CN101794074A - 感光性树脂组合物 - Google Patents
感光性树脂组合物 Download PDFInfo
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- CN101794074A CN101794074A CN201010106751A CN201010106751A CN101794074A CN 101794074 A CN101794074 A CN 101794074A CN 201010106751 A CN201010106751 A CN 201010106751A CN 201010106751 A CN201010106751 A CN 201010106751A CN 101794074 A CN101794074 A CN 101794074A
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- Prior art keywords
- acid
- acrylate
- methyl
- color filter
- sensitive resin
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 26
- 239000011347 resin Substances 0.000 claims abstract description 34
- 229920005989 resin Polymers 0.000 claims abstract description 34
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 239000011159 matrix material Substances 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 17
- 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 claims abstract description 16
- 230000032050 esterification Effects 0.000 claims abstract description 14
- 238000005886 esterification reaction Methods 0.000 claims abstract description 14
- 239000000049 pigment Substances 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 20
- OCVSBJXTWPHUPQ-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical group CC(=C)C(O)=O.CC(=C)C(=O)OCC1=CC=CC=C1 OCVSBJXTWPHUPQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000004973 liquid crystal related substance Substances 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 7
- 239000000178 monomer Substances 0.000 abstract description 44
- 239000000758 substrate Substances 0.000 abstract description 13
- 238000011161 development Methods 0.000 abstract description 12
- 230000006978 adaptation Effects 0.000 abstract description 10
- 206010034960 Photophobia Diseases 0.000 abstract description 9
- 208000013469 light sensitivity Diseases 0.000 abstract description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 description 30
- -1 (methyl) 2-Hydroxy ethyl Chemical group 0.000 description 29
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 16
