KR20140017128A - Colored photosensitive resin composition for green pixel - Google Patents
Colored photosensitive resin composition for green pixel Download PDFInfo
- Publication number
- KR20140017128A KR20140017128A KR1020120083499A KR20120083499A KR20140017128A KR 20140017128 A KR20140017128 A KR 20140017128A KR 1020120083499 A KR1020120083499 A KR 1020120083499A KR 20120083499 A KR20120083499 A KR 20120083499A KR 20140017128 A KR20140017128 A KR 20140017128A
- Authority
- KR
- South Korea
- Prior art keywords
- weight
- photosensitive resin
- pigment
- resin composition
- parts
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 56
- 239000000049 pigment Substances 0.000 claims abstract description 112
- 239000006185 dispersion Substances 0.000 claims abstract description 52
- 239000002270 dispersing agent Substances 0.000 claims abstract description 44
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 37
- 239000002904 solvent Substances 0.000 claims abstract description 21
- 150000001412 amines Chemical class 0.000 claims abstract description 20
- 238000004040 coloring Methods 0.000 claims abstract description 18
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 9
- 238000003384 imaging method Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- -1 metal complex salts Chemical class 0.000 description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 17
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- 230000000052 comparative effect Effects 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
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- PGEHNUUBUQTUJB-UHFFFAOYSA-N anthanthrone Chemical compound C1=CC=C2C(=O)C3=CC=C4C=CC=C5C(=O)C6=CC=C1C2=C6C3=C54 PGEHNUUBUQTUJB-UHFFFAOYSA-N 0.000 description 7
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 6
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- 239000011324 bead Substances 0.000 description 5
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- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 5
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- 239000010409 thin film Substances 0.000 description 5
- 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 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 4
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- 239000002318 adhesion promoter Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- 239000001023 inorganic pigment Substances 0.000 description 4
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000001588 bifunctional effect 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
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- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 3
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- 239000000758 substrate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
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- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 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
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
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- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 2
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- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
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- 230000032683 aging Effects 0.000 description 2
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- 239000003086 colorant Substances 0.000 description 2
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- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- KGGOIDKBHYYNIC-UHFFFAOYSA-N ditert-butyl 4-[3,4-bis(tert-butylperoxycarbonyl)benzoyl]benzene-1,2-dicarboperoxoate Chemical compound C1=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=CC=C1C(=O)C1=CC=C(C(=O)OOC(C)(C)C)C(C(=O)OOC(C)(C)C)=C1 KGGOIDKBHYYNIC-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- MZWHIEFYUAYOJU-UHFFFAOYSA-N hexanedioic acid;oxetane Chemical compound C1COC1.C1COC1.OC(=O)CCCCC(O)=O MZWHIEFYUAYOJU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- GQKZBCPTCWJTAS-UHFFFAOYSA-N methoxymethylbenzene Chemical compound COCC1=CC=CC=C1 GQKZBCPTCWJTAS-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- KRGGVEDZUSPSAC-UHFFFAOYSA-N oxetan-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCO1 KRGGVEDZUSPSAC-UHFFFAOYSA-N 0.000 description 1
- AMUUFLNQHMIHRP-UHFFFAOYSA-N oxetan-3-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1 AMUUFLNQHMIHRP-UHFFFAOYSA-N 0.000 description 1
- WCAOBJJSISYNMN-UHFFFAOYSA-N oxetane;terephthalic acid Chemical compound C1COC1.C1COC1.OC(=O)C1=CC=C(C(O)=O)C=C1 WCAOBJJSISYNMN-UHFFFAOYSA-N 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229940067265 pigment yellow 138 Drugs 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
- G03F7/0295—Photolytic halogen compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Materials For Photolithography (AREA)
Abstract
The present invention comprises a pigment dispersion composition (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D) and a solvent (E), wherein the pigment dispersion composition (A) is used as a pigment. Pigment Green 58, wherein the amine number of the dispersant contained in the composition is 10 ~ 50mgKOH / g, the coloring photosensitive resin composition for green pixels, a color filter prepared using the same and a liquid crystal comprising the color filter A display device or an imaging device is provided.
Description
The present invention relates to a colored photosensitive resin composition for a green color, a colored pattern formed from the composition, a color filter including the colored pattern, a liquid crystal display device having the same, and an imaging device.
