JP5073342B2 - Photosensitive resin composition and color filter using the same - Google Patents
Photosensitive resin composition and color filter using the same Download PDFInfo
- Publication number
- JP5073342B2 JP5073342B2 JP2007091505A JP2007091505A JP5073342B2 JP 5073342 B2 JP5073342 B2 JP 5073342B2 JP 2007091505 A JP2007091505 A JP 2007091505A JP 2007091505 A JP2007091505 A JP 2007091505A JP 5073342 B2 JP5073342 B2 JP 5073342B2
- Authority
- JP
- Japan
- Prior art keywords
- resin composition
- component
- photosensitive resin
- color filter
- weight
- 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 description 32
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000000049 pigment Substances 0.000 claims description 32
- 239000002270 dispersing agent Substances 0.000 claims description 29
- 239000004593 Epoxy Substances 0.000 claims description 22
- 239000006185 dispersion Substances 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- -1 for example Chemical compound 0.000 description 38
- 238000000034 method Methods 0.000 description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 19
- 238000011161 development Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 13
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 10
- 229930185605 Bisphenol Natural products 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000004973 liquid crystal related substance Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 150000007519 polyprotic acids Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 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 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- YWFPGFJLYRKYJZ-UHFFFAOYSA-N 9,9-bis(4-hydroxyphenyl)fluorene Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 YWFPGFJLYRKYJZ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 1
- RUJPNZNXGCHGID-UHFFFAOYSA-N (Z)-beta-Terpineol Natural products CC(=C)C1CCC(C)(O)CC1 RUJPNZNXGCHGID-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- XHXSXTIIDBZEKB-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octamethylanthracene-9,10-dione Chemical compound CC1=C(C)C(C)=C2C(=O)C3=C(C)C(C)=C(C)C(C)=C3C(=O)C2=C1C XHXSXTIIDBZEKB-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- UYFJYGWNYQCHOB-UHFFFAOYSA-N 1-(4-tert-butylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(C(C)(C)C)C=C1 UYFJYGWNYQCHOB-UHFFFAOYSA-N 0.000 description 1
- ONCICIKBSHQJTB-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=C(N(C)C)C=C1 ONCICIKBSHQJTB-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
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- HDYFAPRLDWYIBU-UHFFFAOYSA-N 1-silylprop-2-en-1-one Chemical class [SiH3]C(=O)C=C HDYFAPRLDWYIBU-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- OAMHTTBNEJBIKA-UHFFFAOYSA-N 2,2,2-trichloro-1-phenylethanone Chemical compound ClC(Cl)(Cl)C(=O)C1=CC=CC=C1 OAMHTTBNEJBIKA-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-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
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- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-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
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N 2,6-dibromo-4-[(3,5-dibromo-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-UHFFFAOYSA-N 0.000 description 1
- VYTXKAABSCYYEU-UHFFFAOYSA-N 2,6-dibromo-4-[9-(3,5-dibromo-4-hydroxyphenyl)fluoren-9-yl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2C2=CC=CC=C21 VYTXKAABSCYYEU-UHFFFAOYSA-N 0.000 description 1
- TXYQFJWVHVYIHB-UHFFFAOYSA-N 2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenoxy)phenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1OC1=CC(Cl)=C(O)C(Cl)=C1 TXYQFJWVHVYIHB-UHFFFAOYSA-N 0.000 description 1
- YYDJTJGFHTVGGF-UHFFFAOYSA-N 2,6-dichloro-4-(3,5-dichloro-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Cl)C(O)=C(Cl)C=C1S(=O)(=O)C1=CC(Cl)=C(O)C(Cl)=C1 YYDJTJGFHTVGGF-UHFFFAOYSA-N 0.000 description 1
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- JWAPUVVSOVJCJB-UHFFFAOYSA-N bis(4-hydroxy-3,5-dimethylphenyl)methanone Chemical compound CC1=C(O)C(C)=CC(C(=O)C=2C=C(C)C(O)=C(C)C=2)=C1 JWAPUVVSOVJCJB-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- 239000001055 blue pigment Substances 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
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- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
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- MASNVFNHVJIXLL-UHFFFAOYSA-N ethenyl(ethoxy)silicon Chemical compound CCO[Si]C=C MASNVFNHVJIXLL-UHFFFAOYSA-N 0.000 description 1
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- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 1
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- 125000000524 functional group Chemical group 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000001056 green pigment Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 238000003384 imaging method Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000007733 ion plating Methods 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
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 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
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- YLBPOJLDZXHVRR-UHFFFAOYSA-N n'-[3-[diethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CCO[Si](C)(OCC)CCCNCCN YLBPOJLDZXHVRR-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
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- 231100000289 photo-effect Toxicity 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
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- 238000009832 plasma treatment Methods 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 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
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- QJVXKWHHAMZTBY-GCPOEHJPSA-N syringin Chemical compound COC1=CC(\C=C\CO)=CC(OC)=C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 QJVXKWHHAMZTBY-GCPOEHJPSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
Description
本発明は感光性樹脂組成物及びそれを用いたカラーフィルターに関し、詳しくは、カラーフィルター用のインクに適した感光性樹脂組成物に関する。 The present invention relates to a photosensitive resin composition and a color filter using the same, and more particularly to a photosensitive resin composition suitable for an ink for a color filter.
カラー液晶表示装置は、光の透過量あるいは反射量を制御する液晶部とカラーフィルターを構成要素とするが、そのカラーフィルターの製造方法は、通常、ガラス、プラスチックシート等の透明基板の表面に黒色のマトリックスを形成し、続いて、赤、緑、青の異なる色相を順次、ストライプ状あるいはモザイク状等の色パターンで形成する方法が用いられている。パターンサイズはカラーフィルターの用途並びにそれぞれの色により異なるが赤、緑、青の画素は200〜300μmから100μmへ、ブラックマトリックスは20μmから10μmへ細線化され、これにともなって感光性樹脂材料には高い寸法精度が求められている。
ここ数年、液晶テレビ、液晶モニター、カラー液晶携帯電話などあらゆる分野でカラー液晶表示装置が用いられてきた。カラーフィルターはカラー液晶表示装置の視認性を左右する重要な部材の一つであり、視認性の向上、すなわち、鮮明な画像を得るためには、カラーフィルターを構成する赤、緑、青などの画素を今まで以上に高色純度化、及び、ブラックマトリックスでは高遮光化を達成する必要があり、感光性樹脂組成物に着色剤を従来より多量に添加しなければならない。
A color liquid crystal display device includes a liquid crystal unit for controlling the amount of light transmitted or reflected and a color filter as components, and the method for producing the color filter is usually black on the surface of a transparent substrate such as glass or plastic sheet. Next, a method is used in which different colors of red, green, and blue are sequentially formed in a color pattern such as a stripe shape or a mosaic shape. The pattern size varies depending on the use of the color filter and each color, but red, green and blue pixels are thinned from 200 to 300 μm to 100 μm, and the black matrix is thinned from 20 μm to 10 μm. High dimensional accuracy is required.
In recent years, color liquid crystal display devices have been used in various fields such as liquid crystal televisions, liquid crystal monitors, and color liquid crystal mobile phones. The color filter is one of the important members that influence the visibility of the color liquid crystal display device. In order to improve the visibility, that is, to obtain a clear image, the color filters such as red, green, and blue are used. It is necessary to achieve a higher color purity of the pixels than ever before, and to achieve a higher light shielding in the black matrix, and it is necessary to add a colorant to the photosensitive resin composition in a larger amount than before.
カラーフィルターの製造法には電着法、染色法、印刷法および顔料分散法などがあるが、最近では顔料分散法が主流となっている。顔料分散法は、基板に塗布された感光性樹脂に顔料を分散したカラーレジスト、あるいは非感光樹脂に顔料を分散したカラーペーストを、フォトリソ加工法を用いてパターン形成する方法であり、染色工程が不要なため製造工程が簡略化でき、また得られた着色画素は、耐光、耐熱性に優れ、高精度の画素を形成できるという利点がある。
しかし一方、基板上に画素を形成する際に、顔料を含んだ感光性の膜の基板への密着性が低いために、現像時に画素が剥離するという問題があった。そこで、従来からシランカップリング剤を組成物に添加して密着性の向上を図ってきたが、シランカップリング剤を多量に用いた場合、基板の未露光部に現像残渣が残るという問題点が新たに発生する。
Color filter production methods include electrodeposition, dyeing, printing, and pigment dispersion, but the pigment dispersion method has become the mainstream recently. The pigment dispersion method is a method in which a color resist in which a pigment is dispersed in a photosensitive resin applied to a substrate or a color paste in which a pigment is dispersed in a non-photosensitive resin is patterned using a photolithographic method, and the dyeing process is performed. Since it is unnecessary, the manufacturing process can be simplified, and the obtained colored pixel has the advantage that it has excellent light resistance and heat resistance and can form a highly accurate pixel.
