CN110573964B - 负型感光性树脂组合物及固化膜 - Google Patents
负型感光性树脂组合物及固化膜 Download PDFInfo
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- CN110573964B CN110573964B CN201880027730.7A CN201880027730A CN110573964B CN 110573964 B CN110573964 B CN 110573964B CN 201880027730 A CN201880027730 A CN 201880027730A CN 110573964 B CN110573964 B CN 110573964B
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- negative photosensitive
- photosensitive resin
- glass
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- 239000011342 resin composition Substances 0.000 title claims abstract description 101
- 239000011521 glass Substances 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 125000003566 oxetanyl group Chemical group 0.000 claims abstract description 40
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 37
- 229920002050 silicone resin Polymers 0.000 claims abstract description 29
- 239000000178 monomer Substances 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 8
- 239000000758 substrate Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 239000013522 chelant Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000005341 toughened glass Substances 0.000 claims description 2
- -1 polysiloxane Polymers 0.000 description 141
- 239000000243 solution Substances 0.000 description 36
- 125000004432 carbon atom Chemical group C* 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 31
- 238000011156 evaluation Methods 0.000 description 26
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 20
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 20
- 229910052726 zirconium Inorganic materials 0.000 description 20
- 239000006059 cover glass Substances 0.000 description 19
- 239000004094 surface-active agent Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 18
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 15
- 239000010410 layer Substances 0.000 description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 239000011737 fluorine Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- FPFOSIXCIBGKOH-MTOQALJVSA-J (z)-4-oxopent-2-en-2-olate;zirconium(4+) Chemical compound [Zr+4].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O FPFOSIXCIBGKOH-MTOQALJVSA-J 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- WGRZHLPEQDVPET-UHFFFAOYSA-N 2-methoxyethoxysilane Chemical compound COCCO[SiH3] WGRZHLPEQDVPET-UHFFFAOYSA-N 0.000 description 6
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 6
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 6
- 239000012965 benzophenone Substances 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 6
- 229940093858 ethyl acetoacetate Drugs 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 5
