KR102131170B1 - Black photosensitive resin composition, Black matrix and Image display device having the same - Google Patents
Black photosensitive resin composition, Black matrix and Image display device having the same Download PDFInfo
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- KR102131170B1 KR102131170B1 KR1020130116418A KR20130116418A KR102131170B1 KR 102131170 B1 KR102131170 B1 KR 102131170B1 KR 1020130116418 A KR1020130116418 A KR 1020130116418A KR 20130116418 A KR20130116418 A KR 20130116418A KR 102131170 B1 KR102131170 B1 KR 102131170B1
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- South Korea
- Prior art keywords
- group
- carbon atoms
- black
- formula
- resin composition
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 38
- 239000011159 matrix material Substances 0.000 title claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 48
- 239000011347 resin Substances 0.000 claims abstract description 48
- 239000000049 pigment Substances 0.000 claims abstract description 42
- 239000011230 binding agent Substances 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 239000003999 initiator Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- -1 2-benzothienyl group Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000101 thioether group Chemical group 0.000 claims description 6
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 4
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000008034 disappearance Effects 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000004018 acid anhydride group Chemical group 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 19
- 239000002270 dispersing agent Substances 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- 239000006229 carbon black Substances 0.000 description 16
- 238000010586 diagram Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PYEZDQILSQGOLS-UHFFFAOYSA-N C1=CC=CC=2OC3=CC=CC=C3C(C12)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O.C1=CC=CC=2OC3=CC=CC=C3C(C12)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O Chemical compound C1=CC=CC=2OC3=CC=CC=C3C(C12)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O.C1=CC=CC=2OC3=CC=CC=C3C(C12)(C1=CC=C(C=C1)O)C1=CC=C(C=C1)O PYEZDQILSQGOLS-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 241000981595 Zoysia japonica Species 0.000 description 2
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 2
- CWBLMSQPWRHFFH-UHFFFAOYSA-N [dimethoxy(propyl)silyl] 2-methylprop-2-enoate Chemical compound CCC[Si](OC)(OC)OC(=O)C(C)=C CWBLMSQPWRHFFH-UHFFFAOYSA-N 0.000 description 2
- 229920005822 acrylic binder Polymers 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 235000010187 litholrubine BK Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- CQKAPARXKPTKBK-UHFFFAOYSA-N tert-butylazanium;bromide Chemical compound Br.CC(C)(C)N CQKAPARXKPTKBK-UHFFFAOYSA-N 0.000 description 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- HHQAGBQXOWLTLL-UHFFFAOYSA-N (2-hydroxy-3-phenoxypropyl) prop-2-enoate Chemical compound C=CC(=O)OCC(O)COC1=CC=CC=C1 HHQAGBQXOWLTLL-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- KMOUUZVZFBCRAM-UHFFFAOYSA-N 1,2,3,6-tetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21 KMOUUZVZFBCRAM-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- PAEWNKLGPBBWNM-UHFFFAOYSA-N 1,3,5-tris[2-(3-sulfanylbutoxy)ethyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(S)CCOCCN1C(=O)N(CCOCCC(C)S)C(=O)N(CCOCCC(C)S)C1=O PAEWNKLGPBBWNM-UHFFFAOYSA-N 0.000 description 1
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- BOGFHOWTVGAYFK-UHFFFAOYSA-N 1-[2-(2-propoxyethoxy)ethoxy]propane Chemical compound CCCOCCOCCOCCC BOGFHOWTVGAYFK-UHFFFAOYSA-N 0.000 description 1
- OSNILPMOSNGHLC-UHFFFAOYSA-N 1-[4-methoxy-3-(piperidin-1-ylmethyl)phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CN1CCCCC1 OSNILPMOSNGHLC-UHFFFAOYSA-N 0.000 description 1
- UEXNGZJDTGTAOG-UHFFFAOYSA-N 1-[diethoxy(propyl)silyl]oxyethyl 2-methylprop-2-enoate Chemical compound CCC[Si](OCC)(OCC)OC(C)OC(=O)C(C)=C UEXNGZJDTGTAOG-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- UIJSCOPBBPNHFC-UHFFFAOYSA-N 2,2-dichloro-2-phenylethanethioic s-acid Chemical compound SC(=O)C(Cl)(Cl)C1=CC=CC=C1 UIJSCOPBBPNHFC-UHFFFAOYSA-N 0.000 description 1
- XAMXITINZBKDFX-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylethanethioic S-acid Chemical compound COC(C(=S)O)(C1=CC=CC=C1)OC XAMXITINZBKDFX-UHFFFAOYSA-N 0.000 description 1
- QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
- JRPBSTGRRSTANR-UHFFFAOYSA-N 2,6-bis(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=CC(CC(C)C)=C1O JRPBSTGRRSTANR-UHFFFAOYSA-N 0.000 description 1
- ASUQXIDYMVXFKU-UHFFFAOYSA-N 2,6-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=C(Br)C=C3C2=C1 ASUQXIDYMVXFKU-UHFFFAOYSA-N 0.000 description 1
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 1
- SIVZFLKJXSKCGT-UHFFFAOYSA-N 2-(naphthalen-1-ylamino)acetic acid Chemical compound C1=CC=C2C(NCC(=O)O)=CC=CC2=C1 SIVZFLKJXSKCGT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BXYWKXBAMJYTKP-UHFFFAOYSA-N 2-[2-[2-[2-(3-sulfanylpropanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCCOCCOCCOCCOC(=O)CCS BXYWKXBAMJYTKP-UHFFFAOYSA-N 0.000 description 1
- IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BYCFRIATIOXYQB-UHFFFAOYSA-N 2-chloro-2-phenylethanethioic s-acid Chemical compound SC(=O)C(Cl)C1=CC=CC=C1 BYCFRIATIOXYQB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
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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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- 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
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G02F1/133512—Light shielding layers, e.g. black matrix
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- G—PHYSICS
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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
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Abstract
본 발명은 흑색 감광성 수지 조성물 및 이를 이용하여 형성된 블랙매트릭스에 관한 것으로, 보다 상세하게는 알칼리 가용성 바인더 수지(A), 광중합성 화합물(B), 광중합 개시제(C), 흑색 안료(D) 및 용매(E)를 포함하고, 상기 알칼리 가용성 바인더 수지(A)는 화학식 1로 표시되는 화합물을 포함하여 중합되는 카도계 바인더 수지를 포함하고, 상기 광중합 개시제(C)는 화학식 2로 표시되는 화합물 중에서 선택된 적어도 1종을 포함함으로써, 고해상도를 위한 미세 패턴이 가능하며, 기판에 대한 접착성이 우수하고, 경화 후 내구성이 우수한 흑색 감광성 수지 조성물에 관한 것이다.The present invention relates to a black photosensitive resin composition and a black matrix formed using the same, and more specifically, an alkali-soluble binder resin (A), a photopolymerizable compound (B), a photopolymerization initiator (C), a black pigment (D) and a solvent (E), wherein the alkali-soluble binder resin (A) comprises a cardo-based binder resin that is polymerized by including the compound represented by Formula 1, and the photopolymerization initiator (C) is selected from compounds represented by Formula 2 By including at least one, it is possible to fine patterns for high resolution, excellent adhesion to a substrate, and to a black photosensitive resin composition excellent in durability after curing.
Description
본 발명은 흑색 감광성 수지 조성물에 관한 것이다.
The present invention relates to a black photosensitive resin composition.
디스플레이의 화질은 컬러 필터에 의해 좌우된다. 컬러 필터의 컬러 픽셀 사이에는 블랙매트릭스라고 불리는 격자 상의 흑색패턴이 배치되는 되며, 넓은 스크린 면적과 높은 콘트라스트를 실현하기 위하여, 컬러 필터의 블랙매트릭스는 충분한 광차광성을 가지고 고해상도로 패터닝 될 것이 요구된다. The quality of the display depends on the color filter. A black pattern on a grid called a black matrix is disposed between the color pixels of the color filter, and in order to realize a large screen area and high contrast, the black matrix of the color filter is required to be patterned at a high resolution with sufficient light blocking properties.
종래의 블랙매트릭스는 크롬을 사용하였는데, 이 공정은 크롬을 유리기판 전체에 증착시키고 에칭 처리에 의해 패턴을 형성하는 방식으로 공정상 고비용이 요구되고, 크롬의 고반사율, 크롬 폐액에 의한 환경오염 등의 문제점이 있었다. 이와 같은 이유로 미세가공이 가능한 안료 분산법에 의한 레진 블랙매트릭스의 연구가 활발히 이루어지고 있다.Conventional Black Matrix used chromium. This process requires a high cost in the process by depositing chromium on the entire glass substrate and forming a pattern by etching treatment, high reflectivity of chromium, environmental pollution by chromium waste liquid, etc. There was a problem. For this reason, research on resin black matrix by a pigment dispersion method capable of fine processing has been actively conducted.
또한, 카본 블랙 이외의 착색 안료로 흑색 조성물을 제조하는 연구도 진행되고 있으나, 카본 블랙 이외의 착색 안료는 차광성이 약하기 때문에 그 배합량을 극히 많이 해야 하고, 그 결과 조성물의 점도가 증가하여 취급이 곤란해지거나 형성된 피막의 강도 또는 기판에 대한 밀착성이 현저히 저하된다는 문제점이 있다. 현재, 업계의 지속적인 성능 향상에 대한 요청에 따라 다양한 연구들이 진행되고 있다. In addition, studies have been conducted to produce black compositions with colored pigments other than carbon black, but colored pigments other than carbon black have poor light-shielding properties, and thus the amount of the mixture must be extremely high. As a result, the viscosity of the composition increases and handling is increased. There is a problem that the strength of the formed film becomes difficult or the adhesion to the substrate is significantly reduced. Currently, various studies are being conducted in response to requests for continuous performance improvement in the industry.