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000004793 Polystyrene Substances 0.000 description 12
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 12
- 239000004926 polymethyl methacrylate Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 125000005395 methacrylic acid group Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 6
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012860 organic pigment Substances 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 3
- 239000001054 red pigment Substances 0.000 description 3
- 238000003892 spreading Methods 0.000 description 3
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 2
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical class 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
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000012675 alcoholic extract Substances 0.000 description 2
- 239000012670 alkaline solution Substances 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
- 239000012965 benzophenone Substances 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
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 239000000113 methacrylic resin Substances 0.000 description 2
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 2
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- SUDVPELGFZKOMD-UHFFFAOYSA-N 1,2-di(propan-2-yl)thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=C(C(C)C)C(C(C)C)=CC=C3SC2=C1 SUDVPELGFZKOMD-UHFFFAOYSA-N 0.000 description 1
- GJZFGDYLJLCGHT-UHFFFAOYSA-N 1,2-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(CC)C(CC)=CC=C3SC2=C1 GJZFGDYLJLCGHT-UHFFFAOYSA-N 0.000 description 1
- UYEDESPZQLZMCL-UHFFFAOYSA-N 1,2-dimethylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=C(C)C(C)=CC=C3SC2=C1 UYEDESPZQLZMCL-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
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- LMAUULKNZLEMGN-UHFFFAOYSA-N 1-ethyl-3,5-dimethylbenzene Chemical compound CCC1=CC(C)=CC(C)=C1 LMAUULKNZLEMGN-UHFFFAOYSA-N 0.000 description 1