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003377 acid catalyst Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 239000002390 adhesive tape Substances 0.000 description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- XAOGXQMKWQFZEM-UHFFFAOYSA-N isoamyl propanoate Chemical compound CCC(=O)OCCC(C)C XAOGXQMKWQFZEM-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000006606 n-butoxy group Chemical group 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
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- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 4
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- AHNLTPNNRFETEC-UHFFFAOYSA-N 2-(3-trimethoxysilylpropyl)butanedioic acid Chemical compound CO[Si](OC)(OC)CCCC(C(O)=O)CC(O)=O AHNLTPNNRFETEC-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- JSGVZVOGOQILFM-UHFFFAOYSA-N 3-methoxy-1-butanol Chemical compound COC(C)CCO JSGVZVOGOQILFM-UHFFFAOYSA-N 0.000 description 3
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- 241000501754 Astronotus ocellatus Species 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
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- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
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- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- XVTQAXXMUNXFMU-UHFFFAOYSA-N methyl 2-(3-oxo-2-pyridin-2-yl-1h-pyrazol-5-yl)acetate Chemical compound N1C(CC(=O)OC)=CC(=O)N1C1=CC=CC=N1 XVTQAXXMUNXFMU-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
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- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 3
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- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
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- 238000002834 transmittance Methods 0.000 description 3
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 2
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- DOVZUKKPYKRVIK-UHFFFAOYSA-N 1-methoxypropan-2-yl propanoate Chemical compound CCC(=O)OC(C)COC DOVZUKKPYKRVIK-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 2
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- 230000003287 optical effect Effects 0.000 description 1
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- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
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- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000012360 testing method Methods 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- OAVPBWLGJVKEGZ-UHFFFAOYSA-N tributoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCCCC)(OCCCC)OCCCC)CCC2OC21 OAVPBWLGJVKEGZ-UHFFFAOYSA-N 0.000 description 1