또한, 디스플레이의 슬림화와 보다 넓은 화면의 요구에 따라, 모듈의 상, 하판 합착 부분에 있어서도 최소한의 면적을 사용함으로써 1인치라도 화면을 크게 가져가기 위한 기술이 적용되고 있다. 특히 모바일 시장이 점차적으로 커지고 모바일의 특성을 극대화하기 위해 모듈 자체의 슬림화 외에도 장비는 소량화하면서 디스플레이는 최대한으로 가져가기 위한 방안들이 강구되고 있다.In addition, according to the slimming of the display and the demand for a wider screen, a technique for taking a large screen even at an inch by using a minimum area in the upper and lower bonding portions of the module has been applied. In particular, in order to maximize the characteristics of mobile, the mobile market is gradually growing. In addition to the slimming of the module itself, measures are being taken to maximize display while minimizing equipment.
그 방안 중의 하나로, 기존의 합착 방법이 아닌 새로운 형태의 합착 방법을 사용하게 되었다. 기존의 합착 방법에 있어서는 글래스와 블랙매트릭스의 테두리를 동시에 이용하여 합착하는 방법을 진행하였으나, 실제 보여지는 영역보다 더 큰 글래스를 이용하여 합착함으로써 판넬에서의 디스플레이 효율성이 떨어졌다. 반면 새로운 합착 방법에서는 디스플레이의 효율성을 높이기 위해 합착시 글래스를 이용하지 않고 블랙매트릭스 부분에서만 합착을 진행함으로써 판넬에서 디스플레이의 효율성을 극대화할 수 있게 되었으며, 이 방법에서는 카도계 바인더를 필수적으로 사용하여 공정특성을 확보할 수 있었다. As one of the methods, a new type of bonding method was used instead of the existing bonding method. In the conventional bonding method, a method of bonding using a frame of glass and a black matrix at the same time was carried out, but the display efficiency in the panel was lowered by bonding using a larger glass than the actual visible area. On the other hand, in the new bonding method, it is possible to maximize the efficiency of the display in the panel by performing bonding only in the black matrix part without using glass when bonding, in order to increase the efficiency of the display. Characteristics could be secured.
그러나, 기존 방법에서는 글래스와 블랙매트릭스를 동시에 이용하여 합착을 진행했기 때문에 합착시 가해지는 압력 및 신뢰성 공정 중 실란트의 접착력에 큰 문제가 없었으나, 카도계 바인더를 사용하여 블랙매트릭스 부분에서만 합착을 진행한 경우에는 합착시 가해지는 압력과 신뢰성 공정 중 블랙매트릭스의 기판 접착력이 문제가 되어 실터짐 및 도막 파괴 등이 발생하였으며, 고OD(Optical Density, 광학밀도) 특성과 기판 접착력의 두 조건을 만족시키지 못하는 문제점이 있었다.However, in the conventional method, since the bonding was performed using glass and black matrix at the same time, there was no significant problem in the adhesive force of the sealant during the pressure and reliability process applied during the bonding, but the bonding was performed only in the black matrix part using a cardo-based binder. In one case, the pressure applied during the bonding and the reliability of the substrate of the black matrix during the reliability process became a problem, resulting in sintering and film breakage, and the two conditions of high OD (Optical Density) and substrate adhesion were not satisfied. There was a problem that could not be.
한국등록특허 제1068622 호에는 기판접착력이 향상된 고차광성 블랙매트릭스 조성물이 개시되어 있어 고OD(Optical Density, 광학밀도) 특성과 기판 접착력의 문제는 해결하였으나, 상기 조성물로는 고해상도를 구현할 수 없는 문제점이 있다.
Korean Registered Patent No. 1068622 discloses a high light-shielding black matrix composition with improved substrate adhesion, which solves the problems of high OD (Optical Density) and substrate adhesion, but the composition cannot achieve high resolution. have.
본 발명은 고해상도의 패턴 형성이 가능하고, 기판에 대한 접착성이 우수하고 경화 후 내구성이 뛰어난 흑색 감광성 수지 조성물을 제공하는 것을 목적으로 한다.An object of the present invention is to provide a black photosensitive resin composition capable of forming a high resolution pattern, excellent adhesion to a substrate, and excellent durability after curing.
본 발명은 상기 흑색 감광성 수지 조성물을 이용하여 형성되는 블랙매트릭스를 제공하는 것을 목적으로 한다.An object of the present invention is to provide a black matrix formed by using the black photosensitive resin composition.
또한, 본 발명은 상기 블랙매트릭스를 구비한 액정표시장치를 제공하는 것을 목적으로 한다.
In addition, an object of the present invention is to provide a liquid crystal display device having the black matrix.
1. 알칼리 가용성 바인더 수지(A), 광중합성 화합물(B), 광중합 개시제(C), 흑색 안료(D) 및 용매(E)를 포함하고, 상기 알칼리 가용성 바인더 수지(A)는 하기 화학식 1로 표시되는 화합물을 포함하여 중합되는 카도계 바인더 수지(a1)를 포함하고, 상기 광중합 개시제(C)는 하기 화학식 2로 표시되는 화합물 중에서 선택된 적어도 1종을 포함하는, 흑색 감광성 수지 조성물:1.Alkali-soluble binder resin (A), a photopolymerizable compound (B), a photopolymerization initiator (C), a black pigment (D) and a solvent (E), and the alkali-soluble binder resin (A) is represented by the following formula (1) A black photosensitive resin composition comprising a cardo-based binder resin (a1) that is polymerized, including the compound represented, and the photopolymerization initiator (C) comprising at least one selected from compounds represented by Formula 2 below:
[화학식 1][Formula 1]
(식 중에서, R1 및 R2는 각각 독립적으로, 
X는 수소 원자, 탄소수 1 내지 5의 알킬기 또는 수산기이고, R3는 수소 원자 또는 탄소수 1 내지 5의 알킬기임)X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group, and R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms)
[화학식 2][Formula 2]
(식 중에서, Ch1은 
Het1 및 Het3는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 푸릴기, 티에닐기, 피롤릴기, 피리딜기, 2-벤조티에닐기, 3- 벤조티에닐기, 2- 인돌릴기 또는 3- 인돌릴기이고,Het 1 and Het 3 are each independently a substituted or unsubstituted furyl group, thienyl group, pyrrolyl group, pyridyl group, 2-benzothienyl group, 3- benzothienyl group, 2- indolyl group, or an alkyl group having 1 to 12 carbon atoms, or 3- indolyl group,
Het2 및 Het4는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 티에닐렌기, 피롤릴렌기, 벤조티에닐렌기, 인돌릴렌기 또는 인돌릴렌카보닐기이고,Het 2 and Het 4 are each independently a substituted or unsubstituted thienyl group, pyrrolylene group, benzothienylene group, indolylene group or indolylene carbonyl group having 1 to 12 carbon atoms,
Ar1은 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 
Ar2는 탄소수 6 내지 14의 아릴기 또는 
X1, X2, X3 및 X4는 각각 독립적으로 산소 원자; 황 원자; 또는 -NR6-이고,X 1 , X 2 , X 3 and X 4 are each independently an oxygen atom; Sulfur atom; Or -NR 6 -,
R4는 탄소수 1 내지 12의 알킬기 또는 알콕시기, 또는 탄소수 6 내지 14의 아릴기이고, R 4 is an alkyl group or an alkoxy group having 1 to 12 carbon atoms, or an aryl group having 6 to 14 carbon atoms,
R5는 수소 원자, 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 20의 시클로알킬기 또는 탄소수 6 내지 14의 아릴기이고,R 5 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 14 carbon atoms,
R6는 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 14의 아릴기임).R 6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms).
2. 위 1에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3으로 표시되는 화합물을 이용하여 합성된, 흑색 감광성 수지 조성물:2. In the above 1, the compound represented by Formula 1 is synthesized using the compound represented by Formula 3, black photosensitive resin composition:
[화학식 3][Formula 3]
3. 위 1에 있어서, 상기 카도계 바인더 수지(a1)는 9,9-비스(3,4-메타크릴릭 디에스테르)잔텐을 포함하여 중합된, 흑색 감광성 수지 조성물.3. In the above 1, wherein the cardo-based binder resin (a1) is 9,9-bis (3,4-methacrylic diester) xanthene polymerized, including a black photosensitive resin composition.
4. 위 1에 있어서, 흑색 감광성 수지 조성물 100중량부에 대하여 상기 알칼리 가용성 바인더 수지(A) 1 내지 40중량부, 광중합성 화합물(B) 1 내지 20중량부, 광중합 개시제(C) 0.1 내지 10중량부, 흑색 안료(D) 5 내지 20중량부 및 용매(E) 20 내지 85중량부를 포함하는, 흑색 감광성 수지 조성물.4. In the above 1, 1 to 40 parts by weight of the alkali-soluble binder resin (A), 1 to 20 parts by weight of the photopolymerizable compound (B), photopolymerization initiator (C) 0.1 to 10 parts by weight based on 100 parts by weight of the black photosensitive resin composition Black photosensitive resin composition comprising 5 parts to 20 parts by weight of black pigment (D) and 20 to 85 parts by weight of solvent (E).
5. 위 1 내지 4 중 어느 한 한에 따른 흑색 감광성 수지 조성물을 이용하여 형성되는, 블랙매트릭스.5. Black matrix formed using the black photosensitive resin composition according to any one of 1 to 4 above.
6. 위 5에 따른 블랙매트릭스가 구비된 화상표시장치.
6. An image display device equipped with a black matrix according to the above 5.
본 발명에 따른 흑색 감광성 수지 조성물은 기판에 대한 접착력이 우수하고, 경화 후 내구성이 뛰어나다.The black photosensitive resin composition according to the present invention has excellent adhesion to a substrate and excellent durability after curing.
또한, 본 발명에 따른 흑색 감광성 수지 조성물은 고해상도 구현을 위한 미세 패턴 형성이 가능하다.
In addition, the black photosensitive resin composition according to the present invention is capable of forming a fine pattern for realizing high resolution.
