23 or CO,
또는 비개재되거나 또는 1개 이상의 O, CO 또는 NR23이 개재된 C2-C12알케닐이고,Or a non-intervening or one or more O, CO or NR 23 is a C2-C12 alkenyl interposed,
여기서 개재된 C2-C20알킬 및 비개재 또는 개재된 C2-C12알케닐은 비치환되거나 또는 1개 이상의 할로겐에 의해 치환되거나;Wherein the intervening C 2 -C 20 alkyl and the non-interrupted or interrupted C 2 -C 12 alkenyl are unsubstituted or substituted by one or more halogens;
또는 R5는 C4-C8시클로알케닐, C2-C12알키닐, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C10시클로알킬이거나;Or R 5 is C 4 -C 8 cycloalkenyl, C 2 -C 12 alkynyl, or C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
또는 R5는 페닐 또는 나프틸이고, 이들 각각은 비치환되거나 또는 1개 이상의 OR15, SR16, NR17R18, COR22, CN, NO2, 할로겐, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O, S, CO 또는 NR23이 개재된 C2-C20알킬에 의해 치환되거나, 또는 이들 각각은 C3-C10시클로알킬에 의해 또는 1개 이상의 O, S, CO 또는 NR24이 개재된 C3-C10시클로알킬에 의해 치환되고;Or R 5 is phenyl or naphthyl each of which is unsubstituted or substituted by one or more of OR 15 , SR 16 , NR 17 R 18 , COR 22 , CN, NO 2 , halogen, C 1 -C 20 alkyl, C 1 C 4 haloalkyl, C 2 -C 20 alkyl substituted with one or more O, S, CO or NR 23 , or each of which may be substituted by C 3 -C 10 cycloalkyl or by one or more O, S, CO, or NR 24 is interposed a C 3 -C 10 cycloalkyl which is substituted by alkyl;
R6, R7, R8, R9, R10은 수소, 페닐-C1-C3알킬, 비치환되거나 또는 1개 이상의 할로겐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-페닐, (CO)OH, (CO)O(C1-C4알킬), C3-C20시클로알킬, SO2-(C1-C4할로알킬), O(C1-C4할로알킬)에 의해 또는 1개 이상의 O가 개재된 C3-C20시클로알킬에 의해 치환된 C1-C20알킬이거나; R 6 , R 7 , R 8 , R 9 and R 10 are independently selected from hydrogen, phenyl-C 1 -C 3 alkyl, unsubstituted or substituted with one or more of halogen, OH, SH, CN, C 3 -C 6 alkenoxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - ( C 1 -C 4 alkyl), O (CO) - ( C 2 -C 4) alkenyl (C 1 -C 4 alkyl), C 3 -C 20 cycloalkyl, SO 2 - (C 1 -C 4 haloalkyl), O (C) -C 1 -C 4 haloalkyl), or C 1 -C 20 alkyl substituted by one or more O interrupted C 3 -C 20 cycloalkyl;
또는 R6, R7, R8, R9, R10은 1개 이상의 O, S 또는 NR24이 개재된 C2-C20알킬이거나;Or R 6 , R 7 , R 8 , R 9 , R 10 are C 2 -C 20 alkyl interrupted by one or more O, S or NR 24 ;
또는 R6, R7, R8, R9, R10은 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C1-C8알카노일, C2-C12알케닐, C3-C6알케노일, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C20시클로알킬이거나;Or R 6, R 7, R 8 , R 9, R 10 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C C 1 -C 8 alkanoyl, C 2 -C 12 alkenyl, C 3 -C 6 alkenoyl, or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
또는 R6, R7, R8, R9, R10은, 비개재되거나 또는 1개 이상의 O가 개재된 C1-C8알킬-C3-C10시클로알킬이거나;Or R 6 , R 7 , R 8 , R 9 , R 10 are C 1 -C 8 alkyl-C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O;
또는 R6, R7, R8, R9, R10은, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH 또는 C1-C3알콕시에 의해 치환된 벤조일이거나;Or R 6 , R 7 , R 8 , R 9 , R 10 are benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH or C 1 -C 3 alkoxy;
또는 R6, R7, R8, R9, R10은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, OH, C1-C12알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노에 의해 치환되고;Or R 6 , R 7 , R 8 , R 9 and R 10 are phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, OH, C 1 -C 12 alkyl C 1 -C 12 alkoxy, CN, NO 2 , phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2 , Substituted by diphenylamino;
R15는 수소, 페닐-C1-C3알킬, 비치환되거나 또는 1개 이상의 할로겐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-페닐, (CO)OH, (CO)O(C1-C4알킬), C3-C20시클로알킬, SO2-(C1-C4할로알킬), O(C1-C4할로알킬)에 의해 또는 1개 이상의 O가 개재된 C3-C20시클로알킬에의해 치환된 C1-C20알킬이거나;R 15 is hydrogen, phenyl -C 1 -C 3 alkyl, unsubstituted or substituted by one or more halogen, OH, SH, CN, C 3 -C 6 alkenyl-oxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - (C 1 -C 4 alkyl), O (CO) - (C 2 -C 4 ) alkenyl, O , (CO) O (C 1 -C 4 alkyl), C 3 -C 20 cycloalkyl, SO 2 - (C 1 -C 4 haloalkyl), O (C 1 -C 4 haloalkyl) or more O is interposed a C 3 -C 20 cycloalkyl substituted by C 1 -C 20 alkyl;
또는 R15는 1개 이상의 O, S 또는 NR23이 개재된 C2-C20알킬이거나;Or R 15 is C 2 -C 20 alkyl interrupted by one or more O, S or NR 23 ;
또는 R15는 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C1-C8알카노일, C2-C12알케닐, C3-C6알케노일, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C20시클로알킬이거나;Or R 15 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 1 -C 8 alkanoyl, C 2 -C 12 C 3 -C 6 alkenoyl, or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
또는 R15는, 비개재되거나 또는 1개 이상의 O가 개재된 C1-C8알킬-C3-C10시클로알킬이거나;Or R 15 is C 1 -C 8 alkyl-C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O;
또는 R15는, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH 또는 C1-C3알콕시에 의해 치환된 벤조일이거나;Or R 15 is benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH or C 1 -C 3 alkoxy;
또는 R15는 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, OH, C1-C12알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노 또는 에 의해 치환되고;Or R 15 is phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN, NO 2 , Phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2 , diphenylamino or Lt; / RTI >
R16은 수소, C2-C12알케닐, C3-C20시클로알킬 또는 페닐-C1-C3알킬이고, 여기서 C2-C12알케닐, C3-C20시클로알킬 또는 페닐-C1-C3알킬은 비개재되거나 또는 1개 이상의 O, S, CO, NR23 또는 COOR15가 개재되거나;R 16 is hydrogen, C 2 -C 12 alkenyl, C 3 -C 20 cycloalkyl or phenyl-C 1 -C 3 alkyl, wherein C 2 -C 12 alkenyl, C 3 -C 20 cycloalkyl or phenyl- C 1 -C 3 alkyl is interrupted or interrupted by one or more O, S, CO, NR 23 or COOR 15 ;
또는 R16은, 비치환되거나 또는 1개 이상의 OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-(C1-C4알킬), O(CO)-페닐 또는 (CO)OR15에 의해 치환된 C1-C20알킬이거나;Or R 16 is unsubstituted or substituted with one or more of OH, SH, CN, C 3 -C 6 alkenoxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl) (CO) - (C 2 -C 4) alkenylene, O (CO) - (C 1 -C 4 alkyl), O (CO) - phenyl, or (CO) substituted by a C 1 -C 20 alkyl oR 15 ;
또는 R16은 1개 이상의 O, S, CO, NR23 또는 COOR15이 개재된 C2-C20알킬이거나;Or R 16 is C 2 -C 20 alkyl interrupted by one or more O, S, CO, NR 23 or COOR 15 ;
또는 R16은 (CH2CH2O)nH, (CH2CH2O)n(CO)-(C1-C8알킬), C2-C8알카노일 또는 C3-C6알케노일이거나;Or R 16 is (CH 2 CH 2 O) n H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 2 -C 8 alkanoyl or C 3 -C 6 alkenoyl ;
또는 R16은, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH, C1-C4알콕시 또는 C1-C4알킬술파닐에 의해 치환된 벤조일이거나;Or R 16 is benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH, C 1 -C 4 alkoxy or C 1 -C 4 alkylsulfanyl;
또는 R16은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, C1-C12알킬, C1-C4할로알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노, (CO)O(C1-C8알킬), (CO)-C1-C8알킬, (CO)N(C1-C8알킬)2 또는 에 의해 치환되고;Or R 16 is phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C 1 -C 12 alkyl, C 1 -C 4 haloalkyl, C 1 -C 12 alkoxy, CN, NO 2, phenyl, -C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkyl sulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2, diphenylamino, (CO ) O (C 1 -C 8 alkyl), (CO) -C 1 -C 8 alkyl, (CO) N (C 1 -C 8 alkyl) 2 or Lt; / RTI >
R17 및 R18은 서로 독립적으로 수소, C1-C20알킬, C2-C4히드록시알킬, C2-C10알콕시알킬, C2-C5알케닐, C3-C20시클로알킬, 페닐-C1-C3알킬, C1-C8알카노일, C1-C8알카노일옥시, C3-C12알케노일, SO2-(C1-C4할로알킬) 또는 벤조일이거나;R 17 and R 18 independently of one another are hydrogen, C 1 -C 20 alkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 5 alkenyl, C 3 -C 20 cycloalkyl , phenyl, -C 1 -C 3 alkyl, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, C 3 -C 12 alkenyl alkanoyl, SO 2 - (C 1 -C 4 haloalkyl), or benzoyl, or ;
또는 R17 및 R18은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, C1-C4할로알킬, C1-C20알콕시, C1-C12알킬, 벤조일 또는 C1-C12알콕시에 의해 치환되거나;Or R 17 and R 18 are phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C 1 -C 4 haloalkyl, C 1 -C 20 alkoxy, C 1 -C 12 alkyl, benzoyl or C 1 -C 12, or substituted by alkoxy;
또는 R17 및 R18은 이들이 부착되어 있는 N-원자와 함께, 비개재되거나 또는 O, S 또는 NR15이 개재된 5- 또는 6-원 포화 또는 불포화 고리를 형성하고, 상기 5- 또는 6-원 포화 또는 불포화 고리는 비치환되거나 또는 1개 이상의 C1-C20알킬, C1-C20알콕시, =O, OR15, SR16, NR19R20, (CO)R21, NO2, 할로겐, C1-C4-할로알킬, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR15이 개재된 C3-C20시클로알킬에 의해 치환되거나;Or R 17 and R 18 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR 15 , membered saturated or unsaturated ring is unsubstituted or substituted, or one or more C 1 -C 20 alkyl 1, C 1 -C 20 alkoxy, = O, oR 15, SR 16, NR 19 R 20, (CO) R 21, NO 2, Halogen, C 1 -C 4 -haloalkyl, CN, phenyl or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 15 ;
또는 R17 및 R18은 이들이 부착되어 있는 N-원자와 함께, 비치환되거나 또는 1개 이상의 C1-C20알킬, C1-C4할로알킬, C1-C20알콕시, =O, OR15, SR16, NR19R20, (CO)R21, 할로겐, NO2, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR15이 개재된 C3-C20시클로알킬에 의해 치환된 헤테로방향족 고리계를 형성하고;Or R 17 and R 18 together with the N-atom to which they are attached are unsubstituted or substituted by one or more C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 1 -C 20 alkoxy, ═O, OR 15, SR 16, NR 19 R 20, (CO) R 21, halogen, NO 2, CN, or sandwiched by a phenyl or a non-or at least one O, S, CO or NR 15 is a C 3 -C 20 interposed Form a heteroaromatic ring system substituted by cycloalkyl;
R19 및 R20은 서로 독립적으로 수소, C1-C20알킬, C1-C4할로알킬, C3-C10시클로알킬 또는 페닐이거나;R 19 and R 20 are independently of each other hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 3 -C 10 cycloalkyl or phenyl;
또는 R19 및 R20은 이들이 부착되어 있는 N-원자와 함께, 비개재되거나 또는 O, S 또는 NR23이 개재된 5- 또는 6-원 포화 또는 불포화 고리를 형성하고, 상기 5- 또는 6-원 포화 또는 불포화 고리는 축합되지 않거나 또는 상기5- 또는 6-원 포화 또는 불포화 고리에 벤젠 고리가 축합되고;Or R 19 and R 20 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR 23 , The unsubstituted or unsaturated rings are not condensed or the benzene ring is condensed to the 5- or 6-membered saturated or unsaturated ring;