- MYWQGROTKMBNKN-UHFFFAOYSA-N tributoxyalumane Chemical compound [Al+3].CCCC[O-].CCCC[O-].CCCC[O-] MYWQGROTKMBNKN-UHFFFAOYSA-N 0.000 description 1
- UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
- JYVWRCIOZLRMKO-UHFFFAOYSA-N tributyl(hydroxy)silane Chemical compound CCCC[Si](O)(CCCC)CCCC JYVWRCIOZLRMKO-UHFFFAOYSA-N 0.000 description 1
- 229940080117 triethanolamine sulfate Drugs 0.000 description 1
- PMQIWLWDLURJOE-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F PMQIWLWDLURJOE-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 1
- UUVZTKMMRCCGHN-OUKQBFOZSA-N triethoxy-[(e)-2-phenylethenyl]silane Chemical compound CCO[Si](OCC)(OCC)\C=C\C1=CC=CC=C1 UUVZTKMMRCCGHN-OUKQBFOZSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- PSUKBUSXHYKMLU-UHFFFAOYSA-N triethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OCC)(OCC)OCC)CCC2OC21 PSUKBUSXHYKMLU-UHFFFAOYSA-N 0.000 description 1
- WVMSIBFANXCZKT-UHFFFAOYSA-N triethyl(hydroxy)silane Chemical compound CC[Si](O)(CC)CC WVMSIBFANXCZKT-UHFFFAOYSA-N 0.000 description 1
- AAURKQPZJJMXER-UHFFFAOYSA-N triethylsilyl acetate Chemical compound CC[Si](CC)(CC)OC(C)=O AAURKQPZJJMXER-UHFFFAOYSA-N 0.000 description 1
- BSECONLXOCDYBU-UHFFFAOYSA-N triethylsilyl benzoate Chemical compound CC[Si](CC)(CC)OC(=O)C1=CC=CC=C1 BSECONLXOCDYBU-UHFFFAOYSA-N 0.000 description 1
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- JRSJRHKJPOJTMS-MDZDMXLPSA-N trimethoxy-[(e)-2-phenylethenyl]silane Chemical compound CO[Si](OC)(OC)\C=C\C1=CC=CC=C1 JRSJRHKJPOJTMS-MDZDMXLPSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 1
- VFFKJOXNCSJSAQ-UHFFFAOYSA-N trimethylsilyl benzoate Chemical compound C[Si](C)(C)OC(=O)C1=CC=CC=C1 VFFKJOXNCSJSAQ-UHFFFAOYSA-N 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- FZRMIZUBKZAWGO-UHFFFAOYSA-N tris(1,1,2,2,2-pentafluoroethoxy)-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)silane Chemical compound FC(F)(F)C(F)(F)O[Si](OC(F)(F)C(F)(F)F)(OC(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F FZRMIZUBKZAWGO-UHFFFAOYSA-N 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
- CIOXFKGQNIJXKF-UHFFFAOYSA-N tris(2-methoxyethoxy)silane Chemical compound COCCO[SiH](OCCOC)OCCOC CIOXFKGQNIJXKF-UHFFFAOYSA-N 0.000 description 1
- ODJMOVZKYZHQED-UHFFFAOYSA-N tris(trifluoromethoxy)-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)silane Chemical compound FC(F)(F)O[Si](OC(F)(F)F)(OC(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ODJMOVZKYZHQED-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/006—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character