본 발명은 알칼리 가용성 바인더 수지(A), 광중합성 화합물(B), 광중합 개시제(C), 흑색 안료(D) 및 용매(E)를 포함하고, 상기 알칼리 가용성 바인더 수지(A)는 하기 화학식 1로 표시되는 화합물을 포함하여 중합되는 카도계 바인더 수지(a1)를 포함하고, 상기 광중합 개시제(C)는 하기 화학식 2로 표시되는 화합물 중에서 선택된 적어도 1종을 포함함으로써, 고해상도를 위한 미세 패턴이 가능하며, 기판에 대한 접착성이 우수하고 경화 후 내구성이 뛰어난 흑색 감광성 수지 조성물에 관한 것이다.The present invention includes an alkali-soluble binder resin (A), a photopolymerizable compound (B), a photopolymerization initiator (C), a black pigment (D) and a solvent (E), and the alkali-soluble binder resin (A) is represented by the following Chemical Formula 1 Including a compound represented by a cardo-based binder resin (a1) to be polymerized, wherein the photopolymerization initiator (C) comprises at least one selected from compounds represented by the following formula (2), it is possible to fine patterns for high resolution And relates to a black photosensitive resin composition having excellent adhesion to a substrate and excellent durability after curing.
이하, 본 발명을 상세히 설명 한다.
Hereinafter, the present invention will be described in detail.
본 발명의 흑색 감광성 수지 조성물은 알칼리 가용성 바인더 수지(A), 광중합성 화합물(B), 광중합 개시제(C), 흑색 안료(D) 및 용매(E)를 포함한다.The black photosensitive resin composition of the present invention includes an alkali-soluble binder resin (A), a photopolymerizable compound (B), a photopolymerization initiator (C), a black pigment (D) and a solvent (E).
<알칼리 가용성 바인더 수지(A)><Alkali-soluble binder resin (A)>
본 발명에 따른 알칼리 가용성 바인더 수지(A)는 하기 화학식 1의 화합물을 포함하여 중합한 카도계 바인더 수지(a1)를 포함함으로써, 기판과의 접착력을 향상시키고 현상 밀착력이 우수하여 고해상도를 위한 미세 패턴을 구현할 수 있게 한다. The alkali-soluble binder resin (A) according to the present invention comprises a cardo-based binder resin (a1) polymerized by including the compound of Formula 1 below, thereby improving adhesion to a substrate and having excellent developing adhesion, thereby achieving a fine pattern for high resolution. To implement
[화학식 1][Formula 1]
식 중에서, R1 및 R2는 각각 독립적으로, 
X는 수소 원자, 탄소수 1 내지 5의 알킬기 또는 수산기이고, R3는 수소 원자 또는 탄소수 1 내지 5의 알킬기이며, 바람직하게는 X는 수산기 이고, R3는 수소 원자 또는 메틸기인 것이 좋다.X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group, R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably X is a hydroxyl group, and R 3 is preferably a hydrogen atom or a methyl group.
상기 화학식 1로 표시되는 화합물은 하기 화학식 3을 이용하여 합성될 수 있다.The compound represented by Chemical Formula 1 may be synthesized using Chemical Formula 3 below.
[화학식 3][Formula 3]
식 중에서 수산기(-OH)의 위치는 특별히 한정되지 않으며, 예를 들면, 2-위, 3-위 및 4-위일 수 있으며, 바람직하게는 4-위인 것이 좋다(위치 선정은 잔텐과 결합된 탄소를 1-위로 하여 결정한다).In the formula, the position of the hydroxyl group (-OH) is not particularly limited, and may be, for example, 2-position, 3-position, and 4-position, and preferably 4-position (positioning is carbon combined with xanthene). Is determined by 1-up).
결과적으로, 화학식 3의 수산기(-OH)의 위치에 따라, 상기 화학식 1의 R1 및 R2의 치환 위치가 결정될 수 있다.As a result, depending on the position of the hydroxyl group (-OH) of Chemical Formula 3, substitution positions of R 1 and R 2 of Chemical Formula 1 may be determined.
상기 화학식 1로 표시되는 화합물의 보다 구체적인 예를 들면, 9,9-비스(3,4-메타크릴릭 디에스테르)잔텐을 들 수 있으며, 이에 한정되는 것은 아니다.A more specific example of the compound represented by Chemical Formula 1 may include 9,9-bis(3,4-methacrylic diester) xanthene, but is not limited thereto.
상기 알칼리 가용성 바인더(A) 중 상기 카도계 바인더 수지(a1)의 산가는 10 내지 200mgKOH/g일 수 있으며, 바람직하게는 30 내지 150mgKOH/g인 것이 좋다. 10 내지 200mgKOH/g의 산가를 가지는 경우, 충분한 현상 속도를 확보할 수 있어, 고해상도의 블랙매트릭스를 구현할 수 있게 한다.The acid value of the cardo-based binder resin (a1) in the alkali-soluble binder (A) may be 10 to 200 mgKOH/g, preferably 30 to 150 mgKOH/g. When having an acid value of 10 to 200mgKOH / g, it is possible to secure a sufficient development rate, it is possible to implement a high-resolution black matrix.
상기 알칼리 가용성 바인더(A) 중 상기 카도계 바인더 수지(a1)의 중량평균분자량은 1,000 내지 30,000일수 있으며, 바람직하게는 1,500 내지 10,000인 것이 좋다. 상기 범위 내의 중량평균분자량을 가지는 경우, 밀착성 및 현상성이 향상될 수 있다.The weight average molecular weight of the cardo-based binder resin (a1) in the alkali-soluble binder (A) may be 1,000 to 30,000, preferably 1,500 to 10,000. When having a weight average molecular weight within the above range, adhesion and developability may be improved.
상기 알칼리 가용성 바인더 수지(A)의 함량은 특별히 한정되지 않으나, 흑색 감광성 수지 조성물 100중량부에 대하여 1 내지 40중량부로 포함될 수 있으며, 바람직하게는 5 내지 20중량부인 것이 좋다. 바인더 수지의 함량이 상기 범위내인 경우 현상액에서의 용해성이 충분하여 패턴 형성이 용이하다.
The content of the alkali-soluble binder resin (A) is not particularly limited, but may be included in 1 to 40 parts by weight based on 100 parts by weight of the black photosensitive resin composition, preferably 5 to 20 parts by weight. When the content of the binder resin is within the above range, the solubility in the developer is sufficient, and pattern formation is easy.
<광중합성 화합물(B)><Photopolymerizable compound (B)>
본 발명에 따른 광중합성 화합물(B)은 패턴의 강도를 강화시키기 위한 성분으로서, 단관능 단량체, 2관능 단량체 또는 다관능 단량체를 사용할 수 있으며, 바람직하게는 2관능 이상의 단량체를 사용하는 것이 좋다. The photopolymerizable compound (B) according to the present invention is a component for enhancing the strength of the pattern, and a monofunctional monomer, a bifunctional monomer, or a polyfunctional monomer may be used, and preferably, a bifunctional or higher monomer is used.
상기 단관능 단량체의 종류는 특별히 한정되지 않으며, 예를 들면 노닐페닐카르비톨아크릴레이트, 2-히드록시-3-페녹시프로필아크릴레이트, 2-에틸헥실카르비톨아크릴레이트, 2-히드록시에틸아크릴레이트, N-비닐피롤리돈 등을 들 수 있다.The type of the monofunctional monomer is not particularly limited, for example, nonylphenylcarbitolacrylate, 2-hydroxy-3-phenoxypropylacrylate, 2-ethylhexylcarbitolacrylate, 2-hydroxyethylacrylic Rate, N-vinylpyrrolidone, and the like.
상기 2관능 단량체의 종류는 특별히 한정되지 않으며, 예를 들면, 1,6-헥산디올디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 네오펜틸글리콜디(메타)아크릴레이트, 트리에틸렌글리콜디(메타)아크릴레이트, 비스페놀 A의 비스(아크릴로일옥시에틸)에테르, 3-메틸펜탄디올디(메타)아크릴레이트 등을 들 수 있다.The type of the bifunctional monomer is not particularly limited, for example, 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene Glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, and the like.
상기 다관능 단량체의 종류는 특별히 한정되지 않으며, 예를 들면, 트리메틸올프로판트리(메타)아크릴레이트, 에톡실레이티드트리메틸올프로판트리(메타)아크릴레이트, 프로폭실레이티드트리메틸올프로판트리(메타)아크릴레이트, 펜타에리스리톨트리(메타)아크릴레이트, 펜타에리스리톨테트라(메타)아크릴레이트, 디펜타에리스리톨트리(메타)아크릴레이트, 디펜타에리스리톨펜타(메타)아크릴레이트, 에톡실레이티드디펜타에리스리톨헥사(메타)아크릴레이트, 프로폭실레이티드디펜타에리스리톨헥사(메타)아크릴레이트, 디펜타에리스리톨헥사(메타)아크릴레이트 등을 들 수 있다.The type of the polyfunctional monomer is not particularly limited, for example, trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth) )Acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa (Meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and the like.
상기 광중합성 화합물(B) 의 함량은 특별히 한정되지 않으나, 흑색 감광성 수지 조성물 100중량부에 대하여 1 내지 20중량부로 포함될 수 있으며, 바람직하게는 1 내지 10중량부인 것이 좋다. 상기 광중합성 화합물의 함량이 1 중량부 미만인 경우 광감도가 저하될 수 있으며, 20중량부를 초과하는 경우 감광성 수지층의 점착성이 과잉되어 필름의 강도가 충분치 않고 현상이 패턴이 손실될 수 있다.The content of the photopolymerizable compound (B) is not particularly limited, but may be included in 1 to 20 parts by weight based on 100 parts by weight of the black photosensitive resin composition, preferably 1 to 10 parts by weight. When the content of the photopolymerizable compound is less than 1 part by weight, photosensitivity may be deteriorated, and when it exceeds 20 parts by weight, the adhesiveness of the photosensitive resin layer is excessive, so that the strength of the film is insufficient and the pattern may be lost.