R21은 수소, OH, C1-C20알킬, C1-C4할로알킬, 비개재되거나 또는 1개 이상의 O, CO 또는 NR24이 개재된 C2-C20알킬, 비개재되거나 또는 O, S, CO 또는 NR24이 개재된 C3-C20시클로알킬이거나,R 21 is hydrogen, OH, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl which is interrupted or interrupted by one or more O, CO or NR 24 , , S, CO or C 3 -C 20 cycloalkyl interrupted by NR 24 ,
또는 R21은 페닐, 나프틸, 페닐-C1-C4알킬, OR15, SR16 또는 NR19R20이고;Or R 21 is phenyl, naphthyl, phenyl-C 1 -C 4 alkyl, OR 15 , SR 16 or NR 19 R 20 ;
R22는 C6-C20아릴 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 페닐, 할로겐, C1-C4할로알킬, CN, NO2, OR15, SR16, NR17R18에 의해 또는 1개 이상의 O, S 또는 NR23이 개재된 C1-C20알킬에 의해 치환되거나, 또는 이들 각각은, 비치환되거나 또는 1개 이상의 할로겐, COOR15, CONR17R18, 페닐, C3-C8시클로알킬, C3-C20헤테로아릴, C6-C20아릴옥시카르보닐, C3-C20헤테로아릴옥시카르보닐, OR15, SR16 또는 NR17R18에 의해 치환된 1개 이상의 C1-C20알킬에 의해 치환되거나;R 22 is C 6 -C 20 aryl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C 1 -C 4 haloalkyl, CN, NO 2 , OR 15 , SR 16 , NR 17 R 18 , or C 1 -C 20 alkyl interrupted by one or more O, S or NR 23 , or each of which is unsubstituted or substituted by one or more of halogen, COOR 15 , CONR 17 R 18, phenyl, C 3 -C 8 cycloalkyl, C 3 -C 20 heteroaryl, C 6 -C 20 aryloxycarbonyl, C 3 -C 20 heteroaryloxy carbonyl, oR 15, SR 16 or NR 17 or more 1 substituted by R 18 C 1 -C 20 optionally substituted by alkyl;
또는 R22는 수소, 비치환되거나 또는 1개 이상의 할로겐, 페닐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-페닐, (CO)OH 또는 (CO)O(C1-C4알킬)에 의해 치환된 C1-C20알킬이거나;Or R 22 is hydrogen, unsubstituted or substituted by one or more halogen, phenyl, OH, SH, CN, C 3 -C 6 alkenyl-oxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - ( C 1 -C 4 alkyl), O (CO) - phenyl, (CO) OH or (CO) O (C 1 -C 4 alkyl) C 1 -C substituted by 20 alkyl;
또는 R22는 1개 이상의 O, S 또는 NR24가 개재된 C2-C12알킬이거나;Or R 22 is C 2 -C 12 alkyl interrupted by one or more O, S or NR 24 ;
또는 R22는 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C2-C12알케닐 또는 C3-C8시클로알킬이거나;Or R 22 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 2 -C 12 alkenyl or C 3 -C 8 Cycloalkyl;
또는 R22는 SR16에 의해 치환된 페닐이고, 여기서 라디칼 R16은 CO R22 기가 부착되어 있는 카르바졸 모이어티의 페닐 또는 나프틸 고리에 대한 직접 결합을 나타내고;Or R < 22 > is phenyl substituted by SR < 16 & gt ;, wherein the radical R < 16 > represents a direct bond to the phenyl or naphthyl ring of the carbazole moiety to which the CO R < 22 >
n은 1-20이고;n is 1-20;
R23은 수소, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O 또는 CO가 개재된 C2-C20알킬이거나, 또는 페닐-C1-C4알킬, 비개재되거나 또는 1개 이상의 O 또는 CO가 개재된 C3-C8시클로알킬이거나, 또는 (CO)R17이거나, 또는 비치환되거나 또는 1개 이상의 C1-C20알킬, 할로겐, C1-C4할로알킬, OR15, SR16, NR17R18 또는 에 의해 치환된 페닐이고;R 23 is hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl interrupted by one or more O or CO, or phenyl-C 1 -C 4 alkyl, Or C 3 -C 8 cycloalkyl interrupted by one or more O or CO, or (CO) R 17 , or is phenyl which is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, C 1 -C 4 halo alkyl, oR 15, SR 16, NR 17 R 18 or Lt; / RTI >;
R24는 수소, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O 또는 CO가 개재된 C2-C20알킬이거나, 또는 페닐-C1-C4알킬, 비개재되거나 또는 1개 이상의 O 또는 CO가 개재된 C3-C8시클로알킬이거나, 또는 (CO)R17이거나, 또는 비치환되거나 또는 1개 이상의 C1-C20알킬, 할로겐, C1-C4할로알킬, OR15, SR16, NR17R18 또는 에 의해 치환된 페닐이다.R 24 is hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl interrupted by one or more O or CO, or phenyl-C 1 -C 4 alkyl, Or C 3 -C 8 cycloalkyl optionally interrupted by one or more O or CO, or (CO) R 17 , or is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, C 1 -C 4 haloalkyl, OR 15 , SR 16 , NR 17 R 18 or Lt; / RTI >
상기 광중합 개시제는 상기 화학식 1에서 R1, R2, R3, R4는 서로 독립적으로 수소, C1-C20알킬, OR15, 할로겐, 또는 NO2인 화합물을 포함하는 것이 바람직하다.The photopolymerization initiator preferably includes a compound represented by Formula 1 wherein R 1 , R 2 , R 3 , and R 4 independently of one another are hydrogen, C 1 -C 20 alkyl, OR 15 , halogen, or NO 2 .
상기 광중합 개시제는 상기 화학식 에서 R1 및 R2, R2 및 R3, R3 및 R4는 서로 독립적으로 함께 으로서, 이들이 부착되어 있는 탄소 원자와 함께 6-원 고리를 형성하는 것인 화합물을 포함하는 것이 바람직하다.Wherein the photopolymerization initiator is represented by the formula: wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 are independently Together with the carbon atoms to which they are attached, form a 6-membered ring.
상기 광중합 개시제는 상기 화학식 1에서 R1, R2, R3, R4는 서로 독립적으로 수소, C1-C20알킬, OR15, 할로겐, 또는 NO2인 화합물; 및 R1 및 R2, R2 및 R3, R3 및 R4는 서로 독립적으로 함께 으로서, 이들이 부착되어 있는 탄소 원자와 함께 6-원 고리를 형성하는 것인 화합물;을 포함하는 것이 보다 바람직하다.Wherein the photopolymerization initiator is a compound wherein R 1 , R 2 , R 3 , and R 4 are independently of each other hydrogen, C 1 -C 20 alkyl, OR 15 , halogen, or NO 2 ; And R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , , Together with the carbon atoms to which they are attached, form a 6-membered ring.
이러한 광중합 개시제는 흑색 감광성 수지 조성물 총 중량에 대하여 0.01 내지 10 중량%, 바람직하게는 0.01 내지 5 중량%로 사용할 수 있다. 이러한 함량 범위는 광중합성 화합물의 광중합 속도 및 최종 얻어지는 도막의 물성을 고려한 것으로, 상기 범위 미만이면 중합 속도가 낮아 전체적인 공정 시간이 길어질 수 있으며, 반대로 상기 범위를 초과할 경우 과도한 반응에 의해 도막의 물성이 오히려 저하될 수 있기 때문에, 상기 범위 내에서 적절히 사용하는 것이 바람직하다.Such a photopolymerization initiator may be used in an amount of 0.01 to 10% by weight, preferably 0.01 to 5% by weight based on the total weight of the black photosensitive resin composition. Such a content range takes into account the photopolymerization rate of the photopolymerizable compound and the physical properties of the resulting coating film. When the amount is less than the above range, the polymerization rate is low and the overall process time may become long. On the other hand, It may be deteriorated. Therefore, it is preferable to use it appropriately within the above range.
나아가, 본 발명의 흑색 감광성 수지 조성물은 광중합 개시 보조제가 더 포함될 수 있으며, 바람직하게는 아민계 화합물 및 카르복실산계 화합물로 이루어진 군으로부터 선택되는 1종 이상의 화합물이 광중합 개시 보조제로 사용될 수 있다. Further, the black photosensitive resin composition of the present invention may further include a photopolymerization initiator, and preferably at least one compound selected from the group consisting of an amine compound and a carboxylic acid compound may be used as a photopolymerization initiator.
상기 아민계 화합물은, 예를 들면, 트리에탄올아민, 메틸디에탄올아민 및 트리이소프로판올아민 등의 지방족 아민 화합물; 4-디메틸아미노벤조산 메틸, 4-디메틸아미노벤조산 에틸, 4-디메틸아미노벤조산 이소아밀, 4-디메틸아미노벤조산 2-에틸헥실, 벤조산 2-디메틸아미노에틸, N,N-디메틸파라톨루이딘, 4,4'-비스(디메틸아미노)벤조페논 및 4,4'-비스(디에틸아미노)벤조페논 등의 방향족 아민 화합물; 등을 들 수 있으며, 이 중에서도 방향족 아민 화합물이 바람직하다. Examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine; 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4- Aromatic amine compounds such as bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone; Among them, aromatic amine compounds are preferable.
상기 카르복실산계 화합물은, 예를 들면, 페닐티오아세트산, 메틸페닐티오아세트산, 에틸페닐티오아세트산, 메틸에틸페닐티오아세트산, 디메틸페닐티오아세트산, 메톡시페닐티오아세트산, 디메톡시페닐티오아세트산, 클로로페닐티오아세트산, 디클로로페닐티오아세트산, N-페닐글리신, 페녹시아세트산, 나프틸티오아세트산, N-나프틸글리신 및 나프톡시아세트산 등의 방향족 헤테로아세트산류 등을 들 수 있다.The carboxylic acid compound may be, for example, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthio And aromatic heteroacetic acids such as acetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine and naphthoxyacetic acid.
이들 광중합 개시 보조제를 사용하는 경우, 광중합 개시제 1몰당 통상적으로 10몰 이하, 바람직하게는 0.01 내지 5몰의 범위 내에서 사용하는 것이 바람직하다. 상기의 범위에 있으면 흑색 감광성 수지 조성물의 감도가 더 높아지고, 이 조성물을 사용하여 형성되는 화소정의막의 생산성이 향상되는 경향이 있기 때문에 바람직하다.When these photopolymerization initiators are used, they are preferably used in an amount of usually not more than 10 mol, preferably 0.01 to 5 mol per mol of the photopolymerization initiator. Within the above range, the sensitivity of the black photosensitive resin composition is higher, and the productivity of the pixel defining layer formed using the composition tends to be improved, which is preferable.
본 발명의 흑색 감광성 수지 조성물의 한 실시형태에서, 흑색 감광성 수지 조성물은 착색제, 결합제 수지, 광중합성 화합물, 용제 및 첨가제로 이루어진 군으로부터 선택되는 1종 이상의 성분을 더 포함한다. 이하 이들 성분에 대해 구체적으로 설명한다.In one embodiment of the black photosensitive resin composition of the present invention, the black photosensitive resin composition further comprises at least one component selected from the group consisting of a colorant, a binder resin, a photopolymerizable compound, a solvent and an additive. Hereinafter, these components will be described in detail.
착색제coloring agent
본 발명에서 사용되는 착색제는 흑색 안료 또는 염료, 및 유기 안료 또는 염료로 이루어진 군으로부터 선택되는 1종 이상을 포함할 수 있다. The colorant used in the present invention may include at least one selected from the group consisting of black pigments or dyes, and organic pigments or dyes.
본 발명에서 사용되는 착색제는 흑색 안료 또는 염료와 같이 흑색 그 자체일 수도 있고, 여러 안료 또는 염료를 혼합하여 흑색을 얻을 수 있는 경우도 포함된다. 착색제는 가시광선에서 차광성이 존재한다면 특별히 제한되지 않는다.The colorant used in the present invention may be black itself such as a black pigment or a dye, or may be a black pigment obtained by mixing various pigments or dyes. The colorant is not particularly limited as long as light shielding property exists in visible light.
상기 흑색 안료로는, 특별한 제한 없이 공지된 것이 사용될 수 있으나, 구체적으로 아닐린 블랙, 락탐 블랙, 퍼릴렌 블랙, 카본블랙, 산화크롬, 산화철 및 티탄블랙 등이 사용될 수 있으며 이들은 1종 단독 또는 2종 이상의 조합으로 사용될 수 있다. 상기 카본 블랙으로는 채널 블랙, 퍼니스 블랙, 서멀 블랙, 램프 블랙 등을 들 수 있다.Specific examples of the black pigment include, but are not limited to, aniline black, lactam black, perylene black, carbon black, chromium oxide, iron oxide and titanium black. These can be used in combination. Examples of the carbon black include channel black, furnace black, thermal black and lamp black.
필요한 경우 전기 절연성을 위해 표면에 수지가 피복된 카본 블랙이 사용될 수 있다. 상기 수지가 피복된 카본 블랙은 수지가 피복되어 있지 않은 카본 블랙에 비해 도전성이 낮기 때문에, 블랙 매트릭스 또는 화소정의막 형성 시에 우수한 전기 절연성을 부여 할 수 있는 이점이 있다.Carbon black coated with a resin on its surface may be used for electrical insulation if necessary. Since the resin-coated carbon black has a lower conductivity than carbon black not coated with the resin, there is an advantage that excellent electrical insulation can be imparted at the time of forming the black matrix or the pixel defining layer.