- DKTOWFDVEJQWPF-UHFFFAOYSA-N 1-ethylthioxanthen-9-one Chemical class S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2CC DKTOWFDVEJQWPF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- QZKVUSSYPPWURQ-UHFFFAOYSA-N 1-methylthioxanthen-9-one Chemical class S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C QZKVUSSYPPWURQ-UHFFFAOYSA-N 0.000 description 1
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-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
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- AAMTXHVZOHPPQR-UHFFFAOYSA-N 2-(hydroxymethyl)prop-2-enoic acid Chemical compound OCC(=C)C(O)=O AAMTXHVZOHPPQR-UHFFFAOYSA-N 0.000 description 1
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- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical class COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
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- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- ARXVXVOLXMVYIT-UHFFFAOYSA-N 3-methylbutyl 2-(dimethylamino)benzoate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1N(C)C ARXVXVOLXMVYIT-UHFFFAOYSA-N 0.000 description 1
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
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- LLBIOIRWAYBCKK-UHFFFAOYSA-N pyranthrene-8,16-dione Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C=C4C5=CC=CC=C5C(=O)C5=C4C4=C3C2=C1C=C4C=C5 LLBIOIRWAYBCKK-UHFFFAOYSA-N 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
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- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
-
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Abstract
本发明提供感光性树脂组合物,其以现有丙烯酸酯单体不能实现的高平衡性满足与基板的密合性、分辨率、显影性和感光度。一种滤色片、黑色矩阵或垫片用负型感光性树脂组合物,其中,包含下述化学式(1),(式(1)中,a和b为正整数,a+b=6,1≤a≤6,0≤b≤5)表示的羟值为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇丙烯酸酯化物。
Description
技术领域
本发明涉及负型感光性树脂组合物,更具体而言,本发明涉及在彩色液晶显示器、彩色摄像机、彩色数码照相机、电子纸等中使用的滤色片(color filter)、黑色矩阵(black matrix)或垫片(spacer)的制作中使用的感光性树脂组合物及使用该感光性树脂组合物形成图案的滤色片、黑色矩阵及垫片。
背景技术
在以笔记本电脑、液晶电视等为代表的液晶显示器(LCD)等液晶显示装置中需要滤色片、黑色矩阵及垫片。以作为数码照相机、彩色复印机等的输入器件使用的电荷耦合器件(CCD、CMOS)为代表的固体摄像器件(固体撮像素子)的彩色化需要滤色片。
这些液晶显示装置或固体摄像器件中使用的感光性树脂组合物随着装置本身的轻薄短小化也微细化并薄膜化。因此,进行了减少组合物中的树脂成分和省去有机基底膜的研究。