However, when pixels are formed on the substrate, there is a problem that the pixels are peeled off during development because the adhesion of the photosensitive film containing the pigment to the substrate is low. Therefore, conventionally, a silane coupling agent has been added to the composition to improve adhesion, but when a large amount of the silane coupling agent is used, there is a problem in that a development residue remains on an unexposed portion of the substrate. Newly occurs.
このような問題に対し、例えば特開平８−８２７９０号公報（特許文献１）では基板に紫外線およびオゾンを作用させることで残渣を分解除去する方法が提案されている。しかしながら、この提案は残渣を除去するのに長時間を要し、カラーフィルターの着色層やオーバーコート層が劣化してしまうという問題がある。また特開平９−２８１３２３号公報（特許文献２）では、基板上にブラックマトリクスを形成した後、オゾン処理を行い、次いで、非イオン系界面活性剤を含有した洗浄液にて超音波などの洗浄処理を行う方法が開示されている。しかしながら、この残渣除去の方法は感光性樹脂の密着性を低下させることになるため、必ずしも十分であるとはいえない。
従って、本発明の目的は、残渣を生じることなく良好なパターン密着性維持することができるカラーフィルター用感光性樹脂組成物を提供することにある。また、他の目的は、このカラーフィルター用感光性樹脂組成物を用いて形成した塗膜及びカラーフィルターを提供するものである。 Accordingly, an object of the present invention is to provide a photosensitive resin composition for a color filter capable of maintaining good pattern adhesion without generating a residue. Another object of the present invention is to provide a coating film and a color filter formed using the photosensitive resin composition for a color filter.
本発明者らは前記の課題を解決すべく検討を行った結果、ビスフェノール類から誘導される芳香族エポキシ化合物と（メタ）アクリル酸との反応物を更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有化合物を含む感光性樹脂組成物に特定の分散剤を含む顔料分散体を配合することにより、前記の問題点が解決されることを見出し、本発明を完成させた。 As a result of investigations to solve the above problems, the present inventors have further obtained a reaction product of an aromatic epoxy compound derived from bisphenols and (meth) acrylic acid with a polybasic acid carboxylic acid or an anhydride thereof. We have found that the above-mentioned problems can be solved by blending a pigment dispersion containing a specific dispersant into a photosensitive resin composition containing an unsaturated group-containing compound obtained by the reaction, and completed the present invention. I let you.
本発明は、下記（A）〜（D）成分：
(A)グリシジルエーテル基を有するエポキシ化合物と（メタ）アクリル酸との反応物を更に多塩基酸カルボン酸又はその無水物と反応させて得られた不飽和基含有樹脂であるアルカリ現像性バインダー樹脂、
(B)少なくとも1個のエチレン性不飽和結合を有する光重合性モノマー、
(C)光重合開始剤、及び
(D)遮光性顔料分散体
を必須成分として含むカラーフィルター用感光性樹脂組成物であって、上記(A)成分と(B)成分との重量割合（A）／（B）が、６０／４０〜９０／１０であり、(A)成分と(B)成分の合計１００重量部に対して（C）成分を２〜３０重量部含有し、また、（D）成分は、(A)成分と(B)成分の合計１００重量部に対して３０〜２８０重量部の割合で含有される遮光性顔料と、この遮光性顔料１００重量部に対して５０重量部以下の割合で含有される分散剤とを含み、上記分散剤は、製膜後の分散剤膜の表面にイオン交換水を滴下して１０秒後に測定した接触角が７０〜９０°であることを特徴とするカラーフィルター用感光性樹脂組成物である。
The present invention includes the following components (A) to (D):
(A) Alkali developable binder resin which is an unsaturated group-containing resin obtained by further reacting a reaction product of an epoxy compound having a glycidyl ether group and (meth) acrylic acid with a polybasic carboxylic acid or its anhydride ,
(B) a photopolymerizable monomer having at least one ethylenically unsaturated bond,
(C) a photopolymerization initiator, and
(D) A photosensitive resin composition for a color filter containing a light-shielding pigment dispersion as an essential component, wherein the weight ratio (A) / (B) of the component (A) to the component (B) is 60 / was 40~90 / 10, (a) component and (B) per 100 parts by weight of component (C) component contains 2 to 30 parts by weight, also, (D) component, (a) component And a light-shielding pigment contained in a proportion of 30 to 280 parts by weight with respect to 100 parts by weight of the total of component (B) , and a dispersion contained in a proportion of 50 parts by weight or less with respect to 100 parts by weight of the light-shielding pigment The above-mentioned dispersing agent comprises a dispersing agent , and the contact angle measured after 10 seconds after dropping ion-exchanged water on the surface of the dispersing agent film after film formation is 70 to 90 °. It is an adhesive resin composition.
また、本発明は、前記のカラーフィルター用感光性樹脂組成物を硬化させて形成したことを特徴とする塗膜である。更に、本発明は、前記のカラーフィルター用感光性樹脂組成物を透明基板上に塗布し、プリベークした後、紫外線露光装置による露光、アルカリ水溶液による現像、及びポストベークして作製された画素又はブラックマトリクスを備えたことを特徴とするカラーフィルターである。 Moreover, this invention is a coating film formed by hardening the said photosensitive resin composition for color filters. Furthermore, the present invention provides a pixel or black produced by applying the photosensitive resin composition for a color filter on a transparent substrate, pre-baking, then exposing with an ultraviolet exposure device, developing with an alkaline aqueous solution, and post-baking. A color filter including a matrix.
以下、本発明について詳細に説明する。
本発明のカラーフィルター用感光性樹脂組成物（以下、単に組成物ともいう）は、（A）〜（D）成分を必須成分として含有する。ここで、（A）〜（D）の各成分について詳細に説明する。
Hereinafter, the present invention will be described in detail.
The photosensitive resin composition for color filters of the present invention (hereinafter also simply referred to as a composition) contains components (A) to (D) as essential components. Here, each component of (A)-(D) is demonstrated in detail.
（A）成分のアルカリ現像性バインダー樹脂としては、不飽和基含有化合物であって、ビスフェノール類から誘導されるグリシジルエーテル基を有するエポキシ化合物に、（メタ）アクリル酸（これは「アクリル酸及び／又はメタクリル酸」の意味である）を反応させ、得られたヒドロキシ基を有する化合物に多塩基酸カルボン酸又はその無水物を反応させて得られるエポキシ（メタ）アクリレート酸付加物であることが好ましい。また、ビスフェノール類から誘導されるエポキシ化合物とは、ビスフェノール類とエピハロヒドリンを反応させて得られるエポキシ化合物又はこれと同等物を意味する。不飽和基含有化合物は、エチレン性不飽和二重結合とカルボキシル基とを併せ持つため、カラーフィルター用感光性樹脂組成物に優れた光硬化性、良現像性、パターニング特性を与え遮光膜の物性向上をもたらす。 The alkali-developable binder resin (A) is an unsaturated group-containing compound, which is an epoxy compound having a glycidyl ether group derived from bisphenols, and (meth) acrylic acid (this is “acrylic acid and / or Or an epoxy (meth) acrylate acid adduct obtained by reacting a compound having a hydroxy group with a polybasic acid carboxylic acid or its anhydride. . The epoxy compound derived from bisphenols means an epoxy compound obtained by reacting bisphenols with epihalohydrin or an equivalent thereof. Since unsaturated group-containing compounds have both ethylenically unsaturated double bonds and carboxyl groups, they provide excellent photocurability, good developability, and patterning characteristics to photosensitive resin compositions for color filters, and improve the properties of light-shielding films. Bring.