Color filters are widely used in imaging elements, liquid crystal display elements, and the like, and their application range is rapidly expanding. A color filter used for a color liquid crystal display element, an image pickup element, and the like is generally formed by spin coating a colored photosensitive resin composition for a green color containing a colorant corresponding to each color of red, green and blue on a substrate on which a black matrix is pattern- The coating film formed by uniformly applying and then drying by heating (hereinafter also referred to as pre-baking) is exposed and developed, and if necessary, further heat curing (hereinafter also referred to as post-baking) And then repeatedly forming pixels of each color.
In recent years, color filters for liquid crystal displays (LCDs) are gradually becoming larger in liquid crystal displays, and continuous high quality images are required. To this end, the color of the green pixel is changed to C.I. CI Pigment Green 36 having high transmittance and contrast ratio. Pigment Green 58, but C.I. In the case of Pigment Green 58, it is known that it is difficult to secure a satisfactory voltage holding ratio of 90% or more, which causes continuous image display defects. Therefore, researches to solve this problem are continuing, but there is no clear solution.
For example, Korean Patent Laid-Open No. 10-2011-0113137 discloses a colorant containing (A) a pigment, (B) an A block having a repeating unit (1) of 60% by mass or more represented by Formula 1, and represented by Formula 2 A block copolymer having a B block having a repeating unit (2), the amine number of which is at least 50 mgKOH / g and less than 80 mgKOH / g (hereinafter also referred to as "(B) copolymer"), and (C) containing a solvent The coloring composition characterized by the above-mentioned is disclosed.
The said coloring composition uses the block copolymer in which the amine number was specified as a pigment dispersant. However, in the case of the coloring composition, C.I. When Pigment Green 58 is used, the voltage holding characteristic of the color filter causes a problem of degradation.
The present inventors made diligent efforts to solve the above problems of the prior art, and found that the problem of lowering the voltage holding characteristics of the color filter is related to the liquid crystal contamination by the amine-based dispersant.
Therefore, the present invention solves the above problems and solves C.I. Even when Pigment Green 58 is used, an object of the present invention is to provide a colored photosensitive resin composition for green pixels, which exhibits excellent voltage holding property of 90% or more in a color filter.
This invention contains a pigment dispersion composition (A), alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E),
The pigment dispersion composition (A) is a pigment as C.I. Pigment Green 58 is provided, The amine value of the dispersing agent contained in the composition is 10-50 mgKOH / g, The coloring photosensitive resin composition for green pixels is provided.
The present invention also provides a color filter including a color pattern formed by forming the colored photosensitive resin composition for a green color in a predetermined pattern, followed by exposure and development.
Further, the present invention provides a liquid crystal display element and an imaging element including the color filter.
The coloring photosensitive resin composition for green pixels of this invention uses a dispersing agent whose amine number is 10-50 mgKOH / g as a pigment dispersant, and uses C.I. Even when Pigment Green 58 is used, the color filter exhibits excellent voltage retention of more than 90%.
Therefore, the coloring photosensitive resin composition for green pixels of the present invention can be very usefully used for the production of color filters.
This invention contains a pigment dispersion composition (A), alkali-soluble resin (B), a photopolymerizable compound (C), a photoinitiator (D), and a solvent (E),
The pigment dispersion composition (A) comprises CI Pigment Green 58 as a pigment, and relates to a colored photosensitive resin composition for green pixels, wherein the amine value of the dispersant contained in the composition is 10 to 50 mgKOH / g.
Hereinafter, the coloring photosensitive resin composition for green pixels of this invention is demonstrated in detail for every component.
Pigment Dispersion Composition (A)
Pigment (a1)
The pigment contains CI Pigment Green 58 as an essential component, and further, green, yellow organic pigments or inorganic pigments generally used in the art may be used. The above-mentioned pigments can be used in various kinds of pigments used in printing ink, ink jet ink and the like. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, And an anthanthrone pigment, an anthanthrone pigment, a pravanthrone pigment, a pyranthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, an anthanthrone pigment, a pyranthrone pigment, pyranthrone pigments, diketopyrrolopyrrole pigments, and the like. Examples of the inorganic pigments include metallic compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigments include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black Or composite metal oxides. In particular, the organic pigments and inorganic pigments include compounds that are specifically classified as pigments in the color index (Published by The society of Dyers and Colourists), and more specifically, the color index (CI) number of Although a pigment is mentioned, It is not necessarily limited to these.