为了适应该微细化及薄膜化的潮流,进行了一些钻研。例如,在专利文献1中,记载了对薄膜化所带来的黑色矩阵与玻璃的密合性下降进行补偿的方法。另外,专利文献2中,通过在滤色片的粘合树脂上下功夫来实现良好的分辨率和薄膜化。但是,这些方法都不能全部解决与基板的密合性、分辨率和显影性。
专利文献1:日本特开2004-004651号公报
专利文献2:日本专利第3218256号公报
发明内容
本发明的目的在于获得在滤色片、黑色矩阵、垫片的用途中,与基板的密合性、分辨率(解像性)、显影性、感光度(感度)均优良的负型感光性树脂组合物。
本发明人为了解决上述问题进行了广泛深入的研究,结果发现,通过使用下述化学式(1)表示的二季戊四醇丙烯酸酯化物(羟值:70mgKOH/g以上、130mgKOH/g以下),可以得到与基板的密合性、分辨率、显影性、感光度均优良的树脂组合物,并且完成了本发明。
式(1)中,a和b为正整数,a+b=6,1≤a≤6,0≤b≤5。
即,本发明涉及以下各项。
(1)一种滤色片、黑色矩阵或垫片用负型感光性树脂组合物,其中,包含下述化学式(1)表示的羟值为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇丙烯酸酯化物,
式(1)中,a和b为正整数,a+b=6,1≤a≤6,0≤b≤5。
(2)上述(1)所述的负型感光性树脂组合物,其中,还包含粘合剂聚合物、颜料和光聚合引发剂。
(3)上述(2)所述的负型感光性树脂组合物,其中,粘合剂聚合物为甲基丙烯酸-甲基丙烯酸苄酯共聚物。
(4)通过将上述(1)至(3)中任一项所述的负型感光性树脂组合物固化而得到的滤色片、黑色矩阵或垫片。
(5)一种液晶显示装置,其具备上述(4)所述的滤色片、黑色矩阵或垫片。
(6)一种固体摄像器件,其具备上述(4)所述的滤色片、黑色矩阵或垫片。
发明效果
通过使用羟值为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇丙烯酸酯化物,可以得到与基板的密合性、分辨率、显影性、感光度的平衡性良好、并且具有单独和混合使用现有丙烯酸酯单体均不能得到的高性能的滤色片、黑色矩阵和垫片用负型感光性树脂组合物。
具体实施方式
本发明的负型感光性树脂组合物,是含有特定的光聚合性单体之外,根据需要还含有粘合剂聚合物、特定光聚合性单体以外的光聚合性单体、颜料、光聚合引发剂及有机溶剂、表面活性剂、热固化剂、阻聚剂等各种添加物的负型感光性树脂组合物。
本发明中使用的光聚合性单体没有特别的限制,但是,至少使用下述化学式(1)表示的羟值为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇丙烯酸酯化物。本发明的组合物中也可以混合使用其它光聚合性单体。
式(1)中,a和b为正整数,a+b=6,1≤a≤6,0≤b≤5。
所述光聚合性单体的羟值如果小于70mgKOH/g,则与现有的二季戊四醇六丙烯酸酯相比,在与基板的密合性、分辨率、显影性、感光度方面得不到显著的差异。另外,羟值如果大于130mgKOH/g,则在显影工序中图案表面会观察到粗糙,不适合作为用于滤色片、黑色矩阵及垫片的感光性组合物用光聚合性单体。
羟基为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇丙烯酸酯化物可以通过利用通常使用的方法将二季戊四醇丙烯酸酯化来得到。为了得到所需的羟值,可以适当调节丙烯酸相对于二季戊四醇的投料量,具体而言,相对于二季戊四醇的羟基摩尔数优选为约0.9当量~约1.2当量。
作为本发明中可以使用的其它光聚合性单体的具体例,可以列举:(甲基)丙烯酸-2-羟基乙酯、(甲基)丙烯酸-2-羟基丙酯、(甲基)丙烯酸-2-乙基己酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇(甲基)丙烯酸酯、四乙二醇(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、季戊四醇二(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、羟值小于70mgKOH/g的二季戊四醇丙烯酸酯化物、甘油(甲基)丙烯酸酯、双酚A型环氧二(甲基)丙烯酸酯、双酚F型环氧二(甲基)丙烯酸酯、双酚芴型环氧二(甲基)丙烯酸酯等。
这些光聚合性单体可以单独使用也可以两种以上组合使用。光聚合性单体以在本发明的组合物的总固形分中通常占5~60质量%、优选占10~50质量%的比例使用。
可作为负型感光性树脂组合物的成分使用的粘合剂聚合物,只要能够提高组合物的成膜性则没有特别限制。优选可溶于在滤色片制造时的显影处理工序中使用的显影液中。作为可溶于显影液的粘合剂聚合物可以列举例如:碱可溶性树脂或水溶性树脂。