- C03C17/007—Surface treatment of glass, not in the form of fibres or filaments, by coating with materials of composite character containing a dispersed phase, e.g. particles, fibres or flakes, in a continuous phase
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- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/16—Cyclic ethers having four or more ring atoms
- C08G65/18—Oxetanes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
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Abstract
负型感光性树脂组合物,其含有:(A)具有自由基聚合性基团、和羧基及/或二羧酸酐基的硅氧烷树脂、(B)反应性单体、(C)光自由基聚合引发剂、(D)二氧化硅粒子、及(E)具有氧杂环丁基的硅氧烷化合物。提供负型感光性树脂组合物,其能形成玻璃表面强度高、且与无机膜、有机膜的密合性优异的固化膜。
Description
技术领域
本发明涉及含有硅氧烷树脂、反应性单体、光自由基聚合引发剂、二氧化硅粒子及具有氧杂环丁基的硅氧烷化合物的负型感光性树脂组合物、和使用了其的固化膜。
背景技术
近年来,可穿戴终端、智能手机、平板PC(个人电脑)等各种显示终端具有在液晶显示装置、有机EL(电致发光)显示装置等显示面板的前表面贴合由印刷用着色油墨等形成了装饰膜的覆盖玻璃而成的结构。另外,在一部分显示终端中,也已应用在玻璃上具有透明电极的、赋予了触摸传感器功能的覆盖玻璃。然而,这些显示终端存在下述问题:由于覆盖玻璃的玻璃本身的强度不足、或因玻璃上的透明电极等无机膜而导致的玻璃强度的下降,导致在显示终端掉落时覆盖玻璃容易破损。
作为具有触摸传感器功能的覆盖玻璃,提出了下述覆盖玻璃一体型触摸面板:在覆盖玻璃上直接形成了导电膜及传感器,且1片玻璃具有覆盖玻璃和触摸传感器这两者的功能。这样的结构中,通常,在玻璃上形成遮光层,在遮光层上进一步形成导电膜、ITO等布线。作为覆盖玻璃一体型触摸面板的制造方法,例如,提出了依次包括下述工序的装饰覆盖玻璃一体型触摸面板的制造方法:利用丝网印刷法在覆盖玻璃基板上形成装饰部的工序;对覆盖玻璃基板上的装饰部进行抛光的工序;在覆盖玻璃基板上涂布覆盖涂层的工序;在覆盖涂层上形成触摸面板传感器的工序;和连同触摸面板传感器将覆盖玻璃基板裁断的工序(例如,参见专利文献1)。然而,这样的制造方法中,存在玻璃表面强度不足这样的课题。
因此,作为提高强度的技术,例如,提出了:具备玻璃板、透明导电膜、和由透明的有机化合物形成的基底绝缘膜的传感器一体型覆盖玻璃(例如,参见专利文献2);具有透光性化学强化玻璃基板、和树脂层的显示装置用的保护板用基板(例如,参见专利文献3);具有强化处理玻璃、透明导电膜、和固化膜的图像显示装置的前面板(例如,参见专利文献4);等等。
另外,作为应用于触摸面板的表面保护膜的组合物,例如,提出了含有聚硅氧烷(其是使包含具有羧基的三烷氧基硅烷、和具有甲基丙烯酰基及/或丙烯酰基的三烷氧基硅烷的三烷氧基硅烷进行水解及缩合而得到的)、光自由基引发剂、具有(甲基)丙烯酰基及异氰脲酸酯结构的化合物、及无机粒子的感光性硅氧烷组合物(例如,参见专利文献5)等。
现有技术文献
专利文献
专利文献1:日本特开2012-155644号公报
专利文献2:国际公开第2014/30599号
专利文献3:日本特开2014-228615号公报
专利文献4:日本特开2016-124720号公报
专利文献5:日本特开2015-64516号公报
发明内容
发明所要解决的课题
通过专利文献2~3记载的技术,虽然能提高玻璃表面强度,但要求更高的玻璃表面强度。另外,近年来,为了提高设计性,已进行了在覆盖玻璃上形成光学调节层等无机层、着色膜等有机层的研究。若在专利文献2~3记载的树脂层上形成无机膜、有机膜,则由于热膨胀系数的差异,容易在层叠界面发生剥离,与无机膜、有机膜的密合性存在问题。通过专利文献4记载的技术,虽然能提高玻璃表面强度,但存在与无机膜、有机膜的密合性不充分的课题。另外,关于专利文献5记载的固化膜,也存在与无机膜的密合性不充分的课题。
本发明是鉴于上述现有技术的课题而作出的,目的在于提供能形成玻璃表面强度高、且与无机膜、有机膜的密合性优异的固化膜的负型感光性树脂组合物。
用于解决课题的手段
本申请的发明人为了解决现有技术的课题而进行了深入研究,结果发现,通过将具有特定结构的硅氧烷树脂、二氧化硅粒子及具有氧杂环丁基的硅氧烷化合物进行组合,能解决本发明的课题。
即,本发明的目的可通过以下的构成实现。
负型感光性树脂组合物,其至少含有:(A)具有自由基聚合性基团、和羧基及/或二羧酸酐基的硅氧烷树脂、(B)反应性单体、(C)光自由基聚合引发剂、(D)二氧化硅粒子、及(E)具有氧杂环丁基的硅氧烷化合物。
发明的效果
通过本发明,可得到玻璃表面强度高、且与无机膜、有机膜的密合性优异的固化膜。
具体实施方式
以下,进一步详细地说明本发明。
本发明的负型感光性树脂组合物的特征在于,至少含有:(A)具有自由基聚合性基团、和羧基及/或二羧酸酐基的硅氧烷树脂(以下,有时记载为“(A)硅氧烷树脂”)、(B)反应性单体、(C)光自由基聚合引发剂、(D)二氧化硅粒子、及(E)具有氧杂环丁基的硅氧烷化合物。通过含有(A)硅氧烷树脂及(C)光聚合引发剂,从而在光照射部中(A)硅氧烷树脂的自由基聚合性基团及(B)反应性单体的聚合进行,能进行光照射部不溶解的负型的图案加工。此外,通过含有(D)二氧化硅粒子,从而(A)硅氧烷树脂与(D)二氧化硅粒子的硅烷醇缩合反应与自由基聚合一同进行,因此,能提高固化膜的交联密度,能提高玻璃表面强度。此外,通过含有(E)具有氧杂环丁基的硅氧烷化合物,除了发生(A)硅氧烷树脂与(E)具有氧杂环丁基的硅氧烷化合物的硅烷醇缩合反应、(D)二氧化硅粒子与具有氧杂环丁基的硅氧烷化合物的硅烷醇缩合反应之外,还发生氧杂环丁烷环的开环反应,因此,能降低热膨胀系数,能降低固化膜的膜应力,能得到与无机膜、有机膜的密合性优异的固化膜。