C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 And 185
C.I. Pigment Green 7, 10, 15, 25, 36, 47
These pigments can be used individually or in combination of 2 or more types, respectively.
In particular, one or more pigments selected from CI pigment yellow 138, CI pigment yellow 150, CI pigment green 7, and CI pigment green 36 exemplified above can be preferably used.
The content of the pigment (a1) is in the range of 20 to 90% by weight, preferably 30 to 70% by weight, based on the total weight of solids in the pigment dispersion composition (A). If the content of the pigment is in the range of 20 to 90% by weight based on the above standards, it is preferable because the viscosity is low, the storage stability is excellent, and the dispersion efficiency is high, which is effective in increasing the contrast ratio.
In addition, the pigment (a1) is preferably included in the weight fraction of 5 to 60% by weight relative to the total weight of the solid color of the coloring photosensitive resin composition for green pixels. When included in the above-described range, even if a thin film is formed, the color density of the pixel is sufficient, and since the omission property of the non-pixel portion during development does not decrease, it is preferable because the residue hardly occurs.
Dispersants ( a2 )
In preparing the pigment dispersion composition (A) of the present invention, the amine number of the dispersant should be 10-50 mgKOH / g.
If the amine value of the dispersant is less than 10 mgKOH / g, the dispersibility is low, the storage stability is poor. If the amine value is more than 50 mgKOH / g, the VHR characteristics of the color filter made of a color photosensitive resin composition is less than 90%, there is a problem in the liquid crystal drive Easy to occur
The dispersant (a2) is added to deagglomerate and maintain stability of the pigment, it is not particularly limited as long as the amine value of the dispersant is satisfied. Preferably, It is preferable to contain an acrylate dispersant (hereinafter referred to as an acrylic dispersant) containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate). In this case, it is preferable to apply the acrylic dispersant prepared by the living control method as shown in Korean Patent Application Publication No. 2004-0014311, a commercially available product of the acrylate-based dispersant prepared through the living control method DISPER BYK- 2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150, etc. are mentioned.
The acrylic dispersants exemplified above may be used alone or in combination of two or more.
As the dispersant (a2) according to the present invention, a pigment dispersant of another resin type may be used in addition to the acrylic dispersant described above. The other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine 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 ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide, and phosphate esters. DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-160, BYK (trade name) 164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; EFKA-4060, EFKA-4060, EFKA-4055, EFKA-4055, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 / 10; Kawaken Fine Chemical's trade names: HINOACT T-6000, Hinoact T-7000, Hinoact T-8000; Trade names of Ajinomoto Co., Ltd .: AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823; The brand names of Kyoeisha Chemical Co., Ltd .: FLORENE DOPA-17HF, Floren DOPA-15BHF, Floren DOPA-33, Floren DOPA-44, etc. are mentioned. In addition to the acrylic dispersant described above, pigment dispersants of other resin types may be used alone or in combination of two or more thereof, or may be used in combination with an acrylic dispersant.
The usage-amount of the said dispersing agent (a2) is 5-60 weight part with respect to 100 weight part of solid content of the pigment (a1) used, More preferably, it is 15-50 weight part. When the content of the dispersing agent (a2) exceeds 60 parts by weight, the viscosity may be increased. When the content of the dispersant (a2) is less than 5 parts by weight, it may be difficult to atomize the pigment or may cause problems such as gelation after dispersion.
Dispersion solvent a3 )
The dispersion solvent (a3) is not particularly limited, and various organic solvents used in the art may 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, and diethylene glycol. Diethylene glycol dialkyl ethers such as 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, and propylene glycol mono Alkylene glycol alkyl ether acetates, such as ethyl ether acetate, a propylene glycol monopropyl ether acetate, a methoxy butyl acetate, and a methoxy pentyl acetate, aromatic hydrocarbons, such as benzene, toluene, xylene, and mesitylene, methyl ethyl ketone, acetone,Ketones such as tilamyl ketone, methyl isobutyl ketone, cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, ethyl 3-ethoxypropionate, 3-methoxypropionic acid Ester, such as methyl, Cyclic ester, such as (gamma) -butyrolactone, etc. are mentioned. Preferably, alkylene glycol alkyl ether acetates, ketones, esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate can be used, and more preferably propylene glycol monomethyl ether acetate and propylene glycol mono Ethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, etc. can be used. The dispersion solvents (a3) exemplified above may be used alone or in combination of two or more thereof.