착색제로 사용되는 흑색 안료 또는 염료, 및 유기 안료 또는 염료는 화소정의막에 요구되는 특성에 알맞게 함량을 조절할 수 있다. 상기 착색제는 상기 흑색 감광성 수지 조성물 전체 100중량%에 대하여 1 내지 50 중량%, 바람직하게는 5 내지 40 중량%으로 포함될 수 있다. 착색제의 함량이 상기 범위 미만인 경우 차광성이 충분하지 않으며, 상기 범위를 초과하는 경우 패터닝 후 얻어진 패턴의 품질이 저하될 우려가 있다.Black pigments or dyes used as colorants, and organic pigments or dyes can be adjusted in content to suit the properties required for the pixel definition film. The colorant may be contained in an amount of 1 to 50% by weight, preferably 5 to 40% by weight based on 100% by weight of the entire black photosensitive resin composition. When the content of the colorant is less than the above range, the light shielding property is not sufficient. If the content exceeds the above range, the quality of the pattern obtained after patterning may be deteriorated.
본 발명에 따른 흑색 감광성 수지 조성물은 이 외에도 당업계에서 통상적으로 사용되는 결합제 수지, 광중합성 화합물, 용제 및 첨가제로 이루어진 군에서 선택되는 1종 이상을 더 포함할 수 있다.The black photosensitive resin composition according to the present invention may further include at least one member selected from the group consisting of a binder resin, a photopolymerizable compound, a solvent, and additives commonly used in the art.
결합제 수지Binder resin
본 발명의 일 실시형태에 있어서, 결합제 수지는 하기 화학식 2의 화합물(이하, A1이라고 함)을 포함한 공중합 반응으로 얻어지는 공중합체를 포함할 수 있다.In one embodiment of the present invention, the binder resin may include a copolymer obtained by a copolymerization reaction including a compound represented by the following formula (hereinafter referred to as A1).
[화학식 2](2)
상기 화학식 2에서,In Formula 2,
R25는 수소원자; 또는 수산기로 치환 또는 비치환된 C1 내지 C4의 알킬기이고, R 25 represents a hydrogen atom; Or a C 1 to C 4 alkyl group substituted or unsubstituted with a hydroxyl group,
R26은 단순결합; 또는 헤테로 원자가 포함되거나 포함되지 않는 C1 내지 C20의 지방족 또는 방향족 탄화수소기이다.R 26 is a simple bond; Or a C 1 to C 20 aliphatic or aromatic hydrocarbon group containing or not containing a hetero atom.
본 발명에서 상기 알킬은 직쇄 또는 분지쇄일 수 있으며 예컨대, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸, tert-부틸, sec-부틸, 이들에 한정되지 않는다.In the present invention, the alkyl may be linear or branched and is not limited to, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and sec-butyl.
본 발명에서 헤테로 원자는 N, O 및 S로 이루어진 군으로부터 선택될 수 있다.In the present invention, the hetero atom may be selected from the group consisting of N, O and S.
본 발명에서 지방족 탄화수소기는 직쇄 지방족 탄화수소기와 분지쇄 지방족 탄화수소기, 포화 지방족 탄화수소기와 불포화 지방족 탄화수소기를 모두 포함할 수 있다. 예컨대, 메틸기, 에틸기, 노말-프로필기, 이소-프로필기, 노말-부틸기, sec-부틸기, 이소-부틸기, 터-부틸기, 펜틸기, 헥실기 등의 알킬기; 스티릴과 같은 이중결합을 갖는 알케닐기; 및 아세틸렌기와 같은 삼중결합을 갖는 알키닐기가 있으나, 이에만 한정되는 것은 아니다.In the present invention, the aliphatic hydrocarbon group may include both a straight chain aliphatic hydrocarbon group, a branched chain aliphatic hydrocarbon group, a saturated aliphatic hydrocarbon group and an unsaturated aliphatic hydrocarbon group. An alkyl group such as methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, iso-butyl group, tert-butyl group, pentyl group and hexyl group; An alkenyl group having a double bond such as styryl; And an alkynyl group having a triple bond such as an acetylene group, but the present invention is not limited thereto.
본 발명에서 방향족 탄화수소기는 예컨대, 페닐, 비페닐, 터페닐 등의 단환식 방향족환, 및 나프틸, 안트라세닐, 파이레닐, 페릴레닐등의 다환식 방향족환 등이 있으나, 이에만 한정되는 것은 아니다.Examples of the aromatic hydrocarbon group in the present invention include monocyclic aromatic rings such as phenyl, biphenyl and terphenyl, and polycyclic aromatic rings such as naphthyl, anthracenyl, pyrenyl, and perylenyl, and the like. no.
본 발명의 또 다른 실시형태에 있어서, 결합제 수지는 상기 화학식 2의 화합물(A1)과, 불포화 카르복실산 함유 단량체(이하, A2이라고 함); 및 상기 화학식 2의 화합물(A1) 및 불포화 카르복실산 함유 단량체(A2)와 공중합이 가능한 불포화 결합을 갖는 화합물(이하, A3이라고 함)로 이루어진 군으로부터 선택되는 1종 이상을 더 포함하여 공중합 반응으로 얻어지는 공중합체를 포함할 수 있다. In still another embodiment of the present invention, the binder resin comprises the compound (A1) of the above formula (2) and the unsaturated carboxylic acid-containing monomer (hereinafter referred to as A2); And a compound having an unsaturated bond capable of copolymerizing with the compound (A1) and the unsaturated carboxylic acid-containing monomer (A2) (hereinafter referred to as A3) of the formula (2) ≪ / RTI >
상기 결합제 수지(A)의 구성단위의 전체 몰수에 대한 상기 (A1)으로부터 유도되는 구성단위의 비율은 20 내지 90몰%인 것이 바람직하며, 더욱 바람직하게는 40 내지 70몰%로 포함될 수 있다. 상기 (A1)이 20몰% 미만으로 포함되는 경우에는 아웃가스 발생량을 감소시키는 효과가 부족해 지며, 90몰%를 초과하는 경우에는 현상액에 대한 용해도가 낮아져 패턴 형성이 어려운 문제가 발생되어 바람직하지 않다.The proportion of the structural unit derived from (A1) to the total number of the structural units of the binder resin (A) is preferably 20 to 90 mol%, more preferably 40 to 70 mol%. When the content of (A1) is less than 20 mol%, the effect of decreasing the outgassing amount is insufficient. When the content of (A1) is more than 90 mol%, the solubility in the developer is lowered, .
상기 결합제 수지(A)에 상기 (A2)가 함유되는 경우, 상기 결합제 수지(A)의 구성단위의 합계 몰수에 대한 상기 (A2)로부터 유도되는 구성단위의 비율은 0 초과 70몰% 이하인 것이 바람직하다. 상기 결합제 수지(A)에 상기 (A3)가 함유되는 경우, 상기 결합제 수지(A)의 구성단위의 합계 몰수에 대한 상기 (A3)로부터 유도되는 구성단위의 비율은 0 초과 70몰% 이하인 것이 바람직하다. 상기 (A2) 및 (A3)가 상기 범위 내로 포함될 경우, 현상액에 대한 용해도가 높아져 패턴 형성이 용이한 이점이 있으므로 바람직하다.When the binder resin (A) contains the above-mentioned (A2), the ratio of the constituent unit derived from the above (A2) to the total moles of the constituent units of the binder resin (A) is preferably from more than 0 to 70 mol% Do. When the binder resin (A) contains the above-mentioned (A3), the proportion of the structural unit derived from the above (A3) to the total mols of the constituent units of the binder resin (A) is preferably from more than 0 to 70 mol% Do. When the above-mentioned (A2) and (A3) are included within the above-mentioned range, the solubility in a developer is increased and pattern formation is facilitated, which is preferable.
상기 결합제 수지(A)는 광이나 열의 작용에 의한 반응성 및 알칼리 용해성을 가지며, 착색제를 비롯한 고형분의 분산매로서 작용하며, 결착 수지의 기능을 수행하는 것을 의미한다. The binder resin (A) has reactivity and alkali solubility due to the action of light or heat, and acts as a dispersion medium for solids such as a colorant, and functions as a binder resin.
상기 불포화 카르복실기 함유 단량체(A2)로는, 예를 들어, 불포화 모노카르복실산이나, 불포화 디카르복실산, 불포화 트리카르복실산 등의 분자 중에 1개 이상의 카르복실기를 갖는 불포화 카르복실산 등을 들 수 있다.Examples of the unsaturated carboxyl group-containing monomer (A2) include unsaturated carboxylic acids having at least one carboxyl group in the molecule such as unsaturated monocarboxylic acid, unsaturated dicarboxylic acid and unsaturated tricarboxylic acid. have.
상기 불포화 모노카르복실산으로는, 예를 들어, 아크릴산, 메타크릴산, 크로톤산, α-클로로아크릴산, 신남산 등을 들 수 있다Examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid,? -Chloroacrylic acid, cinnamic acid, and the like
상기 불포화 디카르복실산으로서는, 예를 들어, 말레산, 푸마르산, 이타콘산, 시트라콘산, 메사콘산 등을 들 수 있다.Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid.
상기 불포화 다가 카르복실산은 산무수물일수도 있으며, 구체적으로는 말레산 무수물, 이타콘산 무수물, 시트라콘산 무수물 등을 들 수 있다. 또한, 상기 불포화 다가 카르복실산은 그의 모노(2-메타크릴로일옥시알킬)에스테르일 수도 있으며, 예컨대, 숙신산모노(2-아크릴로일옥시에틸), 숙신산모노(2-메타크릴로일옥시에틸), 프탈산모노(2-아크릴로일옥시에틸), 프탈산모노(2-메타크릴로일옥시에틸) 등 일 수 있다. 상기 불포화 다가 카르복실산은 그 양말단 디카르복시중합체의 모노(메타)아크릴레이트일 수도 있으며, 예컨대, ω-카르복시폴리카프로락톤모노아크릴레이트, ω-카르복시폴리카프로락톤모노메타크릴레이트 등을 들수 있다.The unsaturated polycarboxylic acid may be an acid anhydride, and specific examples thereof include maleic anhydride, itaconic anhydride, citraconic anhydride and the like. The unsaturated polycarboxylic acid may also be mono (2-methacryloyloxyalkyl) ester thereof, and examples thereof include mono (2-acryloyloxyethyl) succinate, mono (2-methacryloyloxyethyl) ), Phthalic acid mono (2-acryloyloxyethyl), phthalic acid mono (2-methacryloyloxyethyl), and the like. The unsaturated polycarboxylic acid may be mono (meth) acrylate of the dicarboxylic polymer at both ends thereof, and examples thereof include ω-carboxypolycaprolactone monoacrylate and ω-carboxypolycaprolactone monomethacrylate.
상기 카르복실기 함유 단량체는 각각 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.The carboxyl group-containing monomers may be used alone or in combination of two or more.
