JP5144971B2 - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- JP5144971B2 JP5144971B2 JP2007157422A JP2007157422A JP5144971B2 JP 5144971 B2 JP5144971 B2 JP 5144971B2 JP 2007157422 A JP2007157422 A JP 2007157422A JP 2007157422 A JP2007157422 A JP 2007157422A JP 5144971 B2 JP5144971 B2 JP 5144971B2
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- meth
- acrylate
- resin composition
- photosensitive resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- 239000002904 solvent Substances 0.000 claims abstract description 63
- 238000009835 boiling Methods 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000000049 pigment Substances 0.000 claims abstract description 22
- 229920006026 co-polymeric resin Polymers 0.000 claims abstract description 16
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003999 initiator Substances 0.000 claims abstract description 13
- 239000002270 dispersing agent Substances 0.000 claims abstract description 10
- 238000007607 die coating method Methods 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 5
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 claims description 4
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical group COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 abstract description 51
- 239000011248 coating agent Substances 0.000 abstract description 47
- 239000000758 substrate Substances 0.000 abstract description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 82
- 238000001035 drying Methods 0.000 description 29
- 238000001704 evaporation Methods 0.000 description 24
- 230000008020 evaporation Effects 0.000 description 24
- -1 N-substituted maleimide Chemical class 0.000 description 21
- 238000000034 method Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 150000003923 2,5-pyrrolediones Chemical class 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 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 4
- GTYRFVGHYNRSKT-UHFFFAOYSA-N 3-benzylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC=CC=2)=C1 GTYRFVGHYNRSKT-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- MZZSDCJQCLYLLL-UHFFFAOYSA-N Secalonsaeure A Natural products COC(=O)C12OC3C(CC1=C(O)CC(C)C2O)C(=CC=C3c4ccc(O)c5C(=O)C6=C(O)CC(C)C(O)C6(Oc45)C(=O)OC)O MZZSDCJQCLYLLL-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 239000003086 colorant 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
- 238000007598 dipping method Methods 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- VKQJCUYEEABXNK-UHFFFAOYSA-N 1-chloro-4-propoxythioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(OCCC)=CC=C2Cl VKQJCUYEEABXNK-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- VTRZMLZNHGCYLK-UHFFFAOYSA-N 1-ethenyl-2-(methoxymethyl)benzene Chemical compound COCC1=CC=CC=C1C=C VTRZMLZNHGCYLK-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- HDEWQSUXJCDXIX-UHFFFAOYSA-N 1-ethenyl-3-(methoxymethyl)benzene Chemical compound COCC1=CC=CC(C=C)=C1 HDEWQSUXJCDXIX-UHFFFAOYSA-N 0.000 description 1
- PECUPOXPPBBFLU-UHFFFAOYSA-N 1-ethenyl-3-methoxybenzene Chemical compound COC1=CC=CC(C=C)=C1 PECUPOXPPBBFLU-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- XVXKXOPCFWAOLN-UHFFFAOYSA-N 1-ethenyl-4-(methoxymethyl)benzene Chemical compound COCC1=CC=C(C=C)C=C1 XVXKXOPCFWAOLN-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- OEYNWAWWSZUGDU-UHFFFAOYSA-N 1-methoxypropane-1,2-diol Chemical compound COC(O)C(C)O OEYNWAWWSZUGDU-UHFFFAOYSA-N 0.000 description 1
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical compound C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-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
- 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
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- UXCIJKOCUAQMKD-UHFFFAOYSA-N 2,4-dichlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC(Cl)=C3SC2=C1 UXCIJKOCUAQMKD-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PUBNJSZGANKUGX-UHFFFAOYSA-N 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=C(C)C=C1 PUBNJSZGANKUGX-UHFFFAOYSA-N 0.000 description 1
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 1
- JFWFAUHHNYTWOO-UHFFFAOYSA-N 2-[(2-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC=C1COCC1OC1 JFWFAUHHNYTWOO-UHFFFAOYSA-N 0.000 description 1
- OCKQMFDZQUFKRD-UHFFFAOYSA-N 2-[(3-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC(COCC2OC2)=C1 OCKQMFDZQUFKRD-UHFFFAOYSA-N 0.000 description 1
- ZADXFVHUPXKZBJ-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methoxymethyl]oxirane Chemical compound C1=CC(C=C)=CC=C1COCC1OC1 ZADXFVHUPXKZBJ-UHFFFAOYSA-N 0.000 description 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical class OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-N 2-chloroacrylic acid Chemical compound OC(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-N 0.000 description 1
- YBXYCBGDIALKAK-UHFFFAOYSA-N 2-chloroprop-2-enamide Chemical compound NC(=O)C(Cl)=C YBXYCBGDIALKAK-UHFFFAOYSA-N 0.000 description 1
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N 2-methylbut-2-enoic acid Chemical group CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
本発明は、感光性樹脂組成物に関し、特に、カラーフィルター作製に有用な感光性樹脂組成物に関する。 The present invention relates to a photosensitive resin composition, and in particular, to a photosensitive resin composition useful for color filter production.
従来、カラーフィルタを製造するに当たっては、基板上に感光性樹脂組成物の塗膜を形成し、所望のパターン形状を有するフォトマスクを介して紫外線、遠紫外線、可視光線、電子線などの電離放射線を照射した後、現像して未露光部を溶解除去し、その後クリーンオーブンやホットプレートを用いてポストベイクすることにより、各色の画素を得る方法（例えば、特許文献１、特許文献２参照。）が知られている。このような方法によりカラーフィルタを製造する場合、従来はスピンコート法により基板上に感光性樹脂組成物を塗布していたが、この方法では、着色層は構成に必要な量より数十倍の量を塗布し、スピンにより均一面を得ているので、コスト対策と環境対策の必要性から液量削減が望まれていた。この対策として、最近ではダイコート法による塗布技術が開発され、特に大型ガラス基板での塗布はダイコート法による塗布が行われている。 Conventionally, when manufacturing a color filter, a coating film of a photosensitive resin composition is formed on a substrate, and ionizing radiation such as ultraviolet rays, far ultraviolet rays, visible rays, and electron beams is passed through a photomask having a desired pattern shape. , And developing to dissolve and remove unexposed portions, and then post-baking using a clean oven or hot plate to obtain pixels of each color (see, for example, Patent Document 1 and Patent Document 2). Are known. In the case of producing a color filter by such a method, a photosensitive resin composition has been conventionally applied on a substrate by a spin coating method, but in this method, the colored layer is several tens of times larger than the amount necessary for the configuration. Since a uniform surface was obtained by applying an amount and spinning, it was desired to reduce the amount of liquid because of the need for cost measures and environmental measures. As a countermeasure, recently, a coating technique using a die coating method has been developed. In particular, coating on a large glass substrate is performed by a die coating method.
この塗布方法では、スピンコート法で発生することがある前工程の段差によるスピンムラは発生しないが、ノズルの開口が狭く少量での塗布となるので、感光性組成物の乾燥した付着物の影響による塗布ムラや乾燥速度の違いによる乾燥ムラが発生しやすく、塗布装置の使用条件や感光性組成物の管理が困難であった。このことがカラーフィルターの歩留まりに影響し、生産性を上げることを難しくしていた。
発生する乾燥付着物を大幅に少なくするため、特許文献３では、色材成分、溶剤成分、バインダ樹脂及び／又はその単量体を含有し、溶剤成分の沸点と、組成物と溶媒それぞれの溶解度パラメータ値を限定したダイコート用硬化性樹脂組成物が提案されている。
しかしながら、乾燥速度の違いによる乾燥ムラ及び乾燥付着物の影響による塗布ムラが発生するという問題や、塗布後の減圧乾燥の工程で、溶媒の蒸発時に組成物中に含まれる微小な気泡が塗膜表面に現れ、乾燥後もそのままクレーター状の欠陥（以下、「突沸孔」という。）として残ってしまうという問題が依然としてあった。
In this coating method, spin unevenness due to a step in the previous process that may occur in the spin coating method does not occur, but since the nozzle opening is narrow and the coating is performed with a small amount, it is due to the influence of the dried deposit of the photosensitive composition. The coating unevenness and the drying unevenness due to the difference in the drying speed are likely to occur, and it is difficult to manage the use conditions of the coating apparatus and the photosensitive composition. This has affected the yield of color filters and made it difficult to increase productivity.
In order to significantly reduce the amount of dry deposits generated, Patent Document 3 contains a colorant component, a solvent component, a binder resin and / or a monomer thereof, the boiling point of the solvent component, and the solubility of each of the composition and the solvent. A curable resin composition for die coating with limited parameter values has been proposed.
However, there are problems such as uneven drying due to the difference in drying speed and uneven coating due to the influence of dry deposits, and minute bubbles contained in the composition during evaporation of the solvent during the vacuum drying process after coating. There was still a problem that it appeared on the surface and remained as a crater-like defect (hereinafter referred to as “bump hole”) after drying.