The content of the dispersion solvent (a3) is usually 60 to 90% by weight, preferably 70 to 85% by weight based on the total weight of the pigment dispersion composition including the same. It is preferable that the content is in the range of 60 to 90% by weight because the storage stability of the pigment dispersion composition becomes good.
Dispersion aids ( a4 )
In preparing the pigment dispersion composition (A), a dispersing aid may be further added for dispersion stability or increase in business card ratio.
Patent Publication No. 11-49974, Japanese Patent Publication No. 2006-265528, Korean Patent Publication No. 2006-0093659 and the like can be used, but is not limited thereto. Specific examples thereof include SOLSPERSE-5000, SOLSPERSE-12000, SOLSPERSE-22000 from Lubrizol, BYK-SYNERGIST 2100, BYK-SINERGIST 2105 from BYK, EFKA-6745 and EFKA-6750 from BASF. In addition, the dispersing aid may be used those described in detail in Korean Patent Publication No. 2006-0111415.
The use amount of the dispersion aid (a4) is usually 1 to 70 parts by weight, more preferably 1 to 50 parts by weight based on 100 parts by weight of the solid content of the pigment (a1). When the content of the dispersion aid (a4) exceeds 70 parts by weight, there is a problem of discoloration due to hard baking during the color filter manufacturing process.
Content of the said pigment dispersion composition (A) is 10-90 weight% in weight fraction with respect to the total weight of the coloring photosensitive resin composition for green pixels, Preferably it is 20-80 It is preferred to be included in weight percent. In the case where the pigment dispersion composition (A) is included in the above-described range, even when a thin film is formed, the color density of the pixel is sufficient, and the residue is unlikely to occur because the omission of the non-pixel portion during development is not reduced. .
Alkali-soluble resin (B)
In the case of the alkali-soluble resin, it is preferable to have an acid value in order to have solubility in an alkaline developer in consideration of the developability of the coloring photosensitive resin composition.
The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the acrylic polymer, and can be determined by titration using an aqueous potassium hydroxide solution.
In the case of an alkali-soluble resin having an acid value, it is possible to produce a copolymer of a compound having an unsaturated bond which is copolymerizable with a compound having a carboxyl group and an unsaturated bond and a compound having a carboxyl group and an unsaturated bond.
Specific examples of the compound having an unsaturated bond with a carboxylic acid group include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid; And anhydrides of the dicarboxylic acids; mono (meth) acrylates of polymers having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and the like, and acrylic acid and methacrylic acid are preferred.
The compounds exemplified above may be used alone or in combination of two or more thereof.
Specific examples of the compound having an unsaturated bond capable of copolymerization are as follows, but are not necessarily limited thereto.
Styrene, vinyltoluene,? -Methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethylether, m-vinylbenzylmethylether, p-vinyl Aromatic vinyl compounds such as benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether or p-vinyl benzyl glycidyl ether;
Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate or t-butyl (meth) acrylate;
(Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate or isobornyl (meth) acrylate;
Aryl (meth) acrylates such as phenyl (meth) acrylate or benzyl (meth) acrylate;
Hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate or 2-hydroxypropyl (meth) acrylate;
N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide;
Unsaturated amide compounds such as (meth) acrylamide and N, N-dimethyl (meth) acrylamide;
3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) -3-ethyloxetane, 3- (methacryloyloxymethyl) -2-trifluoromethyloxetane, 3- (methacryloyloxymethyl) -2-phenyloxetane, 2- (methacryloyloxymethyl) oxetane or 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, etc. And unsaturated oxetane compounds.
The above-exemplified compounds may be used alone or in combination of two or more.
The alkali-soluble resin (B) according to the present invention can be used by further mixing various other alkali-soluble resins known in the art commonly used in the art.
The alkali-soluble resin (B) according to the present invention preferably has a weight average molecular weight in terms of polystyrene in the range of 3,000 to 100,000, more preferably in the range of 5,000 to 50,000. When the weight average molecular weight of the alkali-soluble resin is less than 3,000 or more than 100,000, there is a disadvantage in that the film reduction is not prevented during development, so that a pattern portion may be omitted.