상기 (A1) 및 (A2)와 공중합이 가능한 불포화 결합을 갖는 화합물(A3)로는, 예를 들면 스티렌, α-메틸스티렌, o-비닐톨루엔, m-비닐톨루엔, p-비닐톨루엔, p-클로로스티렌, o-메톡시스티렌, m-메톡시스티렌, p-메톡시스티렌, o-비닐벤질메틸에테르, m-비닐벤질메틸에테르, p-비닐벤질메틸에테르, o-비닐벤질글리시딜에테르,m-비닐벤질글리시딜에테르, p-비닐벤질글리시딜에테르, 인덴 등의 방향족 비닐 화합물; 메틸아크릴레이트, 메틸메타크릴레이트, 에틸아크릴레이트, 에틸메타크릴레이트, n-프로필아크릴레이트, n-프로필메타크릴레이트, i-프로필아크릴레이트, i-프로필메타크릴레이트, n-부틸아크릴레이트, n-부틸메타크릴레이트, i-부틸아크릴레이트, i-부틸메타크릴레이트, sec-부틸아크릴레이트, sec-부틸메타크릴레이트, t-부틸아크릴레이트, t-부틸메타크릴레이트, 2-히드록시에틸아크릴레이트, 2-히드록시에틸메타크릴레이트, 2-히드록시프로필아크릴레이트, 2-히드록시프로필메타크릴레이트, 3-히드록시프로필아크릴레이트, 3-히드록시프로필메타크릴레이트, 2-히드록시부틸아크릴레이트, 2-히드록시부틸메타크릴레이트, 3-히드록시부틸아크릴레이트, 3-히드록시부틸메타크릴레이트, 4-히드록시부틸아크릴레이트, 4-히드록시부틸메타크릴레이트, 알릴아크릴레이트, 알릴메타크릴레이트, 벤질아크릴레이트, 벤질메타크릴레이트, 시클로헥실아크릴레이트, 시클로헥실메타크릴레이트, 페닐아크릴레이트, 페닐메타크릴레이트, 2-메톡시에틸아크릴레이트, 2-메톡시에틸메타크릴레이트, 2-페녹시에틸아크릴레이트, 2-페녹시에틸메타크릴레이트, 메톡시디에틸렌글리콜아크릴레이트, 메톡시디에틸렌글리콜메타크릴레이트, 메톡시트리에틸렌글리콜아크릴레이트, 메톡시트리에틸렌글리콜메타크릴레이트, 메톡시프로필렌글리콜아크릴레이트, 메톡시프로필 렌글리콜메타크릴레이트, 메톡시디프로필렌글리콜아크릴레이트, 메톡시디프로필렌글리콜메타크릴레이트, 이소보르닐아크릴레이트, 이소보르닐메타크릴레이트, 디시클로펜타디에닐아크릴레이트, 디시클로펜타디에틸메타크릴레이트, 2-히드록시-3-페녹시프로필아크릴레이트, 2-히드록시-3-페녹시프로필메타크릴레이트, 글리세롤모노아크릴레이트, 글리세롤모노메타크릴레이트 등의 불포화 카르복실산 에스테르류; 2-아미노에틸아크릴레이트, 2-아미노에틸메타크릴레이트, 2-디메틸아미노에틸아크릴레이트, 2-디메틸아미노에틸메타크릴레이트, 2-아미노프로필아크릴레이트, 2-아미노프로필메타크릴레이트, 2-디메틸아미노프로필아크릴레이트, 2-디메틸아미노프로필메타크릴레이트, 3-아미노프로필아크릴레이트, 3-아미노프로필메타크릴레이트, 3-디메틸아미노프로필아크릴레이트, 3-디메틸아미노프로필메타크릴레이트 등의 불포화 카르복실산 아미노알킬에스테르류; 글리시딜아크릴레이트, 글리시딜메타크릴레이트 등의 불포화 카르복실산 글리시딜에스테르류; 아세트산비닐, 프로피온산비닐, 부티르산비닐, 벤조산비닐 등의 카르복실산 비닐에스테르류; 비닐메틸에테르, 비닐에틸에테르, 알릴글리시딜에테르 등의 불포화에테르류; 아크릴로니트릴, 메타크릴로니트릴, α-클로로아크릴로니트릴, 시안화비닐리덴 등의 시안화 비닐 화합물; 아크릴아미드, 메타크릴아미드, α-클로로아크릴아미드, N-2-히드록시에틸아크릴아미드, N-2-히드록시에틸메타크릴아미드 등의 불포화 아미드류; 말레이미드, N-페닐말레이미드. N-시클로헥실말레이미드 등의 불포화 이미드류; 1,3-부타디엔, 이소프렌, 클로로프렌 등의 지방족 공액 디엔류; 및 폴리스티렌, 폴리메틸아크릴레이트, 폴리메틸메타크릴레이트, 폴리-n-부틸아크릴레이트, 폴리-n-부틸메타크릴레이트, 폴리실록산의 중합체 분자쇄의 말단에 모노아크릴로일기 또는 모노메타크릴로일기를 갖는 거대 단량체류 등을 들 수 있다. 이들 단량체는 각각 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.Examples of the compound (A3) having an unsaturated bond capable of copolymerizing with the above-mentioned (A1) and (A2) include styrene,? -Methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, Styrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, aromatic vinyl compounds such as m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, and indene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, Ethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, Acrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl Methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxy diethylene glycol acrylate, methoxy diethylene glycol methacrylate, methoxy triethylene glycol acrylate, methoxy triethylene glycol methacrylate Acrylate, methoxypropylene glycol methacrylate, methoxypropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentane Dienyl acrylate, dicyclopentadiethyl methacrylate, 2-hydroxy-3-phenoxy Unsaturated carboxylic acid esters such as cyproxy acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate, and glycerol monomethacrylate; Aminoethyl methacrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2- Unsaturated carboxylates such as methyl acrylate, ethyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, Acid amino alkyl esters; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile,? -Chloroacrylonitrile, and vinylidene cyanide; Unsaturated amides such as acrylamide, methacrylamide,? -Chloroacrylamide, N-2-hydroxyethyl acrylamide and N-2-hydroxyethyl methacrylamide; Maleimide, N-phenylmaleimide. Unsaturated imides such as N-cyclohexylmaleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; And a monoacryloyl group or monomethacryloyl group at the end of the polymer molecular chain of polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, And the like. These monomers may be used alone or in combination of two or more.
상기 결합제 수지(A)는 흑색 감광성 수지 조성물 총 100중량%에 대하여 5 내지 80 중량%, 바람직하게는 5 내지 50 중량%으로 사용될 수 있다. 이러한 함량은 현상액에 대한 용해도와, 패턴 형성 등을 다각적으로 고려하여 선정된 범위로서, 상기 범위 내에서 사용할 경우 현상액에 대한 용해성이 충분하여 패턴 형성이 용이하며, 현상시에 노광부의 화소 부분의 막감소가 방지되어 비화소 부분의 누락성이 양호해진다.The binder resin (A) may be used in an amount of 5 to 80% by weight, preferably 5 to 50% by weight based on 100% by weight of the black photosensitive resin composition. Such a content is a range selected considering various factors such as solubility in a developing solution, pattern formation, etc. When used within the above range, solubility in a developing solution is sufficient and pattern formation is easy, So that the dropout of the non-pixel portion is improved.
또한, 본 발명의 또 다른 실시형태에 있어서, 결합제 수지는 당해 기술분야에서 일반적으로 사용되는 카도계 수지를 사용할 수 있다. 상기 카도계 수지는 구체적으로 비스(4-히드록시페닐)설폰, 비스(4-히드록시-3,5-디메틸페닐)설폰 및 비스(4-히드록시-3,5-디클로로페닐)설폰, 비스(4-히드록시페닐)헥사플루오로프로판, 비스(4-히드록시-3,5-디메틸페닐)헥사플루오로프로판 및 비스(4-히드록시-3,5-디클로로페닐)헥사플루오로프로판, 비스(4-히드록시페닐)디메틸실란, 비스(4-히드록시-3,5-디메틸페닐)디메틸실란 및 비스(4-히드록시-3,5-디클로로페닐)디메틸실란, 비스(4-히드록시페닐)메탄, 비스(4-히드록시-3,5-디클로로페틸)메탄 및 비스(4-히드록시-3,5-디브로모페닐)메탄, 2,2-비스(4-히드록시페닐)프로판, 2,2-비스(4-히드록시-3,5-디메틸페닐)프로판, 2,2-비스(4-히드록시-3,5-디클로로페닐)프로판, 2,2-비스(4-히드록시-3-메틸페닐)프로판 및 2,2-비스(4-히드록시-3-클로로페닐)프로판, 비스(4-히드록시페닐)에테르, 비스(4-히드록시-3,5-디메틸페닐)에테르 및 비스(4-히드록시-3,5-디클로페닐)에테르, 9,9-비스(4-히드록시페닐)플루오렌, 9,9-비스(4-히드록시-3-메틸페닐)플루오렌, 9,9-비스(4-히드록시-3-클로로페닐)플루오렌, 9,9-비스(4-히드록시-3-브로모페닐)플루오렌, 9,9-비스(4-히드록시-3-플루오로페닐)플루오렌, 9,9-비스(4-히드록시-3-메톡시페닐)플루오렌, 9,9-비스(4-히드록시-3,5-디메틸페닐)플루오렌, 9,9-비스(4-히드록시-3,5-디클로로페닐)플루오렌 및 9,9-비스(4-히드록시-3,5-디브로모페닐)플루오렌 등으로부터 얻어진 것일 수 있으나, 이에 한정되는 것은 아니다.Further, in another embodiment of the present invention, the binder resin may be a carded resin commonly used in the art. Specific examples of the cation resin include bis (4-hydroxyphenyl) sulfone, bis (4-hydroxy-3,5-dimethylphenyl) sulfone, bis (4-hydroxyphenyl) hexafluoropropane, bis (4-hydroxy-3,5-dimethylphenyl) hexafluoropropane and bis (4-hydroxy-3,5-dichlorophenyl) hexafluoropropane, Bis (4-hydroxyphenyl) dimethylsilane, bis (4-hydroxy-3,5-dimethylphenyl) dimethylsilane and bis Bis (4-hydroxyphenyl) methane, bis (4-hydroxy-3,5-dichlorophenyl) methane and bis Propane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 2,2- Propane and 2,2-bis (4-hydroxy-3-chlorophenyl) propane, bis (4-hydroxyphenyl) ) Ether, bis (4-hydroxy-3,5-dimethylphenyl) ether and bis (4-hydroxy-3,5-dichlorophenyl) ether, 9,9- , 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis Fluorophenyl) fluorene, 9,9-bis (4-hydroxy-3-fluorophenyl) fluorene, (4-hydroxy-3,5-dimethylphenyl) fluorene, 9,9-bis (4-hydroxy-3,5-dichlorophenyl) fluorene and 9,9- -3,5-dibromophenyl) fluorene, and the like, but the present invention is not limited thereto.
상기 카도계 수지가 결합제 수지로 사용되는 경우, 결합제 수지의 함량은 본 발명의 흑색 감광성 수지 조성물의 고형분 총 중량을 기준으로 바람직하게는 10 내지 80 중량%, 보다 바람직하게는 10 내지 70 중량%으로 사용될 수 있다. 상기 결합제 수지의 함량이 10 내지 80 중량% 범위를 만족하는 경우 현상액의 용해성이 충분하여 패턴 형성이 용이하며, 현상 시에 노광부의 화소 부분의 막 감소가 방지되어 비화소 부분의 누락성이 양호해지므로 바람직하다.When the cation resin is used as a binder resin, the content of the binder resin is preferably 10 to 80% by weight, more preferably 10 to 70% by weight, based on the total solid weight of the black photosensitive resin composition of the present invention Can be used. When the content of the binder resin is in the range of 10 to 80% by weight, the solubility of the developer is sufficient and the pattern formation is easy. In the development, the reduction of the film thickness of the pixel portion of the exposure portion is prevented, .
광중합성 화합물Photopolymerizable compound
광중합성 화합물은 특별히 한정되지 않으나, 카르복실기 함유 불포화 단량체의 중합체, 카르복실기 함유 불포화 단량체 및 그와 공중합 가능한 불포화 결합을 갖는 단량체와의 공중합체 및 이들의 조합으로 이루어진 군에서 선택된 1종 이상이 사용될 수 있다.The photopolymerizable compound is not particularly limited, but at least one selected from the group consisting of a polymer of a carboxyl group-containing unsaturated monomer, a copolymer of a carboxyl group-containing unsaturated monomer and a monomer having an unsaturated bond copolymerizable therewith, and a combination thereof can be used .
상기 카르복실기 함유 불포화 단량체로는 불포화 모노카르복실산, 불포화 디카르복실산, 불포화 트리카르복실산 등이 사용가능하다. 구체적으로, 불포화 모노카르복실산으로서는, 예를 들면 아크릴산, 메타크릴산, 크로톤산, ?-클로로아크릴산, 신남산 등을 들 수 있다. 불포화 디카르복실산으로서는, 예를 들면 푸마르산, 메사콘산, 이타콘산, 시트라콘산 등을 들 수 있다. 불포화 다가 카르복실산은 산무수물일 수도 있으며, 구체적으로는 말레산 무수물, 이타콘산 무수물, 시트라콘산 무수물 등을 들 수 있다. 또한, 불포화 다가 카르복실산은 ?-카르복시폴리카프로락톤모노(메타)아크릴레이트 등의 양 말단에 카르복실기와 수산기를 갖는 폴리머의 모노(메타)아크릴레이트류, 모노메틸말레인산, 5-노보넨-2-카르복실산, 모노-2-((메타)아크릴로일옥시)에틸프탈레이트, 모노-2-((메타)아크릴로일옥시)에틸숙시네이트 등이 가능하다. 이들 불포화 카르복실기를 갖는 화합물들은 각각 단독으로 또는 둘 이상을 조합하여 사용할 수 있으며, 그중 아크릴산 및 메타크릴산이 공중합 반응성 및 현상액에 대한 용해성이 우수하여 바람직하게 사용될 수 있다.As the carboxyl group-containing unsaturated monomer, unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, and unsaturated tricarboxylic acids can be used. Specific examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid,? -Chloroacrylic acid, cinnamic acid, and the like. Examples of the unsaturated dicarboxylic acid include fumaric acid, mesaconic acid, itaconic acid and citraconic acid. The unsaturated polycarboxylic acid may be an acid anhydride, and specific examples thereof include maleic anhydride, itaconic anhydride, citraconic anhydride and the like. Examples of the unsaturated polycarboxylic acid include mono (meth) acrylates, monomethyl maleic acid, 5-norbornene-2-one (meth) acrylate of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -Carboxypolycaprolactone mono (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, and the like. These unsaturated carboxyl group-containing compounds may be used singly or in combination of two or more thereof, and acrylic acid and methacrylic acid among them may be preferably used because of their excellent copolymerization reactivity and solubility in a developing solution.
또한, 카르복실기 함유 불포화 단량체와 공중합이 가능한 단량체로는 방향족 비닐 화합물, 불포화 카르복실레이트 화합물, 불포화 아미노알킬카르복실레이트 화합물, 비닐시아나이드 화합물, 불포화 옥세탄카르복실레이트 화합물 등이 사용될 수 있으며, 이들은 1종 단독으로 또한 2종 이상을 조합하여 사용할 수 있다.As the monomer capable of copolymerizing with the carboxyl group-containing unsaturated monomer, an aromatic vinyl compound, an unsaturated carboxylate compound, an unsaturated aminoalkyl carboxylate compound, a vinyl cyanide compound, and an unsaturated oxetanecarboxylate compound can be used. One kind may be used singly or two or more kinds may be used in combination.