（A）成分である不飽和基含有化合物としては、好ましくは、下記一般式(Ｉ)で表されるエポキシ化合物から誘導されるのがよい。このエポキシ化合物はビスフェノール類から誘導される。したがって、ビスフェノール類を説明することによって、不飽和基含有化合物が理解されるので、好ましい具体例をビスフェノール類により説明する。なお、一般式 (Ｉ)において、Ｒ11 及びＲ12 は、独立に水素原子、炭素数１〜５のアルキル基又はハロゲン原子を示すが、好ましくは水素原子であり、また、Ｘは、‐CO‐、−SO2−、‐C(CF3)2−、-Si(CH3)2‐、-CH2‐、-C(CH3)2‐、-O-、9,9-フルオレニル基又は不存在を示すが、好ましくは9,9-フルオレニル基である。ｎは０〜１０の整数であるが、好ましくは０又は平均値として０〜２の範囲である。ここで、9,9-フルオレニル基は、下記式（II）で表される基をいう。
好ましい不飽和基含有化合物の原料となるビスフェノール類としては、次のようなものが挙げられる。ビス（４−ヒドロキシフェニル）ケトン、ビス（４−ヒドロキシ−３，５−ジメチルフェニル）ケトン、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）ケトン、ビス（４−ヒドロキシフェニル）スルホン、ビス（４−ヒドロキシ−３，５−ジメチルフェニル）スルホン、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）スルホン、ビス（４−ヒドロキシフェニル）ヘキサフルオロプロパン、ビス（４−ヒドロキシ−３，５−ジメチルフェニル）ヘキサフルオロプロパン、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）ヘキサフルオロプロパン、ビス（４−ヒドロキシフェニル）ジメチルシラン、ビス（４−ヒドロキシ−３，５−ジメチルフェニル）ジメチルシラン、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）ジメチルシラン、ビス（４−ヒドロキシフェニル）メタン、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）メタン、ビス（４−ヒドロキシ−３，５−ジブロモフェニル）メタン、２，２−ビス（４−ヒドロキシフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３−メチルフェニル）プロパン、２，２−ビス（４−ヒドロキシ−３−クロロフェニル）プロパン、ビス（４−ヒドロキシフェニル）エーテル、ビス（４−ヒドロキシ−３，５−ジメチルフェニル）エーテル、ビス（４−ヒドロキシ−３，５−ジクロロフェニル）エーテル等を含む化合物や、Ｘが前記の９,９−フルオレニル基である９,９−ビス（４−ヒドロキシフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３−メチルフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３−クロロフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３−ブロモフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３−フルオロフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３−メトキシフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３，５−ジメチルフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３，５−ジクロロフェニル）フルオレン、９，９−ビス（４−ヒドロキシ−３，５−ジブロモフェニル）フルオレン等や、更には４，４'−ビフェノール、３，３'−ビフェノール等の化合物が挙げられる。 The following are mentioned as bisphenol used as the raw material of a preferable unsaturated group containing compound. Bis (4-hydroxyphenyl) ketone, bis (4-hydroxy-3,5-dimethylphenyl) ketone, bis (4-hydroxy-3,5-dichlorophenyl) ketone, bis (4-hydroxyphenyl) sulfone, bis (4 -Hydroxy-3,5-dimethylphenyl) sulfone, bis (4-hydroxy-3,5-dichlorophenyl) sulfone, bis (4-hydroxyphenyl) hexafluoropropane, bis (4-hydroxy-3,5-dimethylphenyl) Hexafluoropropane, bis (4-hydroxy-3,5-dichlorophenyl) hexafluoropropane, bis (4-hydroxyphenyl) dimethylsilane, bis (4-hydroxy-3,5-dimethylphenyl) dimethylsilane, bis (4- Hydroxy-3,5-dichlorophenyl) dimethyl Silane, bis (4-hydroxyphenyl) methane, bis (4-hydroxy-3,5-dichlorophenyl) methane, bis (4-hydroxy-3,5-dibromophenyl) methane, 2,2-bis (4-hydroxyphenyl) ) Propane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 2,2-bis (4-hydroxy-3,5-dichlorophenyl) propane, 2,2-bis (4-hydroxy-) 3-methylphenyl) propane, 2,2-bis (4-hydroxy-3-chlorophenyl) propane, bis (4-hydroxyphenyl) ether, bis (4-hydroxy-3,5-dimethylphenyl) ether, bis (4 -Hydroxy-3,5-dichlorophenyl) ether or the like, or X is the 9,9-fluorenyl group 9,9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (4-hydroxy-3-methylphenyl) fluorene, 9,9-bis (4-hydroxy-3-chlorophenyl) fluorene, 9,9 -Bis (4-hydroxy-3-bromophenyl) fluorene, 9,9-bis (4-hydroxy-3-fluorophenyl) fluorene, 9,9-bis (4-hydroxy-3-methoxyphenyl) fluorene, 9, 9-bis (4-hydroxy-3,5-dimethylphenyl) fluorene, 9,9-bis (4-hydroxy-3,5-dichlorophenyl) fluorene, 9,9-bis (4-hydroxy-3,5-dibromo Phenyl) fluorene and the like, and further compounds such as 4,4′-biphenol and 3,3′-biphenol.
この不飽和基含有化合物は、上記のようなビスフェノール類から誘導されるエポキシ化合物から得ることができるが、かかるエポキシ化合物の他にフェノールノボラック型エポキシ化合物や、クレゾールノボラック型エポキシ化合物等もグリシジルエーテル基を有する化合物を有意に含むものであれば使用することができる。また、ビスフェノール類をグリシジルエーテル化する際に、オリゴマー単位が混入することになるが、式(Ｉ)におけるｎの平均値が０〜１０、好ましくは０〜２の範囲であれば、本樹脂組成物の性能には問題はない。 This unsaturated group-containing compound can be obtained from an epoxy compound derived from bisphenols as described above. In addition to such an epoxy compound, a phenol novolac type epoxy compound, a cresol novolak type epoxy compound, etc. are also glycidyl ether groups. Any compound can be used as long as it contains a compound having a significant difference. Further, when bisphenols are glycidyl etherified, oligomer units are mixed. If the average value of n in the formula (I) is in the range of 0 to 10, preferably 0 to 2, the present resin composition There is no problem in the performance of things.
また、このようなエポキシ化合物と（メタ）アクリル酸とを反応させて得られたエポキシ（メタ）アクリレート分子中のヒドロキシ基と反応し得る多塩基酸カルボン酸又はその酸無水物としては、例えば、マレイン酸、コハク酸、イタコン酸、フタル酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、メチルエンドメチレンテトラヒドロフタル酸、クロレンド酸、メチルテトラヒドロフタル酸、トリメリット酸、ピロメリット酸等やその酸無水物、更には、ベンゾフェノンテトラカルボン酸、ビフェニルテトラカルボン酸、ビフェニルエーテルテトラカルボン酸等の芳香族多価カルボン酸やその酸二無水物等が挙げられる。そして、酸無水物と酸二無水物の使用割合については、露光、アルカリ現像操作によって微細なパターンを形成するのに適した割合を選択することができる。 In addition, as the polybasic acid carboxylic acid or its acid anhydride that can react with the hydroxy group in the epoxy (meth) acrylate molecule obtained by reacting such an epoxy compound with (meth) acrylic acid, for example, Maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, methylendomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, trimellitic acid, pyromellitic acid and the acid anhydride thereof, Furthermore, aromatic polyvalent carboxylic acids such as benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, biphenyl ether tetracarboxylic acid, and acid dianhydrides thereof can be used. And about the usage-amount of an acid anhydride and an acid dianhydride, the ratio suitable for forming a fine pattern by exposure and alkali image development operation can be selected.
（A）成分のアルカリ現像性バインダー樹脂については、その１種のみを使用しても、２種以上の混合物を使用することもできる。また、エポキシ化合物と（メタ）アクリル酸との反応で得られたエポキシ（メタ）アクリレートと多塩基酸又はその酸無水物を反応させて不飽和基含有化合物を製造する方法については、特に限定されるものでなく、その一例を示せば、例えば次のようにして製造することができる。すなわち、先ず、９，９−ビス（４−ヒドロキシフェニル）フルオレンとエピクロロヒドリンとを反応させて下記一般式（III）で表されるビスフェノールフルオレン型エポキシ化合物を合成し、この一般式（III）のビスフェノールフルオレン型エポキシ化合物と下記一般式（IV）で表される（メタ）アクリル酸とを反応させて下記一般式（Ｖ）で表されるビスフェノールフルオレン型エポキシアクリレート樹脂を合成し、次いでプロピレングリコールモノメチルエーテルアセテート溶媒中で一般式（Ｖ）のビスフェノールフルオレン型エポキシアクリレート樹脂と上記多塩基酸又はその酸無水物とを加熱下に反応させ、目的の不飽和基含有化合物を製造する。ここで式（III）〜（Ｖ）において、Ｒ11，Ｒ12は、前記と同じであり、Ｒ13は、独立にＨ又はCH3である。 About (A) component alkali developable binder resin, even if it uses only 1 type, the mixture of 2 or more types can also be used. In addition, the method for producing an unsaturated group-containing compound by reacting an epoxy (meth) acrylate obtained by reaction of an epoxy compound with (meth) acrylic acid and a polybasic acid or an acid anhydride thereof is particularly limited. If it shows not an example but the example, it can manufacture as follows, for example. That is, first, 9,9-bis (4-hydroxyphenyl) fluorene and epichlorohydrin are reacted to synthesize a bisphenolfluorene type epoxy compound represented by the following general formula (III). ) Bisphenolfluorene type epoxy compound and (meth) acrylic acid represented by the following general formula (IV) are reacted to synthesize a bisphenolfluorene type epoxy acrylate resin represented by the following general formula (V), and then propylene The target unsaturated group-containing compound is produced by reacting the bisphenolfluorene type epoxy acrylate resin of general formula (V) with the polybasic acid or acid anhydride thereof in a glycol monomethyl ether acetate solvent under heating. In the formulas (III) to (V), R 11 and R 12 are the same as described above, and R 13 is independently H or CH 3 .
なお、この際の反応については、酸無水物がエポキシアクリレート樹脂の０Ｈ基１モル当たり１／２モルとなるように定量的に反応させることが望ましく、そのために反応温度としては９０〜１３０℃、好ましくは９５〜１２５℃である。この反応については、一般式（Ｉ）の単位構造を有する化合物全体について同様である。 In addition, about the reaction in this case, it is desirable to make it react quantitatively so that an acid anhydride may become 1/2 mol per 1 mol of 0H groups of an epoxy acrylate resin, Therefore As reaction temperature, it is 90-130 degreeC, Preferably it is 95-125 degreeC. About this reaction, it is the same about the whole compound which has a unit structure of general formula (I).