本発明は、このような状況下で、塗布ムラ、乾燥ムラ、乾燥付着物や突沸孔が発生しにくく基材面内の色度均一性に優れる感光性樹脂組成物を提供することを課題とするものである。 It is an object of the present invention to provide a photosensitive resin composition having excellent chromaticity uniformity within a substrate surface, in which coating unevenness, drying unevenness, dry deposits and bumps are unlikely to occur under such circumstances. To do.
本発明者は、前記課題を達成するために鋭意研究を重ねた結果、特定の樹脂成分と沸点の異なる二種以上の溶剤とを組み合わせて用いることにより上記課題を達成し得ることを見出した。本発明は、かかる知見に基づいて完成したものである。
すなわち、本発明は、マレイミド系共重合樹脂、光重合性モノマー、顔料、分散剤、光重合開始剤及び溶剤を含む感光性樹脂組成物であって、該溶剤が大気圧の沸点として１００℃以上かつ１６５℃未満である溶剤Ａ及び大気圧の沸点として１６５℃以上かつ２００℃以下である溶剤Ｂからなることを特徴とする感光性樹脂組成物である。
As a result of intensive studies to achieve the above problems, the present inventor has found that the above problems can be achieved by using a specific resin component and two or more solvents having different boiling points in combination. The present invention has been completed based on such findings.
That is, the present invention is a photosensitive resin composition comprising a maleimide copolymer resin, a photopolymerizable monomer, a pigment, a dispersant, a photopolymerization initiator, and a solvent, wherein the solvent has a boiling point of 100 ° C. or higher as the atmospheric pressure. And a solvent A having a boiling point of 165 ° C. or more and 200 ° C. or less as a boiling point at atmospheric pressure and a solvent B having a temperature of less than 165 ° C.
本発明によれば、塗布ムラ、乾燥ムラ、乾燥付着物や突沸孔が発生しにくく基材面内の色度均一性に優れる感光性樹脂組成物を提供することができる。 According to the present invention, it is possible to provide a photosensitive resin composition that is less likely to cause coating unevenness, drying unevenness, dry deposits, and bumping holes, and is excellent in chromaticity uniformity in the substrate surface.
本発明は、マレイミド系共重合樹脂、光重合性モノマー、顔料、分散剤、光重合開始剤及び溶剤を含む感光性樹脂組成物であり、該溶剤が大気圧の沸点として１００℃以上かつ１６５℃未満である溶剤Ａ及び大気圧の沸点として１６５℃以上かつ２００℃以下である溶剤Ｂからなることを特徴とする。
溶剤Ａの大気圧での沸点が１００℃以上であることを要するのは、沸点が１００℃より低いと、塗布工程などにおいて乾燥が促進されるため、塗布ムラや乾燥ムラの原因になるばかりでなく、突沸孔の発生や乾燥付着物の発生原因となり、品質上の不具合を生じる場合があるからであり、一方、１６５℃未満であることを要するのは、適度なスピードで乾燥する為、塗布ムラや乾燥ムラが発生し難いからである。
また、溶剤Ｂの大気圧での沸点が１６５℃以上であることを要するのは、乾燥性が遅く、乾燥付着物の発生が抑制されるばかりでなく、突沸孔や塗布ムラや乾燥ムラが発生し難いからである。一方、２００℃以下であることを要するのは、沸点が２００℃より高いと、硬化性樹脂組成物の乾燥性抑制の効果は高いが、プリベイク後においても塗膜中に残留溶剤が多く存在し、品質上の不具合を生じる場合があるからである。
上述の沸点範囲を有する溶剤Ａと溶剤Ｂとを組み合わせて用いることにより、感光性樹脂組成物が塗布ムラ、乾燥ムラ、乾燥付着物や突沸孔の発生を起こしにくくなり、基材面内の色度均一性が大幅に良好となる。
The present invention is a photosensitive resin composition comprising a maleimide copolymer resin, a photopolymerizable monomer, a pigment, a dispersant, a photopolymerization initiator, and a solvent, and the solvent has a boiling point of 100 ° C. or higher and 165 ° C. as the boiling point of atmospheric pressure. It consists of the solvent A which is 165 degreeC or more and 200 degrees C or less as a boiling point of the solvent A which is less than atmospheric pressure.
The reason why the boiling point of the solvent A at atmospheric pressure is 100 ° C. or higher is that if the boiling point is lower than 100 ° C., drying is promoted in the coating process and the like. This is because it may cause bumping holes and dry deposits and may cause defects in quality. On the other hand, it is necessary to be below 165 ° C. because it dries at an appropriate speed. This is because unevenness and drying unevenness hardly occur.
In addition, it is necessary that the boiling point of the solvent B at atmospheric pressure is 165 ° C. or more. Not only the drying property is slow and the generation of dry deposits is suppressed, but also bumping holes, coating unevenness and drying unevenness occur. Because it is difficult. On the other hand, if the boiling point is higher than 200 ° C., the effect of suppressing the drying property of the curable resin composition is high when the boiling point is higher than 200 ° C., but there are many residual solvents in the coating film even after pre-baking. This is because quality problems may occur.
By using a combination of the solvent A and the solvent B having the above boiling range, the photosensitive resin composition is less likely to cause coating unevenness, drying unevenness, dry deposits, and bumping holes, and the color within the substrate surface The degree of uniformity is greatly improved.
さらに、溶剤Ａの比蒸発速度が酢酸ブチルの蒸発速度を１００とした場合において２０〜５０であり、溶剤Ｂの比蒸発速度が酢酸ブチルの蒸発速度を１００とした場合において５〜２５であることが好ましい。溶剤Ａの比蒸発速度が２０以上であれば、適度なスピードで乾燥する為、塗布ムラや乾燥ムラが発生し難いので好ましい。一方、溶剤Ａの比蒸発速度が５０より大きいと、塗布工程などにおいて乾燥が促進されるため、塗布ムラや乾燥ムラの原因になるばかりでなく、突沸孔の発生や乾燥付着物の発生原因となり、品質上の不具合を生じる場合があるので、５０以下であることが好ましい。また、溶剤Ｂの比蒸発速度が５未満であると、硬化性樹脂組成物の乾燥性抑制の効果は高いが、プリベイク後においても塗膜中に残留溶剤が多く存在し、品質上の不具合を生じる場合があるので、比蒸発速度が５以上であることが好ましい。一方、溶剤Ｂの比蒸発速度が２５以下であれば、乾燥性が遅く、乾燥付着物の発生が抑制されるばかりでなく、塗布ムラ、乾燥ムラや突沸孔が発生し難く、プリベイク時に残留溶剤が残留し難いので好ましい。
また、上記の溶剤Ａと溶剤Ｂの比蒸発速度において、溶剤Ａの比蒸発速度が溶剤Ｂの比蒸発速度より高いことが好ましい。
なお、上記の比蒸発速度は、ＡＳＴＭ Ｄ３５３９−８７に準拠して測定した値である。
上記の溶剤Ａと溶剤Ｂは、それぞれ１種又は２種以上の溶剤が用いられる。そして、溶剤Ｂの含有量が、全溶剤（すなわち、溶剤Ａと溶剤Ｂとの総量）基準で５〜５０質量％質量％であることが、突沸孔の発生が抑制され、乾燥異物や乾燥ムラのない面内均一性に優れた着色層を得ることが出来るので好ましい。
Further, the specific evaporation rate of solvent A is 20 to 50 when the evaporation rate of butyl acetate is 100, and the specific evaporation rate of solvent B is 5 to 25 when the evaporation rate of butyl acetate is 100. Is preferred. If the specific evaporation rate of the solvent A is 20 or more, it is preferable because drying is performed at an appropriate speed, so that coating unevenness and drying unevenness hardly occur. On the other hand, if the specific evaporation rate of the solvent A is greater than 50, drying is promoted in the coating process and the like, which not only causes coating unevenness and drying unevenness, but also causes bumping holes and dry deposits. Since it may cause a defect in quality, it is preferably 50 or less. In addition, if the specific evaporation rate of the solvent B is less than 5, the effect of suppressing the drying property of the curable resin composition is high, but there are many residual solvents in the coating film even after pre-baking, which causes a problem in quality. Since it may occur, the specific evaporation rate is preferably 5 or more. On the other hand, if the specific evaporation rate of the solvent B is 25 or less, the drying property is slow, and not only the generation of dry deposits is suppressed, but also coating unevenness, drying unevenness and bump holes are difficult to occur. Is preferable because it is difficult to remain.
Further, in the specific evaporation rate of the solvent A and the solvent B, the specific evaporation rate of the solvent A is preferably higher than the specific evaporation rate of the solvent B.
In addition, said specific evaporation rate is the value measured based on ASTMD3539-87.
As the solvent A and the solvent B, one type or two or more types of solvents are used. The content of the solvent B is 5 to 50% by mass on the basis of the total solvent (that is, the total amount of the solvent A and the solvent B). This is preferable because a colored layer having no in-plane uniformity can be obtained.