The acid value of the alkali-soluble resin (B) is 50 to 150 KOH mg / g, preferably 60 to 140 KOH mg / g, more preferably 80 to 135 KOH mg / g, most preferably 80 to 130 KOH mg / g. g. When the acid value of the said alkali-soluble resin (B) is 50-150 KOHmg / g, since the solubility to a developing solution improves and a residual film rate improves, it is preferable.
The alkali-soluble resin (B) is in the range of 10 to 80% by weight, preferably 10 to 70% by weight relative to the total weight of solids of the colored photosensitive resin composition for green pixels of the present invention. When the content of the alkali-soluble resin (B) is 10 to 80% by weight on the basis of the above-mentioned criteria, the solubility of the developer is sufficient and the pattern formation is easy. In the development, the film portion of the pixel portion of the exposed portion is prevented from being reduced, So that it is preferable.
Photopolymerization The compound (C)
The photopolymerizable compound (C) is a compound capable of polymerizing under the action of the following photopolymerization initiator (D), and may be a monofunctional monomer, a bifunctional monomer or a polyfunctional monomer, and preferably a bifunctional or higher polyfunctional monomer. Can be used.
Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N- But are not limited thereto.
Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) , Bis (acryloyloxyethyl) ether of bisphenol A or 3-methylpentanediol di (meth) acrylate, but are not limited thereto.
Specific examples of the polyfunctional monomer include trimethylol propane tri (meth) acrylate, ethoxylated trimethylol propane tri (meth) acrylate, propoxylated trimethylol propane tri (meth) acrylate, and pentaerythritol tree. (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) ) Acrylate or dipentaerythritol hexa (meth) acrylate, and the like, but is not limited thereto.
The photopolymerizable compound (C) is preferably contained in an amount of 5 to 45% by weight, more preferably 7 to 45% by weight based on the total weight of the solid components in the colored photosensitive resin composition for a green color. When the photopolymerizable compound (C) is included in the range described above, it is preferable because the strength and smoothness of the pixel portion can be improved.
Light curing Initiator (D)
The photoinitiator (D) can be used without particular limitation as long as it can polymerize the photopolymerizable compound (C). In particular, the photopolymerization initiator (D) is an acetophenone compound, a benzophenone compound, a triazine compound, a biimidazole compound, an oxime compound and a tee from the viewpoint of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price. It is preferable to use at least one compound selected from the group consisting of oxatone compounds.
Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 2-hydroxy-1- [4- (2-hydroxy Hydroxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane-1 -One, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like.
Examples of the benzophenone compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.
Specific examples of the triazine-based compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6 -(4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2- Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl ) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine and the like.
Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'-bis (2,3- Phenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) , 2,2'-bis (2,6-dichlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) Imidazole compounds in which 4'5,5'-tetraphenyl-1,2'-biimidazole or phenyl groups at 4,4 ', 5,5' positions are substituted by carboalkoxy groups. Among them, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole is preferably used do.
Specific examples of the oxime compound include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one and the like, and OXE01 and OXE02 manufactured by BASF Corporation are typical examples.
As said thioxanthone type compound, 2-isopropyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- dichloro thioxanthone, 1-chloro-4- propoxy thioxanthone, etc. are mentioned, for example. There is this.
In addition, the photopolymerization initiator (D) may further include a photopolymerization initiation assistant (d2) in order to improve the sensitivity of the colored photosensitive resin composition for green pixels of the present invention. The coloring photosensitive resin composition for green pixels which concerns on this invention contains a photoinitiation start adjuvant (d2), and can raise a sensitivity further and can improve productivity.
As the above (d2), at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group can be preferably used.
It is preferable to use an aromatic amine compound as the amine compound, and specifically, aliphatic amine compounds such as triethanolamine, methyl diethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4- Dimethylaminobenzoic acid isoamyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (common name: Michler's ketone ), 4,4'-bis (diethylamino) benzophenone and the like can be used.
The carboxylic acid compound is preferably an aromatic heteroacetic acid, specifically, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthio Acetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid, and the like.
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-mercaptobutyloxyethyl)- 1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, trimethylolpropanetris (3-mergaptopropionate), pentaerythritol tetrakis (3-mercaptobutyl Late), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptopropionate), etc. are mentioned. Can be.