(B)成分の少なくとも1個のエチレン性不飽和結合を有する光重合性モノマーとしては、例えば、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、２−エチルヘキシル（メタ）アクリレート等の水酸基を有するモノマーや、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（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、テトラメチレングリコールジ（メタ）アクリレート、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ジ（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、グリセロール（メタ）アクリレート等の（メタ）アクリル酸エステル類を挙げることができ、これらの化合物は、その１種のみを単独で使用できるほか、２種以上を併用して使用することもできる。 Examples of the photopolymerizable monomer (B) having at least one ethylenically unsaturated bond include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. Monomers having a hydroxyl group such as ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, tetramethylene glycol di (meth) acrylate, Trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythrito (Meth) acrylic acid esters such as diol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, glycerol (meth) acrylate, and the like. Only one type can be used alone, or two or more types can be used in combination.
これら(A)成分と(B)成分の配合割合は、重量比（A）/（B）で６０／４０〜９０／１０であり、好ましくは７０／３０〜８０／２０である。(A)成分の配合割合が６０／４０より少ないと、光硬化後の硬化物が脆くなり、また、未露光部において塗膜の酸価が低いためにアルカリ現像液に対する溶解性が低下し、パターンエッジがぎざつきシャープにならないといった問題が生じ、また、９０／１０よりも多いと、樹脂に占める光反応性官能基の割合が少なく架橋構造の形成が十分でなく、更に、樹脂成分における酸価度が高過ぎて、露光部におけるアルカリ現像液に対する溶解性が高くなることから、形成されたパターンが目標とする線幅より細ったり、パターンの欠落が生じ易くなるといった問題が生じるおそれがある。 The blending ratio of these component (A) and component (B) is 60/40 to 90/10, preferably 70/30 to 80/20 in weight ratio (A) / (B). When the blending ratio of the component (A) is less than 60/40, the cured product after photocuring becomes brittle, and the acid value of the coating film is low in the unexposed area, so that the solubility in an alkali developer is lowered. There arises a problem that the pattern edge is not jagged and sharp, and when it is more than 90/10, the ratio of the photoreactive functional group in the resin is small and the formation of a crosslinked structure is insufficient. Since the valence is too high and the solubility in the alkaline developer in the exposed area is increased, there is a possibility that the formed pattern is thinner than the target line width or the pattern is easily lost. .
(C)成分の光重合開始剤としては、紫外線光等の照射によりラジカル種を発生し、光重合性の化合物に付加してラジカル重合を開始させ、組成物を硬化させるものであり、このような光重合開始剤として例えば、アセトフェノン、２，２−ジエトキシアセトフェノン、ｐ−ジメチルアセトフェノン、ｐ−ジメチルアミノプロピオフェノン、ジクロロアセトフェノン、トリクロロアセトフェノン、ｐ−ｔｅｒｔ−ブチルアセトフェノン等のアセトフェノン類、ベンゾフェノン、２−クロロベンゾフェノン、ｐ，ｐ'−ビスジメチルアミノベンゾフェノン等のベンゾフェノン類、ベンジル、ベンゾイン、ベンゾインメチルエーテル、ベンゾインイソプロピルエーテル、ベンゾインイソブチルエーテル、等のベンゾインエーテル類、2-(o-クロロフェニル)-4,5-フェニルビイミダゾール、2-(o-クロロフェニル)-4,5-ジ(m-メトキシフェニル)ビイミダゾール、2-(o-フルオロフェニル)-4,5-ジフェニルビイミダゾール、2-(o-メトキシフェニル)-4,5-ジフェニルビイミダゾール、2、4,5-トリアリールビイミダゾール等のビイミダゾール系化合物類、2-トリクロロメチル−5−スチリル−1,3,4−オキサジアゾール、2−トリクロロメチル-5-(p-シアノスチリル)-1,3, 4-オキサジアゾール、2-トリクロロメチル-5-(p-メトキシスチリル)-1,3,4-オキサジアゾール等のハロメチルチアゾール化合物類、2,4,6-トリス（トリクロロメチル）-1,3,5-トリアジン、2-メチル−4,6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-フェニル-4、6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-(4-クロロフェニル)-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-(4-メトキシフェニル)-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-(4-メトキシナフチル)-4,6-ビス（トリクロロRメチル）-1, 3,5-トリアジン、2-(4-メトキシスチリル)-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-(3,4,5-トリメトキシスチリル)-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン、2-(4-メチルチオスチリル)-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン等のハロメチル−Ｓ−トリアジン系化合物類、1,2-オクタンジオン,1-［4-（フェニルチオ）フェニル］-,2-（O-ベンゾイルオキシム）、1-(4-フェニルスルファニルフェニル)ブタン-1，2-ジオン-2-オキシム-O-ベンゾアート、1-(4-メチルスルファニルフェニル)ブタン-1， 2-ジオン-2-オキシム-O-アセタート、1-(4-メチルスルファニルフェニル)ブタン-1−オンオキシム-O-アセタート、エタノン,1-［9-エチル-6-（2-メチルベンジル）-9H-カルバゾール-3-イル］-1-（O-アセチルオキシム）等、O-アシルオキシム系化合物類、ベンジルジメチルケタール、チオキサンソン、２−クロロチオキサンソン、２，４−ジエチルチオキサンソン、２−メチルチオキサンソン、２−イソプロピルチオキサンソン、等のイオウ化合物、２−エチルアントラキノン、オクタメチルアントラキノン、１，２−ベンズアントラキノン、２，３−ジフェニルアントラキノン等のアントラキノン類、アゾビスイソブチルニトリル、ベンゾイルパーオキサイド、クメンパーオキシド等の有機過酸化物、２−メルカプトベンゾイミダゾール、２−メルカプトベンゾオキサゾール、２−メルカプトベンゾチアゾール等のチオール化合物等が挙げられる。 As the photopolymerization initiator of component (C), radical species are generated by irradiation with ultraviolet light or the like, added to the photopolymerizable compound to initiate radical polymerization, and the composition is cured. Examples of the photopolymerization initiator include acetophenones such as acetophenone, 2,2-diethoxyacetophenone, p-dimethylacetophenone, p-dimethylaminopropiophenone, dichloroacetophenone, trichloroacetophenone, p-tert-butylacetophenone, benzophenone, Benzophenones such as 2-chlorobenzophenone and p, p'-bisdimethylaminobenzophenone, benzoin ethers such as benzyl, benzoin, benzoin methyl ether, benzoin isopropyl ether and benzoin isobutyl ether, 2- (o-chlorophenyl) -4,5-phenylbiimidazole, 2- (o-chlorophenyl) -4,5-di (m-methoxyphenyl) biimidazole, 2- (o-fluorophenyl) -4,5-diphenylbiimidazole, 2- (o-methoxyphenyl) -4,5-diphenylbiimidazole, biimidazole compounds such as 2,4,5-triarylbiimidazole, 2-trichloromethyl-5-styryl-1,3,4-oxadi Azole, 2-trichloromethyl-5- (p-cyanostyryl) -1,3,4-oxadiazole, 2-trichloromethyl-5- (p-methoxystyryl) -1,3,4-oxadiazole, etc. Halomethylthiazole compounds, 2,4,6-tris (trichloromethyl) -1,3,5-triazine, 2-methyl-4,6-bis (trichloromethyl) -1,3,5-triazine, 2 -Phenyl-4,6-bis (trichloromethyl) -1,3,5-triazine, 2- (4-chlorophenyl) -4,6-bis (trichloromethyl) -1,3,5-triazi 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -1,3,5-triazine, 2- (4-methoxynaphthyl) -4,6-bis (trichloroRmethyl) -1, 3,5-triazine, 2- (4-methoxystyryl) -4,6-bis (trichloromethyl) -1,3,5-triazine, 2- (3,4,5-trimethoxystyryl) -4,6 Halomethyl-S-triazine compounds such as 2-bis (trichloromethyl) -1,3,5-triazine, 2- (4-methylthiostyryl) -4,6-bis (trichloromethyl) -1,3,5-triazine 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), 1- (4-phenylsulfanylphenyl) butane-1,2-dione-2-oxime -O-benzoate, 1- (4-methylsulfanylphenyl) butane-1,2-dione-2-oxime-O-acetate, 1- (4-methylsulfanylphenyl) butan-1-oneoxime-O-acetate, Etano , 1- [9-ethyl-6- (2-methylbenzyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), O-acyloxime compounds, benzyldimethyl ketal, thioxanthone Sulfur compounds such as 2-chlorothioxanthone, 2,4-diethylthioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 2-ethylanthraquinone, octamethylanthraquinone, 1,2-benzanthraquinone Anthraquinones such as 2,3-diphenylanthraquinone, organic peroxides such as azobisisobutylnitrile, benzoyl peroxide, cumene peroxide, 2-mercaptobenzimidazole, 2-mercaptobenzoxazole, 2-mercaptobenzothiazole, etc. Examples include thiol compounds.