<광중합 개시제(C)><Photopolymerization initiator (C)>
본 발명에 따른 광중합 개시제(C)는 하기 화학식 2로 표시되는 옥심에스테르계 화합물을 포함함으로써, 광감도를 향상시키고 기판과의 접착력 및 현상 밀착력을 향상시켜 고해상도를 위한 미세패턴을 구현할 수 있게 한다.The photopolymerization initiator (C) according to the present invention includes an oxime ester-based compound represented by the following Chemical Formula 2, thereby improving light sensitivity, improving adhesion to a substrate, and developing adhesion, thereby realizing a fine pattern for high resolution.
[화학식 2] [Formula 2]
식 중에서, Ch1은 
Het1 및 Het3는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 푸릴기, 티에닐기, 피롤릴기, 피리딜기, 2-벤조티에닐기, 3- 벤조티에닐기, 2- 인돌릴기 또는 3- 인돌릴기이고, Het 1 and Het 3 are each independently a substituted or unsubstituted furyl group, thienyl group, pyrrolyl group, pyridyl group, 2-benzothienyl group, 3- benzothienyl group, 2- indolyl group, or an alkyl group having 1 to 12 carbon atoms, or 3- indolyl group,
Het2 및 Het4는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 티에닐렌기, 피롤릴렌기, 벤조티에닐렌기, 인돌릴렌기 또는 인돌릴렌카보닐기이고,Het 2 and Het 4 are each independently a substituted or unsubstituted thienyl group, pyrrolylene group, benzothienylene group, indolylene group or indolylene carbonyl group having 1 to 12 carbon atoms,
Ar1은 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 
Ar2는 탄소수 6 내지 14의 아릴기 또는 
X1, X2, X3 및 X4는 각각 독립적으로 산소 원자; 황 원자; 또는 -NR6-이고,X 1 , X 2 , X 3 and X 4 are each independently an oxygen atom; Sulfur atom; Or -NR 6 -,
R4는 탄소수 1 내지 12의 알킬기 또는 알콕시기, 또는 탄소수 6 내지 14의 아릴기이고, 상기 아릴기는 페닐기인 것이 바람직하다.R 4 is an alkyl group or an alkoxy group having 1 to 12 carbon atoms, or an aryl group having 6 to 14 carbon atoms, and the aryl group is preferably a phenyl group.
R5는 수소 원자, 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 20의 시클로알킬기 또는 탄소수 6 내지 14의 아릴기이고, 상기 아릴기는 페닐기인 것이 바람직하다.R 5 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 14 carbon atoms, and the aryl group is preferably a phenyl group.
R6는 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 14의 아릴기이고, 상기 아릴기는 페닐기인 것이 바람직하다.R 6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms, and the aryl group is preferably a phenyl group.
본 발명의 광중합 개시제(C)의 구체적인 예를 들면, 1-[9-에틸-6-(티오펜-2-카보닐)-9.H.-카바졸-3-일]-에타논 옥심 O-아세테이트 등을 들 수 있으며, 사용 가능한 시판되고 있는 제품의 예를 들면, Irgacure OXE-02(시바사), N-1919(아데카사) 등을 들 수 있으며, 이에 제한 되는 것은 아니다.Specific examples of the photopolymerization initiator (C) of the present invention include 1-[9-ethyl-6-(thiophen-2-carbonyl)-9.H.-carbazol-3-yl]-ethanone oxime O -Acetate, etc., and examples of commercially available products that can be used include, for example, Irgacure OXE-02 (Shiba Corporation), N-1919 (Adeka Corporation), and the like, but are not limited thereto.
상기 광중합 개시제(C)는 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. The photopolymerization initiator (C) may be used alone or in combination of two or more.
또한, 상기 광중합 개시제(D)는 본 발명의 흑색 감광성 수지 조성물의 감도를 향상시키기 위해서, 광중합 개시 보조제를 더 포함할 수 있다. 본 발명에 따른 흑색 감광성 수지 조성물은 광중합 개시 보조제를 함유함으로써, 감도가 더욱 높아져 생산성을 향상시킬 수 있다.In addition, in order to improve the sensitivity of the black photosensitive resin composition of the present invention, the photopolymerization initiator (D) may further include a photopolymerization initiator. The black photosensitive resin composition according to the present invention contains a photopolymerization initiation aid, so that the sensitivity becomes higher and productivity can be improved.
상기 광중합 개시 보조제로는, 아민 화합물, 카르복실산 화합물 및 티올기를 가지는 유기 황화합물로 이루어진 군으로부터 선택되는 1종 이상의 화합물을 들 수 있다.Examples of the photopolymerization initiation aid include one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds, and organic sulfur compounds having thiol groups.
상기 아민 화합물의 구체적인 예를 들면, 트리에탄올아민, 메틸디에탄올아민, 트리이소프로판올아민 등의 지방족 아민 화합물, 4-디메틸아미노벤조산메틸, 4-디메틸아미노벤조산에틸, 4-디메틸아미노벤조산이소아밀, 4-디메틸아미노벤조산2-에틸헥실, 벤조산2-디메틸아미노에틸, N,N-디메틸파라톨루이딘, 4,4'-비스(디메틸아미노)벤조페논(통칭: 미힐러 케톤), 4,4'-비스(디에틸아미노)벤조페논 등을 들 수 있으며, 방향족 아민 화합물을 사용하는 것이 바람직하다.Specific examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 4 -Dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Mihiler ketone), 4,4'-bis (Diethylamino)benzophenone, and the like, and it is preferable to use an aromatic amine compound.
상기 카르복실산 화합물의 구체적인 예를 들면, 방향족 헤테로아세트산류인 것이 바람직하며, 예를 들면. 페닐티오아세트산, 메틸페닐티오아세트산, 에틸페닐티오아세트산, 메틸에틸페닐티오아세트산, 디메틸페닐티오아세트산, 메톡시페닐티오아세트산, 디메톡시페닐티오아세트산, 클로로페닐티오아세트산, 디클로로페닐티오아세트산, N-페닐글리신, 페녹시아세트산, 나프틸티오아세트산, N-나프틸글리신, 나프톡시아세트산 등을 들 수 있다. Specific examples of the carboxylic acid compound are preferably aromatic heteroacetic acids, for example. Phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine , Phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.
상기 티올기를 가지는 유기 황화합물의 구체적인 예를 들면, 2-머캅토벤조티아졸, 1,4-비스(3-머캅토부티릴옥시)부탄, 1,3,5-트리스(3-머캅토부틸옥시에틸)-1,3,5-트리아진-2,4,6(1H,3H,5H)-트리온, 트리메틸올프로판트리스(3-머캅토프로피오네이트), 펜타에리스리톨테트라키스(3-머캅토부틸레이트), 펜타에리스리톨테트라키스(3-머캅토프로피오네이트), 디펜타에리스리톨헥사키스(3-머캅토프로피오네이트), 테트라에틸렌글리콜비스(3-머캅토프로피오네이트) 등을 들 수 있다.Specific examples of the organic sulfur compound having the thiol group include 2-mercaptobenzothiazole, 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyloxy Ethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropanetris(3-mercaptopropionate), pentaerythritol tetrakis(3-mer Captobutylate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptopropionate), etc. Can.
상기 광중합 개시제(C)의 함량은 특별히 한정되지 않으나, 흑색 감광성 수지 조성물 100중량부에 대하여 0.1 내지 10중량부로 포함될 수 있으며, 바람직하게는 0.5 내지 5중량부인 것이 좋다. 0.1중량부 미만으로 포함되는 경우, 감도가 저하되어 현상 공정 중 패턴의 탈락이 발생할 수 있으며, 10중량부를 초과하는 경우 주름이 발생할 수 있다.
The content of the photopolymerization initiator (C) is not particularly limited, but may be included in 0.1 to 10 parts by weight based on 100 parts by weight of the black photosensitive resin composition, preferably 0.5 to 5 parts by weight. When included in less than 0.1 parts by weight, the sensitivity is lowered, so that the pattern may be dropped during the development process, and when it exceeds 10 parts by weight, wrinkles may occur.
<흑색 안료(D)><Black pigment (D)>
본 발명에 사용되는 흑색 안료(D)는 카본 블랙, 유기블랙안료, 티타늄 블랙 및 적색, 청색, 녹색을 혼합한 안료 등을 사용할 수 있다.As the black pigment (D) used in the present invention, carbon black, organic black pigment, titanium black, and pigments of red, blue, and green may be used.