上記の溶剤Ａとしては、エチレングリコールモノエチルエーテル（沸点：１３６℃、比蒸発速度：３２）、エチレングリコールモノメチルエーテルアセテート（沸点：１４５℃、比蒸発速度：３１）、プロピレングリコールモノメチルエーテルアセテート（沸点：１４６℃、比蒸発速度：３４）及びジエチレングリコールジメチルエーテル（沸点：１６２℃、比蒸発速度：３６）が好適に例示される。
また、上記の溶剤Ｂとしては、３−メトキシブチルアセテート（沸点：１７１℃、比蒸発速度：１４）及び３−メチル−３−メトキシブチルアセテート（沸点：１８８℃、比蒸発速度：１０）が好適に例示される。
Examples of the solvent A include ethylene glycol monoethyl ether (boiling point: 136 ° C., specific evaporation rate: 32), ethylene glycol monomethyl ether acetate (boiling point: 145 ° C., specific evaporation rate: 31), propylene glycol monomethyl ether acetate (boiling point). 146 ° C., specific evaporation rate: 34) and diethylene glycol dimethyl ether (boiling point: 162 ° C., specific evaporation rate: 36).
As the solvent B, 3-methoxybutyl acetate (boiling point: 171 ° C., specific evaporation rate: 14) and 3-methyl-3-methoxybutyl acetate (boiling point: 188 ° C., specific evaporation rate: 10) are preferable. Is exemplified.
本発明の感光性樹脂組成物は、その不揮発成分全量基準で、マレイミド系共重合樹脂、光重合性モノマー及び必要に応じブレンドされる他の樹脂成分の総量として２０〜９５質量％が好ましく、より具体的には、マレイミド系共重合樹脂が１０〜５０質量％、光重合性モノマーが２〜５０質量％、他の樹脂成分が０〜３０質量％であることがさらに好ましい。
また、上記の不揮発成分全量基準で、光重合開始剤が０．１〜２０質量％であることが好ましい。
顔料及び分散剤並びに溶剤は、本発明の感光性樹脂組成物の目的とする用途に応じて、所定量含有される。
The photosensitive resin composition of the present invention is preferably 20 to 95% by mass as the total amount of the maleimide copolymer resin, the photopolymerizable monomer, and other resin components blended as necessary, based on the total amount of nonvolatile components. Specifically, it is more preferable that the maleimide copolymer resin is 10 to 50% by mass, the photopolymerizable monomer is 2 to 50% by mass, and the other resin components are 0 to 30% by mass.
Moreover, it is preferable that a photoinitiator is 0.1-20 mass% on said non-volatile component whole quantity basis.
The pigment, the dispersant, and the solvent are contained in a predetermined amount according to the intended use of the photosensitive resin composition of the present invention.
本発明の感光性樹脂組成物に用いられるマレイミド系共重合樹脂とは、無置換又は置換マレイミドと他の共重合性不飽和単量体との共重合体をいう。
ここで、置換マレイミドとしては、例えば、Ｎ−ベンジルマレイミド、Ｎ−フェニルマレイミド、Ｎ−シクロヘキシルマレイミド、Ｎ−メチルマレイミド、Ｎ−エチルマレイミド、Ｎ−（ｎ−ブチル）マレイミド、Ｎ−ラウリルマレイミド、などのＮ−置換マレイミドなどが挙げられる。これらの内、Ｎ−ベンジルマレイミドが好ましい。
また、他の共重合性不飽和単量体としては、カルボキシル基含有不飽和単量体、芳香族ビニル化合物、脂肪族共役ジエン類、インデン類、不飽和カルボン酸エステル類、不飽和カルボン酸アミノアルキルエステル類、カルボン酸ビニルエステル類、不飽和エーテル類、シアン化ビニル化合物、不飽和アミド類、脂肪族共役ジエン類、重合体分子鎖の末端にモノ（メタ）アクリロイル基を有するマクロモノマー類などが挙げられる。これらの共重合性不飽和単量体は、単独で又は２種以上を混合して使用することができる。
無置換又は置換マレイミドと他の共重合性不飽和単量体との共重合体の共重合の質量比は、（無置換もしくは置換マレイミド）／（他の共重合性不飽和単量体）が（９０／１０）〜（５／９５）であることが好ましく、（８０／２０）〜（１０／９０）であることがさらに好ましい。無置換又は置換マレイミドを用いるのは、耐熱黄変性に優れて硬度が高く、しかも、溶剤への溶解性に優れているので、本発明の溶剤組成と組み合わせることにより、塗布ムラ、乾燥ムラ、乾燥付着物や突沸孔が発生し難くなるからである。
本発明の感光性樹脂組成物において、必要に応じブレンドされる他の樹脂成分としては、上述の他の共重合性不飽和単量体の単独重合体又は共重合体などが挙げられる。
The maleimide copolymer resin used in the photosensitive resin composition of the present invention refers to a copolymer of an unsubstituted or substituted maleimide and another copolymerizable unsaturated monomer.
Here, examples of the substituted maleimide include N-benzylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, N-methylmaleimide, N-ethylmaleimide, N- (n-butyl) maleimide, N-laurylmaleimide, and the like. N-substituted maleimide and the like. Of these, N-benzylmaleimide is preferred.
Other copolymerizable unsaturated monomers include carboxyl group-containing unsaturated monomers, aromatic vinyl compounds, aliphatic conjugated dienes, indenes, unsaturated carboxylic acid esters, unsaturated carboxylic acid amino acids. Alkyl esters, carboxylic acid vinyl esters, unsaturated ethers, vinyl cyanide compounds, unsaturated amides, aliphatic conjugated dienes, macromonomers having a mono (meth) acryloyl group at the end of the polymer molecular chain, etc. Is mentioned. These copolymerizable unsaturated monomers can be used alone or in admixture of two or more.
The weight ratio of copolymerization of the copolymer of unsubstituted or substituted maleimide and other copolymerizable unsaturated monomer is (unsubstituted or substituted maleimide) / (other copolymerizable unsaturated monomer) It is preferably (90/10) to (5/95), more preferably (80/20) to (10/90). The use of unsubstituted or substituted maleimide is excellent in heat-resistant yellowing, has high hardness, and is excellent in solubility in a solvent. By combining with the solvent composition of the present invention, coating unevenness, drying unevenness, drying This is because deposits and bump holes are less likely to occur.
In the photosensitive resin composition of the present invention, examples of other resin components blended as necessary include homopolymers or copolymers of the above-mentioned other copolymerizable unsaturated monomers.
本発明の感光性樹脂組成物に用いられるマレイミド系共重合樹脂は、顔料に対してバインダーとして作用し、かつカラーフィルタなどを製造する際に、その現像処理工程において用いられる現像液、特に好ましくはアルカリ性現像液に対して可溶性を有するマレイミド系共重合樹脂が好ましい。 The maleimide copolymer resin used in the photosensitive resin composition of the present invention acts as a binder for the pigment, and when producing a color filter or the like, a developer used in the development processing step, particularly preferably A maleimide copolymer resin having solubility in an alkaline developer is preferred.
上記のカルボキシル基含有不飽和単量体としては、例えば、（メタ）アクリル酸、クロトン酸、α−クロルアクリル酸、けい皮酸などの不飽和モノカルボン酸類；マレイン酸、無水マレイン酸、フマル酸、イタコン酸、無水イタコン酸、シトラコン酸、無水シトラコン酸、メサコン酸などの不飽和ジカルボン酸またはその無水物類；３価以上の不飽和多価カルボン酸またはその無水物類；こはく酸モノ〔２−（メタ）アクリロイロキシエチル〕、フタル酸モノ〔２−（メタ）アクリロイロキシエチル〕などの２価以上の多価カルボン酸のモノ〔（メタ）アクリロイロキシアルキル〕エステル類；ω−カルボキシポリカプロラクトンモノ（メタ）アクリレートなどの両末端にカルボキシ基と水酸基とを有するポリマーのモノ（メタ）アクリレート類などを挙げることができる。 Examples of the carboxyl group-containing unsaturated monomer include unsaturated monocarboxylic acids such as (meth) acrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid; maleic acid, maleic anhydride, and fumaric acid. , Itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid and other unsaturated dicarboxylic acids or anhydrides thereof; trivalent or higher unsaturated polycarboxylic acids or anhydrides thereof; succinic acid mono [2 -[Meth] acryloyloxyethyl], mono [(meth) acryloyloxyalkyl] esters of polyvalent carboxylic acids such as phthalic acid mono [2- (meth) acryloyloxyethyl]; Mono (meth) acrylate of polymer having carboxy group and hydroxyl group at both ends such as carboxypolycaprolactone mono (meth) acrylate And the like.