これらの光重合開始剤は、その１種のみを単独で使用できるほか、２種以上を組み合わせて使用することもできる。また、それ自体では光重合開始剤として作用しないが、増感剤を上記の化合物と組み合わせて用いることにより、光重合開始剤の能力を増大させ得るような化合物を添加することもできる。そのような化合物としては、例えば、ベンゾフェノンと組み合わせて使用すると効果のあるトリエタノールアミン等の第３級アミンを挙げることができる。 These photopolymerization initiators can be used alone or in combination of two or more. In addition, a compound that does not act as a photopolymerization initiator per se but can increase the ability of the photopolymerization initiator can be added by using a sensitizer in combination with the above compound. Examples of such compounds include tertiary amines such as triethanolamine which are effective when used in combination with benzophenone.
(C)成分の光重合開始剤の使用量は、(A)、(B)の各成分の合計１００重量部を基準として２〜３０重量部であり、好ましくは５〜２０重量部である。(C)成分の配合割合が２重量部未満の場合には、光重合の速度が遅くなって、感度が低下し、一方、３０重量部を超える場合には、感度が強すぎて、パターン線幅がパターンマスクに対して太った状態になり、マスクに対して忠実な線幅が再現できない、又は、パターンエッジがぎざつきシャープにならないといった問題が生じるおそれがある。 The amount of the photopolymerization initiator used as the component (C) is 2 to 30 parts by weight, preferably 5 to 20 parts by weight, based on a total of 100 parts by weight of the components (A) and (B). When the blending ratio of component (C) is less than 2 parts by weight, the rate of photopolymerization becomes slow and the sensitivity decreases. On the other hand, when it exceeds 30 parts by weight, the sensitivity is too strong and the pattern line The width becomes thicker than the pattern mask, and there is a possibility that a line width that is faithful to the mask cannot be reproduced, or that the pattern edge does not become jagged and sharp.
（D）成分の遮光性顔料分散体は遮光性顔料と分散剤とを含んでなる分散体であり、必要に応じ、分散助剤として顔料誘導体を添加することができる。 The light-shielding pigment dispersion of component (D) is a dispersion comprising a light-shielding pigment and a dispersant, and a pigment derivative can be added as a dispersion aid if necessary.
上記分散剤については、水に対する接触角が７０〜９０°となるものを使用する。ここで言う接触角とは、分散剤を適当な濃度に希釈し、スピンコーターでガラス上に塗布、熱風乾燥機を用いてポストベークした後、製膜された分散剤膜表面にイオン交換水を滴下し、１０秒後に測定したイオン交換水のぬれ角度を示すものである。 About the said dispersing agent, the contact angle with respect to water will be 70-90 degrees. The contact angle referred to here means that the dispersant is diluted to an appropriate concentration, coated on glass with a spin coater, post-baked with a hot air dryer, and then ion-exchanged water is applied to the surface of the formed dispersant film. It shows the wetting angle of ion-exchanged water that was dropped and measured 10 seconds later.
遮光性顔料分散体に用いられる分散剤としては、例えば、カチオン系、アニオン系、ノニオン系、両性、シリコーン系、フッ素系等の界面活性剤を挙げることができる。前記界面活性剤の具体例としては、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類；ポリオキシエチレンｎ−オクチルフェニルエーテル、ポリオキシエチレンｎ−ノニルフェニルエーテル等のポリオキシエチレンアルキルフェニルエーテル類；ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレート等のポリエチレングリコールジエステル類；ソルビタン脂肪酸エステル類；脂肪酸変性ポリエステル類；３級アミン変性ポリウレタン類；ポリエチレンイミン類等のほか、以下商品名で、ＫＰ（信越化学工業（株）製）、ポリフロー（共栄社化学（株）製）、エフトップ（トーケムプロダクツ社製）、メガファック（大日本インキ化学工業（株）製）、フロラード（住友スリーエム（株）製）、アサヒガード、サーフロン（以上、旭硝子（株）製）、Ｄｉｓｐｅｒｂｙｋ（ビックケミー・ジャパン（株）製）、ソルスパース（ゼネカ（株）製）、ＥＦＫＡ（エフカーケミカルズビーブイ（ＥＦＫＡ）社製）、等を挙げることができる。これらの界面活性剤は、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。界面活性剤の使用量は、遮光性顔料１００重量部に対して、通常、５０重量部以下、好ましくは３０重量部以下である。 Examples of the dispersant used in the light-shielding pigment dispersion include cationic, anionic, nonionic, amphoteric, silicone, and fluorine surfactants. Specific examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether; polyoxyethylene n-octylphenyl ether, polyoxyethylene n- Polyoxyethylene alkylphenyl ethers such as nonylphenyl ether; polyethylene glycol diesters such as polyethylene glycol dilaurate and polyethylene glycol distearate; sorbitan fatty acid esters; fatty acid-modified polyesters; tertiary amine-modified polyurethanes; In addition to the following trade names, KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), F-Top (manufactured by Tochem Products), Gafac (Dainippon Ink Chemical Co., Ltd.), Florard (Sumitomo 3M Co., Ltd.), Asahi Guard, Surflon (above, Asahi Glass Co., Ltd.), Disperbyk (Bicchemy Japan Co., Ltd.), Sol Sparse ( Zeneca Co., Ltd.), EFKA (manufactured by EFKA Chemicals Beebuy (EFKA)) and the like. These surfactants can be used alone or in admixture of two or more. The amount of the surfactant used is usually 50 parts by weight or less, preferably 30 parts by weight or less with respect to 100 parts by weight of the light-shielding pigment.
本発明において分散剤を製膜した際の接触角が一定の範囲において有効であるのは、接触角と水溶性に相関があり、分散剤の水溶性（すなわち水との親和性）が現像性に影響するためと考えられる。そのため、適切な水溶性を有することが必須の要件である。分散剤の接触角が小さい、すなわち水との親和性が高いと現像パターンの密着性が低下し、また、分散剤の接触角が大きい、すなわち水との親和性が低いと未露光部に残渣残りが発生するため、分散剤の極性基（ポリエーテル、アミン等）と非極性基（ポリエステル等）とのバランスを考慮して、適正範囲のものを選択する必要がある。 In the present invention, the contact angle when forming a film of the dispersant is effective within a certain range because the contact angle and the water solubility are correlated, and the water solubility (that is, affinity for water) of the dispersant is developability. This is thought to affect Therefore, it is an essential requirement to have appropriate water solubility. If the contact angle of the dispersant is small, that is, if the affinity with water is high, the adhesion of the development pattern will decrease, and if the contact angle of the dispersant is large, that is, if the affinity with water is low, residues will remain in the unexposed areas. Since the remainder is generated, it is necessary to select an appropriate one in consideration of the balance between the polar group (polyether, amine, etc.) and the nonpolar group (polyester, etc.) of the dispersant.
（D）成分の遮光性顔料分散体に用いる遮光性顔料としては、黒色有機顔料、混色有機顔料又は遮光材などが挙げられ、このうち、黒色有機顔料としては、例えばペリレンブラック、シアニンブラック等が挙げられる。混色有機顔料としては、赤、青、緑、紫、黄色、シアニン、マゼンタ等から選ばれる少なくとも２種以上の顔料を混合して擬似黒色化されたものが挙げられる。遮光材としては、カーボンブラック、酸化クロム、酸化鉄、チタンブラック、アニリンブラック、シアニンブラックを挙げることができ、２種以上を適宜選択して用いることもできるが、特にカーボンブラックが、遮光性、表面平滑性、分散安定性、樹脂との相溶性が良好な点で好ましい。 Examples of the light-shielding pigment used for the light-shielding pigment dispersion of component (D) include black organic pigments, mixed-color organic pigments, or light-shielding materials. Among these, examples of black organic pigments include perylene black and cyanine black. Can be mentioned. Examples of mixed color organic pigments include those obtained by mixing at least two pigments selected from red, blue, green, purple, yellow, cyanine, magenta and the like into a pseudo black color. Examples of the light shielding material include carbon black, chromium oxide, iron oxide, titanium black, aniline black, and cyanine black. Two or more types can be appropriately selected and used. The surface smoothness, dispersion stability, and compatibility with the resin are preferable.