作为碱可溶性树脂,只要是可以溶解于碱性溶液或碱性水溶液的树脂则可以没有特别限制地使用。作为这样的碱可溶性树脂,可以列举例如具有羟基的聚合物。作为具有羧基的聚合物,优选包含具有一个以上羧基的烯属不饱和单体(以下仅称为“具有羧基的不饱和单体”)与其它可共聚的烯属不饱和单体(以下称为“其它不饱和单体”)的单体混合物的共聚物(以下仅称为“具有羧基的共聚物”)。作为具有羧基的不饱和单体的具体例,可以列举:丙烯酸、甲基丙烯酸、巴豆酸、α-氯丙烯酸、乙基丙烯酸、肉桂酸等不饱和一元羧酸类;马来酸、马来酸酐、富马酸、衣康酸、衣康酸酐、柠康酸、柠康酸酐、甲基富马酸等不饱和二元羧酸类或它们的酸酐;三元以上的不饱和多元羧酸类或其酸酐等。这些具有羧基的不饱和单体可以单独使用或者两种以上混合使用。
另外,作为所述其它不饱和单体的具体例,可以列举:苯乙烯、α-甲基苯乙烯、邻乙烯基甲苯、间乙烯基甲苯、对乙烯基甲苯、邻氯苯乙烯、间氯苯乙烯、对氯苯乙烯、对甲氧基苯乙烯等芳香族乙烯基化合物;丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丙酯、丙烯酸异丙酯、甲基丙烯酸正丙酯、甲基丙烯酸异丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸仲丁酯、丙烯酸叔丁酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸仲丁酯、甲基丙烯酸叔丁酯、丙烯酸-2-羟基乙酯、甲基丙烯酸-2-羟基乙酯、丙烯酸苄酯、甲基丙烯酸苄酯等不饱和羧酸酯类;丙烯酸-2-氨基乙酯、甲基丙烯酸-2-氨基乙酯、丙烯酸-2-氨基丙酯、甲基丙烯酸-2-氨基丙酯、丙烯酸-3-氨基丙酯、甲基丙烯酸-3-氨基丙酯等不饱和羧酸氨基烷基酯类;丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯等不饱和羧酸缩水甘油酯类;乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯、苯甲酸乙烯酯等羧酸乙烯酯类;乙烯基甲基醚、乙烯基乙基醚、烯丙基缩水甘油基醚、甲代烯丙基缩水甘油基醚等不饱和醚类;丙烯腈、甲基丙烯腈、α-氯丙烯腈、偏二氰基乙烯等氰化乙烯基化合物;丙烯酰胺、甲基丙烯酰胺、α-氯丙烯酰胺、N-(2-羟基乙基)丙烯酰胺、N-(2-羟基乙基)甲基丙烯酰胺、马来酰亚胺等不饱和酰胺或不饱和酰亚胺类;1,3-丁二烯、异戊二烯、氯丁二烯等脂肪族共轭二烯类;在聚苯乙烯、聚丙烯酸甲酯、聚甲基丙烯酸甲酯、聚丙烯酸正丁酯、聚甲基丙烯酸正丁酯、聚硅氧烷(polysilicone)等聚合物分子链的末端具有单丙烯酰基或单甲基丙烯酰基的大分子单体类等。这些其它不饱和单体可以单独使用或者两种以上混合使用。
作为这些具有羧基的不饱和单体与其它不饱和单体的优选组合,可以列举:丙烯酸和/或甲基丙烯酸与选自由甲基丙烯酸甲酯、丙烯酸-2-羟基乙酯、甲基丙烯酸-2-羟基乙酯、丙烯酸苄酯、甲基丙烯酸苄酯、苯乙烯、聚苯乙烯大分子单体和聚甲基丙烯酸甲酯大分子单体组成的组中的至少一种其它不饱和单体。作为具有羧基的聚合物的优选具体例,可以列举:丙烯酸-丙烯酸苄酯共聚物、丙烯酸-丙烯酸苄酯-苯乙烯共聚物、丙烯酸-丙烯酸甲酯-苯乙烯共聚物、丙烯酸-丙烯酸苄酯-聚苯乙烯大分子单体共聚物、丙烯酸-丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物、丙烯酸-丙烯酸甲酯-聚苯乙烯大分子单体共聚物、丙烯酸-丙烯酸甲酯-聚甲基丙烯酸甲酯大分子单体共聚物、丙烯酸-甲基丙烯酸苄酯共聚物、丙烯酸-甲基丙烯酸苄酯-苯乙烯共聚物、丙烯酸-甲基丙烯酸甲酯-苯乙烯共聚物、丙烯酸-甲基丙烯酸苄酯-聚苯乙烯大分子单体共聚物、丙烯酸-甲基丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物、丙烯酸-甲基丙烯酸甲酯-聚苯乙烯大分子单体共聚物、丙烯酸-甲基丙烯酸甲酯-聚甲基丙烯酸甲酯大分子单体共聚物、丙烯酸-甲基丙烯酸-2-羟基乙酯-甲基丙烯酸苄酯-聚苯乙烯大分子单体共聚物、丙烯酸-甲基丙烯酸-2-羟基乙酯-甲基丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物等丙烯酸共聚物;甲基丙烯酸-丙烯酸苄酯共聚物、甲基丙烯酸-丙烯酸苄酯-苯乙烯共聚物、甲基丙烯酸-丙烯酸甲酯-苯乙烯共聚物、甲基丙烯酸-丙烯酸苄酯-聚苯乙烯大分子单体共聚物、甲基丙烯酸-丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物、甲基丙烯酸-丙烯酸甲酯-聚苯乙烯大分子单体共聚物、甲基丙烯酸-丙烯酸甲酯-聚甲基丙烯酸甲酯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸苄酯共聚物、甲基丙烯酸-甲基丙烯酸苄酯-苯乙烯共聚物、甲基丙烯酸-甲基丙烯酸甲酯-苯乙烯共聚物、甲基丙烯酸-甲基丙烯酸苄酯-聚苯乙烯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸甲酯-聚苯乙烯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸甲酯-聚甲基丙烯酸甲酯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸-2-羟基乙酯-甲基丙烯酸苄酯-聚苯乙烯大分子单体共聚物、甲基丙烯酸-甲基丙烯酸-2-羟基乙酯-甲基丙烯酸苄酯-聚甲基丙烯酸甲酯大分子单体共聚物等甲基丙烯酸共聚物等。