보다 구체적으로 상기 흑색 안료는 카본 블랙과 2가지 이상의 착색 안료를 혼합하여 밀링한 착색 분산액을 제조하여 사용할 수 있다. 사용 가능한 카본블랙으로는 미쿠니색소사의 CHBK-17; 동해카본(주)의 시스토 5HIISAF-HS, 시스토 KH, 시스토 3HHAF-HS, 시스토 NH, 시스토 3M, 시스토 300HAF-LS, 시스토 116HMMAF-HS, 시스토 116MAF, 시스토 FMFEF-HS, 시스토 SOFEF, 시스토 VGPF, 시스토 SVHSRF-HS, 및 시스토 SSRF; 미쯔비시화학(주)의 다이어그램 블랙 Ⅱ, 다이어그램 블랙 N339, 다이어그램 블랙 SH, 다이어그램 블랙 H, 다이어그램 LH, 다이어그램 HA, 다이어그램 SF, 다이어그램 N550M, 다이어그램 M, 다이어그램 E, 다이어그램 G, 다이어그램 R, 다이어그램 N760M, 다이어그램 LR, #2700, #2600, #2400, #2350, #2300, #2200, #1000, #980, #900, MCF88, #52, #50, #47, #45, #45L, #25, #CF9, #95, #3030, #3050, MA7, MA77, MA8, MA11, OIL7B, OIL9B, OIL11B, OIL30B, 및 OIL31B; 대구사(주)의 PRINTEX-U, PRINTEX-V, PRINTEX-140U, PRINTEX-140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, PRINTEX-25, PRINTEX-200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, 및 LAMP BLACK-101; 콜롬비아 카본(주)의 RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN-820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN-2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, 및 RAVEN-1170 등을 들 수 있다.More specifically, the black pigment may be prepared by mixing a carbon black and two or more colored pigments and milling the colored dispersion. Carbon black that can be used is CHBK-17 from Mikuni Colors; Donghae Carbon's Systo 5HIISAF-HS, Systo KH, Systo 3HHAF-HS, Systo NH, Systo 3M, Systo 300HAF-LS, Systo 116HMMAF-HS, Systo 116MAF, Systo FMFEF- HS, Systo SOFEF, Systo VGPF, Systo SVHSRF-HS, and Systo SSRF; Diagram Black Ⅱ of Mitsubishi Chemical, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Diagram LR, #2700, #2600, #2400, #2350, #2300, #2200, #1000, #980, #900, MCF88, #52, #50, #47, #45, #45L, #25, # CF9, #95, #3030, #3050, MA7, MA77, MA8, MA11, OIL7B, OIL9B, OIL11B, OIL30B, and OIL31B; PRINTEX-U, PRINTEX-V, PRINTEX-140U, PRINTEX-140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, of Daegu Corporation PRINTEX-25, PRINTEX-200, PRINTEX-40, PRINTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, and LAMP BLACK-101; RAVEN-1100ULTRA, RAVEN-1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, of Columbia Carbon Co., Ltd. RAVEN-850, RAVEN-820, RAVEN-790ULTRA, RAVEN-780ULTRA, RAVEN-760ULTRA, RAVEN-520, RAVEN-500, RAVEN-460, RAVEN-450, RAVEN-430ULTRA, RAVEN-420, RAVEN-410, RAVEN- 2500ULTRA, RAVEN-2000, RAVEN-1500, RAVEN-1255, RAVEN-1250, RAVEN-1200, RAVEN-1190ULTRA, and RAVEN-1170.
상기 카본블랙과 혼합하여 사용 가능한 착색 안료로는 카민 6B(C.I.12490), 프탈로시아닌 그린(C.I. 74260), 프탈로시아닌 블루(C.I. 74160), 미쓰비시 카본 블랙 MA100, 페릴렌 블랙(BASF K0084. K0086), 시아닌 블랙, 리놀옐로우(C.I.21090), 리놀 옐로우GRO(C.I. 21090), 벤지딘 옐로우4T-564D, 미쓰비시 카본 블랙 MA-40, 빅토리아 퓨어 블루(C.I.42595), C.I. PIGMENT RED97, 122, 149, 168, 177, 180, 192, 215, C.I. PIGMENT GREEN 7, 36, C.I. PIGMENT 15:1, 15:4, 15:6, 22, 60, 64, C.I. PIGMENT 83, 139 C.I. PIGMENT VIOLET 23 등이 있으며, 이 밖에 백색 안료, 형광 안료 등을 사용할 수도 있다.The coloring pigments that can be used in combination with the carbon black include carmine 6B (CI12490), phthalocyanine green (CI 74260), phthalocyanine blue (CI 74160), Mitsubishi carbon black MA100, perylene black (BASF K0084. K0086), cyanine black. , Linol Yellow (CI21090), Linol Yellow GRO (CI 21090), Benzidine Yellow 4T-564D, Mitsubishi Carbon Black MA-40, Victoria Pure Blue (CI42595), CI PIGMENT RED97, 122, 149, 168, 177, 180, 192, 215, C.I. PIGMENT GREEN 7, 36, C.I. PIGMENT 15:1, 15:4, 15:6, 22, 60, 64, C.I. PIGMENT 83, 139 C.I. PIGMENT VIOLET 23, etc. In addition, white pigment, fluorescent pigment, etc. may be used.
상기 카본 블랙은 차광성이 있는 안료이면 특별히 한정되지 않으며, 공지된 카본 블랙을 사용할 수 있다. 상기 흑색 안료인 카본 블랙으로는 구체적으로 채널 블랙(channel black), 퍼니스 블랙(furnace black), 서멀 블랙(thermal black), 램프 블랙(lamp black) 등을 들 수 있다.The carbon black is not particularly limited as long as it is a light-shielding pigment, and a known carbon black can be used. As the black pigment, carbon black, specifically, channel black, furnace black, thermal black, lamp black, and the like.
또한, 상기 흑색 안료인 카본 블랙은 수지가 피복된 카본 블랙을 이용할 수도 있다. 상기 수지가 피복된 카본 블랙은 수지가 피복되어 있지 않은 카본 블랙에 비해 도전성이 낮기 때문에 블랙 매트릭스 또는 블랙 컬럼스페이서 형성시에 우수한 전기 절연성을 부여 할 수 있다.In addition, carbon black, which is the black pigment, may use carbon black coated with a resin. Since the carbon black coated with the resin has lower conductivity than the carbon black without the resin coating, it can provide excellent electrical insulation when forming a black matrix or black column spacer.
상기 흑색 안료는 흑색 안료의 입경이 균일하게 분산된 안료 분산액으로 사용할 수 있다. 안료의 입경을 균일하게 분산시키기 위한 방법의 예로는 안료 분산제(d1)를 함유시켜 분산 처리하는 방법 등을 들 수 있으며, 상기 방법에 따라 안료가 용액 중에 균일하게 분산된 상태의 안료 분산액을 얻을 수 있다.The black pigment may be used as a pigment dispersion in which the particle diameter of the black pigment is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of a pigment may include a method of dispersing by containing a pigment dispersant (d1), and according to the above method, a pigment dispersion liquid in which the pigment is uniformly dispersed in a solution can be obtained. have.
(( d1d1 )안료 ) Pigment 분산제Dispersant
상기 안료 분산제의 구체적인 예로는 양이온계, 음이온계, 비이온계, 양성, 폴리에스테르계, 폴리아민계 등의 계면활성제 등을 들 수 있고, 이들은 각각 단독 또는 2종이상을 조합하여 사용할 수 있다.Specific examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester-based, polyamine-based surfactants, and the like, and these may be used alone or in combination of two or more.
또한, 부틸메타아크릴레이트(BMA) 또는 N,N-디메틸아미노에틸메타아크릴레이트(DMAEMA)를 포함하는 아크릴레이트계 분산제 (이하, 아크릴레이트계 분산제라고 함)를 포함하는 것이 바람직하다. 상기 아크릴레이트계 분산제의 시판품으로는 DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070 또는 DISPER BYK-2150 등을 들 수 있으며, 상기 아크릴레이트계 분산제는 각각 단독 또는 2종이상을 조합하여 사용할 수 있다.In addition, it is preferable to include an acrylate-based dispersant (hereinafter referred to as an acrylate-based dispersant) containing butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA). Commercial products of the acrylate-based dispersant include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, or DISPER BYK-2150, and the acrylate-based dispersants can be used alone or in combination of two or more. Can.
상기 안료 분산제(d1)는 상기한 아크릴 분산제 이외에 다른 수지 타입의 안료 분산제를 사용할 수도 있다. 상기 다른 수지 타입의 안료 분산제로는 공지된 수지 타입의 안료 분산제, 특히 폴리우레탄, 폴리아크릴레이트로 대표되는 폴리카르복실산 에스테르, 불포화 폴리아미드, 폴리카르복실산, 폴리카르복실산의 (부분적)아민 염, 폴리카르복실산의 암모늄 염, 폴리카르복실산의 알킬아민 염, 폴리실록산, 장쇄 폴리아미노아미드 포스페이트 염, 히드록실기-함 폴리카르복실산의 에스테르 및 이들의 개질 생성물, 또는 프리(free) 카르복실기를 갖는 폴리에스테르와 폴리(저급 알킬렌이민)의 반응에 의해 형성된 아미드 또는 이들의 염과 같은 유질의 분산제; (메트)아크릴산-스티렌 코폴리머, (메트)아크릴산-(메트)아크릴레이트 에스테르 코폴리머, 스티렌-말레산 코폴리머, 폴리비닐 알코올 또는 폴리비닐 피롤리돈과 같은 수용성 수지 또는 수용성 폴리머 화합물; 폴리에스테르; 개질 폴리아크릴레이트; 에틸렌 옥사이드/프로필렌 옥사이드의 부가생성물 및 포스페이트 에스테르 등을 들 수 있다. 상기한 수지형 분산제의 시판품으로는 양이온계 수지 분산제로서는, 예를 들면, BYK(빅) 케미사의 상품명: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162,DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182,DISPER BYK-184; BASF사의 상품명: EFKA-44, EFKA-46, EFKA-47, EFKA-48,EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800 ; Lubirzol사의 상품명:SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 /10; 카와켄 파인 케미컬사의 상품명: 히노액트(HINOACT) T-6000, 히노액트 T-7000, 히노액트 T-8000; 아지노모토사의 상품명: 아지스퍼(AJISPUR) PB-821, 아지스퍼 PB-822, 아지스퍼 PB-823; 쿄에이샤 화학사의 상품명: 플로렌 (FLORENE) DOPA-17HF, 플로렌 DOPA-15BHF, 플로렌 DOPA-33, 플로렌 DOPA-44 등을 들 수 있다. 상기한 아크릴 분산제 이외에 다른 수지 타입의 안료 분산제는 각각 단독 또는 2종이상을 조합하여 사용할 수 있으며, 아크릴 분산제와 병용하여 사용할 수도 있다.The pigment dispersant (d1) may be a resin dispersant other than the acrylic dispersant described above. As said other resin type pigment dispersant, a known resin type pigment dispersant, in particular of polyurethane, polycarboxylic acid esters represented by polyacrylates, unsaturated polyamides, polycarboxylic acids, (partial) of polycarboxylic acids Amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oily dispersants such as amides or salts thereof formed by the reaction of a polyester having a carboxyl group with poly(lower alkyleneimine); Water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; Modified polyacrylates; And ethylene oxide/propylene oxide adducts and phosphate esters. As commercially available products of the resin-type dispersing agent described above, as the cationic resin dispersing agent, for example, trade names of BYK (Big) Chemicals: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK- 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF's product names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names of Lubirzol: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 /10; Trade names of Kawaken Fine Chemicals: HINOACT T-6000, Hinoact T-7000, Hinoact T-8000; Ajinomoto's trade names: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Trade names of Kyoeisha Chemicals: FLORENE DOPA-17HF, Floren DOPA-15BHF, Floren DOPA-33, Floren DOPA-44, and the like. Pigment dispersants of other resin types other than the above-described acrylic dispersants may be used alone or in combination of two or more, or may be used in combination with acrylic dispersants.