また、顔料の分散性の向上、分散安定性の向上のために分散助剤として以下のような顔料誘導体等を添加しても良い。顔料誘導体としてはアゾ系、フタロシアニン系、キナクリドン系、ベンズイミダゾロン系、キノフタロン系、イソインドリノン系、ジオキサジン系、アントラキノン系、インダンスレン系、ペリレン系、ペリノン系、ジケトピロロピロール系、ジオキサジン系等の誘導体が挙げられるが、中でもフタロシアニン系が好ましい。顔料誘導体の置換基としてはスルホン酸基、スルホンアミド基及びその４級塩、フタルイミドメチル基、ジアルキルアミノアルキル基、水酸基、カルボキシル基、アミド基等が顔料骨格に直接またはアルキル基、アリール基、複素環基等を介して結合したものが挙げられ、好ましくはスルホン酸基である。またこれら置換基は一つの顔料骨格に複数置換していても良い。顔料誘導体の具体例としてはフタロシアニンのスルホン酸誘導体、キノフタロンのスルホン酸誘導体、アントラキノンのスルホン酸誘導体、キナクリドンのスルホン酸誘導体、ジケトピロロピロールのスルホン酸誘導体、ジオキサジンのスルホン酸誘導体等が挙げられる。顔料誘導体の添加量は顔料に対して通常０．１〜３０重量％、好ましくは０．１〜２０重量％以下、より好ましくは０．１〜１０重量％、さらに好ましくは０．１〜５重量％以下である。 In addition, the following pigment derivatives and the like may be added as a dispersion aid in order to improve the dispersibility and dispersion stability of the pigment. As pigment derivatives, azo, phthalocyanine, quinacridone, benzimidazolone, quinophthalone, isoindolinone, dioxazine, anthraquinone, indanthrene, perylene, perinone, diketopyrrolopyrrole, dioxazine Examples thereof include phthalocyanine derivatives. Substituents of pigment derivatives include sulfonic acid groups, sulfonamide groups and quaternary salts thereof, phthalimidomethyl groups, dialkylaminoalkyl groups, hydroxyl groups, carboxyl groups, amide groups, etc. directly on the pigment skeleton or alkyl groups, aryl groups, and complex groups. Examples thereof include those bonded via a ring group and the like, and a sulfonic acid group is preferable. Further, a plurality of these substituents may be substituted on one pigment skeleton. Specific examples of the pigment derivative include phthalocyanine sulfonic acid derivatives, quinophthalone sulfonic acid derivatives, anthraquinone sulfonic acid derivatives, quinacridone sulfonic acid derivatives, diketopyrrolopyrrole sulfonic acid derivatives, and dioxazine sulfonic acid derivatives. The addition amount of the pigment derivative is usually 0.1 to 30% by weight, preferably 0.1 to 20% by weight or less, more preferably 0.1 to 10% by weight, still more preferably 0.1 to 5% by weight based on the pigment. % Or less.
本発明における（D）成分の遮光性顔料の使用量は、（A）成分、（B）成分の総量１００重量部に対して３０〜２８０重量部、好ましくは５０〜２３０重量部の範囲がよい。３０重量部より少ないと、遮光性が十分でなくなり、望ましい遮光性を得るためには膜厚を厚くしなければならなくなり、カラーフィルターの面平滑性が得にくい。反対に、２８０重量部を越えると、（D）成分を含むカラーフィルター用感光性樹脂組成物の分散安定性が低下し、また、バインダーとなる感光性樹脂の配合割合が相対的に減少するため、現像特性を損なうと共に膜形成能が損なわれるという好ましくない問題が生じるおそれがある。 The amount of the light-shielding pigment used as the component (D) in the present invention is in the range of 30 to 280 parts by weight, preferably 50 to 230 parts by weight based on 100 parts by weight of the total amount of the components (A) and (B). . When the amount is less than 30 parts by weight, the light shielding property is not sufficient, and in order to obtain a desired light shielding property, it is necessary to increase the film thickness, and it is difficult to obtain the surface smoothness of the color filter. On the other hand, if it exceeds 280 parts by weight, the dispersion stability of the photosensitive resin composition for color filters containing the component (D) is lowered, and the blending ratio of the photosensitive resin as the binder is relatively reduced. In addition, the development characteristics may be impaired and the film forming ability may be impaired.
本発明のカラーフィルター用感光性樹脂組成物においては、上記（A）〜（D）成分の他に溶剤を使用することが好ましい。溶剤としては、例えば、メタノール、エタノール、ｎ−プロパノール、イソプロパノール、エチレングリコール、プロピレングリコール等のアルコール類、α−若しくはβ−テルピネオール等のテルペン類等、アセトン、メチルエチルケトン、シクロヘキサノン、Ｎ−メチル−２−ピロリドン等のケトン類、トルエン、キシレン、テトラメチルベンゼン等の芳香族炭化水素類、セロソルブ、メチルセロソルブ、エチルセロソルブ、カルビトール、メチルカルビトール、エチルカルビトール、ブチルカルビトール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル等のグリコールエーテル類、酢酸エチル、酢酸ブチル、セロソルブアセテート、エチルセロソルブアセテート、ブチルセロソルブアセテート、カルビトールアセテート、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテルアセテート、３−エトキシプロピオン酸エチル等のエステル類等が挙げられ、これらを用いて溶解、混合させることにより、均一な溶液状の組成物とすることができる。 In the photosensitive resin composition for a color filter of the present invention, it is preferable to use a solvent in addition to the components (A) to (D). Examples of the solvent include alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol, propylene glycol, terpenes such as α- or β-terpineol, acetone, methyl ethyl ketone, cyclohexanone, N-methyl-2- Ketones such as pyrrolidone, aromatic hydrocarbons such as toluene, xylene, tetramethylbenzene, cellosolve, methyl cellosolve, ethyl cellosolve, carbitol, methyl carbitol, ethyl carbitol, butyl carbitol, propylene glycol monomethyl ether, propylene Glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monomethyl ether, Glycol ethers such as reethylene glycol monoethyl ether, ethyl acetate, butyl acetate, cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, carbitol acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether acetate, propylene glycol mono Examples include esters such as ethyl ether acetate and ethyl 3-ethoxypropionate. By using these to dissolve and mix, a uniform solution-like composition can be obtained.
また、本発明のカラーフィルター用感光性樹脂組成物には、必要に応じて硬化促進剤、熱重合禁止剤、可塑剤、充填材、溶剤、消泡剤、レべリング剤、カップリング剤等の添加剤を配合することができる。熱重合禁止剤としては、ハイドロキノン、ハイドロキノンモノメチルエーテル、ピロガロール、tert-ブチルカテコール、フェノチアジン等を挙げることができ、可塑剤としては、ジブチルフタレート、ジオクチルフタレート、トリクレジル等を挙げることができ、充填材としては、グラスファイバー、シリカ、マイカ、アルミナ等を挙げることができ、また、消泡剤、レべリング剤としては、例えば、シリコン系、フッ素系、アクリル系の化合物を挙げることができ、また、カップリング剤としてはビニルトリス（β−メトキシエトキシ）シラン、ビニルエトキシシラン、ビニルトリメトキシシラン、等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の（メタ）アクリルシラン類、β−（３，４−エポキシシクロヘキシル）エチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリメトキシシラン、β−（３，４−エポキシシクロヘキシル）エチルトリエトキシシラン、β−（３，４−エポキシシクロヘキシル）メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン、等のエポキシシラン類、Ｎ−β（アミノエチル）γ−アミノプロピルトリメトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルトリエトキシシラン、Ｎ−β（アミノエチル）γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリメトキシシラン、Ｎ−フェニル−γ−アミノプロピルトリエトキシシラン、等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン、等のチオシラン類等のシランカップリング剤等を挙げることができる。 The photosensitive resin composition for color filters of the present invention includes a curing accelerator, a thermal polymerization inhibitor, a plasticizer, a filler, a solvent, an antifoaming agent, a leveling agent, a coupling agent and the like as necessary. Additives can be blended. Examples of the thermal polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, pyrogallol, tert-butylcatechol, phenothiazine, and the like. Examples of the plasticizer include dibutyl phthalate, dioctyl phthalate, tricresyl, and the like. Can include glass fiber, silica, mica, alumina, and the like, and examples of the antifoaming agent and leveling agent include silicon-based, fluorine-based, and acrylic compounds. As coupling agents, vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3, 4-epoxycyclohexyl ) Ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) methyltriethoxysilane , Γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, and other epoxy silanes, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ -Aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxy Silane, N-phenyl-γ-aminopropyl Examples include aminosilanes such as triethoxysilane, and silane coupling agents such as thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane.
本発明のカラーフィルター用感光性樹脂組成物は、上記（A）〜（D）成分又はこれらと溶剤を主成分として含有する。溶剤を除いた固形分（固形分には硬化後に固形分となるモノマーを含む）中に、（A）〜（D）成分が合計で70wt％以上、好ましくは80wt％、より好ましくは90wt％以上含むことが望ましい。溶剤の量は、目標とする粘度によって変化するが、20〜80wt％の範囲が望ましい。 The photosensitive resin composition for color filters of the present invention contains the above components (A) to (D) or these and a solvent as main components. In the solid content excluding the solvent (the solid content includes monomers that become solid content after curing), the total of components (A) to (D) is 70 wt% or more, preferably 80 wt%, more preferably 90 wt% or more It is desirable to include. The amount of the solvent varies depending on the target viscosity, but is preferably in the range of 20 to 80 wt%.