另外,在上述具有羧基的聚合物的侧链上进一步引入不饱和双键的聚合物对本发明也有用。作为这样的聚合物的例子,可以列举例如:使丙烯酸羟乙酯等具有醇羟基的丙烯酸酯或甲基丙烯酸缩水甘油酯等具有环氧基的丙烯酸酯同马来酸酐与可以和马来酸酐共聚的苯乙烯、乙烯基苯酚、丙烯酸、丙烯酸酯、丙烯酰胺等的共聚物的马来酸酐部反应而半酯化的化合物及进一步使丙烯酸同丙烯酸、丙烯酸酯与丙烯酸羟乙酯等具有醇羟基的丙烯酸酯的共聚物的羟基反应而得到的化合物。
作为水溶性树脂,可以列举丙烯酸类树脂、甲基丙烯酸类树脂、聚乙烯醇类树脂、聚乙烯基吡咯烷酮类树脂、丙烯酰吗啉类树脂等。丙烯酸类树脂的例子可以列举丙烯酸、丙烯酸钠、丙烯酰胺等的聚合物及共聚物等,甲基丙烯酸类树脂的例子可以列举甲基丙烯酸、甲基丙烯酸钠、2-羟基甲基丙烯酸等的聚合物或共聚物。
作为能够溶解前述的碱可溶性树脂或水溶性树脂的碱性溶液或碱性水溶液,可以列举例如:氢氧化钠水溶液、氢氧化钾水溶液、碳酸钠水溶液、碳酸钾水溶液、碳酸氢钠水溶液、碳酸氢钾水溶液、四甲基氢氧化铵水溶液、二乙醇胺水溶液、乙醇胺水溶液等以及在上述溶液中适当混合表面活性剂而得到的混合物等,但是,本发明不限于这些。
本发明中,所述粘合剂聚合物可以单独使用或者两种以上混合使用。本发明中的粘合剂聚合物在使用时,以在本发明的负型感光性树脂组合物的总固形分(除有机溶剂以外的其它成分;下同)中通常占5~80质量%、优选占10~60质量%的比例使用。粘合剂聚合物的含量低于5质量%时,例如可能使碱显影性下降或者在形摄像素的部分以外的区域产生本底灰雾或膜残留等。
粘合剂聚合物的重均分子量(Mw)通常为2000~1000000、优选3000~400000。重均分子量为2000以下时、或者重均分子量为400000以上时,感光度及显影性可能变差。
本发明的负型着色感光性树脂组合物中根据需要可以使用颜料等。另外,作为本发明中使用的颜料,只要是具有适当分光光谱的颜料则可以没有特别限制地使用有机颜料、无机颜料。
作为本发明中可以使用的有机颜料的例子,可以列举例如:蒽醌类、酞菁类、苯并咪唑酮类、喹吖酮类、偶氮螯合物类、偶氮类、异吲哚啉类、异吲哚啉酮类、皮蒽酮类、阴丹酮类、蒽嘧啶(anthrapyrimidine)类、二溴蒽嵌蒽醌(dibromoanthanthrone)类、黄烷士酮类、苝类、紫环酮(perinone)类、喹酞酮类、硫靛蓝类、二噁嗪类等颜料、用各种沉淀剂使酸性染料、碱性染料、直接染料等沉淀而得到的色淀颜料、染色的色淀颜料等。这些有机颜料根据需要可以单独使用或者两种以上组合使用。
作为本发明中可以使用的无机颜料的例子,可以列举:复合金属氧化物颜料、炭黑、黑色低价氮氧化钛(低次酸窒化チタン)、氧化钛、硫酸钡、锌华、硫酸铅、铬黄、三氧化二铁、群青、铁蓝、氧化铬、锑白、铁黑、铅丹、硫化锌、镉黄、镉红、锌、锰紫、钴紫、硫酸钡、碳酸镁等金属氧化物、金属硫化物、硫酸盐、金属氢氧化物、金属碳酸盐等。这些无机颜料根据需要可以单独使用或者两种以上组合使用。
本发明中使用颜料时,以在本发明的负型着色感光性树脂组合物的总固形分中通常占5~70质量%、优选占10~60质量%的比例使用。色素的含量可以根据固化膜所需的膜厚、分光特性等适当确定。另外,本发明中使用的色素的色调可以列举红色、蓝色、绿色、黑色、黄色、洋红色、青色等色调。
本发明的组合物中根据需要可以使用光聚合引发剂。作为本发明中可以使用的光聚合引发剂,只要是对作为曝光光源普遍使用的超高压水银灯射出的紫外线具有充分感光度的光聚合引发剂则可以没有特别限制地使用。作为光聚合引发剂的具体例,可以列举:联苯酰、苯偶姻醚、苯偶姻丁基醚、苯偶姻丙基醚、二苯甲酮、3,3’-二甲基-4-甲氧基二苯甲酮、苯甲酰苯甲酸、苯甲酰苯甲酸的酯化物、4-苯甲酰-4’-甲基二苯硫醚、联苯酰二甲基缩酮、4-甲氨基苯甲酸-2-丁氧基乙酯、氯代噻吨酮、甲基噻吨酮、乙基噻吨酮、异丙基噻吨酮、二甲基噻吨酮、二乙基噻吨酮、二异丙基噻吨酮、苯甲酸二甲氨基甲酯、二甲氨基苯甲酸异戊酯、1-(4-十二烷基苯基)-2-羟基-2-甲基丙烷-1-酮、1-羟基环己基苯基酮、2-羟基-2-甲基-1-苯基丙烷-1-酮、1-(4-异丙基苯基)-2-羟基-2-甲基丙烷-1-酮、苯甲酰甲酸甲酯、2-甲基-1-(4-甲硫基苯基)-2-吗啉代丙烷-1-酮、2-苄基-2-二甲氨基-1-(4-吗啉代苯基)丁烷-1-酮、2,2’-双(2-氯苯基)-4,4’,5