The photopolymerization initiator (D) is 0.1 to 40 parts by weight based on 100 parts by weight of the total weight of alkali-soluble resin (B) and the photopolymerizable compound (C) included in the colored photosensitive resin composition for green pixels of the present invention based on solid content. , Preferably 1 to 30 parts by weight
It may be included as. When the photopolymerization initiator (D) is contained within the above-described range, the photosensitive resin composition is highly sensitive and the exposure time is shortened, which is preferable because productivity can be improved and high resolution can be maintained. Further, in the case of using a composition having the above-described conditions, the strength and surface smoothness of the formed pixel portion can be improved.
In addition, the photopolymerization start adjuvant (d2) is included in an amount of 10 to 100 parts by weight, preferably 20 to 100 parts by weight, based on 100 parts by weight of the photopolymerization initiator (D). When the photopolymerization start adjuvant (d2) is included in the above-described range, a decrease in sensitivity and occurrence of a short circuit of the pattern during the developing step are prevented.
Solvent (E)
As long as the solvent (E) is effective for dissolving other components contained in the colored photosensitive resin composition for a green color, a solvent used in a conventional photosensitive resin composition can be used without particular limitation, and in particular, an ether, an aromatic hydrocarbon, Ketones, alcohols, esters, amides and the like can be preferably used.
The solvent (E) specifically includes 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 dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether; Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin; Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone.
The solvent (E) is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C on the application and drying surface, more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl Lactate, butylacetate, 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 thereof, and may be combined with the dispersion solvent contained in the pigment dispersion composition (A) based on the total weight of the colored photosensitive resin composition for green pixels of the present invention. 60 to 90% by weight, preferably 70 to 85% by weight may be included. When the solvent (E) is included in the above-mentioned range, it is possible to improve the coating property when applied with a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater Can be obtained.
Additive (F)
The additive (F) may be optionally added, for example, other polymer compounds, a curing agent, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber, and an antiflocculant.
Specific examples of the other polymer compound include curable resins such as epoxy resins and maleimide resins, thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, polyurethanes, and the like. Can be mentioned.
The curing agent is used to increase the core hardening and mechanical strength, and specific examples of the curing agent include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, oxetane compounds and the like.
Specific examples of the epoxy compound in the curing agent include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, noblock type epoxy resin, other aromatic epoxy resin, alicyclic epoxy resin , Aliphatic, cycloaliphatic or aromatic epoxy compounds other than glycidyl ester resins, glycidylamine resins, or brominated derivatives of these epoxy resins, epoxy resins and brominated derivatives thereof, butadiene (co) polymer epoxides, isoprene ( Co) polymer epoxide, glycidyl (meth) acrylate (co) polymer, triglycidyl isocyanurate, and the like.
Specific examples of the oxetane compound in the curing agent include carbonates bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane, and the like.
The curing agent may be used together with a curing agent in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound. The curing assistant compound includes, for example, polyvalent carboxylic acids, polyvalent carboxylic anhydrides, and acid generators. The polyvalent carboxylic acid anhydrides may be those commercially available as an epoxy resin curing agent. Specific examples of the above-mentioned epoxy resin curing agent include epoxy resin curing agents such as epoxy resins, epoxy resins, epoxy resins, epoxy resins, epoxy resins, epoxy resins, Manufactured by Japan Ehwa Co., Ltd.). The curing agents exemplified above may be used alone or in combination of two or more.
The surfactant may be used to further improve the film formability of the photosensitive resin composition, and a fluorine-based surfactant or a silicone-based surfactant may be preferably used.
The silicone surfactants include, for example, DC3PA, DC7PA, SH11PA, SH21PA, SH8400, etc. of Dow Corning Toray Silicone Co., Ltd., and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF- 4460, TSF-4452, and the like. Examples of the fluorine-based surfactant include Megapieces F-470, F-471, F-475, F-482, and F-489 manufactured by Dainippon Ink & Chemicals Co., Ltd. as commercially available products. The above-exemplified surfactants may be used alone or in combination of two or more.
Specific examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (2-aminoethyl) (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- Methoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, and the like. The adhesion promoters exemplified above may be used alone or in combination of two or more. The adhesion promoter may be generally included in a weight fraction of 0.01 to 10% by weight, preferably 0.05 to 2% by weight based on the total weight of solids of the colored photosensitive resin composition for green pixels.
Specific examples of the antioxidant include 2,2'-thiobis (4-methyl-6-t-butylphenol), 2,6-di-t-butyl-4-methylphenol and the like.