次に、感光性樹脂組成物を用いたカラーフィルターの製造法について説明する。まず、基板の表面上に、必要に応じて、画素を形成する部分を区画するように遮光層を形成する。次に遮光層が形成された基板上に、例えば赤色の顔料が分散された感光性樹脂組成物の液状組成物を塗布したのち、プレベークを行って溶剤を蒸発させ、塗膜を形成する。次いで、この塗膜にフォトマスクを介して露光したのち、アルカリ性現像液を用いて現像して、塗膜の未露光部を溶解除去し、その後ポストベークすることにより、赤色の画素パターンが所定の配列で配置された画素アレイを形成する。その後、緑色又は青色の顔料が分散された感光性樹脂組成物の液状組成物を用い、前記と同様にして、各液状組成物の塗布、プリベーク、露光、現像及びポストベークを行って、緑色の画素アレイ及び青色の画素アレイを同一基板上に順次形成することにより、赤色、緑色及び青色の三原色の画素アレイが基板上に配置されたカラーフィルターを得る。 Next, the manufacturing method of the color filter using the photosensitive resin composition is demonstrated. First, a light shielding layer is formed on the surface of the substrate so as to partition a portion where a pixel is formed, if necessary. Next, after applying a liquid composition of a photosensitive resin composition in which, for example, a red pigment is dispersed on a substrate on which a light shielding layer is formed, pre-baking is performed to evaporate the solvent, thereby forming a coating film. Next, after exposing the coating film through a photomask, development using an alkaline developer is performed to dissolve and remove the unexposed portion of the coating film, and then post-baking to form a predetermined red pixel pattern. A pixel array arranged in an array is formed. Thereafter, using the liquid composition of the photosensitive resin composition in which the green or blue pigment is dispersed, the liquid composition is applied, pre-baked, exposed, developed, and post-baked in the same manner as described above. By sequentially forming the pixel array and the blue pixel array on the same substrate, a color filter in which the pixel arrays of the three primary colors of red, green, and blue are arranged on the substrate is obtained.
感光性樹脂組成物を液状組成物の状態で基板に塗布する際には、公知の溶液浸漬法、スプレー法の他、ローラーコーター機、ランドコーター機やスピナー機を用いる方法等の何れの方法をも採用することができる。これらの方法によって、所望の厚さに塗布した後、溶剤を除去する（プリベーク）ことにより、被膜が形成される。プリベークはオーブン、ホットプレート等により加熱することによって行われる。プリベークにおける加熱温度及び加熱時間は使用する溶剤に応じて適宜選択され、例えば８０〜１２０℃の温度で１〜１０分間行われる。 When the photosensitive resin composition is applied to the substrate in the liquid composition state, any method such as a method using a roller coater machine, a land coater machine, or a spinner machine in addition to a known solution dipping method or spray method is used. Can also be adopted. After applying to a desired thickness by these methods, the film is formed by removing the solvent (pre-baking). Pre-baking is performed by heating with an oven, a hot plate or the like. The heating temperature and heating time in the pre-baking are appropriately selected according to the solvent used, and for example, the heating is performed at a temperature of 80 to 120 ° C. for 1 to 10 minutes.
カラーフィルターを作製する際に使用される放射線としては、例えば、可視光線、紫外線、遠紫外線、電子線、Ｘ線等を使用することができるが、波長が２５０〜４５０ｎｍの範囲にある放射線が好ましい。また、このアルカリ現像に適した現像液としては、例えば、アルカリ金属やアルカリ土類金属の炭酸塩の水溶液、アルカリ金属の水酸化物の水溶液等を挙げることができるが、特に炭酸ナトリウム、炭酸カリウム、炭酸リチウム等の炭酸塩を０.０５〜１０重量％含有する弱アルカリ性水溶液を用いて２０〜３０℃の温度で現像するのがよく、市販の現像機や超音波洗浄機等を用いて微細な画像を精密に形成することができる。なお、アルカリ現像後は、通常、水洗する。現像処理法としては、シャワー現像法、スプレー現像法、ディップ（浸漬）現像法、パドル（液盛り）現像法等を適用することができる。現像条件は、常温で１０〜１２０秒が好ましい。 As the radiation used when producing the color filter, for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray and the like can be used, and radiation having a wavelength in the range of 250 to 450 nm is preferable. . Examples of the developer suitable for the alkali development include, for example, an aqueous solution of an alkali metal or alkaline earth metal carbonate, an aqueous solution of an alkali metal hydroxide, and the like. It is better to develop at a temperature of 20 to 30 ° C. using a weak alkaline aqueous solution containing 0.05 to 10% by weight of a carbonate such as lithium carbonate, and finely develop it using a commercially available developing machine or ultrasonic cleaner. An accurate image can be formed. In addition, it is usually washed with water after alkali development. As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied. The development conditions are preferably 10 to 120 seconds at room temperature.
このようにして現像した後、１８０〜２５０℃の温度、及び２０〜１００分の条件で熱処理（ポストベーク）が行われる。このポストベークは、パターニングされた塗膜と基板との密着性を高めるため等の目的で行われる。これはプリベークと同様に、オーブン、ホットプレート等により加熱することによって行われる。本発明のパターニングされた塗膜は、以上のフォトリソグラフィー法による各工程を経て形成される。
また、ブラックマトリックスは、遮光感光性樹脂組成物を用い、前記画素アレイの場合と同様にして形成することができる。
After the development as described above, a heat treatment (post-bake) is performed at a temperature of 180 to 250 ° C. and a condition of 20 to 100 minutes. This post-baking is performed for the purpose of improving the adhesion between the patterned coating film and the substrate. This is performed by heating with an oven, a hot plate or the like, as in the pre-baking. The patterned coating film of this invention is formed through each process by the above photolithography method.
The black matrix can be formed in the same manner as in the pixel array using a light-shielding photosensitive resin composition.
画素及び／又はブラックマトリックスを備えたカラーフィルターを形成する際に使用される基板としては、例えば、ガラス、透明フィルム（例えば、ポリカーボネート、ポリエチレンテレフタレート、ポリエーテルスルフォン等）上にＩＴＯ、金等の透明電極が蒸着あるいはパターニングされたもの等が用いられる。また、これらの基板には、所望により、シランカップリング剤等による薬品処理、プラズマ処理、イオンプレーティング、スパッタリング、気相反応法、真空蒸着等の適宜の前処理を施しておくこともできる。 As a substrate used when forming a color filter having pixels and / or a black matrix, for example, glass, transparent film (for example, polycarbonate, polyethylene terephthalate, polyethersulfone, etc.), transparent such as ITO, gold, etc. A material in which an electrode is deposited or patterned is used. In addition, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.
本発明のカラーフィルター用感光性樹脂組成物は、残渣を生じることなく良好なパターン密着性を維持することができ、このため、本発明のカラーフィルター用感光性樹脂組成物は、カラー液晶表示装置、カラーファクシミリ、イメージセンサー等の各種の多色表示体や、光学機器等に使用されるカラーフィルター用の着色インク、及び、これらによって形成されたブラックマトリックスを有するカラーフィルターや、テレビ、ビデオモニター、あるいは、コンピューターのディスプレー等に好適に使用することができる。また、このようにして得られたカラーフィルターは、例えば、透過型あるいは反射型のカラー液晶表示装置、カラー撮像管素子、カラーセンサー等に極めて有用である。 The photosensitive resin composition for a color filter of the present invention can maintain good pattern adhesion without generating a residue. Therefore, the photosensitive resin composition for a color filter of the present invention is a color liquid crystal display device. Various color display materials such as color facsimiles and image sensors, colored inks for color filters used in optical devices, etc., and color filters having a black matrix formed by these, televisions, video monitors, Alternatively, it can be suitably used for a computer display or the like. The color filter thus obtained is extremely useful for, for example, a transmissive or reflective color liquid crystal display device, a color imaging tube element, a color sensor, and the like.
以下、実施例及び比較例に基づいて、本発明を具体的に説明するが、本発明はこれらに限定されるものではない。ここで、実施例、比較例のカラーフィルターの製造で用いた原料及び略号は以下の通りである。 EXAMPLES Hereinafter, although this invention is demonstrated concretely based on an Example and a comparative example, this invention is not limited to these. Here, the raw materials and abbreviations used in the production of the color filters of Examples and Comparative Examples are as follows.
(A)：フルオレン骨格を有するエポキシアクリレートの酸無水物重縮合物のプロピレングリコールモノメチルエーテルアセテート溶液（樹脂固形分濃度=56.5重量%、新日鐵化学（株）製 商品名V259ME） (A): propylene glycol monomethyl ether acetate solution of acid anhydride polycondensate of epoxy acrylate having a fluorene skeleton (resin solid content concentration = 56.5% by weight, trade name V259ME manufactured by Nippon Steel Chemical Co., Ltd.)