본 발명의 흑색 안료(D)는 흑색 감광성 수지 조성물 100중량부에 대하여 5 내지 20중량부로 포함될 수 있으며, 바람직하게는 5 내지 10중량부인 것이 좋다.The black pigment (D) of the present invention may be included in 5 to 20 parts by weight based on 100 parts by weight of the black photosensitive resin composition, preferably 5 to 10 parts by weight.
<용매(E)><Solvent (E)>
본 발명에 따른 용매(E)는 본 발명의 흑색 감광성 수지 조성물의 다른 성분들을 용해시키기 위해 사용되는 것으로서, 통상적으로 사용되는 흑색 감광성 수지 조성물에 사용되는 용매라면 특별히 제한하지 않고 사용될 수 있으며, 에테르류, 방향족 탄화수소류, 케톤류, 알코올류, 에스테르류, 아미드류 등이 바람직하다.The solvent (E) according to the present invention is used to dissolve other components of the black photosensitive resin composition of the present invention, and any solvent used in a commonly used black photosensitive resin composition may be used without particular limitation, and ethers , Aromatic hydrocarbons, ketones, alcohols, esters, amides and the like are preferred.
상기 용매(E)의 구체적인 예를 들면, 에틸렌글리콜모노메틸에테르, 에틸렌글리콜모노에틸에테르, 에틸렌글리콜모노프로필에테르, 에틸렌글리콜모노부틸에테르 등의 에틸렌글리콜모노알킬에테르류;Specific examples of the solvent (E) include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether;
프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르 등의 프로필렌글리콜모노알킬에테르류;Propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether;
디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 디에틸렌글리콜디프로필에테르, 디에틸렌글리콜디부틸에테르 등의 디에틸렌글리콜디알킬에테르류;Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether;
메틸셀로솔브아세테이트, 에틸셀로솔브아세테이트 등의 에틸렌글리콜알킬에테르아세테이트류;Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate;
프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트, 메톡시부틸아세테이트, 메톡시펜틸아세테이트 등의 알킬렌글리콜알킬에테르아세테이트류;Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate;
벤젠, 톨루엔, 크실렌, 메시틸렌 등의 방향족 탄화수소류;Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene;
메틸에틸케톤, 아세톤, 메틸아밀케톤, 메틸이소부틸케톤, 시클로헥사논 등의 케톤류;Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone;
에탄올, 프로판올, 부탄올, 헥사놀, 시클로헥산올, 에틸렌글리콜, 글리세린 등의 알코올류;Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin;
3-에톡시프로피온산에틸, 3-메톡시프로피온산메틸 등의 에스테르류, γ-부티롤락톤 등의 환상 에스테르류 등을 들 수 있다.And esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone.
상기 용매(E)는 도포성 및 건조성 면에서 비점이 100 내지 200℃인 유기 용매가 바람직하며, 예를 들면 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 시클로헥사논, 에틸락테이트, 부틸락테이트, 3-에톡시프로피온산에틸, 3-메톡시프로피온산메틸 등을 들 수 있다. 상기 예시한 용매(E)는 각각 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다. The solvent (E) is preferably an organic solvent having a boiling point of 100 to 200°C in terms of coatability and dryness, for example, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate , Butyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like. The solvents (E) exemplified above may be used alone or in combination of two or more.
상기 용매(E)의 함량은 특별히 한정되지 않으나, 흑색 감광성 수지 조성물 100중량부 대하여 20 내지 85중량부로 포함될 수 있으며, 상기 범위내로 포함되는 경우 도포성이 양호해질 수 있다.
The content of the solvent (E) is not particularly limited, but may be included in an amount of 20 to 85 parts by weight with respect to 100 parts by weight of the black photosensitive resin composition.
또한, 본 발명의 감광성 수지 조성물은 밀착촉진제, 계면활성제, 분산제, 산화방지제, 자외선흡수제, 열중합방지제, 및 레벨링제 중에서 선택되는 1종 이상의 첨가제를 추가로 포함할 수 있다.In addition, the photosensitive resin composition of the present invention may further include one or more additives selected from adhesion promoters, surfactants, dispersants, antioxidants, ultraviolet absorbers, thermal polymerization inhibitors, and leveling agents.
상기 밀착촉진제로는 메타아크릴로일옥시 프로필트리메톡시 실란, 메타아크릴로일옥시 프로필 디메톡시 실란, 메타아크릴로일옥시 프로필트리에톡시 실란, 메타아크릴로일옥시 프로필디메톡시실란 등의 메타아크릴로일 실란 커플링제로 이루어진 군에서 선택된 적어도 1종을 사용할 수 있고, 알킬 트리메톡시 실란으로서 옥틸트리메톡시 실란, 도데실트리메톡시 실란, 옥타데실트리메톡시 실란으로 이루어진 군에서 선택된 적어도 1종을 사용할 수 있다.Examples of the adhesion promoter include methacryl such as methacryloyloxy propyl trimethoxy silane, methacryloyloxy propyl dimethoxy silane, methacryloyloxy propyl triethoxy silane, and methacryloyloxy propyl dimethoxysilane. At least one selected from the group consisting of a loyl silane coupling agent may be used, and at least 1 selected from the group consisting of octyltrimethoxy silane, dodecyltrimethoxy silane, and octadecyltrimethoxy silane as the alkyl trimethoxy silane. Species can be used.
상기 계면 활성제로는 MCF 350SF, F-475, F-488, F-552(이하 DIC 사)등을 사용할 수 있으나 이들에만 한정하는 것은 아니며, 경우에 따라 좀 더 그 범위가 확대될 수 있다.As the surfactant, MCF 350SF, F-475, F-488, F-552 (hereinafter referred to as DIC) may be used, but the present invention is not limited thereto, and the range may be further expanded in some cases.
상기 분산제 및 레벨링제로는 당업계에서 일반적으로 쓰이는 것들이 모두 사용될 수 있다.As the dispersant and the leveling agent, all those commonly used in the art can be used.
상기 산화방지제로는 2,2-티오비스(4-메틸-6-t-부틸페놀), 2,6-g,t-부틸페놀 등을 사용할 수 있고, 상기 자외선 흡수제로는 2-(3-t-부틸-5-메틸-2-히드록시페닐)-5-클로로-벤조트리아졸, 알콕시 벤조페논 등을 사용할 수 있다. 상기 열중합방지제로는 히드로퀴논, p-메톡시페놀, 디-t-부틸-p-크레졸, 피로가롤, t-부틸카테콜, 벤조퀴논, 4,4-티오비스(3-메틸-6-t-부틸페놀), 2,2-메틸렌비스(4-메틸-6-t-부틸페놀), 2-머캅토이미다졸 등을 사용할 수 있다.As the antioxidant, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol, and the like can be used, and the ultraviolet absorber 2-(3- t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, and the like can be used. Examples of the thermal polymerization inhibitor include hydroquinone, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, t-butyl catechol, benzoquinone, 4,4-thiobis(3-methyl-6- t-butylphenol), 2,2-methylenebis(4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and the like.
그리고, 본 발명의 감광성 수지 조성물은 카본블랙 분산물, 기능성을 가지는 수지바인더, 모노머, 감방사선성 화합물, 및 그 밖의 첨가제 중에서 선택되는 1 종 이상의 2차 첨가제를 추가로 포함할 수 있다.In addition, the photosensitive resin composition of the present invention may further include one or more secondary additives selected from carbon black dispersions, resin binders having functionality, monomers, radiation-sensitive compounds, and other additives.
또한, 본 발명은 상기 흑색 감광성 수지 조성물로 제조된 블랙매트리스 및 이를 구비하는 화상 표시 장치를 제공하는 것을 목적으로 한다.In addition, an object of the present invention is to provide a black mattress made of the black photosensitive resin composition and an image display device having the same.
본 발명의 화상 표시 장치는 상기 블랙매트릭스를 구비한 것으로서, 구체적인 예를 들면, 액정 디스플레이, OLED, 플렉서블 디스플레이 등을 들 수 있으며, 이에 한정되는 것은 아니다. The image display device of the present invention is provided with the black matrix, and specific examples thereof include a liquid crystal display, an OLED, and a flexible display, but are not limited thereto.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 기재하나, 이들 실시예는 본 발명을 예시하는 것일 뿐 첨부된 특허 청구범위를 제한하는 것이 아니며, 본 발명의 범주 및 기술사상 범위 내에서 실시예에 대한 다양한 변경 및 수정이 가능함은 당업자에게 있어서 명백한 것이며, 이러한 변형 및 수정이 첨부된 특허청구범위에 속하는 것도 당연한 것이다.
Hereinafter, preferred embodiments will be described in order to help the understanding of the present invention, but these embodiments are merely illustrative of the present invention and do not limit the appended claims, and the embodiments within the scope and technical scope of the present invention. It is apparent to those skilled in the art that various changes and modifications to the present invention are possible, and it is natural that such modifications and modifications fall within the scope of the appended claims.