,5’-四苯基联咪唑、2,2’-双(2-氯苯基)-4,4’,5,5’-四(4-甲氧基苯基)联咪唑、2,4-双(三氯甲基)-6-(4-甲氧基苯基)-1,3,5-均三嗪、2,4,6-三(三氯甲基)-1,3,5-均三嗪、2,4-双(三溴甲基)-6-(4’-甲氧基苯基)-1,3,5-均三嗪、2,4,6-三(三溴甲基)-1,3,5-均三嗪、2,4-双(三氯甲基)-6-(1,3-苯并二氧杂环戊烷-5-基)-1,3,5-均三嗪、二苯甲酮、1-(4-苯硫基苯基)丁烷-1,2-二酮-2-肟-O-苯甲酸酯、1-(4-甲硫基苯基)丁烷-1,2-二酮-2-肟-O-乙酸酯、1-(4-甲硫基苯基)丁烷-1-酮肟-O-乙酸酯、1-[9-乙基-6-(2-甲基苯甲酰)-9H-咔唑-3-基]乙酮-1-(O-乙酰基肟)等。
这些光聚合引发剂可以单独使用或者两种以上组合使用。本发明中,当使用光聚合引发剂时,以在本发明组合物的总固形分中通常占0.5~30质量%、优选占1~25质量%的比例使用。
本发明的组合物中根据需要可以使用有机溶剂。本发明中使用的有机溶剂可以适当选择能够溶解作为本发明的负型感光性树脂组合物的构成成分的粘合剂聚合物、光聚合性单体、光聚合引发剂等的有机溶剂。作为有机溶剂的具体例,可以列举:苯、甲苯、二甲苯等苯类;甲基溶纤剂、乙基溶纤剂、丁基溶纤剂等溶纤剂类;甲基溶纤剂乙酸酯、乙基溶纤剂乙酸酯、丁基溶纤剂乙酸酯等溶纤剂乙酸酯类;丙二醇单甲醚乙酸酯、丙二醇单***乙酸酯、丙二醇单丁醚乙酸酯等丙二醇单烷基醚乙酸酯类;甲氧基丙酸甲酯、甲氧基丙酸乙酯、乙氧基丙酸甲酯、乙氧基丙酸乙酯等丙酸酯类;乳酸甲酯、乳酸乙酯、乳酸丁酯等乳酸酯类;二乙二醇单甲醚、二乙二醇单***等二乙二醇类;乙酸甲酯、乙酸乙酯、乙酸丁酯等乙酸酯类;二甲醚、二***、四氢呋喃、二氧杂环己烷等醚类;丙酮、甲乙酮、甲丁酮、环己酮等酮类;等。
这些有机溶剂可以单独使用或者两种以上组合使用。另外,本发明中,当使用有机溶剂时,相对于负型着色感光性组合物的总固形分100质量份,有机溶剂的含量通常为50~2000质量份,优选100~1000质量份。
本发明的负型感光性树脂组合物可以通过将上述粘合剂聚合物、光聚合性单体、光聚合引发剂、染料和有机溶剂用溶解器、高速搅拌机(homomixer)等搅拌、溶解或分散来制造。
本发明的负型感光性树脂组合物中根据需要还可以含有各种添加剂,例如填充剂、表面活性剂、热聚合抑制剂、密合促进剂、抗氧化剂、紫外线吸收剂、防凝聚剂。另外,本发明的负型感光性树脂组合物在制备后为了除去异物等也可以用过滤器等进行精密过滤。
下面,对本发明的滤色片、黑色矩阵及垫片的制造方法进行说明。首先,利用旋涂法、辊涂法、刮棒涂布法等方法将本发明的负型感光性树脂组合物涂布到玻璃基板、硅基板等基板上,使膜厚为约0.1μm~约7μm,并在温度60~120℃、时间1~50分钟的条件下进行预烘焙处理来制膜。然后,利用光刻法通过预定的掩模图案照射放射线(例如,电子射线、紫外线,优选紫外线),并用表面活性剂水溶液、碱性(水)溶液或(表面活性剂+碱剂)水溶液进行显影,除去未固化的部分,并用水冲洗,得到基板上的本发明的负型感光性树脂组合物的固化物图案。
上述中,作为表面活性剂,可以使用聚氧乙烯烷基醚、聚氧化烯烷基醚等。使用表面活性剂时,通常使用它们的0.05~1.0质量%的水溶液。另外,作为碱,可以使用碳酸钠、碳酸钾、氢氧化钠、氢氧化钾、二乙醇胺、四甲基氢氧化铵等,通常使用它们的0.05~1.0质量%的水溶液。本发明中,优选使用含有上述碱和表面活性剂的水溶液。显影在温度通常为10~50℃、优选20~40℃,时间通常为30~180秒、优选30~120秒的条件下进行。
本发明的负型感光性树脂组合物的固化物,作为用于液晶显示装置的滤色片、黑色矩阵及垫片、以及用于数码照相机的固体摄像器件用滤色片有用。
本发明的液晶显示装置例如可以按照将背光源、偏振膜、显示电极、液晶、取向膜、共用电极、本发明的滤色片、偏振膜等依次层叠的结构来制造。
本发明的固体摄像器件例如可以通过在设置有转移电极、光电二极管的硅晶片上设置本发明的滤色片层、然后层叠微透镜来制作。
实施例
以下,通过实施例更详细地说明本发明。实施例中,%表示质量%。
实施例1
将32g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的丙二醇单甲醚乙酸酯(以下简记为PGMEA)22%溶液、7g作为光聚合性单体的羟值70mgKOH/g的二季戊四醇的丙烯酸酯化物、1g作为光聚合引发剂的イルガキユア一907(チバスペシヤルテイケミカルズ制造)、0.5gカヤキユア一DETX-S(日本化药制)、86g作为颜料的红色颜料分散液(重量比:C.I.颜料红177/C.I.颜料黄83/分散剂/PGMEA=16/4/5/75)和30g作为溶剂的PGMEA混合,得到本发明的红色的负型感光性组合物1。
比较例1