上記の芳香族ビニル化合物としては、例えば、スチレン、α−メチルスチレン、ｏ−ビニルトルエン、ｍ−ビニルトルエン、ｐ−ビニルトルエン、ｐ−クロルスチレン、ｏ−メトキシスチレン、ｍ−メトキシスチレン、ｐ−メトキシスチレン、ｏ−ビニルベンジルメチルエーテル、ｍ−ビニルベンジルメチルエーテル、ｐ−ビニルベンジルメチルエーテル、ｏ−ビニルベンジルグリシジルエーテル、ｍ−ビニルベンジルグリシジルエーテル、ｐ−ビニルベンジルグリシジルエーテルなどを挙げることができる。
上記の脂肪族共役ジエン類としては、例えば、１，３−ブタジエン、イソプレン、クロロプレンなどを挙げることができる。
上記のインデン類としては、例えば、インデン、１−メチルインデンなどを挙げることができる。
Examples of the aromatic vinyl compound include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p- Examples include methoxystyrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, and the like. .
Examples of the aliphatic conjugated dienes include 1,3-butadiene, isoprene, chloroprene and the like.
Examples of the indene include indene and 1-methylindene.
上記の不飽和カルボン酸エステル類としては、例えば、メチル（メタ）アクリレート、エチル（メタ）アクリレート、ｎ−プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、ｎ−ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、ｓｅｃ−ブチル（メタ）アクリレート、ｔ−ブチル（メタ）アクリレート、２−ヒドロキシエチル（メタ）アクリレート、２−ヒドロキシプロピル（メタ）アクリレート、３−ヒドロキシプロピル（メタ）アクリレート、２−ヒドロキシブチル（メタ）アクリレート、３−ヒドロキシブチル（メタ）アクリレート、４−ヒドロキシブチル（メタ）アクリレート、アリル（メタ）アクリレート、ベンジル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、フェニル（メタ）アクリレート、２−メトキシエチル（メタ）アクリレート、２−フェノキシエチル（メタ）アクリレート、メトキシジエチレングルコール（メタ）アクリレート、メトキシトリエチレングルコール（メタ）アクリレート、メトキシプロピレングルコール（メタ）アクリレート、メトキシジプロピレングルコール（メタ）アクリレート、イソボルニル（メタ）アクリレート、トリシクロ[５．２．１．０2,6]デカン−８−イル（メタ）アクリレート、２−ヒドロキシ−３−フェノキシプロピル（メタ）アクリレート、グリセロールモノ（メタ）アクリレート、グリシジル（メタ）アクリレートなどを挙げることができる。 Examples of the unsaturated carboxylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth) ) Acrylate, sec-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (Meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl ( ) Acrylate, 2-methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, Methoxydipropylene glycol (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decan-8-yl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) Examples include acrylate, glycerol mono (meth) acrylate, and glycidyl (meth) acrylate.
上記の不飽和カルボン酸アミノアルキルエステル類としては、例えば、２−アミノエチル（メタ）アクリレート、２−ジメチルアミノエチル（メタ）アクリレート、２−アミノプロピル（メタ）アクリレート、２−ジメチルアミノプロピル（メタ）アクリレート、３−アミノプロピル（メタ）アクリレート、３−ジメチルアミノプロピル（メタ）アクリレートなどを挙げることができる。
上記のカルボン酸ビニルエステル類としては、例えば、酢酸ビニル、プロピオン酸ビニル、酪酸ビニル、安息香酸ビニルなどを挙げることができる。
Examples of the unsaturated carboxylic acid aminoalkyl esters include 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate, 2-dimethylaminopropyl (meth) ) Acrylate, 3-aminopropyl (meth) acrylate, 3-dimethylaminopropyl (meth) acrylate, and the like.
Examples of the carboxylic acid vinyl esters include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate, and the like.
上記の不飽和エーテル類としては、例えば、ビニルメチルエーテル、ビニルエチルエーテル、アリルグリシジルエーテルなどを挙げることができる。
上記のシアン化ビニル化合物としては、例えば、（メタ）アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデンなどを挙げることができる。
上記の不飽和アミド類としては、例えば、（メタ）アクリルアミド、α−クロロアクリルアミド、Ｎ−２−ヒドロキシエチル（メタ）アクリルアミドなどを挙げることができる。
Examples of the unsaturated ethers include vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.
Examples of the vinyl cyanide compound include (meth) acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide, and the like.
Examples of the unsaturated amides include (meth) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide and the like.
上述のマレイミド系共重合樹脂に用いられる共重合性不飽和単量体としては、(メタ)アクリル酸、(メタ)アクリル酸エステルなどが好ましく、好ましい(メタ)アクリル酸エステルとしては、メチル(メタ)アクリレート、グリシジル(メタ)アクリレートなどが例示される。 As the copolymerizable unsaturated monomer used in the above-mentioned maleimide copolymer resin, (meth) acrylic acid, (meth) acrylic acid ester and the like are preferable, and preferable (meth) acrylic acid ester is methyl (methacrylic acid). ) Acrylate, glycidyl (meth) acrylate and the like.
本発明の感光性樹脂組成物に用いられる光重合性モノマーとしては、前記のマレイミド系共重合樹脂と相溶性のあるエチレン性不飽和二重結合を少なくとも２つ有する化合物が挙げられる。上記のエチレン性不飽和二重結合を少なくとも２つ有する化合物としては、二官能（メタ）アクリレートおよび三官能以上の（メタ）アクリレートなど、好ましくは三官能以上の（メタ）アクリレートが挙げられる。
ここで、（メタ）アクリレートとはアクリレート又はメタクリレートをいう。
Examples of the photopolymerizable monomer used in the photosensitive resin composition of the present invention include compounds having at least two ethylenically unsaturated double bonds that are compatible with the maleimide copolymer resin. Examples of the compound having at least two ethylenically unsaturated double bonds include bifunctional (meth) acrylates and trifunctional or higher functional (meth) acrylates, preferably trifunctional or higher functional (meth) acrylates.
Here, (meth) acrylate refers to acrylate or methacrylate.
また、上記の二単官能（メタ）アクリレートとしては、例えば、１，３−ブタンジオールジ（メタ）アクリレート、１，４−ブタンジオールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、１，６−ヘキサンジオールジ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート、トリエチレングリコールジ（メタ）アクリレート、テトラエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ビスフェノールＡジ（メタ）アクリレート、３−メチルペンタンジオールジ（メタ）アクリレート、フタル酸ジ（メタ）アクリレート、シクロヘキシレングリコールジ（メタ）アクリレートなどが挙げられる。 Examples of the bifunctional (meth) acrylate include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1 , 6-hexanediol di (meth) acrylate, polypropylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, bisphenol A di (meth) ) Acrylate, 3-methylpentanediol di (meth) acrylate, phthalic acid di (meth) acrylate, cyclohexylene glycol di (meth) acrylate, and the like.
また、上記の三官能以上の（メタ）アクリレートとしては、例えば、トリメチロールプロパントリ（メタ）アクリレート、トリメチロールエタントリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート(ＤＰＨＡ)、ジペンタエリスリトールペンタ（メタ）アクリレート、カルボン酸変性ジペンタエリスリトールペンタアクリレートなどが挙げられる。 Examples of the trifunctional or higher functional (meth) acrylate include trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, and pentaerythritol tetra (meth) acrylate. , Dipentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate (DPHA), dipentaerythritol penta (meth) acrylate, carboxylic acid-modified dipentaerythritol pentaacrylate, and the like.
これらの多官能性モノマーのうち、三官能以上の（メタ）アクリレートが好ましく、具体的には、トリメチロールプロパントリ（メタ）アクリレート、ペンタエリスリトールトリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレートなどが好ましく、特に、トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレートおよびジペンタエリスリトールヘキサアクリレートが、着色層の強度および表面平滑性に優れ、かつ未露光部の基板上および遮光層上に地汚れ、膜残りなどを発生し難い点で好ましい。
上記の光重合性モノマーは、単独でまたは２種以上を混合して使用することができる。
Of these polyfunctional monomers, tri- or higher functional (meth) acrylates are preferred, specifically, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, Dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and the like are preferable. It is preferable in that it is excellent and hardly causes scumming or film residue on the unexposed substrate and the light shielding layer.
Said photopolymerizable monomer can be used individually or in mixture of 2 or more types.
本発明における光重合性モノマーの使用量は、マレイミド系共重合樹脂１００質量部に対して、好ましくは５〜５００質量部、さらに好ましくは１０〜３００質量部、特に好ましくは１０〜２００質量部である。この場合、光重合性モノマーの使用量が５質量部未満では、着色層の強度や表面平滑性が低下する傾向があり、一方５００質量部を超えると、例えば、アルカリ現像性が低下したり、未露光部の基板上あるいは遮光層上に地汚れ、膜残りなどが発生しやすくなる傾向がある。
また、本発明においては、光重合性モノマーの一部を、重合性不飽和結合を１個有する単官能性モノマーに置き換えることもできる。
The amount of the photopolymerizable monomer used in the present invention is preferably 5 to 500 parts by mass, more preferably 10 to 300 parts by mass, and particularly preferably 10 to 200 parts by mass with respect to 100 parts by mass of the maleimide copolymer resin. is there. In this case, if the amount of the photopolymerizable monomer used is less than 5 parts by weight, the strength and surface smoothness of the colored layer tend to be reduced. On the other hand, if it exceeds 500 parts by weight, for example, alkali developability is reduced, There is a tendency that stains, film residue, and the like are likely to occur on the unexposed portion of the substrate or the light shielding layer.