제조예Manufacturing example 1 : 화학식 1의 화합물의 합성 1: Synthesis of Compound of Formula 1
3000ml 삼구 라운드 플라스크에 4,4′-(9H-잔텐-9,9-디일)디페놀 (4,4′-(9H-xanthene-9,9-diyl)diphenol)364.4g과 t-부틸암모늄 브로마이드 0.4159g을 혼합하고, 에피클로로히드린 2359g을 넣고 90℃로 가열하여 반응시켰다. 액체크로마토그래피로 분석하여 4,4′-(9H-잔텐-9,9-디일)디페놀 (4,4′-(9H-xanthene-9,9-diyl)diphenol)이 완전히 소진되면 30℃로 냉각하여 50% NaOH 수용액(3당량)을 천천히 첨가하였다. 액체 크로마토그래피로 분석하여 에피클로로히드린이 완전히 소진되었으면, 디클로로메탄으로 추출한 후 3회 수세한 후 유기층을 황산마그네슘으로 건조시킨 후 디클로로메탄을 감압 증류하고 디클로로메탄과 메탄올 혼합비 50:50을 사용하여 재결정하였다.364.4 g and t-butylammonium bromide in 4,4′-(9H-xanthene-9,9-diyl)diphenol (4,4′-(9H-xanthene-9,9-diyl)diphenol) in a 3000ml three-necked round flask 0.4159g was mixed, 2359g of epichlorohydrin was added, and the mixture was heated to 90°C for reaction. It was analyzed by liquid chromatography, and when 4,4′-(9H-xanthene-9,9-diyl)diphenol (4,4′-(9H-xanthene-9,9-diyl)diphenol) was completely exhausted, it was increased to 30℃. After cooling, 50% NaOH aqueous solution (3 eq.) was slowly added. When epichlorohydrin is completely exhausted by liquid chromatography, the mixture is extracted with dichloromethane, washed three times, and then the organic layer is dried over magnesium sulfate, dichloromethane is distilled under reduced pressure, and a dichloromethane and methanol mixture ratio of 50:50 is used. Recrystallized.
이렇게 합성된 에폭시 화합물 1당량과 t-부틸암모늄 브로마이드 0.004당량, 2,6-디이소부틸페놀 0.001당량, 아크릴산 2.2당량을 혼합한 후 용매 프로필렌글리콜모노메틸에테르아세테이트 24.89g을 넣어 혼합하였다. 이 반응 용액에 공기를 25ml/min으로 불어넣으면서 온도를 90~100℃로 가열 용해하였다. 반응 용액이 백탁한 상태에서 온도를 120℃까지 가열하여 완전히 용해시켰다. 용액이 투명해지고 점도가 높아지면 산가를 측정하여 산가가 1.0mgKOH/g미만이 될 때까지 교반하였다. 산가가 목표(0.8)에 이를 때까지 11시간이 필요했다. 반응 종결 후 반응기의 온도를 실온으로 내려 무색 투명한 화학식 1의 화합물을 얻었다.1 equivalent of the epoxy compound thus synthesized, 0.004 equivalent of t-butylammonium bromide, 0.001 equivalent of 2,6-diisobutylphenol, and 2.2 equivalents of acrylic acid were mixed, followed by adding 24.89 g of a solvent propylene glycol monomethyl ether acetate. The reaction solution was heated and dissolved at 90 to 100°C while blowing air at 25 ml/min. While the reaction solution was cloudy, the temperature was heated to 120°C to dissolve completely. When the solution became transparent and the viscosity increased, the acid value was measured and stirred until the acid value became less than 1.0 mgKOH/g. It took 11 hours to reach the target (0.8). After completion of the reaction, the temperature of the reactor was lowered to room temperature to obtain a colorless and transparent compound of formula (1).
제조예Manufacturing example 2: 2: 카도계Cardo system 바인더 수지(A-1)의 합성 Synthesis of binder resin (A-1)
제조예 1의 화학식 1의 화합물 307.0g에 프로필렌글리콜모노메틸에테르아세테이트 600g을 첨가하여 용해한 후, 비페닐테트라카르복실산 2무수물 78g 및 브롬화테트라에틸암모늄 1g을 혼합하고 서서히 승온시켜 110∼115℃ 에서 4시간 동안 반응시켰다. 산 무수물기의 소실을 확인한 후, 1,2,3,6-테트라히드로무수프탈산 38.0g을 혼합하여 90℃ 에서 6시간 동안 반응시켜 카도계 바인더 수지로 중합하였다. 무수물의 소실은 IR 스펙트럼에 의해 확인하였다.After adding and dissolving 600 g of propylene glycol monomethyl ether acetate to 307.0 g of the compound of Formula 1 of Preparation Example 1, 78 g of biphenyltetracarboxylic dianhydride and 1 g of tetraethylammonium bromide were mixed and gradually heated to 110 to 115°C. The reaction was carried out for 4 hours. After confirming the disappearance of the acid anhydride group, 1,2,3,6-tetrahydrophthalic anhydride 38.0g was mixed and reacted at 90°C for 6 hours to polymerize with a cardo-based binder resin. The disappearance of the anhydride was confirmed by IR spectrum.
제조예Manufacturing example 3 : 바인더 수지(A-2)합성 3: Synthesis of binder resin (A-2)
반응용매로 THF(테트라하이드로퓨란) 용액 200g을 500ml 4구 플라스크에 투입하고 50℃로 유지시킨다. 상기 [화학식 4]로 표시되는 화합물 89g을 투입하고 [화학식 5]로 표시되는 에피클로히드린 용액을 44.5g을 드롭핑 펀넬을 이용하여 분당 5.25g의 속도로 투입하여 1시간 30분간 반응시켰다. 반응으로 얻어진 비스페놀계 플루오렌형 에폭시 레진 화합물 348g을 1000mL 반응기에 투입하고 아크릴산 용액 140.52g을 넣고 80℃로 승온하여 반응을 시켰다. 이 후, 테트라에틸 암모늄 브로마이드 13.5g을 서서히 투입하여 60시간 동안 반응을 시켰다. 상기 반응물 150g을 반응기에 넣고 산무수물(무수프탈산) 180.5g과 산2무수물(무수피로메리트산) 348.8g을 투입한 후 120℃로 유지시킨다. 이때 촉매로써 Fascat 4101을 0.718g을 서서히 넣고 5시간 동안 반응시켜 바인더 수지를 제조한다.200 g of THF (tetrahydrofuran) solution was added to a 500 ml 4-neck flask as a reaction solvent and maintained at 50°C. 89 g of the compound represented by [Formula 4] was added, and 44.5 g of the epiclohydrin solution represented by [Formula 5] was added at a rate of 5.25 g per minute using a dropping funnel and reacted for 1 hour and 30 minutes. 348 g of the bisphenol-based fluorene-type epoxy resin compound obtained by the reaction was introduced into a 1000 mL reactor, and 140.52 g of an acrylic acid solution was added thereto, and the mixture was heated to 80° C. to react. Thereafter, 13.5 g of tetraethyl ammonium bromide was slowly added to react for 60 hours. 150 g of the reactants were put into a reactor, and 180.5 g of acid anhydride (phthalic anhydride) and 348.8 g of acid 2 anhydride (pyromeric anhydride) were added and maintained at 120°C. At this time, 0.718 g of Fascat 4101 was slowly added as a catalyst and reacted for 5 hours to prepare a binder resin.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
실시예Example 및 And 비교예Comparative example
하기 표 1의 성분 및 함량을 사용하여 감광성 수지 조성물을 제조하였다.A photosensitive resin composition was prepared using the components and contents of Table 1 below.
(중량부)division
(Parts by weight)
안료(D)black
Pigment (D)
(E)menstruum
(E)
촉진제(F)stick
Accelerator (F)
A-1: 제조예 2의 카도계 바인더 수지(본 발명의 카도계 바인더 수지)
A-2: 제조예 3의 바인더 수지
A-3: 아크릴계 바인더(벤질메타아크릴레이트/N-페닐말레이미드/스티렌/메타아크릴산)
(몰비 55/9/11/25, Mw=20,000, 산가 100 ㎎KOH /g)
광중합성 화합물(B): 디펜타에리스리톨트리아크릴레이트
광중합 개시제
C-1: N-1919(아데카사)
C-2: OXE-02(시바사)
C-3: Triazine-EB(Tronly사)
흑색 안료(D): CHBK-17(미쿠니색소사)
용매(E): 프로필렌글리콜모노메틸에테르아세테이트
밀착촉진제(F): 3-메타아크릴로일옥시 프로필트리메톡시 실란(신에츠사)Binder resin
A-1: Cardo-based binder resin of Production Example 2 (cardo-based binder resin of the present invention)
A-2: Binder resin of Production Example 3
A-3: Acrylic binder (benzyl methacrylate/N-phenylmaleimide/styrene/methacrylic acid)
(Molar ratio 55/9/11/25, Mw=20,000, acid value 100 mgKOH/g)
Photopolymerizable compound (B): dipentaerythritol triacrylate
Photopolymerization initiator
C-1: N-1919 (Adeka Corporation)
C-2: OXE-02 (Shiba Corporation)
C-3: Triazine-EB (Tronly)
Black pigment (D): CHBK-17 (Mikuni color)
Solvent (E): Propylene glycol monomethyl ether acetate
Adhesion promoter (F): 3-methacryloyloxy propyltrimethoxy silane (Shin-Etsu)
시험방법Test Methods
(1) 접착력 평가(1) Evaluation of adhesion
실시예 및 비교예의 감광성 수지 조성물을 도포하고, 핫플레이트 상에서 100℃에서 1분 동안 건조시켜 도막을 수득하였다. 이후, 도막 위에 패턴 두께가 1 내지 20㎛까지 1㎛단위로 새겨진 마스크를 사용하여 365㎚의 파장을 가진 고압 수은 램프를 사용하여 노광 공정을 수행하였다. 노광 공정까지 진행한 도면에 대해 현상을 진행하지 않고 230℃의 컨벡션 오븐에서 100분간 포스트베이크(post-bake)한 후 PCT(Pressure-cookertest) 를 실시 후, Cross-cut 테스트로 글라스와 코팅편의 박리여부를 판단하였다. The photosensitive resin compositions of Examples and Comparative Examples were applied, and dried on a hot plate at 100° C. for 1 minute to obtain a coating film. Subsequently, an exposure process was performed using a high pressure mercury lamp having a wavelength of 365 nm using a mask engraved in 1 µm units with a pattern thickness of 1 to 20 µm on the coating film. Post-bake for 100 minutes in a convection oven at 230°C without developing for the drawings that have been exposed to the exposure process, and then perform PCT (Pressure-cookertest), and then peel off the glass and coating pieces by cross-cut test It was judged whether or not.