구체적으로, 상기 공중합이 가능한 단량체로는 스티렌, ?-메틸스티렌, 비닐톨루엔 등의 방향족 비닐 화합물; 메틸아크릴레이트, 메틸메타크릴레이트, 에틸아크릴레이트, 에틸메타크릴레이트, 부틸아크릴레이트, 부틸메타크릴레이트, 2-히드록시에틸아크릴레이트, 2-히드록시에틸메타크릴레이트, 벤질아크릴레이트, 벤질메타크릴레이트 등의 불포화 카르복실레이트 화합물; 아미노에틸아크릴레이트 등의 불포화 아미노알킬카르복실레이트 화합물; 글리시딜메타크릴레이트 등의 불포화 글리시딜카르복실레이트 화합물; 비닐아세테이트, 비닐프로피오네이트 등의 비닐카르복실레이트 화합물; 아크릴로니트릴, 메타크릴로니트릴, ?-클로로아크릴로니트릴 등의 비닐시아나이드 화합물; 3-메틸-3-아크릴옥시메틸옥세탄, 3-메틸-3-메타크릴옥시메틸옥세탄, 3-에틸-3-아크릴옥시메틸옥세탄, 3-에틸-3-메타크릴옥시메틸옥세탄, 3-메틸-3-아크릴옥시에틸옥세탄, 3-메틸-3-메타크릴옥시에틸옥세탄, 3-메틸-3-아크릴옥시에틸옥세탄, 3-메틸-3-메타크릴옥시에틸옥세탄 등의 불포화 옥세탄카르복실레이트 화합물 등을 들 수 있다.Specifically, examples of the copolymerizable monomer include aromatic vinyl compounds such as styrene,? -Methylstyrene, and vinyltoluene; Acrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate, Unsaturated carboxylate compounds such as acrylate; Unsaturated aminoalkyl carboxylate compounds such as aminoethyl acrylate; Unsaturated glycidyl carboxylate compounds such as glycidyl methacrylate; Vinyl carboxylate compounds such as vinyl acetate and vinyl propionate; Vinylcyanide compounds such as acrylonitrile, methacrylonitrile and? -Chloroacrylonitrile; 3-methyl-3-acryloxymethyloxetane, 3-methyl-3-acryloxymethyloxetane, 3-methyl-3-methacryloxymethyloxetane, Methyl-3-acryloxyethyl oxetane, 3-methyl-3-acryloxyethyl oxetane, 3-methyl-3-methacryloxyethyl oxetane, Unsaturated oxetanecarboxylate compounds, and the like.
상기 예시한 불포화 카르복실기를 갖는 화합물들과 공중합 가능한 다른 단량체는 각각 단독으로 또는 둘 이상을 조합하여 사용할 수 있다. The above-exemplified monomers copolymerizable with the compounds having an unsaturated carboxyl group may be used alone or in combination of two or more thereof.
용제solvent
본 발명의 흑색 감광성 수지 조성물에 함유되는 용제는 특별히 제한되지 않으며 흑색 감광성 수지 조성물의 분야에서 사용되고 있는 각종 유기 용제를 사용할 수 있다. 그의 구체예로서는 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노프로필에테르,에틸렌글리콜모노부틸에테르 등의 에틸렌글리콜모노알킬에테르류, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜디프로필에테르, 디에틸렌글리콜디부틸에테르 등의 디에틸렌글리콜디알킬에테르류,메틸셀로솔브아세테이트, 에틸셀로솔브아세테이트 등의 에틸렌글리콜알킬에테르아세테이트류, 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트, 메톡시부틸아세테이트 및 메톡시펜틸아세테이트 등의 알킬렌글리콜알킬에테르아세테이트류, 벤젠, 톨루엔, 크실렌, 메시틸렌 등의 방향족 탄화수소류, 메틸에틸케톤, 아세톤, 메틸아밀케톤, 메틸이소부틸케톤, 시클로헥사논등의 케톤류, 에탄올, 프로판올, 부탄올, 헥사놀, 시클로헥산올, 에틸렌글리콜, 글리세린 등의 알코올류, 3-에톡시프로피온산 에틸, 3-메톡시프로피온산 메틸 등의 에스테르류, γ-부티롤락톤 등의 환상 에스테르류 등을 들수 있다. 상기의 용제 중, 도포성, 건조성면에서 바람직하게는 상기 용제 중에서 비점이 100℃ 내지 200℃인 유기 용제를 들 수 있고, 보다 바람직하게는 알킬렌글리콜알킬에테르아세테이트류, 케톤류, 3-에톡시프로피온산 에틸이나, 3-메톡시프로피온산 메틸 등의 에스테르류를 들 수 있으며, 더욱 바람직하게는 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 시클로헥사논, 3-에톡시프로피온산 에틸, 3-메톡시프로피온산 메틸 등을 들 수 있다. 이들 용제는 각각 단독으로 또는 2종류 이상 혼합하여 사용할 수 있다.The solvent contained in the black photosensitive resin composition of the present invention is not particularly limited and various organic solvents used in the field of the black photosensitive resin composition can be used. Specific examples thereof include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene Diethylene glycol dialkyl ethers such as diethylene glycol diethyl ether, glycol dipropyl ether and diethylene glycol dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, Alkylene glycol alkyl ether acetates such as monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, methyl ethyl ketone, acetone , Ketones such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin, ethyl 3-methoxypropionate, Esters such as methyl, and cyclic esters such as? -Butyrolactone. Among the above solvents, organic solvents having a boiling point of 100 占 폚 to 200 占 폚 in the solvent are preferably used from the viewpoint of coatability and dryness, more preferably alkylene glycol alkyl ether acetates, ketones, 3-ethoxy Propylene glycol monomethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, 3-ethoxypropionate, and 3-methoxypropionate are more preferable. Examples of the solvent include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, Methyl methoxypropionate, and the like. These solvents may be used alone or in combination of two or more.
상기 용제는 흑색 감광성 수지 조성물이 100 중량%를 만족하도록 잔량으로 포함될 수 있다. 이러한 함량은 조성의 분산 안정성 및 제조 공정에서의 공정 용이성(예, 도포성)을 고려하여 선정된 범위이다. The solvent may be contained in a balance such that the black photosensitive resin composition satisfies 100 wt%. Such a content is selected in consideration of dispersion stability of the composition and easiness of process in the production process (for example, applicability).
첨가제additive
본 발명의 흑색 감광성 수지 조성물에는 필요에 따라 충진제, 다른 고분자 화합물, 안료 분산제. 밀착 촉진제, 산화 방지제, 자외선 흡수제, 응집 방지제 등의 첨가제를 병행하는 것도 가능하다. In the black photosensitive resin composition of the present invention, filler, other polymer compound, pigment dispersant, An adhesion promoter, an antioxidant, an ultraviolet absorber, an anti-aggregation agent, and the like.
충진제의 구체적인 예는 유리, 실리카, 알루미나 등이 예시된다. 다른 고분자 화합물로서는 구체적으로 에폭시 수지, 말레이미드 수지 등의 경화성 수지, 폴리비닐알코올, 폴리아크릴산, 폴리에틸렌글리콜모노알킬에테르, 폴리플루오로알킬아크릴레이트, 폴리에스테르, 폴리우레탄 등의 열가소성 수지 등을 들 수 있다. 안료 분산제로서는 시판되는 계면 활성제를 이용할 수 있고, 예를 들면 실리콘계, 불소계, 에스테르계, 양이온계, 음이온계, 비이온계, 양성 등의 계면 활성제 등을 들 수 있다. 이들은 각각 단독으로 또는 2종 이상을 조합하여 사용될 수 있다. Specific examples of the filler include glass, silica, alumina and the like. Specific examples of other polymer compounds include curable resins such as epoxy resin and maleimide resin, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane have. As the pigment dispersant, commercially available surfactants can be used, and examples thereof include surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic, and amphoteric surfactants. These may be used alone or in combination of two or more.
상기의 계면 활성제로서, 예를 들면 폴리옥시에틸렌알킬에테르류, 폴리옥시에틸렌알킬페에테르류, 폴리에틸렌글리콜 디에스테르류, 소르비탄 지방상 에스테르류, 지방산 변성 폴리에스테르류, 3급아민 변성 폴리우레탄류, 폴리에틸렌이민류 등이 있으며 이외에, 상품명으로 KP(신에쯔 가가꾸 고교㈜ 제조), 폴리플로우(POLYFLOW)(교에이샤 가가꾸㈜ 제조), 에프톱(EFTOP)(토켐 프로덕츠사 제조), 메가팩(MEGAFAC)(다이닛본 잉크 가가꾸 고교㈜ 제조), 플로라드(Flourad)(스미또모 쓰리엠㈜ 제조), 아사히가드(Asahi guard), 서플(Surflon)(이상, 아사히 글라스㈜ 제조), 솔스퍼스(SOLSPERSE)(제네까㈜ 제조), EFKA(EFKA 케미칼스사 제조), PB 821(아지노모또㈜ 제조) 등을 들 수 있다. Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkylpethers, polyethylene glycol diesters, sorbitan fatty esters, fatty acid modified polyesters, tertiary amine modified polyurethanes (Manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by TOKEM PRODUCTS CO., LTD.), And polyethyleneimine, (Manufactured by Dainippon Ink and Chemicals, Inc.), Flourad (manufactured by Sumitomo 3M Limited), Asahi guard, Surflon (manufactured by Asahi Glass Co., Ltd.), Sol SOLSPERSE (manufactured by Genene), EFKA (manufactured by EFKA Chemical), PB 821 (manufactured by Ajinomoto), and the like.
밀착 촉진제로서, 예를 들면 비닐트리메톡시실란, 비닐트리에톡시실란, 비닐트리스(2-메톡시에톡시)실란, N-(2-아미노에틸)-3-아미노프로필메틸디메톡시실란, N-(2-아미노에틸)-3-아미노프로필트리메톡시실란, 3-아미노프로트리에톡시실란, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필메틸디메톡시실란, 2-(3,4-에폭시시클로헥실)에틸트리메톡시실란, 3-클로로프로필메틸디메톡시실란, 3-클로로프로필트리메톡시실란, 3-메타크릴옥시프로필트리메톡시실란, 3-머캅토프로필트리메톡시실란 등을 들 수 있다. 산화 방지제로서는 구체적으로 2,2'-티오비스(4-메틸-6-t-부틸페놀), 2,6-디-t-부틸-4-메틸페놀 등을 들 수 있다. Examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N Aminopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (2-aminoethyl) (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- Methoxysilane and the like. Specific examples of the antioxidant include 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.
자외선 흡수제로서는 구체적으로 2-(3-tert-부틸-2-히드록시-5-메틸페닐)-5-클로로벤조티리아졸, 알콕시벤조페논 등을 들 수 있다. Specific examples of the ultraviolet absorber include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.
응집 방지제로서는 구체적으로 폴리아크릴산 나트륨 등을 들 수 있다.Specific examples of the anti-aggregation agent include sodium polyacrylate.
상기 첨가제는 본 발명의 효과를 저해하지 않는 범위에서 당업자가 적절히 추가하여 사용이 가능하다.The additive can be suitably added and used by those skilled in the art within a range not hindering the effect of the present invention.
<표시장치><Display device>
본 발명의 다른 양태는, 상기 흑색 감광성 수지 조성물의 경화물을 포함하는 화소정의막을 포함하는 표시장치에 관한 것이다. 본 발명에 따른 표시장치는 유기발광소자 또는 양자점발광소자를 포함하는 표시장치를 포함할 수 있다.Another aspect of the present invention relates to a display device including a pixel defining layer including a cured product of the black photosensitive resin composition. The display device according to the present invention may include a display device including an organic light emitting device or a quantum dot light emitting device.
포토리쏘그래피 방법에 따른 화소정의막을 형성하는 통상의 패터닝 공정은 다음과 같은 단계를 포함하여 이루어진다:A typical patterning process for forming a pixel defining layer according to a photolithography method comprises the following steps:
a) 기판에 흑색 감광성 수지 조성물을 도포하는 단계;a) applying a black photosensitive resin composition to a substrate;
b) 용매를 건조하는 프리베이크 단계; b) prebaking step of drying the solvent;
c) 얻어진 피막 위에 포토 마스크를 대어 활성 광선을 조사해 노광부를 경화시키는 단계; c) applying a photomask onto the obtained film to irradiate an actinic ray to cure the exposed portion;
d) 알칼리 수용액을 이용하여 미노광부를 용해하는 현상 공정을 수행하는 단계; 및 d) performing a developing step of dissolving the unexposed portion using an aqueous alkali solution; And
e) 건조 및 포스트 베이크 수행단계e) drying and post-baking steps
상기 도포는 원하는 두께를 얻을 수 있도록 롤 코터, 스핀 코터, 슬릿 앤드 스핀 코터, 슬릿 코터(다이 코터라고도 하는 경우가 있음), 잉크젯 등의 도포 장치를 이용한 습식 코팅 방법에 의해 수행될 수 있다.The application may be performed by a wet coating method using a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater (which may be referred to as a die coater), an ink jet or the like so as to obtain a desired thickness.