In the present invention, a part of the photopolymerizable monomer can be replaced with a monofunctional monomer having one polymerizable unsaturated bond.
上記の重合性不飽和結合を１個有する単官能性モノマーとしては、単官能（メタ）アクリレートが好ましい。単官能（メタ）アクリレートとしては、例えば、ヒドロキシエチル（メタ）アクリレート、ヒドロキシプロピル（メタ）アクリレート、２−エチルヘキシル（メタ）アクリレート、ポリエチレングリコールモノ（メタ）アクリレート、ポリプロピレングリコールモノ（メタ）アクリレート、ブタンジオールモノ（メタ）アクリレート、アリル（メタ）アクリレート、ブトキシエチル（メタ）アクリレート、ｔ−ブチルアミノエチル（メタ）アクリレート、ブチル（メタ）アクリレート、ヘキシル（メタ）アクリレート、ラウリル（メタ）アクリレート、オクチル（メタ）アクリレート、グリシジル（メタ）アクリレートなどが挙げられる。
本発明における光重合性モノマーと単官能性モノマーとの合計使用量は、マレイミド系共重合樹脂１００質量部に対して、好ましくは５〜５００質量部、さらに好ましくは１０〜３００質量部である。
As the monofunctional monomer having one polymerizable unsaturated bond, monofunctional (meth) acrylate is preferable. Examples of the monofunctional (meth) acrylate include hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, polyethylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, and butane. Diol mono (meth) acrylate, allyl (meth) acrylate, butoxyethyl (meth) acrylate, t-butylaminoethyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, lauryl (meth) acrylate, octyl ( Examples include meth) acrylate and glycidyl (meth) acrylate.
The total use amount of the photopolymerizable monomer and the monofunctional monomer in the present invention is preferably 5 to 500 parts by mass, more preferably 10 to 300 parts by mass with respect to 100 parts by mass of the maleimide copolymer resin.
本発明の感光性樹脂組成物に用いられる顔料としては、カラーフィルターを形成する各画素用の顔料として、着色力、透明性、コントラスト、耐光性、耐熱性、耐薬品性などに優れている顔料であればいずれも使用することができる。また、必要に応じて染料も使用することができる。 The pigment used in the photosensitive resin composition of the present invention is a pigment excellent in coloring power, transparency, contrast, light resistance, heat resistance, chemical resistance, etc. as a pigment for each pixel forming a color filter. Any of them can be used. Moreover, dye can also be used as needed.
上記の顔料としては、例えば、Ｃ．Ｉ．ピグメントイエロー１２、１３、１４、１７、２０、２４、３１、５５、８３、９３、１０９、１１０、１３７、１３８、１３９、１５０、１５３、１５４、１６６、１６８、１７３；Ｃ．Ｉ．ピグメントレッド９、９７、１２２、１２３、１４９、１７６、１７７、１８０、２１５、２２４、２５４；Ｃ．Ｉ．ピグメントグリーン７、３６；Ｃ．Ｉ．ピグメントブルー１５、（１５：３）、（１５：６）、（１５：４）；Ｃ．Ｉ．ピグメントオレンジ３６、４３、５１；Ｃ．Ｉ．ピグメントブラウン２３、２５；Ｃ．Ｉ．ピグメントバイオレット１４、１９、２３、２９、３２、３３、３６、３７；Ｃ．Ｉ．ピグメントブラック１、７などが挙げられる。 Examples of the pigment include C.I. I. Pigment Yellow 12, 13, 14, 17, 20, 24, 31, 55, 83, 93, 109, 110, 137, 138, 139, 150, 153, 154, 166, 168, 173; I. Pigment Red 9, 97, 122, 123, 149, 176, 177, 180, 215, 224, 254; I. Pigment green 7, 36; I. Pigment Blue 15, (15: 3), (15: 6), (15: 4); C.I. I. Pigment orange 36, 43, 51; C.I. I. Pigment brown 23, 25; I. Pigment violet 14, 19, 23, 29, 32, 33, 36, 37; C.I. I. Pigment Black 1, 7 and the like.
また、本発明の感光性樹脂組成物に用いられる分散剤としては、公知の分散剤を使用することができる。具体的には、変性ポリウレタン，変性ポリアクリレート、変性ポリエステル、変性ポリアミド等の高分子分散剤．リン酸エステル、アルキルアミン、ポリオキシエチレンアルキルフェニルエーテル等の界面活性剤や顔料誘導体を挙げることができる。本発明においては、これらの中でも、高分子分散剤が好ましく、具体的な商品名としてはＥＦＫＡ−４０４６、ＥＦＫＡ−４０４７、ＥＦＫＡポリマー１００、ＥＦＫＡポリマー４００、ＥＦＫＡポリマー４０１、ＥＦＫＡポリマー４３００、ＥＦＫＡポリマー４３３０（以上、エフカケミカルズ社製）、Disperbyk１１１、Disperbyk１６１、Disperbyk１６５、Disperbyk１８２、Disperbyk２０００、Disperbyk２００１（以上、ビックケミー社製）、SOLSPERSE２４０００、SOLSPERSE２７０００、SOLSPERSE２８０００（以上、ルーブリゾール社製）、アジスパー８２１（味の素ファインテクノ（株）製）等を挙げることができる。 Moreover, a well-known dispersing agent can be used as a dispersing agent used for the photosensitive resin composition of this invention. Specifically, polymer dispersants such as modified polyurethane, modified polyacrylate, modified polyester, and modified polyamide. Surfactants and pigment derivatives such as phosphate esters, alkylamines, and polyoxyethylene alkylphenyl ethers can be mentioned. Among these, a polymer dispersant is preferable in the present invention, and specific trade names include EFKA-4046, EFKA-4047, EFKA polymer 100, EFKA polymer 400, EFKA polymer 401, EFKA polymer 4300, and EFKA polymer 4330. (Above, manufactured by Efka Chemicals), Disperbyk111, Disperbyk161, Disperbyk165, Disperbyk182, Disperbyk2000, Disperbyk2001 (above, manufactured by BYK Chemie), SOLSPERSE24000, SOLSPERSE27000, SOLSPERSE28000 (above, made by LubrizolTechnology), Ajispurintechno 821 And the like).
本発明の感光性樹脂組成物に用いられる光重合開始剤としては、公知の光重合開始剤を使用することができ、好ましくはイミダゾール系、アセトフェノン系、オキシムエステル系、ベンゾフェノン系、ベンゾインエーテル系、チオキサントン系、トリアジン系、ベンジル系、アントラキノン系、チオール系およびイオウ化合物系光重合開始剤から選ばれる少なくとも１種であり、とくに好ましくはイミダゾール系、アルキルフェノン系、ベンゾフェノン系、アセトフェノン系およびチオキサントン系光重合開始剤から選ばれる少なくとも１種である。 As the photopolymerization initiator used in the photosensitive resin composition of the present invention, known photopolymerization initiators can be used, preferably imidazole series, acetophenone series, oxime ester series, benzophenone series, benzoin ether series, At least one selected from thioxanthone-based, triazine-based, benzyl-based, anthraquinone-based, thiol-based and sulfur compound-based photopolymerization initiators, particularly preferably imidazole-based, alkylphenone-based, benzophenone-based, acetophenone-based, and thioxanthone-based light It is at least one selected from polymerization initiators.
上記のイミダゾール系光重合開始剤としては、ヘキサアリールビスイミダゾール系化合物などが挙げられ、これらの化合物としては、例えば、２，２'−ビス（ｏ−クロルフェニル）−４，４'，５，５'−テトラフェニルビスイミダゾリル、２，２'−ビス（ｏ−クロルフェニル）−４，４'，５，５'−テトラ−（ｐ−メトキシフェニル）ビスイミダゾリル、２，２'−ビス（２クロロフェニル）−４，４'−５，５'テトラキスフェニル−１，２'ビイミダゾールなどが挙げられる。 Examples of the imidazole photopolymerization initiator include hexaarylbisimidazole compounds. Examples of these compounds include 2,2′-bis (o-chlorophenyl) -4,4 ′, 5, 5′-tetraphenylbisimidazolyl, 2,2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetra- (p-methoxyphenyl) bisimidazolyl, 2,2′-bis (2 Chlorophenyl) -4,4′-5,5′tetrakisphenyl-1,2′biimidazole and the like.