Specific examples of the ultraviolet absorber include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole, alkoxybenzophenone and the like.
Specific examples of the anti-aggregation agent include sodium polyacrylate and the like.
In the present invention, the additive (F) may be included in an amount of about 0.01 to 15% by weight based on the total weight of solids in the colored photosensitive resin composition for green pixels.
The present invention also relates to a color filter including a color pattern formed by forming the colored photosensitive resin composition for a green color in a predetermined pattern, followed by exposure and development.
The color filter may be manufactured by a conventional method well known in the art.
The present invention also relates to a liquid crystal display element and an image pickup device including the color filter.
The liquid crystal display element and the image pickup element include configurations known to those skilled in the art, except that the color filter is provided. That is, the liquid crystal display element and the image pickup element to which the color filter of the present invention can be applied are all included in the present invention.
Hereinafter, the present invention will be described in more detail based on examples. However, the embodiments of the present invention described below are illustrative only, and the scope of the present invention is not limited to these embodiments. The scope of the present invention is indicated in the claims, and moreover, includes all changes within the meaning and range of equivalency of the claims. In the following Production Examples, Examples and Comparative Examples, "%" and "part" representing the content are based on weight unless otherwise specified.
Manufacturing example 1: Synthesis of Alkali Soluble Resin
108 parts of propylene glycol monomethyl ether acetate, 72 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 18 parts of methacrylic acid, 22 parts of benzyl methacrylate in a flask equipped with a stirrer, a thermometer reflux condenser, a dropping lot and a nitrogen introduction tube. , 50 parts of 4-methylstyrene, 10 parts of methyl methacrylate, and 3 parts of n-dodecyl mercapto were added and nitrogen-substituted. Thereafter, the temperature of the reaction solution was raised to 110 DEG C with stirring, and the reaction was carried out for 3 hours. The alkali-soluble resin thus synthesized had a solid content of 115 mgKOH / g and a weight-average molecular weight Mw of about 22,100 as measured by GPC.
Manufacturing example 2: pigment dispersion composition ( M1 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine 17 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether by bead mill for 12 hours Pigment dispersion M1 was prepared.
Manufacturing example 3: pigment dispersion composition ( M2 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine of 29 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether for 12 hours by mixing / dispersing with a bead mill. Pigment dispersion M2 was prepared.
Manufacturing example 4: pigment dispersion composition ( M3 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine value of 40 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether as a solvent for 12 hours. Pigment dispersion M3 was prepared.
Manufacturing example 5: pigment dispersion composition ( M4 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine value 54 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether by bead mill for 12 hours Pigment dispersion M4 was prepared.
Manufacturing example 6: pigment dispersion composition ( M5 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine value 62 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether by bead mill for 12 hours Pigment dispersion M5 was prepared.
Manufacturing example 7: pigment dispersion composition ( M6 )
12.0 parts by weight of CI Pigment Green 58 as a pigment, 6.0 parts by weight of a dispersant having an amine value 71 as a dispersant, 44 parts by weight of propylene glycol methyl ether acetate and 40 parts by weight of propylene glycol methyl ether by bead mill for 12 hours Pigment dispersion M6 was prepared.
Example 1: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M1, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), 34.1 parts by weight of propylene glycol monomethyl ether acetate Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Example 2: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M2, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), 34.1 parts by weight of propylene glycol monomethyl ether acetate Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Example 3: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M3, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), 34.1 parts by weight of propylene glycol monomethyl ether acetate Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Comparative Example 1: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M4, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), and 34.1 parts by weight of propylene glycol monomethyl ether acetate. Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Comparative Example 2: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M5, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), and 34.1 parts by weight of propylene glycol monomethyl ether acetate Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Comparative Example 3: green For pixels Preparation of colored photosensitive resin composition
22.5 parts by weight of the pigment dispersion composition M6, 9.7 parts by weight of the resin of Preparation Example 1, 3.2 parts by weight of KAYARAD DPHA (manufactured by Nippon Kayaku), 0.6 parts by weight of OXE-01 (manufactured by BASF), 34.1 parts by weight of propylene glycol monomethyl ether acetate Then, 8.5 parts by weight of propylene glycol monomethyl ether was mixed to prepare a colored photosensitive resin composition.
Test Example One.
(1) Manufacture of color filters
Color filters were prepared using the colored photosensitive resin compositions prepared in Examples 1 to 3 and Comparative Examples 1 to 3.