(PCT 공정조건: 2기압, 습도 120% 4hr/1cycle)(PCT process conditions: 2 atm, humidity 120% 4hr/1cycle)
(2) 현상 밀착성 평가(2) Evaluation of developing adhesion
두께 1㎜의 유리기판 상에 1㎛의 두께로 실시예 및 비교예의 감광성 수지 조성물을 도포하고, 핫플레이트 상에서 100℃에서 1분 동안 건조시켜 도막을 수득하였다. 이후, 도막 위에 패턴의 폭이 1 내지 20㎛까지 1㎛단위로 새겨진 마스크를 사용하여 365㎚의 파장을 가진 고압 수은 램프를 사용하여 노광한 후, 1% KOH계 수용액을 사용하여 30℃, 상압 하에서 일정 시간 동안 현상을 진행하였다. 패턴이 잔존하는 마스크 사이즈를 기준으로 최소패턴을 측정하였다.The photosensitive resin compositions of Examples and Comparative Examples were coated on a 1 mm thick glass substrate with a thickness of 1 μm, and dried on a hot plate at 100° C. for 1 minute to obtain a coating film. Subsequently, after exposure using a high pressure mercury lamp having a wavelength of 365 nm using a mask engraved in 1 µm increments from 1 to 20 µm in width on the coating film, 30° C. and normal pressure using a 1% KOH-based aqueous solution. The development was carried out for a period of time under. The minimum pattern was measured based on the mask size in which the pattern remains.
상기 표 2 에서 보는 바와 같이, 본 발명에 따른 흑색 감광성 수지 조성물을 사용한 실시예의 경우, 현상 밀착력이 우수하여 패턴의 유실 없이 형성 가능한 최소 패턴의 크기가 현저히 작아 고해상도의 컬러 필터를 구현할 수 있고, 기판에 대한 접착력도 우수하여 내구성 또한 우수한 것을 확인할 수 있었다.As shown in Table 2, in the case of the embodiment using the black photosensitive resin composition according to the present invention, the developmental adhesion is excellent and the size of the minimum pattern that can be formed without loss of the pattern is remarkably small, so that a high-resolution color filter can be implemented, and the substrate It was also confirmed that the adhesion to the product was excellent and the durability was also excellent.
알칼리 가용성 바인더 수지와 광중합 개시제를 다소 과량으로 포함하는 실시예 5 및 6의 경우, 비교예 보다는 최소패턴의 크기가 작고 기판접착력이 우수하였으나, 다른 실시예와 비교하면 최소패턴의 크기가 큰 것을 확인할 수 있었다.In the case of Examples 5 and 6 containing the alkali-soluble binder resin and the photopolymerization initiator in an excessive amount, the size of the minimum pattern was smaller and the adhesion of the substrate was better than that of the comparative example, but it was confirmed that the size of the minimum pattern was large compared to other examples. Could.
본 발명의 화학식 1과 다른 구조를 가지는 화합물로부터 중합한 바인더 수지를 사용한 비교예 1의 경우, 현상 밀착력이 저하되어 최소 패턴의 크기가 컸고, 내습열 조건에서의 기판력이 저하되어 내구성이 약한 것을 확인할 수 있었다.In the case of Comparative Example 1 using a binder resin polymerized from a compound having a structure different from Formula 1 of the present invention, it was confirmed that the developing adhesive strength was reduced, the size of the minimum pattern was large, and the substrate strength was lowered in the heat and humidity conditions, resulting in weak durability. Could.
아크릴계 바인더 수지를 사용한 비교예 2의 경우, 기판에 대한 접착력은 우수하였으나, 현상 밀착력이 저하된 것을 확인할 수 있었다.In the case of Comparative Example 2 using an acrylic binder resin, the adhesive strength to the substrate was excellent, but it was confirmed that the developing adhesion was lowered.
본 발명의 옥심에스테르계 광개시제 대신 트리아진계 광개시제를 사용한 비교예 3의 경우, 현상 밀착력과 기판에 대한 접착성이 모두 저하된 것을 확인할 수 있었다.
In the case of Comparative Example 3 in which the triazine-based photoinitiator was used instead of the oxime ester-based photoinitiator of the present invention, it was confirmed that both the developing adhesion and the adhesion to the substrate were reduced.
Claims (6)
상기 알칼리 가용성 바인더 수지(A)는 하기 화학식 1로 표시되는 화합물들이 산무수물기의 소실을 통해 중합되며 10 내지 200mgKOH/g의 산가를 갖고 1,000 내지 30,000의 중량평균분자량을 갖는 카도계 바인더 수지(a1)를 포함하고,
상기 광중합 개시제(C)는 하기 화학식 2로 표시되는 화합물 중에서 선택된 적어도 1종을 포함하는, 블랙매트릭스 형성용 흑색 감광성 수지 조성물:
[화학식 1]
(식 중에서, R1 및 R2는 각각 독립적으로,
X는 수소 원자, 탄소수 1 내지 5의 알킬기 또는 수산기이고, R3는 수소 원자 또는 탄소수 1 내지 5의 알킬기임)
[화학식 2]
(식 중에서, Ch1은
Het1 및 Het3는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 푸릴기, 티에닐기, 피롤릴기, 피리딜기, 2-벤조티에닐기, 3- 벤조티에닐기, 2- 인돌릴기 또는 3- 인돌릴기이고,
Het2 및 Het4는 각각 독립적으로 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된 티에닐렌기, 피롤릴렌기, 벤조티에닐렌기, 인돌릴렌기 또는 인돌릴렌카보닐기이고,
Ar1은 탄소수 1 내지 12의 알킬기로 치환 또는 비치환된
Ar2는 탄소수 6 내지 14의 아릴기 또는
X1, X2, X3 및 X4는 각각 독립적으로 산소 원자; 황 원자; 또는 -NR6-이고,
R4는 탄소수 1 내지 12의 알킬기 또는 알콕시기, 또는 탄소수 6 내지 14의 아릴기이고,
R5는 수소 원자, 탄소수 1 내지 20의 알킬기, 탄소수 3 내지 20의 시클로알킬기 또는 탄소수 6 내지 14의 아릴기이고,
R6는 탄소수 1 내지 20의 알킬기 또는 탄소수 6 내지 14의 아릴기임).
Alkali-soluble binder resin (A), photopolymerizable compound (B), photopolymerization initiator (C), black pigment (D), and solvent (E).
In the alkali-soluble binder resin (A), the compounds represented by the following Chemical Formula 1 are polymerized through the disappearance of an acid anhydride group, and have an acid value of 10 to 200 mgKOH/g, and a cardo-based binder resin (a1) having a weight average molecular weight of 1,000 to 30,000. ),
The photopolymerization initiator (C) comprises at least one selected from compounds represented by the following formula (2), a black photosensitive resin composition for forming a black matrix:
[Formula 1]
(In the formula, R 1 and R 2 are each independently,
X is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a hydroxyl group, and R 3 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms)
[Formula 2]
(In the formula, Ch 1 is
Het 1 and Het 3 are each independently a substituted or unsubstituted furyl group, thienyl group, pyrrolyl group, pyridyl group, 2-benzothienyl group, 3- benzothienyl group, 2- indolyl group, or an alkyl group having 1 to 12 carbon atoms, or 3- indolyl group,
Het 2 and Het 4 are each independently a substituted or unsubstituted thienyl group, pyrrolylene group, benzothienylene group, indolylene group or indolylene carbonyl group having 1 to 12 carbon atoms,
Ar 1 is substituted or unsubstituted with an alkyl group having 1 to 12 carbon atoms.
Ar 2 is an aryl group having 6 to 14 carbon atoms, or
X 1 , X 2 , X 3 and X 4 are each independently an oxygen atom; Sulfur atom; Or -NR 6 -,
R 4 is an alkyl group or an alkoxy group having 1 to 12 carbon atoms, or an aryl group having 6 to 14 carbon atoms,
R 5 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an aryl group having 6 to 14 carbon atoms,
R 6 is an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 14 carbon atoms).
[화학식 3]
The method according to claim 1, wherein the compound represented by Formula 1 is synthesized using the compound represented by Formula 3, black photosensitive resin composition for forming a black matrix:
[Formula 3]
The black photosensitive resin composition for forming a black matrix according to claim 1, wherein the cardo-based binder resin (a1) is polymerized with 9,9-bis (3,4-methacrylic diester) xanthene.
The method according to claim 1, 1 to 40 parts by weight of the alkali-soluble binder resin (A), 1 to 20 parts by weight of the photopolymerizable compound (B), 0.1 to 10 parts by weight of the photopolymerization initiator (C) with respect to 100 parts by weight of the black photosensitive resin composition , Black pigment (D) 5 to 20 parts by weight, and solvent (E) 20 to 85 parts by weight, a black photosensitive resin composition for forming a black matrix.
A black matrix formed by using the black photosensitive resin composition for forming a black matrix according to any one of claims 1 to 4.
An image display device provided with a black matrix according to claim 5.
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| JP2013105066A (en) | 2011-11-15 | 2013-05-30 | Kaneka Corp | New production kit for photosensitive resin composition, and use of the same |
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| KR101068622B1 (en) | 2009-12-22 | 2011-09-28 | 주식회사 엘지화학 | The high lightshielding blackmatrix composition having improved adhesion properties |
| KR101486560B1 (en) * | 2010-12-10 | 2015-01-27 | 제일모직 주식회사 | Photosensitive resin composition and black matrix using the same |
| KR101432604B1 (en) * | 2011-11-16 | 2014-08-22 | 제일모직주식회사 | Black photosensitive resin composition and light blocking layer using the same |
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