(B)：ペンタエリスリトールテトラアクリレート（サートマー・ジャパン社製、商品名SR-295） (B): Pentaerythritol tetraacrylate (Sartomer Japan, trade name SR-295)
(C)−1：エタノン,1-［9-エチル-6-（2-メチルベンジル）-9H-カルバゾール-3-イル］-1-（O-アセチルオキシム）（チバスペシャリティケミカル社製 商品名 イルガキュアOXE-02）
(C)−2：4-（4'-エチルビフェニル）-4,6-ビス（トリクロロメチル）-1,3,5-トリアジン（レスペ・ケミカル社製 商品名 STR-2BP）
(C)−3：2−ベンジル−2−ジメチルアミノ−1−（4−モルフォリノフェニル）−ブタノン−1（チバスペシャリティケミカル社製 商品名 イルガキュア369）
(C) -1: Ethanone, 1- [9-ethyl-6- (2-methylbenzyl) -9H-carbazol-3-yl] -1- (O-acetyloxime) (trade name, Irgacure, manufactured by Ciba Specialty Chemicals) OXE-02)
(C) -2: 4- (4'-Ethylbiphenyl) -4,6-bis (trichloromethyl) -1,3,5-triazine (trade name STR-2BP manufactured by Respe Chemical Co., Ltd.)
(C) -3: 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone-1 (trade name Irgacure 369, manufactured by Ciba Specialty Chemicals)
(D)：カーボンブラック（平均粒径135〜160nm）濃度20重量%、高分子分散剤濃度5重量%、分散助剤濃度0.5重量%のプロピレングリコールモノメチルエーテルアセテート分散液（固形分25.5%）
分散剤(a)：ウレタン系分散剤DiperＢＹＫ−１６３（ビックケミー社製）
分散剤(b)：ウレタン系分散剤DiperＢＹＫ−１６７（ビックケミー社製）
分散剤(c)：ウレタン系分散剤DiperＢＹＫ−１８２（ビックケミー社製）
分散助剤：フタロシアニンスルホン酸誘導体
(D): Propylene glycol monomethyl ether acetate dispersion with carbon black (average particle size 135 to 160 nm) concentration of 20% by weight, polymer dispersant concentration of 5% by weight, and dispersion aid concentration of 0.5% by weight (solid content: 25.5%)
Dispersant (a): Urethane dispersant DiperBYK-163 (manufactured by Big Chemie)
Dispersant (b): Urethane-based dispersant DiperBYK-167 (manufactured by Big Chemie)
Dispersant (c): Urethane dispersant DiperBYK-182 (manufactured by Big Chemie)
Dispersing aid: phthalocyanine sulfonic acid derivative
(E)：プロピレングリコールモノメチルエーテルアセテート
(F)：γ−グリシドキシプロピルトリメトキシシラン（チッソ社製 商品名 サイラエース510）
(G)：フッ素系界面活性剤（ディック社製 商品名 メガファック470）
(E): Propylene glycol monomethyl ether acetate
(F): γ-glycidoxypropyltrimethoxysilane (product name: Thyra Ace 510, manufactured by Chisso Corporation)
(G): Fluorosurfactant (Dick's brand name Megafuck 470)
［実施例１〜２及び比較例１］
上記配合成分を表１の割合で配合して、実施例１〜２及び比較例１の組成物を調製した。
[Examples 1 and 2 and Comparative Example 1]
The compositions of Examples 1 and 2 and Comparative Example 1 were prepared by blending the above blending components at the ratio shown in Table 1.
上記各成分を均一に混合して得たカラーフィルター用感光性樹脂組成物（実施例１〜２、及び比較例１）を、スピンコーターを用いて125mm×125mmのガラス基板上にポストベーク後の厚膜が1.0μmとなるように塗布し、80℃で1分間プリベークした。次いで、乾燥塗膜の上に、ネガ型フォトマスクを被せ、I線照度30mW/cm2の超高圧水銀ランプで100mj/cm2の紫外線を照射し感光部分の光効果反応を行った。次に、この露光済み塗板を0.04%水酸化カリウム水溶液中、23℃にて60秒の1kgf/cm2圧シャワー現像及び2.5kgf/cm2圧のスプレー水洗を行い、塗膜の未露光部分を除去し、ガラス基板上に画素パターンを形成した際の細線パターンの密着性を評価した。 The color filter photosensitive resin compositions (Examples 1 and 2 and Comparative Example 1) obtained by uniformly mixing the above components were post-baked on a 125 mm × 125 mm glass substrate using a spin coater. The thick film was applied to a thickness of 1.0 μm and prebaked at 80 ° C. for 1 minute. Next, a negative photomask was covered on the dried coating film, and an ultraviolet light of 100 mj / cm 2 was irradiated with an ultra-high pressure mercury lamp with an I-line illuminance of 30 mW / cm 2 to carry out a photoeffect reaction of the photosensitive part. Then, in a 0.04% aqueous potassium hydroxide solution the exposed coated plate performs spray rinsing for 60 seconds 1 kgf / cm 2 pressure shower development and 2.5 kgf / cm 2 pressure at 23 ° C., the unexposed portions of the coating The adhesion of the thin line pattern when the pixel pattern was formed on the glass substrate was evaluated.
また、上記と同様に乾燥塗膜を作成し、未露光で0.04%水酸化カリウム水溶液中、23℃にて60秒の1kgf/cm2圧シャワー現像及び2.5kgf/cm2圧のスプレー水洗を行い、塗膜の未露光部分を除去した後、自然乾燥したガラス板で残渣を評価した。
実施例及び比較例における評価項目とその方法については以下の通りである。
It also creates the same manner as described above dry film, in 0.04% aqueous potassium hydroxide solution at unexposed performs spray rinsing of 1 kgf / cm 2 pressure shower development and 2.5 kgf / cm 2 pressure for 60 seconds at 23 ° C. After removing the unexposed part of the coating film, the residue was evaluated with a naturally dried glass plate.
Evaluation items and methods in Examples and Comparative Examples are as follows.
接触角：分散剤を適当な濃度に希釈し、スピンコーターでガラス上に塗布、熱風乾燥機を用いてポストベークした後、製膜された分散剤膜表面にイオン交換水を滴下し、１０秒後の接触角を測定した。
密着性：測長顕微鏡（（株）ニコン製 商品名XD-20）を用い、マスク幅10μmの細線パターンが確認できたときを○＜良好＞、確認できなかったときを×＜不良＞と判定した。
残渣：乾燥後のガラス板上を、アセトンをしみ込ませたウエスで拭き取り、ウエス上に付着した残渣の着色の程度を持って残渣を評価した。
Contact angle: The dispersant is diluted to an appropriate concentration, applied onto glass with a spin coater, post-baked using a hot air dryer, and then ion-exchanged water is dropped on the surface of the formed dispersant film for 10 seconds. The subsequent contact angle was measured.
Adhesion: Using a measuring microscope (trade name XD-20, manufactured by Nikon Corporation), when a fine line pattern with a mask width of 10 μm was confirmed, ○ <good>, and when it was not confirmed, judged as x <defect> did.
Residue: The glass plate after drying was wiped off with a cloth soaked with acetone, and the residue was evaluated with the degree of coloring of the residue adhered on the cloth.
結果を表２に示す。
表１に示した配合においては実施例、比較例とも残渣は良好であったが、比較例のように分散剤の接触角が小さすぎると密着性が×となった。
The results are shown in Table 2.
In the formulation shown in Table 1, the residue was good in both Examples and Comparative Examples, but when the contact angle of the dispersant was too small as in the Comparative Examples, the adhesion became x.
Claims (6)
(B)少なくとも1個のエチレン性不飽和結合を有する光重合性モノマー、
(C)光重合開始剤、及び
(D)遮光性顔料分散体
を必須成分として含むカラーフィルター用感光性樹脂組成物であって、上記(A)成分と(B)成分との重量割合（A）／（B）が、６０／４０〜９０／１０であり、(A)成分と(B)成分の合計１００重量部に対して（C）成分を２〜３０重量部含有し、また、（D）成分は、(A)成分と(B)成分の合計１００重量部に対して３０〜２８０重量部の割合で含有される遮光性顔料と、この遮光性顔料１００重量部に対して５０重量部以下の割合で含有される分散剤とを含み、上記分散剤は、製膜後の分散剤膜の表面にイオン交換水を滴下して１０秒後に測定した接触角が７０〜９０°であることを特徴とするカラーフィルター用感光性樹脂組成物。 (A) Alkali developable binder resin which is an unsaturated group-containing resin obtained by further reacting a reaction product of an epoxy compound having a glycidyl ether group and (meth) acrylic acid with a polybasic carboxylic acid or its anhydride ,
(B) a photopolymerizable monomer having at least one ethylenically unsaturated bond,
(C) a photopolymerization initiator, and
(D) A photosensitive resin composition for a color filter containing a light-shielding pigment dispersion as an essential component, wherein the weight ratio (A) / (B) of the component (A) to the component (B) is 60 / was 40~90 / 10, (a) component and (B) per 100 parts by weight of component (C) component contains 2 to 30 parts by weight, also, (D) component, (a) component And a light-shielding pigment contained in a proportion of 30 to 280 parts by weight with respect to 100 parts by weight of the total of component (B) , and a dispersion contained in a proportion of 50 parts by weight or less with respect to 100 parts by weight of the light-shielding pigment The above-mentioned dispersing agent comprises a dispersing agent , and the contact angle measured after 10 seconds after dropping ion-exchanged water on the surface of the dispersing agent film after film formation is 70 to 90 °. Resin composition.
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