また、上記のアセトフェノン系光重合開始剤としては、例えば、ジエトキシアセトフェノン、２−ヒドロキシ−１−［４−（２−ヒドロキシエトキシ）フェニル］−２−メチルプロパン−１−オン、２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノン−１（例えば、チバスペシャリティーケミカルズ社製、商標「ＩＲＧＡＣＵＲＥ ３６９」）、２−（ジメチルアミノ）−２−［（４−メチルフェニル）メチル］−１−［４−（４−モルホリニル）フェニル］−１−ブタノン、ベンジルジメチルケタール、１−ヒドロキシシクロヘキシルフェニルケトン、２−メチル−１−（４−メチルチオフェニル）−２−モルホリノプロパン−１−オン（例えば、チバスペシャリティーケミカルズ社製、商標「ＩＲＧＡＣＵＲＥ ９０７」）、２−ヒドロキシ−２−メチル−１−フェニルプロパン−１−オン、２−ヒドロキシ−１−｛４−［４−（２−ヒドロキシ−２−メチル−プロピオニル）−ベンジル］フェニル｝−２−メチルプロパン−１−オン、２，２−ジメトキシ−１，２−ジフェニルエタン−１−オンなどが挙げられる。 Examples of the acetophenone photopolymerization initiator include diethoxyacetophenone, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 2-benzyl- 2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (for example, trade name “IRGACURE 369” manufactured by Ciba Specialty Chemicals), 2- (dimethylamino) -2-[(4-methylphenyl) Methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, benzyldimethyl ketal, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1 -ON (for example, trade name “IRGACUR, manufactured by Ciba Specialty Chemicals, Inc.) E 907 "), 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-1- {4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl} -2-methylpropan-1-one, 2,2-dimethoxy-1,2-diphenylethane-1-one, and the like.
また、上記のベンゾフェノン系光重合開始剤としては、例えば、ベンゾフェノン、４−フェニルベンゾフェノン、４−ベンゾイル−４'−メチルジフェニルサルファイド、３，３'，４，４'−テトラ（ｔｅｒｔ−ブチルパーオキシカルボニル）ベンゾフェノン、２，４，６−トリメチルベンゾフェノン、４，４'−ビス−ジメチルアミノベンゾフェノンなどが挙げられる。 Examples of the benzophenone photopolymerization initiator include benzophenone, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxy). Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 4,4′-bis-dimethylaminobenzophenone, and the like.
また、上記のチオキサントン系光重合開始剤としては、例えば、２−および４−イソプロピルチオキサントン、２，４−ジエチルチオキサントン、１−クロロ−４−プロポキシチオキサントン、２，４−ジクロロチオキサントンなどが挙げられる。 Examples of the thioxanthone photopolymerization initiator include 2- and 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 1-chloro-4-propoxythioxanthone, and 2,4-dichlorothioxanthone.
本発明の感光性樹脂組成物においては、本発明の目的を妨げない範囲において、所望により種々の添加剤を配合しても良い。これらの添加剤としては、カラーフィルター用ガラス基板への上記感光性樹脂組成物の塗膜の濡れ性向上のためのノニオン系、カチオン系、アニオン系などの各種の界面活性剤、また、密着性向上のためにアクリル系シランカップリング剤、エポキシ系シランカップリング剤、ウレイド系シランカップリング剤などのシランカップリング剤、その他、消泡剤、ハジキ防止剤、酸化防止剤、凝集防止剤、紫外線吸収剤などが挙げられる。 In the photosensitive resin composition of this invention, you may mix | blend various additives depending on necessity in the range which does not interfere with the objective of this invention. As these additives, various surfactants such as nonionic, cationic and anionic surfactants for improving the wettability of the coating film of the photosensitive resin composition on the glass substrate for a color filter, and adhesiveness Silane coupling agents such as acrylic silane coupling agents, epoxy silane coupling agents, ureido silane coupling agents, etc., antifoaming agents, repellency inhibitors, antioxidants, anti-aggregation agents, UV rays Examples include absorbents.
本発明の感光性樹脂組成物は、公知の混合機、分散機により混合分散することによって得られる。上記の混合分散は、例えば、ビーズミル、ボールミル、ディゾルバー、ニーダーなど、好ましくはビーズミルを使用して行われ、得られた感光性樹脂組成物は好ましくは濾過して調製する。 The photosensitive resin composition of the present invention can be obtained by mixing and dispersing using a known mixer or disperser. The above-mentioned mixing / dispersing is preferably performed using a bead mill such as a bead mill, a ball mill, a dissolver, a kneader, and the obtained photosensitive resin composition is preferably prepared by filtration.
上記のように調製された本発明の感光性樹脂組成物は、例えば、これを用いて、遮光層がパターン形成されたカラーフィルター用のガラス基板に回転塗布（スピンコート）、流延塗布、浸漬塗布、ロール塗布、特にダイコート法などの公知の塗布方法により塗布し、真空度が０．１〜１．０ｔｏｒｒ程度、例えば０．２ｔｏｒｒに到達するまで真空ベイクを行って０．５〜４μｍ程度（乾燥膜厚）の塗布膜を得る。得られた塗布膜に目的の画素を形成するためのネガ型のフォトマスクを介して高圧水銀灯や超高圧水銀灯などにより１０〜５００ｍJ／ｃｍ2 程度の光量の紫外線を照射し露光する。露光後、光硬化した塗膜を公知のアルカリ現像液を使用してスプレイ法や浸漬法にて現像し、未露光部を溶解して目的とする色に相当する画素を得る。必要に応じて、現像後、２００〜２５０℃程度の温度で１０〜６０分程度、後硬化処理（ポストベイク）することができる。上記の画素を得る工程を、カラーフィルターに必要とされる色の数だけ繰り返すことによって目的とするカラーフィルターが得られる。上記のカラーフィルターは、通常、赤、緑および青の各画素を遮光層がパターン形成されたカラーフィルター用のガラス基板上に配置したものである。 The photosensitive resin composition of the present invention prepared as described above is used, for example, by spin coating (spin coating), casting coating, and dipping on a glass substrate for a color filter having a light shielding layer patterned. Coating is performed by a known coating method such as coating, roll coating, especially die coating, and vacuum baking is performed until the degree of vacuum reaches about 0.1 to 1.0 torr, for example, 0.2 torr, and about 0.5 to 4 μm ( A coating film having a dry film thickness is obtained. The obtained coating film is exposed by irradiating it with ultraviolet light having a light quantity of about 10 to 500 mJ / cm 2 by a high pressure mercury lamp or an ultrahigh pressure mercury lamp through a negative photomask for forming a target pixel. After the exposure, the photocured coating film is developed by a spray method or a dipping method using a known alkaline developer, and the unexposed portion is dissolved to obtain a pixel corresponding to the target color. If necessary, after development, post-curing can be performed at a temperature of about 200 to 250 ° C. for about 10 to 60 minutes. A target color filter can be obtained by repeating the above-described step of obtaining the pixels by the number of colors required for the color filter. The above color filter is usually one in which red, green, and blue pixels are arranged on a glass substrate for a color filter in which a light shielding layer is patterned.
本発明を実施例により、さらに詳細に説明するが、本発明は、これらの例によってなんら限定されるものではない。
なお、感光性樹脂組成物の乾燥塗膜の溶剤再溶解性の評価、塗布ムラ及び乾燥ムラの有無の評価及び突沸孔の有無の評価は、下記の方法に従って実施した。
（１）乾燥塗膜の溶剤再溶解性
ダイコート法における異物欠陥発生の有無を評価する代替法として以下のように乾燥塗膜の溶剤再溶解性評価を行った。溶剤再溶解性が悪いと乾燥物が付着し、塗布ムラの原因となる。
ガラス基板に感光性樹脂組成物を塗布し、恒温恒湿オーブンを用いて、２５℃、湿度５５％の条件下で３０分風乾したのち、乾燥塗膜が付着したガラス基板をプロピレングリコールモノメチルエーテルアセテート中に１０分間浸漬した。このとき、乾燥塗膜の再溶解状態により、下記の３段階で評価した。
○：浸漬中に乾燥塗膜が全て溶解する。
△：１０分間浸漬後も乾燥塗膜の一部が残る。
×：１０分間浸漬後も乾燥塗膜が殆どもしくは全く溶解しない。
（２）塗布ムラ及び乾燥ムラの有無
ガラス基板に、感光性樹脂組成物を、ダイコーターを用いて塗布した後、真空度が０．２ｔｏｒｒに到達するまで真空ベイクを行って、膜厚２．３μｍの塗膜を形成した。その後、得られた基板を、干渉縞検査灯（Ｎａランプ）を用いて観察し、塗膜に発生する塗布ムラ及び乾燥ムラの有無を目視評価した。
○：塗布ムラ及び乾燥ムラが全く認められない。
△：塗布ムラ及び乾燥ムラが僅かに認められる。
×：塗布ムラ及び乾燥ムラが多く認められる。
（３）突沸孔の有無
ガラス基板に、感光性樹脂組成物を、ダイコーターを用いて塗布した後、真空度が０．２ｔｏｒｒに到達するまで真空ベイクを行って、膜厚２．３μｍの塗膜を形成した。その後、得られた基板を光学顕微鏡で観察して、塗膜に発生する突沸孔の有無を目視評価した。
○：突沸孔が全く認められない。
△：突沸孔が僅かに認められる。
×：突沸孔が多く認められる。
Examples The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
In addition, evaluation of the solvent re-solubility of the dry coating film of the photosensitive resin composition, evaluation of the presence or absence of coating unevenness and drying unevenness, and evaluation of the presence or absence of bumping holes were performed according to the following methods.