프리베이크는 오븐, 핫 플레이트 등에 의해 가열함으로써 행해진다. 이때 프리베이크에 있어서의 가열 온도 및 가열 시간은 사용하는 용제에 따라 적의 선택 되어 예를 들면, 80 내지 150의 온도로 1 내지 30분간 행해진다.Prebaking is performed by heating with an oven, a hot plate or the like. At this time, the heating temperature and the heating time in the pre-baking are appropriately selected depending on the solvent to be used, for example, at a temperature of 80 to 150 for 1 to 30 minutes.
또 프리베이크 후에 행해지는 노광은, 노광기에 의해 행해져 포토 마스크를 통하여 노광함으로써 패턴에 대응한 부분만을 감광시킨다. 이때 조사하는 빛은, 예를 들면, 가시광선, 자외선, X선 및 전자선 등이 가능하다.The exposure performed after the pre-baking is performed by an exposure machine, and exposed through a photomask to expose only the portion corresponding to the pattern. The light to be irradiated may be, for example, visible light, ultraviolet light, X-ray, electron beam, or the like.
노광 후의 알칼리 현상 비노광 부분의 제거되지 않는 부분의 감광성 수지 조성물을 제거하는 목적으로 행해져 이 현상에 의해 원하는 패턴이 형성된다. 이 알칼리 현상에 적합한 현상액으로는, 예를 들면 알칼리 금속이나 알칼리 토류 금속의 탄산염의 수용액 등을 사용할 수 있다. 특히, 탄산나트륨, 탄산칼륨, 탄산 리튬등의 탄산염을 1~3 중량%를 함유하는 미만 알칼리 수용액을 이용하여 10~50℃, 바람직하게는 20~40℃의 온도 내에서 현상기 또는 초음파 세정기 등을 이용하여 수행한다.Alkali development after exposure is carried out for the purpose of removing the photosensitive resin composition in the portion where the non-exposed portion is not removed, and a desired pattern is formed by this development. As the developer suitable for the alkali development, for example, an aqueous solution of a carbonate of an alkali metal or an alkaline earth metal may be used. Particularly, a weakly alkaline aqueous solution containing 1 to 3% by weight of a carbonate such as sodium carbonate, potassium carbonate or lithium carbonate is used at a temperature of 10 to 50 ° C, preferably 20 to 40 ° C, using a developing machine or an ultrasonic cleaner .
포스트 베이크는 패터닝 된 막과 기판과의 밀착성을 높이기 위해서 수행하며, 80~220℃에서 10~120 분의 조건으로 열처리를 통해 이루어진다. 포스트 베이크 프리베이크와 같게, 오븐, 핫 플레이트 등을 이용하여 수행한다.The post bake is performed to enhance the adhesion between the patterned film and the substrate, and is performed by heat treatment at 80 to 220 ° C for 10 to 120 minutes. Post-baking Pre-baking is carried out using an oven, hot plate or the like.
본 발명의 흑색 감광성 수지 조성물로 제조된 화소정의막은 광학밀도, 밀착성, 전기 절연성, 차광성 등의 물성이 우수할 뿐만 아니라, 내열성 및 내용제성 등이 우수하여 유기발광소자, 양자점발광소자, 및 상기 유기발광소자 또는 양자점발광소자를 포함하는 표시 장치의 신뢰도를 향상시킬 수 있다.The pixel defining layer made of the black photosensitive resin composition of the present invention is excellent in physical properties such as optical density, adhesion, electrical insulating property and light shielding property, and is excellent in heat resistance and solvent resistance and can be used for an organic light emitting device, a quantum dot light emitting device, The reliability of the display device including the organic light emitting element or the quantum dot light emitting element can be improved.
이하, 본 발명을 구체적으로 설명하기 위해 실시예를 들어 상세히 설명한다. 그러나, 본 발명에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지는 않는다. 본 발명의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 발명을 보다 완전하게 설명하기 위해 제공되는 것이다. 또한, 이하에서 함유량을 나타내는 "%" 및 "부"는 특별히 언급하지 않는 한 중량 기준이다.Hereinafter, the present invention will be described in detail by way of examples with reference to the following examples. However, the embodiments according to the present invention can be modified into various other forms, and the scope of the present invention is not construed as being limited to the above-described embodiments. Embodiments of the invention are provided to more fully describe the present invention to those skilled in the art. In the following, "%" and "part" representing the content are by weight unless otherwise specified.
제조예: 결합제 수지 A의 합성Preparation Example: Synthesis of Binder Resin A
교반기, 온도계 환류 냉각관, 적하 로트 및 질소 도입관을 구비한 플라스크를 준비하였다. 모노머 적하 로트로서, 3,4-에폭시트리시클로데칸-8-일(메타)아크릴레이트와 3,4-에폭시트리시클로데칸-9-일(메타)아크릴레이트를 몰비 50:50으로 혼합한 혼합물 20부, 아크릴산 30부, 시클로헥실말레이미드 80부, 2-히드록시메타크릴레이트 70부 t-부틸퍼옥시-2-에틸헥사노에이트 4부, 프로필렌글리콜모노메틸에테르아세테이트(PGMEA) 40부를 첨가하여 교반을 준비하였다. 연쇄이동제 적하조로서, n-도데칸티올 6부, PGMEA 24부를 첨가하여 교반을 준비하였다. 이후 플라스크에 PGMEA 395부를 첨가하고 플라스크내 분위기를 공기에서 질소로 교환한 후 교반하면서 플라스크의 온도를 90까지 승온시켰다. 그 후 모노머 및 연쇄 이동제를 적하 로트로부터 적하를 개시하였다. 적하는 90를 유지하면서, 각각 2 시간 동안 진행하였고 1 시간 후에 110까지 승온하여 5 시간동안 유지하여 고형분 산가가 100㎎KOH/g인 수지를 얻었다. GPC에 의해 측정한 폴리스티렌 환산의 중량평균분자량은 10,100이고, 분자량 분포(Mw/Mn)는 2.2이었다.A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was prepared. As a monomer dropping lot, a mixture 20 of 3,4-epoxytricyclodecan-8-yl (meth) acrylate and 3,4-epoxytricyclodecan-9-yl (meth) acrylate in a molar ratio of 50:50 , 30 parts of acrylic acid, 80 parts of cyclohexylmaleimide, 70 parts of 2-hydroxymethacrylate, 4 parts of t-butylperoxy-2-ethylhexanoate and 40 parts of propylene glycol monomethyl ether acetate (PGMEA) Stirring was prepared. As a chain transfer agent, 6 parts of n-dodecanethiol and 24 parts of PGMEA were added and stirred. Then 395 parts of PGMEA was added to the flask, and the atmosphere in the flask was replaced with nitrogen in air, and the temperature of the flask was raised to 90 while stirring. The monomer and the chain transfer agent were then started to be added dropwise from the dropping funnel. The mixture was allowed to stand for 2 hours each while maintaining the temperature of 90 ° C. After 1 hour, the temperature was elevated to 110 and maintained for 5 hours to obtain a resin having a solid acid value of 100 mgKOH / g. The weight average molecular weight in terms of polystyrene measured by GPC was 10,100 and the molecular weight distribution (Mw / Mn) was 2.2.
실시예 1 내지 3 및 비교예 1 내지 3: 흑색 감광성 수지 조성물의 제조Examples 1 to 3 and Comparative Examples 1 to 3: Preparation of black photosensitive resin composition
하기 표 1에 기재된 조성 및 함량으로 흑색 감광성 수지 조성물을 제조하였다.A black photosensitive resin composition was prepared according to the compositions and contents shown in Table 1 below.
2) 결합제 수지A
3) 디펜타에리트리톨헥사아크릴레이트(Kayarad DPHA: 닛본 카야꾸㈜))
4) 개시제 1: Irgacure OXE03(Basf사 제)
개시제 2: NCI-831 (Adeka사 제)
개시제 3: 옥심계 화합물, Irgacure 0XE01 (Basf사 제)
개시제 4: 비스아실포스핀계 화합물, Irgacure-819 (Basf사 제)
개시제 5: 아세토페논계 화합물, Irgacure-907 (Basf사 제)
5) 프로필렌글리콜모노메틸에테르아세테이트
6) 안료 분산제 (폴리에스테르계)1) carbon black
2) Binder Resin A
3) Dipentaerythritol hexaacrylate (Kayarad DPHA: Nippon Kayaku Co., Ltd.))
4) Initiator 1: Irgacure OXE03 (manufactured by Basf)
Initiator 2: NCI-831 (manufactured by Adeka)
Initiator 3: Oxime compound, Irgacure 0XE01 (manufactured by Basf)
Initiator 4: Bisacylphosphine-based compound, Irgacure-819 (manufactured by Basf)
Initiator 5: Acetophenone compound, Irgacure-907 (manufactured by Basf)
5) Propylene glycol monomethyl ether acetate
6) Pigment dispersant (polyester type)
상기 표 1에 기재된 각 성분 중, 미리 착색 재료인 안료 및 첨가제인 안료 분산제의 합계량이 안료, 안료 분산제 및 프로필렌글리콜모노메틸에테르아세테이트의 혼합물에 대하여 20질량%가 되도록 혼합하여 비드 밀을 이용하여 안료를 충분히 분산시킨 후 비드 밀을 분리하고, 프로필렌글리콜모노메틸에테르아세테이트의 잔량을 포함하는 나머지 성분을 더 첨가하고 혼합하여 착색 감광성 수지 조성물을 얻었다.Among the components listed in Table 1, the pigment and the pigment dispersant, which were previously used as the coloring material, were mixed so as to be 20 mass% with respect to the mixture of the pigment, the pigment dispersant and the propylene glycol monomethyl ether acetate, The bead mill was separated, and the remaining components including the remaining amount of propylene glycol monomethyl ether acetate were further added and mixed to obtain a colored photosensitive resin composition.
실험예: 아웃가스 특성 평가Experimental Example: Evaluation of outgas characteristics
(1) 착색 기판 제작(1) Preparation of colored substrate
5cm X 5cm의 유리기판(코닝社)을 중성세제 및 물로 세정 후 건조하였다. 상기 유리기판 상에 상기 실시예 및 비교예에서 제조된 흑색 감광성 수지 조성물 각각을 최종 막 두께가 1.5㎛가 되도록 스핀 코팅을 하고, 80 내지 120℃에서 선 소성하여 1 내지 2분간 건조하여 용제를 제거하였다. 그런 다음, 노광량 40 내지 100 mJ/cm2로 노광하여 1cm X 3cm 패턴을 형성하고 알카리 수용액을 사용하여 비노광부를 제거하였다. 이어서 220℃에서 후 소성을 20분간 하여 착색기판을 제조하였다.A 5 cm x 5 cm glass substrate (Corning) was cleaned with a neutral detergent and water and dried. Each of the black photosensitive resin compositions prepared in the above Examples and Comparative Examples was spin-coated on the glass substrate to a final film thickness of 1.5 탆, prebaked at 80 to 120 캜 and dried for 1 to 2 minutes to remove the solvent Respectively. Then, exposure was performed at an exposure dose of 40 to 100 mJ / cm 2 to form a 1 cm x 3 cm pattern, and an unexposed area was removed using an aqueous alkaline solution. Subsequently, the substrate was baked at 220 캜 for 20 minutes to prepare a colored substrate.
(2) 아웃가스 평가(2) Outgassing evaluation
아웃가스 평가는 상기에서 제조된 착색기판을 230℃에서 30분간 열분해시키면서 포집된 화합물을 Py-GC/MS로 분석하는 방법으로 실시되었다. 분석결과는 하기 표 2에 나타내었다.The outgassing was carried out by pyrolyzing the colored substrate prepared above at 230 DEG C for 30 minutes and analyzing the collected compound by Py-GC / MS. The results of the analysis are shown in Table 2 below.
상기 표 2에서 확인되는 바와 같이, 본 발명에 따른 흑색 감광성 수지 조성물인 실시예 1 내지 3를 이용하여 제조한 경우, 비교예 1 내지 3에 따른 감광성 수지 조성물을 이용하여 제조한 경우에 비하여 용출되는 아웃가스량이 현저히 감소하였다.As can be seen from the above Table 2, when the black photosensitive resin compositions according to the present invention were produced using the photosensitive resin compositions according to Examples 1 to 3, the photosensitive resin composition according to Comparative Examples 1 to 3 was eluted The amount of outgas decreased significantly.