Specifically, each of the above colored photosensitive resin compositions was applied on a 2-inch-square glass substrate ("EAGLE XG", manufactured by Corning Inc.) by spin coating, then placed on a heating plate and held at a temperature of 100 ° C. for 3 minutes to form a thin film . Subsequently, ultraviolet rays were irradiated onto the thin film. At this time, the ultraviolet light source was irradiated with a high pressure mercury lamp of 1 KW containing g, h and i lines at an illuminance of 100 mJ / cm 2, and no special optical filter was used. The UV-irradiated thin film was developed by soaking in a KOH aqueous solution developing solution of pH 10.5 for 2 minutes. The thin plate coated glass plate was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 230 ° C. for 25 minutes to prepare a color filter.
The film thickness of the color filter prepared above was 2.0 μm.
(2) measurement of VHR
The VHR of the color filter prepared in the experimental example was measured. Fabrication and measurement conditions of the VHR cell are as follows.
The color resist substrate prepared in the test example is scratched to obtain a powder state. After mixing Resist: LC = 3: 97, Aging was performed at 80 ° C. for 20 hours. After injecting IPA into the VHR measuring cell, ultrasonic cleaning was performed at 35 ° C for 30 minutes. The mixture of LC and Resist after Aging was filtered with 0.2um syringe. The LC obtained after filtering was added to CELL. After soldering, VHR was measured using a Toyo VHR measuring instrument.
The test results are shown in Table 1 below.
As confirmed in Table 1, in Examples 1 to 3, which are the colored photosensitive resin compositions for green pixels according to the present invention, the voltage retention (VHR) was very excellent, of 93% or more, but the greening of Comparative Examples 1 to 3 was performed. The coloring coloring photosensitive resin composition was very low at 87% or less of voltage retention (VHR). And it can be seen that this result is due to the amine number of the dispersant contained in the colored photosensitive resin composition for green pixels.
Claims (8)
The pigment dispersion composition (A) includes CI Pigment Green 58 as a pigment, wherein the amine number of the dispersant contained in the composition is 10 to 50 mgKOH / g, wherein the colored photosensitive resin composition for green pixels is used.
The colored photosensitive resin composition for a green color
20 to 90% by weight of the pigment dispersion composition (A) in a weight fraction based on the total weight of the colored photosensitive resin composition for green pixels;
10 to 80% by weight of an alkali-soluble resin (B) and 5 to 45% by weight of a photopolymerizable compound (C) in weight fractions based on the total weight of the colored photosensitive resin composition solid for green pixels;
0.1 to 40 parts by weight of the photopolymerization initiator (D) based on 100 parts by weight of the total weight of the alkali-soluble resin (B) and the photopolymerizable compound (C);
The coloring for green pixels containing the solvent (E) which is 60-90 weight% of the weight fraction combined with the dispersion solvent contained in the said pigment dispersion composition (A) with respect to the total weight of the coloring photosensitive resin composition for green pixels. Photosensitive resin composition.
The pigment dispersion composition (A) is a pigment of 20 to 90% by weight based on the total weight of solids in the composition,
5 to 60 parts by weight of a dispersant based on 100 parts by weight of solids of the pigment, and
A colored photosensitive resin composition for green pixels, comprising 60 to 90% by weight of a dispersion solvent in a weight fraction based on the total weight of the pigment dispersion composition.
The acid value of the said alkali-soluble resin (B) is 50-150 KOHmg / g, The coloring photosensitive resin composition for green pixels characterized by the above-mentioned.
The alkali-soluble resin (B) has a weight average molecular weight in terms of polystyrene of 3,000 to 100,000, wherein the colored photosensitive resin composition for green pixels is used.
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| KR1020120083499A KR20140017128A (en) | 2012-07-30 | 2012-07-30 | Colored photosensitive resin composition for green pixel |
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| KR1020120083499A KR20140017128A (en) | 2012-07-30 | 2012-07-30 | Colored photosensitive resin composition for green pixel |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170036600A (en) * | 2015-09-24 | 2017-04-03 | 동우 화인켐 주식회사 | A green photosensitive resin composition, color filter and display device comprising the same |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20170036600A (en) * | 2015-09-24 | 2017-04-03 | 동우 화인켐 주식회사 | A green photosensitive resin composition, color filter and display device comprising the same |
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