(1) Solvent resolubility of dry paint film As an alternative method for evaluating the presence or absence of foreign matter defects in the die coating method, solvent resolubility evaluation of the dry paint film was performed as follows. If the solvent re-solubility is poor, dry matter will adhere and cause uneven coating.
A photosensitive resin composition is applied to a glass substrate, air-dried at 25 ° C. and 55% humidity for 30 minutes using a constant temperature and humidity oven, and then the glass substrate to which the dried coating film is attached is propylene glycol monomethyl ether acetate. Soaked in for 10 minutes. At this time, it evaluated in the following three steps by the redissolved state of the dry coating film.
○: All dried coating films dissolve during immersion.
Δ: A part of the dried coating film remains even after immersion for 10 minutes.
X: The dried coating film hardly or not dissolves after immersion for 10 minutes.
(2) Presence / absence of coating unevenness and drying unevenness After the photosensitive resin composition was applied to a glass substrate using a die coater, vacuum baking was performed until the degree of vacuum reached 0.2 torr. A 3 μm coating film was formed. Then, the obtained board | substrate was observed using the interference fringe inspection lamp (Na lamp), and the presence or absence of the coating nonuniformity which generate | occur | produces in a coating film and the dry nonuniformity was evaluated visually.
○: Coating unevenness and drying unevenness are not recognized at all.
Δ: Slight coating unevenness and drying unevenness are observed.
X: Many coating unevenness and drying unevenness are recognized.
(3) Presence / absence of bump holes After the photosensitive resin composition was applied to a glass substrate using a die coater, vacuum baking was performed until the degree of vacuum reached 0.2 torr. A film was formed. Then, the obtained board | substrate was observed with the optical microscope, and the presence or absence of the bump hole which generate | occur | produces in a coating film was evaluated visually.
A: No bump holes are observed at all.
(Triangle | delta): A bump hole is recognized slightly.
X: Many bump holes are recognized.
製造例１ ベンジルマレイミド樹脂の合成
３０Ｌの重合槽に、溶媒としてジエチレングリコールジメチルエーテル（ＤＭＤＧ）４０．０質量部を仕込み、窒素雰囲気下に９０℃に昇温した後、滴下系１としてＮ−ベンジルマレイミド（ＢｚＭＩ）６．１６質量部、ジエチレングリコールジメチルエーテル（ＤＭＤＧ）６．１６質量部、メチルメタクリレート（ＭＭＡ）１２．１２質量部、メタクリル酸（ＭＡＡ）１２．５５質量部、滴下系２として、パーブチルＯ（ＰＢＯ）（商品名、日本油脂社製）０．６２質量部、滴下系３としてｎ‐ドデシルメルカプタン（ｎ‐ＤＭ）１．２３質量部を、それぞれ３時間かけて連続的に供給した。その後、３０分９０℃を保持した後、温度を１０５℃に昇温し、３時間重合を継続した。ガスクロクロマトグラフィー（ＧＣ）測定による未反応モノマーは、ＢｚＭＩが０．１％、ＭＭＡが０．２％、ＭＡＡが０．３％であった。
次いで、この反応液にグリシジルメタクリレート（ＧＭＡ）１２．７３質量部、触媒としてトリエチルアミン０．１３質量部、重合禁止剤として２，２′−メチレンビス（４−メチル−６−ｔ−ブチルフェノール）（商品名「アンテージＷ４００」、川口化学工業社製）０．０７質量部を追加し、５％酸素濃度に調整した空気、窒素混合ガスを２００ｍｌ／分の流量でバブリングしながら８時間反応を継続した。反応液をガスクロマトグラフィー（ＧＣ）で測定したところ未反応のＧＭＡは検出されなかった。ＤＭＤＧ７．５質量部を加えて希釈した後、冷却し、ベンジルマレイミド樹脂溶液を得た。このベンジルマレイミド樹脂の重量平均分子量（Ｍｗ）はポリスチレン換算で１５，０００であり、酸価（ＡＶ）は７４．８ｍｇＫＯＨ／ｇであり、得られた樹脂溶液中の固形分（ＮＶ）は４４．４質量％であった。
Production Example 1 Synthesis of Benzylmaleimide Resin In a 30 L polymerization tank, 40.0 parts by mass of diethylene glycol dimethyl ether (DMDG) was charged as a solvent, heated to 90 ° C. in a nitrogen atmosphere, and then dropped into N-benzylmaleimide ( BzMI) 6.16 parts by mass, diethylene glycol dimethyl ether (DMDG) 6.16 parts by mass, methyl methacrylate (MMA) 12.12 parts by mass, methacrylic acid (MAA) 12.55 parts by mass, dropping system 2 as perbutyl O (PBO) ) (Trade name, manufactured by NOF Corporation) 0.62 parts by mass, and 1.23 parts by mass of n-dodecyl mercaptan (n-DM) as a dropping system 3 were continuously supplied over 3 hours. Then, after maintaining 90 degreeC for 30 minutes, temperature was heated up to 105 degreeC and superposition | polymerization was continued for 3 hours. The unreacted monomer as measured by gas chromatography (GC) was 0.1% BzMI, 0.2% MMA, and 0.3% MAA.
Next, 12.73 parts by mass of glycidyl methacrylate (GMA), 0.13 parts by mass of triethylamine as a catalyst, and 2,2′-methylenebis (4-methyl-6-t-butylphenol) as a polymerization inhibitor (trade name) “ANTAGE W400” (manufactured by Kawaguchi Chemical Industry Co., Ltd.) was added 0.07 part by mass, and the reaction was continued for 8 hours while bubbling a mixed gas of air and nitrogen adjusted to 5% oxygen concentration at a flow rate of 200 ml / min. When the reaction solution was measured by gas chromatography (GC), unreacted GMA was not detected. After diluting by adding 7.5 parts by mass of DMDG, the mixture was cooled to obtain a benzylmaleimide resin solution. The weight average molecular weight (Mw) of this benzyl maleimide resin is 15,000 in terms of polystyrene, the acid value (AV) is 74.8 mgKOH / g, and the solid content (NV) in the obtained resin solution is 44. It was 4% by mass.
製造例２ ベンジルメタクリレート共重合樹脂の合成
ベンジルメタクリレート３０ｇ（０．１７モル）、スチレン３８ｇ（０．３７モル）、メタクリル酸１８ｇ（０．２１モル）及びｔ−ブチルパーオキシ−２−エチルヘキサノエート（日本油脂製、パーブチルＯ）１０ｇの混合液を、プロピレングリコールモノメチルエーテルアセテート１５０ｇを入れた重合槽中に、窒素気流下１００℃で、３時間かけて滴下した。滴下終了後さらに３時間加熱することにより重合体溶液を得た。この重合体溶液の重量平均分子量（Ｍｗ）はポリスチレン換算で８，０００であった。
次に、得られた重合体溶液に、グリシジルメタクリレート１４ｇ（０．１０モル）、トリエチルアミン０．２ｇ及びｐ−メトキシフェノール０．０５ｇを添加し、１１０℃で１０時間加熱することにより主鎖メタクリル酸のカルボン酸基とグリシジルメタクリレートのエポキシ基との反応を行った。反応中は、グリシジルメタクリレートの重合を防ぐため、反応溶液内に空気をバブリングさせた。反応は、溶液の酸価測定により追跡した。得られた反応溶液は固形分（ＮＶ）３８質量％、酸価（ＡＶ）７５ｍｇＫＯＨ／ｇであり、重量平均分子量（Ｍｗ）はポリスチレン換算で１０，０００であった。なお、モル比（ベンジルメタクリレート／スチレン／メタクリル酸／グリシジルメタクリレート）は、（２０／４３／２５／１２）であった。
Production Example 2 Synthesis of benzyl methacrylate copolymer resin benzyl methacrylate 30 g (0.17 mol), styrene 38 g (0.37 mol), methacrylic acid 18 g (0.21 mol) and t-butylperoxy-2-ethylhexano A mixed solution of 10 g of ate (manufactured by NOF Corporation, Perbutyl O) was dropped into a polymerization tank containing 150 g of propylene glycol monomethyl ether acetate at 100 ° C. for 3 hours in a nitrogen stream. After completion of the dropwise addition, a polymer solution was obtained by heating for an additional 3 hours. The weight average molecular weight (Mw) of this polymer solution was 8,000 in terms of polystyrene.