Claims (15)
상기 광중합 개시제가 하기 화학식 1로 표시되는 화합물로 이루어진 군으로부터 선택되는 1종 이상을 포함하는 흑색 감광성 수지 조성물:
[화학식 1]
상기 화학식 1에서,
R1, R2, R3, R4는 서로 독립적으로 수소, C1-C20알킬, OR15, 할로겐, 또는 NO2이거나;
또는 R1 및 R2, R2 및 R3, R3 및 R4는 서로 독립적으로 함께 으로서, 이들이 부착되어 있는 탄소 원자와 함께 6-원 고리를 형성하고;
R11, R12, R13, R14는 서로 독립적으로 수소, 비치환되거나 또는 1개 이상의 할로겐, 페닐, CN, OH, SH, C1-C4-알콕시, (CO)OH에 의해 또는 (CO)O(C1-C4알킬)에 의해 치환된 C1-C20알킬이거나;
또는 R11, R12, R13, R14는 서로 독립적으로 비치환된 페닐 또는 1개 이상의 C1-C6알킬, 할로겐, CN, OR15에 의해 또는 NR17R18에 의해 치환된 페닐이거나;
또는 R11, R12, R13, R14는 서로 독립적으로 할로겐, CN, OR15, SR16, SOR16, SO2R16 또는 NR17R18이고, 여기서 치환기 OR15, SR16 또는 NR17R18은 임의로 나프틸 고리의 탄소 원자 중 1개와 함께 라디칼 R15, R16, R17 및/또는 R18을 통해 5- 또는 6-원 고리를 형성하고;
R5는, 비치환되거나 또는 1개 이상의 할로겐, R15, COOR15, OR15, SR16, CONR17R18, NR17R18에 의해 치환된 C1-C20알킬이거나;
또는 R5는 1개 이상의 O, S, SO, SO2, NR23 또는 CO가 개재된 C2-C20알킬이거나,
또는 비개재되거나 또는 1개 이상의 O, CO 또는 NR23이 개재된 C2-C12알케닐이고,
여기서 개재된 C2-C20알킬 및 비개재 또는 개재된 C2-C12알케닐은 비치환되거나 또는 1개 이상의 할로겐에 의해 치환되거나;
또는 R5는 C4-C8시클로알케닐, C2-C12알키닐, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C10시클로알킬이거나;
또는 R5는 페닐 또는 나프틸이고, 이들 각각은 비치환되거나 또는 1개 이상의 OR15, SR16, NR17R18, COR22, CN, NO2, 할로겐, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O, S, CO 또는 NR23이 개재된 C2-C20알킬에 의해 치환되거나, 또는 이들 각각은 C3-C10시클로알킬에 의해 또는 1개 이상의 O, S, CO 또는 NR24이 개재된 C3-C10시클로알킬에 의해 치환되고;
R6, R7, R8, R9, R10은 수소, 페닐-C1-C3알킬, 비치환되거나 또는 1개 이상의 할로겐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-페닐, (CO)OH, (CO)O(C1-C4알킬), C3-C20시클로알킬, SO2-(C1-C4할로알킬), O(C1-C4할로알킬)에 의해 또는 1개 이상의 O가 개재된 C3-C20시클로알킬에 의해 치환된 C1-C20알킬이거나;
또는 R6, R7, R8, R9, R10은 1개 이상의 O, S 또는 NR24이 개재된 C2-C20알킬이거나;
또는 R6, R7, R8, R9, R10은 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C1-C8알카노일, C2-C12알케닐, C3-C6알케노일, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C20시클로알킬이거나;
또는 R6, R7, R8, R9, R10은, 비개재되거나 또는 1개 이상의 O가 개재된 C1-C8알킬-C3-C10시클로알킬이거나;
또는 R6, R7, R8, R9, R10은, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH 또는 C1-C3알콕시에 의해 치환된 벤조일이거나;
또는 R6, R7, R8, R9, R10은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, OH, C1-C12알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노에 의해 치환되고;
R15는 수소, 페닐-C1-C3알킬, 비치환되거나 또는 1개 이상의 할로겐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-페닐, (CO)OH, (CO)O(C1-C4알킬), C3-C20시클로알킬, SO2-(C1-C4할로알킬), O(C1-C4할로알킬)에 의해 또는 1개 이상의 O가 개재된 C3-C20시클로알킬에의해 치환된 C1-C20알킬이거나;
또는 R15는 1개 이상의 O, S 또는 NR23이 개재된 C2-C20알킬이거나;
또는 R15는 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C1-C8알카노일, C2-C12알케닐, C3-C6알케노일, 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR23이 개재된 C3-C20시클로알킬이거나;
또는 R15는, 비개재되거나 또는 1개 이상의 O가 개재된 C1-C8알킬-C3-C10시클로알킬이거나;
또는 R15는, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH 또는 C1-C3알콕시에 의해 치환된 벤조일이거나;
또는 R15는 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, OH, C1-C12알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노 또는 에 의해 치환되고;
R16은 수소, C2-C12알케닐, C3-C20시클로알킬 또는 페닐-C1-C3알킬이고, 여기서 C2-C12알케닐, C3-C20시클로알킬 또는 페닐-C1-C3알킬은 비개재되거나 또는 1개 이상의 O, S, CO, NR23 또는 COOR15가 개재되거나;
또는 R16은, 비치환되거나 또는 1개 이상의 OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C2-C4)알케닐, O(CO)-(C1-C4알킬), O(CO)-페닐 또는 (CO)OR15에 의해 치환된 C1-C20알킬이거나;
또는 R16은 1개 이상의 O, S, CO, NR23 또는 COOR15이 개재된 C2-C20알킬이거나;
또는 R16은 (CH2CH2O)nH, (CH2CH2O)n(CO)-(C1-C8알킬), C2-C8알카노일 또는 C3-C6알케노일이거나;
또는 R16은, 비치환되거나 또는 1개 이상의 C1-C6알킬, 할로겐, OH, C1-C4알콕시 또는 C1-C4알킬술파닐에 의해 치환된 벤조일이거나;
또는 R16은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, C1-C12알킬, C1-C4할로알킬, C1-C12알콕시, CN, NO2, 페닐-C1-C3알킬옥시, 페녹시, C1-C12알킬술파닐, 페닐술파닐, N(C1-C12알킬)2, 디페닐아미노, (CO)O(C1-C8알킬), (CO)-C1-C8알킬, (CO)N(C1-C8알킬)2 또는 에 의해 치환되고;
R17 및 R18은 서로 독립적으로 수소, C1-C20알킬, C2-C4히드록시알킬, C2-C10알콕시알킬, C2-C5알케닐, C3-C20시클로알킬, 페닐-C1-C3알킬, C1-C8알카노일, C1-C8알카노일옥시, C3-C12알케노일, SO2-(C1-C4할로알킬) 또는 벤조일이거나;
또는 R17 및 R18은 페닐, 나프틸 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 할로겐, C1-C4할로알킬, C1-C20알콕시, C1-C12알킬, 벤조일 또는 C1-C12알콕시에 의해 치환되거나;
또는 R17 및 R18은 이들이 부착되어 있는 N-원자와 함께, 비개재되거나 또는 O, S 또는 NR15이 개재된 5- 또는 6-원 포화 또는 불포화 고리를 형성하고, 상기 5- 또는 6-원 포화 또는 불포화 고리는 비치환되거나 또는 1개 이상의 C1-C20알킬, C1-C20알콕시, =O, OR15, SR16, NR19R20, (CO)R21, NO2, 할로겐, C1-C4-할로알킬, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR15이 개재된 C3-C20시클로알킬에 의해 치환되거나;
또는 R17 및 R18은 이들이 부착되어 있는 N-원자와 함께, 비치환되거나 또는 1개 이상의 C1-C20알킬, C1-C4할로알킬, C1-C20알콕시, =O, OR15, SR16, NR19R20, (CO)R21, 할로겐, NO2, CN, 페닐에 의해 또는 비개재되거나 또는 1개 이상의 O, S, CO 또는 NR15이 개재된 C3-C20시클로알킬에 의해 치환된 헤테로방향족 고리계를 형성하고;
R19 및 R20은 서로 독립적으로 수소, C1-C20알킬, C1-C4할로알킬, C3-C10시클로알킬 또는 페닐이거나;
또는 R19 및 R20은 이들이 부착되어 있는 N-원자와 함께, 비개재되거나 또는 O, S 또는 NR23이 개재된 5- 또는 6-원 포화 또는 불포화 고리를 형성하고, 상기 5- 또는 6-원 포화 또는 불포화 고리는 축합되지 않거나 또는 상기5- 또는 6-원 포화 또는 불포화 고리에 벤젠 고리가 축합되고;
R21은 수소, OH, C1-C20알킬, C1-C4할로알킬, 비개재되거나 또는 1개 이상의 O, CO 또는 NR24이 개재된 C2-C20알킬, 비개재되거나 또는 O, S, CO 또는 NR24이 개재된 C3-C20시클로알킬이거나,
또는 R21은 페닐, 나프틸, 페닐-C1-C4알킬, OR15, SR16 또는 NR19R20이고;
R22는 C6-C20아릴 또는 C3-C20헤테로아릴이고, 이들 각각은 비치환되거나 또는 1개 이상의 페닐, 할로겐, C1-C4할로알킬, CN, NO2, OR15, SR16, NR17R18에 의해 또는 1개 이상의 O, S 또는 NR23이 개재된 C1-C20알킬에 의해 치환되거나, 또는 이들 각각은, 비치환되거나 또는 1개 이상의 할로겐, COOR15, CONR17R18, 페닐, C3-C8시클로알킬, C3-C20헤테로아릴, C6-C20아릴옥시카르보닐, C3-C20헤테로아릴옥시카르보닐, OR15, SR16 또는 NR17R18에 의해 치환된 1개 이상의 C1-C20알킬에 의해 치환되거나;
또는 R22는 수소, 비치환되거나 또는 1개 이상의 할로겐, 페닐, OH, SH, CN, C3-C6알켄옥시, OCH2CH2CN, OCH2CH2(CO)O(C1-C4알킬), O(CO)-(C1-C4알킬), O(CO)-페닐, (CO)OH 또는 (CO)O(C1-C4알킬)에 의해 치환된 C1-C20알킬이거나;
또는 R22는 1개 이상의 O, S 또는 NR24가 개재된 C2-C12알킬이거나;
또는 R22는 (CH2CH2O)n+1H, (CH2CH2O)n(CO)-(C1-C8알킬), C2-C12알케닐 또는 C3-C8시클로알킬이거나;
또는 R22는 SR16에 의해 치환된 페닐이고, 여기서 라디칼 R16은 CO R22 기가 부착되어 있는 카르바졸 모이어티의 페닐 또는 나프틸 고리에 대한 직접 결합을 나타내고;
n은 1-20이고;
R23은 수소, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O 또는 CO가 개재된 C2-C20알킬이거나, 또는 페닐-C1-C4알킬, 비개재되거나 또는 1개 이상의 O 또는 CO가 개재된 C3-C8시클로알킬이거나, 또는 (CO)R17이거나, 또는 비치환되거나 또는 1개 이상의 C1-C20알킬, 할로겐, C1-C4할로알킬, OR15, SR16, NR17R18 또는 에 의해 치환된 페닐이고;
R24는 수소, C1-C20알킬, C1-C4할로알킬, 1개 이상의 O 또는 CO가 개재된 C2-C20알킬이거나, 또는 페닐-C1-C4알킬, 비개재되거나 또는 1개 이상의 O 또는 CO가 개재된 C3-C8시클로알킬이거나, 또는 (CO)R17이거나, 또는 비치환되거나 또는 1개 이상의 C1-C20알킬, 할로겐, C1-C4할로알킬, OR15, SR16, NR17R18 또는 에 의해 치환된 페닐이다.A colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent,
Wherein the photopolymerization initiator comprises at least one compound selected from the group consisting of compounds represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
R 1 , R 2 , R 3 and R 4 independently of one another are hydrogen, C 1 -C 20 alkyl, OR 15 , halogen, or NO 2 ;
Or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , Together with the carbon atoms to which they are attached form a 6-membered ring;
R 11 , R 12 , R 13 and R 14 are each independently of the other hydrogen, unsubstituted or substituted by one or more halogen, phenyl, CN, OH, SH, C 1 -C 4 -alkoxy, CO) O (C 1 -C 4 alkyl) in the substituted C 1 -C 20 alkyl, or by;
Or R 11 , R 12 , R 13 and R 14 are independently of each other unsubstituted phenyl or phenyl substituted by one or more C 1 -C 6 alkyl, halogen, CN, OR 15 or NR 17 R 18 ;
Or R 11 , R 12 , R 13 and R 14 independently of one another are halogen, CN, OR 15 , SR 16 , SOR 16 , SO 2 R 16 or NR 17 R 18 in which substituents OR 15 , SR 16 or NR 17 R 18 together with one of the carbon atoms of the naphthyl ring optionally form a 5- or 6-membered ring via the radicals R 15 , R 16 , R 17 and / or R 18 ;
R 5 is C 1 -C 20 alkyl unsubstituted or substituted by one or more halogens, R 15 , COOR 15 , OR 15 , SR 16 , CONR 17 R 18 , NR 17 R 18 ;
Or R 5 is C 2 -C 20 alkyl interrupted by one or more O, S, SO, SO 2 , NR 23 or CO,
Or a non-intervening or one or more O, CO or NR 23 is a C2-C12 alkenyl interposed,
Wherein the intervening C 2 -C 20 alkyl and the non-interrupted or interrupted C 2 -C 12 alkenyl are unsubstituted or substituted by one or more halogens;
Or R 5 is C 4 -C 8 cycloalkenyl, C 2 -C 12 alkynyl, or C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
Or R 5 is phenyl or naphthyl each of which is unsubstituted or substituted by one or more of OR 15 , SR 16 , NR 17 R 18 , COR 22 , CN, NO 2 , halogen, C 1 -C 20 alkyl, C 1 C 4 haloalkyl, C 2 -C 20 alkyl substituted with one or more O, S, CO or NR 23 , or each of which may be substituted by C 3 -C 10 cycloalkyl or by one or more O, S, CO, or NR 24 is interposed a C 3 -C 10 cycloalkyl which is substituted by alkyl;
R 6 , R 7 , R 8 , R 9 and R 10 are independently selected from hydrogen, phenyl-C 1 -C 3 alkyl, unsubstituted or substituted with one or more of halogen, OH, SH, CN, C 3 -C 6 alkenoxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - ( C 1 -C 4 alkyl), O (CO) - ( C 2 -C 4) alkenyl (C 1 -C 4 alkyl), C 3 -C 20 cycloalkyl, SO 2 - (C 1 -C 4 haloalkyl), O (C) -C 1 -C 4 haloalkyl), or C 1 -C 20 alkyl substituted by one or more O interrupted C 3 -C 20 cycloalkyl;
Or R 6 , R 7 , R 8 , R 9 , R 10 are C 2 -C 20 alkyl interrupted by one or more O, S or NR 24 ;
Or R 6, R 7, R 8 , R 9, R 10 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C C 1 -C 8 alkanoyl, C 2 -C 12 alkenyl, C 3 -C 6 alkenoyl, or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
Or R 6 , R 7 , R 8 , R 9 , R 10 are C 1 -C 8 alkyl-C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O;
Or R 6 , R 7 , R 8 , R 9 , R 10 are benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH or C 1 -C 3 alkoxy;