将32g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的PGMEA 22%溶液、7g作为光聚合性单体的羟值48mgKOH/g的二季戊四醇的丙烯酸酯化物、1g作为光聚合引发剂的イルガキユア一907(チバスペシヤルテイケミカルズ制造)、0.5gカヤキユア一DETX-S(日本化药制)、86g作为颜料的红色颜料分散液(重量比:C.I.颜料红177/C.I.颜料黄83/分散剂/PGMEA=16/4/5/75)和30g作为溶剂的PGMEA混合,得到红色的负型感光性组合物2。
比较例2
将32g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的PGMEA 22%溶液、7g作为光聚合性单体的季戊四醇三丙烯酸酯(羟值130mgKOH/g)、1g作为光聚合引发剂的イルガキユア一907(チバスペシヤルテイケミカルズ制造)、0.5gカヤキユア一DETX-S(日本化药制)、86g作为颜料的红色颜料分散液(重量比:C.I.颜料红177/C.I.颜料黄83/分散剂/PGMEA=16/4/5/75)和30g作为溶剂的PGMEA混合,得到红色的负型感光性组合物3。
实施例2
将23g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的PGMEA 22%溶液、5g作为光聚合性单体的羟值130mgKOH/g的二季戊四醇的丙烯酸酯化物、1g作为光聚合引发剂的イルガキユアOXE02(1-[9-乙基-6-(2-甲基苯甲酰)-9H-咔唑-3-基]乙酮-1-(O-乙酰基肟)、チバスペシヤルテイケミカルズ制造)、45g作为颜料的炭黑分散液的PGMEA 22%溶液和34g作为溶剂的PGMEA混合,得到本发明的黑色的负型感光性组合物4。
比较例3
将23g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的PGMEA 22%溶液、5g作为光聚合性单体的羟值48mgKOH/g的二季戊四醇的丙烯酸酯化物、1g作为光聚合引发剂的イルガキユアOXE02(1-[9-乙基-6-(2-甲基苯甲酰)-9H-咔唑-3-基]乙酮-1-(O-乙酰基肟)、チバスペシヤルテイケミカルズ制造)、45g作为颜料的炭黑分散液的PGMEA 22%溶液和34g作为溶剂的PGMEA混合,得到黑色的负型感光性组合物5。
比较例4
将23g作为粘合剂聚合物的甲基丙烯酸-甲基丙烯酸苄酯共聚物(质量比20/80、重均分子量22000)的PGMEA 22%溶液、5g作为光聚合性单体的季戊四醇三丙烯酸酯(羟值130mgKOH/g)、1g作为光聚合引发剂的イルガキユアOXE02(1-[9-乙基-6-(2-甲基苯甲酰)-9H-咔唑-3-基]乙酮-1-(O-乙酰基肟)、チバスペシヤルテイケミカルズ制造)、45g作为颜料的炭黑分散液的PGMEA 22%溶液和34g作为溶剂的PGMEA混合,得到黑色的负型感光性组合物6。
利用旋涂法以1000rpm将上述得到的本发明的红色负型感光性组合物1和黑色负型感光性组合物4以及红色负型感光性组合物2、3和黑色负型感光性组合物5、6涂布到玻璃基板上,在80℃×100秒的条件下预烘焙后,使用紫外线曝光装置(株式会社オ一ク制作所,型号HMW-680GW)通过描绘有电路图案的掩模(Toppan-Test-Chart-No1-N)分别照射200mJ/cm2和400mJ/cm2的紫外线。曝光后,用添加有表面活性剂的0.1%TMAH水溶液进行60秒喷淋显影,用水冲洗后,在200℃加热处理,得到红色图案和黑色图案。
与玻璃基板的密合性及分辨率通过测定显影后残留的最小线宽(μm)来求出。这些宽线越小则表示密合性、分辨率越好。另外,显影性通过显影时开始溶解的时间(秒)(Breakpoint)进行确认。Breakpoint越短则显影性越好。感光度通过在变动曝光量进行图案化后用光学显微镜确认表面的固化性来判断。
表1
红色负型感光性组合物的图案化结果
表2
红色负型感光性组合物的图案化结果
从上述结果可以明显看出,通过在感光性组合物中使用羟值为70mgKOH/g以上、130mgKOH/g以下的二季戊四醇的丙烯酸酯化物,可以得到使用现有丙烯酸酯单体不能得到的、与无机基板的密合性、分辨率、显影性、感光度均优良的、平衡性好的感光性组合物。
Claims (6)
2.如权利要求1所述的负型感光性树脂组合物,其中,还包含粘合剂聚合物、颜料和光聚合引发剂。
3.如权利要求2所述的负型感光性树脂组合物,其中,粘合剂聚合物为甲基丙烯酸-甲基丙烯酸苄酯共聚物。
4.通过将权利要求1至3中任一项所述的负型感光性树脂组合物固化而得到的滤色片、黑色矩阵或垫片。
5.一种液晶显示装置,其具备权利要求4所述的滤色片、黑色矩阵或垫片。
6.一种固体摄像器件,其具备权利要求4所述的滤色片、黑色矩阵或垫片。
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