Next, 14 g (0.10 mol) of glycidyl methacrylate, 0.2 g of triethylamine and 0.05 g of p-methoxyphenol were added to the obtained polymer solution, and the main chain methacrylic acid was heated by heating at 110 ° C. for 10 hours. The reaction between the carboxylic acid group and the epoxy group of glycidyl methacrylate was carried out. During the reaction, air was bubbled into the reaction solution in order to prevent polymerization of glycidyl methacrylate. The reaction was followed by measuring the acid value of the solution. The obtained reaction solution had a solid content (NV) of 38% by mass, an acid value (AV) of 75 mgKOH / g, and a weight average molecular weight (Mw) of 10,000 in terms of polystyrene. The molar ratio (benzyl methacrylate / styrene / methacrylic acid / glycidyl methacrylate) was (20/43/25/12).
実施例１、５、９、参考例２〜４、６〜８、１０〜１２及び比較例１〜９
表１に示す配合内容により、ビーズミルを使用して均一に混合分散して実施例１、５、９、参考例２〜４、６〜８、１０〜１２及び比較例１〜９の２１種類の感光性樹脂組成物を調製した。これら２１種類の感光性樹脂組成物を上記の方法により、乾燥塗膜の溶剤再溶解性を評価した。
次に、これら２１種類の感光性樹脂組成物を使用して、それぞれ、ガラス基板に、ダイコーターを用いて塗布した後、真空度が０．２ｔｏｒｒに到達するまで真空ベイクを行って、膜厚２．３μｍの塗膜を形成した。
２１種類の塗膜それぞれの塗布ムラ及び乾燥ムラの有無の評価及び突沸孔の有無の評価を上記の方法により実施した。評価結果を表１に示す。
Examples 1 , 5, 9, Reference Examples 2-4, 6-8, 10-12 and Comparative Examples 1-9
According to the blending contents shown in Table 1, it was mixed and dispersed uniformly using a bead mill, and 21 types of Examples 1 , 5, 9, Reference Examples 2-4, 6-8, 10-12 and Comparative Examples 1-9 were used. A photosensitive resin composition was prepared. These 21 types of photosensitive resin compositions were evaluated for solvent resolubility of the dried coating film by the above-described method.
Next, using these 21 types of photosensitive resin compositions, each was applied to a glass substrate using a die coater, and then vacuum baked until the degree of vacuum reached 0.2 torr. A 2.3 μm coating film was formed.
Evaluation of the presence or absence of uneven coating and drying unevenness of each of the 21 types of coating films and the presence or absence of bump holes were carried out by the above methods. The evaluation results are shown in Table 1.
マレイミド系共重合樹脂： 製造例１で調製されたベンジルマレイミド樹脂
ベンジルメタクリレート共重合樹脂： 製造例２で調製された樹脂
光重合性モノマー： ジペンタエリスリトールヘキサアクリレート (ＤＰＨＡ)
光重合開始剤 Ａ： ２−ベンジル−２−ジメチルアミノ−１−（４−モルホリノフェニル）−ブタノンー１、チバスペシャリティーケミカルズ社製、商標「ＩＲＧＡＣＵＲＥ ３６９」
光重合開始剤 Ｂ： ２−メチル−１−(４−メチルチオフェニル)−２−モルホリノプロパン−１−オン、チバスペシャリティーケミカルズ社製、商標「ＩＲＧＡＣＵＲＥ ９０７」
赤顔料 Ａ： ピグメントレッド１７７
赤顔料 Ｂ： ピグメントレッド２５４
黄顔料 Ａ： ピグメントイエロー１３９
緑顔料 Ａ： ピグメントグリーン３６
黄顔料 Ｂ： ピグメントイエロー１３８
黄顔料 Ｃ： ピグメントイエロー１５０
青顔料 Ａ： ピグメントブルー１５：６
分散剤： ビックケミー社製、商標「Ｄｉｓｐｅｒｂｙｋ １６１」
溶剤Ａ−１： プロピレングリコールモノメチルエーテルアセテート（沸点：１４６℃、比蒸発速度：３４）
溶剤Ａ−２： ジエチレングリコールジメチルエーテル（沸点：１６２℃、比蒸発速度：３６）
溶剤Ｂ−１： ３−メトキシブチルアセテート（沸点：１７１℃、比蒸発速度：１４）
溶剤Ｂ−２： ３−メチル−３−メトキシブチルアセテート（沸点：１８８℃、比蒸発速度：１０）
Maleimide copolymer resin: Benzyl maleimide resin prepared in Production Example 1 Benzyl methacrylate copolymer resin: Resin photopolymerizable monomer prepared in Production Example 2: Dipentaerythritol hexaacrylate (DPHA)
Photopolymerization initiator A: 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1, manufactured by Ciba Specialty Chemicals, trade name “IRGACURE 369”
Photopolymerization initiator B: 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, manufactured by Ciba Specialty Chemicals, trade name “IRGACURE 907”
Red pigment A: Pigment Red 177
Red pigment B: Pigment Red 254
Yellow Pigment A: Pigment Yellow 139
Green pigment A: Pigment Green 36
Yellow pigment B: Pigment yellow 138
Yellow Pigment C: Pigment Yellow 150
Blue pigment A: Pigment blue 15: 6
Dispersant: Trademark “Disperbyk 161” manufactured by Big Chemie
Solvent A-1: Propylene glycol monomethyl ether acetate (boiling point: 146 ° C., specific evaporation rate: 34)
Solvent A-2: Diethylene glycol dimethyl ether (boiling point: 162 ° C., specific evaporation rate: 36)
Solvent B-1: 3-methoxybutyl acetate (boiling point: 171 ° C., specific evaporation rate: 14)
Solvent B-2: 3-methyl-3-methoxybutyl acetate (boiling point: 188 ° C., specific evaporation rate: 10)
表１から明らかなように、溶剤Ａと溶剤Ｂを好適に組み合わせて用いた実施例１、５、９の感光性樹脂組成物は、比較例１〜９の感光性樹脂組成物と比較して、塗布ムラ、乾燥ムラ、乾燥付着物や突沸孔の発生を起こさず、基材面内の色度均一性に優れていた。 As is clear from Table 1 , the photosensitive resin compositions of Examples 1 , 5 , and 9 using a suitable combination of solvent A and solvent B were compared with the photosensitive resin compositions of Comparative Examples 1-9. No unevenness of application, unevenness of drying, generation of dry deposits or bump holes, and excellent chromaticity uniformity in the substrate surface.
本発明の着色感光性樹脂組成物は、高精細なカラーフィルター、特に液晶表示装置の大型ガラス基板を有するカラーフィルター用の感光性樹脂組成物として好適に用いられる。 The colored photosensitive resin composition of the present invention is suitably used as a photosensitive resin composition for high-definition color filters, particularly color filters having a large glass substrate for liquid crystal display devices.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007157422A JP5144971B2 (en) | 2007-06-14 | 2007-06-14 | Photosensitive resin composition |
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| JP5121522B2 (en) * | 2008-03-24 | 2013-01-16 | 富士フイルム株式会社 | Colored curable composition, color filter, and liquid crystal display device |
| JP5463029B2 (en) * | 2008-12-25 | 2014-04-09 | 株式会社Ｄｎｐファインケミカル | Method for producing polymerizable copolymer for coating liquid, polymerizable copolymer for coating liquid, and coating liquid |
| JP2021064015A (en) * | 2021-01-28 | 2021-04-22 | 株式会社Ｄｎｐファインケミカル | Colored composition for color filter, color filter and display device |
| US20230185190A1 (en) | 2021-12-10 | 2023-06-15 | Samsung Sdi Co., Ltd. | Photosensitive resin composition, photosensitive resin layer using the same and color filter |
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| JP3360866B2 (en) * | 1993-03-31 | 2003-01-07 | 東京応化工業株式会社 | Photosensitive resin composition for color filters |
| JP3787917B2 (en) * | 1996-10-02 | 2006-06-21 | 日立化成工業株式会社 | Colored image forming photosensitive solution, method for producing color filter using the same, and color filter |
| JP4561101B2 (en) * | 2003-03-06 | 2010-10-13 | Ｊｓｒ株式会社 | Radiation sensitive composition for color filter and color filter |
| JP2005234045A (en) * | 2004-02-17 | 2005-09-02 | Fujifilm Electronic Materials Co Ltd | Color resin composition |
| JP4661384B2 (en) * | 2005-06-16 | 2011-03-30 | Ｊｓｒ株式会社 | Radiation-sensitive composition for forming colored layer and color filter |
| JP4815952B2 (en) * | 2005-08-26 | 2011-11-16 | Ｊｓｒ株式会社 | Polymer, radiation sensitive composition for color filter, color filter and color liquid crystal display panel |
| JP4893327B2 (en) * | 2006-02-08 | 2012-03-07 | Ｊｓｒ株式会社 | Radiation-sensitive composition for forming colored layer, color filter, and liquid crystal display device |
| JP5114979B2 (en) * | 2007-03-13 | 2013-01-09 | Ｊｓｒ株式会社 | Radiation-sensitive composition for forming colored layer, color filter, and color liquid crystal display element |
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