Or R 6 , R 7 , R 8 , R 9 and R 10 are phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, OH, C 1 -C 12 alkyl C 1 -C 12 alkoxy, CN, NO 2 , phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2 , Substituted by diphenylamino;
R 15 is hydrogen, phenyl -C 1 -C 3 alkyl, unsubstituted or substituted by one or more halogen, OH, SH, CN, C 3 -C 6 alkenyl-oxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - (C 1 -C 4 alkyl), O (CO) - (C 2 -C 4 ) alkenyl, O , (CO) O (C 1 -C 4 alkyl), C 3 -C 20 cycloalkyl, SO 2 - (C 1 -C 4 haloalkyl), O (C 1 -C 4 haloalkyl) or more O is interposed a C 3 -C 20 cycloalkyl substituted by C 1 -C 20 alkyl;
Or R 15 is C 2 -C 20 alkyl interrupted by one or more O, S or NR 23 ;
Or R 15 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 1 -C 8 alkanoyl, C 2 -C 12 C 3 -C 6 alkenoyl, or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 23 ;
Or R 15 is C 1 -C 8 alkyl-C 3 -C 10 cycloalkyl which is interrupted or interrupted by one or more O;
Or R 15 is benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH or C 1 -C 3 alkoxy;
Or R 15 is phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, OH, C 1 -C 12 alkyl, C 1 -C 12 alkoxy, CN, NO 2 , Phenyl-C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkylsulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2 , diphenylamino or Lt; / RTI >
R 16 is hydrogen, C 2 -C 12 alkenyl, C 3 -C 20 cycloalkyl or phenyl-C 1 -C 3 alkyl, wherein C 2 -C 12 alkenyl, C 3 -C 20 cycloalkyl or phenyl- C 1 -C 3 alkyl is interrupted or interrupted by one or more O, S, CO, NR 23 or COOR 15 ;
Or R 16 is unsubstituted or substituted with one or more of OH, SH, CN, C 3 -C 6 alkenoxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl) (CO) - (C 2 -C 4) alkenyl, O (CO) - (C 1 -C 4 alkyl), O (CO) - phenyl, or (CO) substituted by a C 1 -C 20 alkyl oR 15 ;
Or R 16 is C 2 -C 20 alkyl interrupted by one or more O, S, CO, NR 23 or COOR 15 ;
Or R 16 is (CH 2 CH 2 O) n H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 2 -C 8 alkanoyl or C 3 -C 6 alkenoyl ;
Or R 16 is benzoyl which is unsubstituted or substituted by one or more C 1 -C 6 alkyl, halogen, OH, C 1 -C 4 alkoxy or C 1 -C 4 alkylsulfanyl;
Or R 16 is phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C 1 -C 12 alkyl, C 1 -C 4 haloalkyl, C 1 -C 12 alkoxy, CN, NO 2, phenyl, -C 1 -C 3 alkyloxy, phenoxy, C 1 -C 12 alkyl sulfanyl, phenylsulfanyl, N (C 1 -C 12 alkyl) 2, diphenylamino, (CO ) O (C 1 -C 8 alkyl), (CO) -C 1 -C 8 alkyl, (CO) N (C 1 -C 8 alkyl) 2 or Lt; / RTI >
R 17 and R 18 independently of one another are hydrogen, C 1 -C 20 alkyl, C 2 -C 4 hydroxyalkyl, C 2 -C 10 alkoxyalkyl, C 2 -C 5 alkenyl, C 3 -C 20 cycloalkyl , phenyl, -C 1 -C 3 alkyl, C 1 -C 8 alkanoyl, C 1 -C 8 alkanoyloxy, C 3 -C 12 alkenyl alkanoyl, SO 2 - (C 1 -C 4 haloalkyl), or benzoyl, or ;
Or R 17 and R 18 are phenyl, naphthyl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of halogen, C 1 -C 4 haloalkyl, C 1 -C 20 alkoxy, C 1 -C 12 alkyl, benzoyl or C 1 -C 12, or substituted by alkoxy;
Or R 17 and R 18 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR 15 , membered saturated or unsaturated ring is unsubstituted or substituted, or one or more C 1 -C 20 alkyl 1, C 1 -C 20 alkoxy, = O, oR 15, SR 16, NR 19 R 20, (CO) R 21, NO 2, Halogen, C 1 -C 4 -haloalkyl, CN, phenyl or C 3 -C 20 cycloalkyl which is interrupted or interrupted by one or more O, S, CO or NR 15 ;
Or R 17 and R 18 together with the N-atom to which they are attached are unsubstituted or substituted by one or more C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 1 -C 20 alkoxy, ═O, OR 15, SR 16, NR 19 R 20, (CO) R 21, halogen, NO 2, CN, or sandwiched by a phenyl or a non-or at least one O, S, CO or NR 15 is a C 3 -C 20 interposed Form a heteroaromatic ring system substituted by cycloalkyl;
R 19 and R 20 are independently of each other hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 3 -C 10 cycloalkyl or phenyl;
Or R 19 and R 20 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is non-interrupted or interrupted by O, S or NR 23 , The unsubstituted or unsaturated rings are not condensed or the benzene ring is condensed to the 5- or 6-membered saturated or unsaturated ring;
R 21 is hydrogen, OH, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl which is interrupted or interrupted by one or more O, CO or NR 24 , , S, CO or C 3 -C 20 cycloalkyl interrupted by NR 24 ,
Or R 21 is phenyl, naphthyl, phenyl-C 1 -C 4 alkyl, OR 15 , SR 16 or NR 19 R 20 ;
R 22 is C 6 -C 20 aryl or C 3 -C 20 heteroaryl, each of which is unsubstituted or substituted by one or more of phenyl, halogen, C 1 -C 4 haloalkyl, CN, NO 2 , OR 15 , SR 16 , NR 17 R 18 , or C 1 -C 20 alkyl interrupted by one or more O, S or NR 23 , or each of which is unsubstituted or substituted by one or more of halogen, COOR 15 , CONR 17 R 18, phenyl, C 3 -C 8 cycloalkyl, C 3 -C 20 heteroaryl, C 6 -C 20 aryloxycarbonyl, C 3 -C 20 heteroaryloxy carbonyl, oR 15, SR 16 or NR 17 or more 1 substituted by R 18 C 1 -C 20 optionally substituted by alkyl;
Or R 22 is hydrogen, unsubstituted or substituted by one or more halogen, phenyl, OH, SH, CN, C 3 -C 6 alkenyl-oxy, OCH 2 CH 2 CN, OCH 2 CH 2 (CO) O (C 1 -C 4 alkyl), O (CO) - ( C 1 -C 4 alkyl), O (CO) - phenyl, (CO) OH or (CO) O (C 1 -C 4 alkyl) C 1 -C substituted by 20 alkyl;
Or R 22 is C 2 -C 12 alkyl interrupted by one or more O, S or NR 24 ;
Or R 22 is (CH 2 CH 2 O) n + 1 H, (CH 2 CH 2 O) n (CO) - (C 1 -C 8 alkyl), C 2 -C 12 alkenyl or C 3 -C 8 Cycloalkyl;
Or R < 22 > is phenyl substituted by SR < 16 & gt ;, wherein the radical R < 16 > represents a direct bond to the phenyl or naphthyl ring of the carbazole moiety to which the CO R < 22 >
n is 1-20;
R 23 is hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl interrupted by one or more O or CO, or phenyl-C 1 -C 4 alkyl, Or C 3 -C 8 cycloalkyl interrupted by one or more O or CO, or (CO) R 17 , or is phenyl which is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, C 1 -C 4 halo alkyl, oR 15, SR 16, NR 17 R 18 or Lt; / RTI >;
R 24 is hydrogen, C 1 -C 20 alkyl, C 1 -C 4 haloalkyl, C 2 -C 20 alkyl interrupted by one or more O or CO, or phenyl-C 1 -C 4 alkyl, Or C 3 -C 8 cycloalkyl optionally interrupted by one or more O or CO, or (CO) R 17 , or is unsubstituted or substituted by one or more C 1 -C 20 alkyl, halogen, C 1 -C 4 haloalkyl, OR 15 , SR 16 , NR 17 R 18 or Lt; / RTI >
흑색 감광성 수지 조성물 전체 100중량%에 대하여, 상기 광중합 개시제는 0.01 내지 10 중량% 포함되는 것인 흑색 감광성 수지 조성물.The method according to claim 1,
Wherein the photopolymerization initiator is contained in an amount of 0.01 to 10% by weight based on 100% by weight of the entire black photosensitive resin composition.
흑색 감광성 수지 조성물 전체 100중량%에 대하여, 착색제 1 내지 50 중량%, 결합제 수지 5 내지 80 중량%, 광중합성 화합물 1 내지 30 중량%, 광중합 개시제 0.01 내지 10 중량%, 및 잔량의 용제를 포함하는 것인 흑색 감광성 수지 조성물.6. The method of claim 5,
Wherein the photosensitive resin composition comprises 1 to 50 wt% of a colorant, 5 to 80 wt% of a binder resin, 1 to 30 wt% of a photopolymerizable compound, 0.01 to 10 wt% of a photopolymerization initiator, Based on the total weight of the black photosensitive resin composition.
광중합 개시 보조제를 더 포함하는 것인 흑색 감광성 수지 조성물.The method according to claim 1,
A photopolymerization initiator, and a photopolymerization initiator.
상기 광중합 개시 보조제는 아민계 화합물 및 카르복실산계 화합물로 이루어진 군으로부터 선택되는 1종 이상을 포함하는 것인 흑색 감광성 수지 조성물.8. The method of claim 7,
Wherein the photopolymerization initiation auxiliary comprises at least one member selected from the group consisting of an amine compound and a carboxylic acid compound.
첨가제를 더 포함하는 것인 흑색 감광성 수지 조성물.The method according to claim 1,
Wherein the black photosensitive resin composition further comprises an additive.
상기 착색제는 흑색 안료 또는 염료, 및 유기 안료 또는 염료로 이루어진 군으로부터 선택되는 1종 이상을 포함하는 것인 흑색 감광성 수지 조성물.The method according to claim 1,
Wherein the coloring agent comprises at least one selected from the group consisting of black pigments or dyes, and organic pigments or dyes.
상기 결합제 수지는 하기 화학식 2의 화합물을 포함한 공중합 반응으로 얻어지는 공중합체를 포함하는 것인 흑색 감광성 수지 조성물:
[화학식 2]
상기 화학식 2에서,
R25는 수소원자; 또는 수산기로 치환 또는 비치환된 C1 내지 C4의 알킬기이고,
R26은 단순결합; 또는 헤테로 원자가 포함되거나 포함되지 않는 C1 내지 C20의 지방족 또는 방향족 탄화수소기이다.The method according to claim 1,
Wherein the binder resin comprises a copolymer obtained by a copolymerization reaction including a compound represented by the following formula (2): < EMI ID =
(2)
In Formula 2,
R 25 represents a hydrogen atom; Or a C 1 to C 4 alkyl group substituted or unsubstituted with a hydroxyl group,
R 26 is a simple bond; Or a C 1 to C 20 aliphatic or aromatic hydrocarbon group containing or not containing a hetero atom.
상기 결합제 수지는 불포화 카르복실산 함유 단량체; 및 상기 화학식 2의 화합물 및 불포화 카르복실산 함유 단량체와 공중합이 가능한 불포화 결합을 갖는 화합물로 이루어진 군으로부터 선택되는 1종 이상을 더 포함하여 공중합 반응으로 얻어지는 공중합체를 포함하는 것인 흑색 감광성 수지 조성물.12. The method of claim 11,
The binder resin comprises an unsaturated carboxylic acid-containing monomer; And a compound having an unsaturated bond capable of copolymerizing with the compound of formula (2) and an unsaturated carboxylic acid-containing monomer, wherein the black photosensitive resin composition further comprises a copolymer obtained by a copolymerization reaction .
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