本发明的负型感光性树脂组合物含有(A)硅氧烷树脂。所谓硅氧烷树脂,是指含有具有硅氧烷骨架的重复单元的聚合物。其中,硅氧烷树脂具有氧杂环丁基时,分类为后述的(E)具有氧杂环丁基的硅氧烷化合物。本发明中的(A)硅氧烷树脂具有自由基聚合性基团、和羧基及/或羧酸酐基,优选为具有自由基聚合性基团的有机硅烷化合物与具有羧基及/或二羧酸酐基的有机硅烷化合物的水解缩合物。从提高涂布特性的观点考虑,(A)硅氧烷树脂的重均分子量(Mw)优选为1,000以上,更优选为2,000以上。另一方面,从提高在进行图案形成时的显影液中的溶解性的观点考虑,(A)硅氧烷树脂的Mw优选为10,000以下,更优选为5,000以下。此处,所谓(A)硅氧烷树脂的Mw,是指利用凝胶渗透色谱法(GPC)测定的聚苯乙烯换算值。
作为自由基聚合性基团,可举出例如乙烯基、α-甲基乙烯基、烯丙基、苯乙烯基、(甲基)丙烯酰基等。从进一步提高固化膜的硬度、图案加工时的敏感度的观点考虑,优选为(甲基)丙烯酰基。
作为具有自由基聚合性基团的有机硅烷化合物,可举出例如乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三(甲氧基乙氧基)硅烷、乙烯基甲基二甲氧基硅烷、乙烯基甲基二乙氧基硅烷、乙烯基甲基二(甲氧基乙氧基)硅烷、烯丙基三甲氧基硅烷、烯丙基三乙氧基硅烷、烯丙基三(甲氧基乙氧基)硅烷、烯丙基甲基二甲氧基硅烷、烯丙基甲基二乙氧基硅烷、烯丙基甲基二(甲氧基乙氧基)硅烷、苯乙烯基三甲氧基硅烷、苯乙烯基三乙氧基硅烷、苯乙烯基三(甲氧基乙氧基)硅烷、苯乙烯基甲基二甲氧基硅烷、苯乙烯基甲基二乙氧基硅烷、苯乙烯基甲基二(甲氧基乙氧基)硅烷、γ-丙烯酰基丙基三甲氧基硅烷、γ-丙烯酰基丙基三乙氧基硅烷、γ-丙烯酰基丙基三(甲氧基乙氧基)硅烷、γ-甲基丙烯酰基丙基三甲氧基硅烷、γ-甲基丙烯酰基丙基三乙氧基硅烷、γ-甲基丙烯酰基丙基三(甲氧基乙氧基)硅烷、γ-甲基丙烯酰基丙基甲基二甲氧基硅烷、γ-甲基丙烯酰基丙基甲基二乙氧基硅烷、γ-丙烯酰基丙基甲基二甲氧基硅烷、γ-丙烯酰基丙基甲基二乙氧基硅烷、γ-甲基丙烯酰基丙基(甲氧基乙氧基)硅烷等。可使用它们中的2种以上。这些中,从进一步提高固化膜的硬度、图案加工时的敏感度的观点考虑,优选γ-丙烯酰基丙基三甲氧基硅烷、γ-丙烯酰基丙基三乙氧基硅烷、γ-甲基丙烯酰基丙基三甲氧基硅烷、γ-甲基丙烯酰基丙基三乙氧基硅烷。
作为具有羧基的有机硅烷化合物,可举出下述通式(1)表示的含有脲基的有机硅烷化合物、下述通式(2)表示的含有氨基甲酸酯基的有机硅烷化合物、后述的通式(6)表示的有机硅烷化合物等。可使用它们中的2种以上。
[化学式1]
上述通式(1)~(2)中,R1、R3及R7表示碳原子数为1~20的2价的有机基团。R2表示氢原子或碳原子数为1~3的烷基。R4~R6表示碳原子数为1~6的烷基、碳原子数为1~6的烷氧基、苯基、苯氧基、碳原子数为2~6的烷基羰基氧基或它们的取代体。其中,R4~R6中,至少一个为烷氧基、苯氧基或乙酰氧基。
作为上述通式(1)~(2)中的R1及R7的优选例,可举出亚甲基、亚乙基、亚正丙基、亚正丁基、亚苯基、-CH2-C6H4-CH2-、-CH2-C6H4-等烃基。这些中,从耐热性的观点考虑,优选亚苯基、-CH2-C6H4-CH2-、-CH2-C6H4-等具有芳香族环的烃基。
从反应性的观点考虑,上述通式(2)中的R2优选为氢或甲基。
作为上述通式(1)~(2)中的R3,可举出例如亚甲基、亚乙基、亚正丙基、亚正丁基、亚正戊基等烃基、氧基亚甲基、氧基亚乙基、氧基亚正丙基、氧基亚正丁基、氧基亚正戊基等。这些中,从合成的容易性的观点考虑,优选亚甲基、亚乙基、亚正丙基、亚正丁基、氧基亚甲基、氧基亚乙基、氧基亚正丙基、氧基亚正戊基。
上述通式(1)~(2)中的R4~R6中,作为烷基的具体例,可举出甲基、乙基、正丙基、异丙基等。从合成的容易性的观点考虑,优选甲基或乙基。另外,作为烷氧基的具体例,可举出甲氧基、乙氧基、正丙氧基、异丙氧基等。从合成的容易性的观点考虑,优选甲氧基或乙氧基。另外,作为取代体的取代基,可举出甲氧基、乙氧基等。具体而言,可举出1-甲氧基丙基、甲氧基乙氧基等。
上述通式(1)表示的含有脲基的有机硅烷化合物可由下述通式(3)表示的氨基羧酸化合物与下述通式(5)表示的含有异氰酸酯基的有机硅烷化合物通过已知的脲化反应得到。另外,上述通式(2)表示的含有氨基甲酸酯基的有机硅烷化合物可由下述通式(4)表示的羟基羧酸化合物与下述通式(5)表示的具有异氰酸酯基的有机硅烷化合物通过已知的氨基甲酸酯化反应得到。
[化学式2]
H-O-R7COOH (4)
上述通式(3)~(5)中,R1、R3及R7表示碳原子数为1~20的2价的有机基团。R2表示氢原子或碳原子数为1~3的烷基。R4~R6表示碳原子数为1~6的烷基、碳原子数为1~6的烷氧基、苯基、苯氧基、碳原子数为2~6的烷基羰基氧基或它们的取代体。其中,R4~R6中,至少一个为烷氧基、苯氧基或乙酰氧基。R1~R7的优选例与关于通式(1)~(2)中的R1~R7而在上文中说明的相同。
[化学式3]
上述通式(6)中,R8表示碳原子数为1~6的烷基、碳原子数为1~6的烷氧基、苯基、苯氧基、碳原子数为2~6的烷基羰基氧基或它们的取代体。其中,1为2以上时,多个R8可以相同也可以不同,至少一个为烷氧基、苯氧基或乙酰氧基。l表示1~3的整数。m表示2~20的整数。
作为具有二羧酸酐基的有机硅烷化合物的具体例,可举出下述通式(7)~(9)中任意式表示的有机硅烷化合物。可使用它们中的2种以上。
[化学式4]
上述通式(7)~(9)中,R9~R11、R13~R15及R17~R19表示碳原子数为1~6的烷基、碳原子数为1~6的烷氧基、苯基、苯氧基、碳原子数为2~6的烷基羰基氧基或它们的取代体。R12、R16及R20表示单键、链状脂肪族烃基、环状脂肪族烃基、羰基、醚基、酯基、酰胺基、芳香族基团、或具有上述任意基团的2价的基团。这些基团可以被取代。h及k表示0~3的整数。
作为R12、R16及R20的具体例,可举出-C2H4-、-C3H6-、-C4H8-、-O-、-C3H6OCH2CH(OH)CH2O2C-、-CO-、-CO2-、-CONH-、以下列举的有机基团等。
[化学式5]
作为上述通式(7)表示的有机硅烷化合物的具体例,可举出3-三甲氧基甲硅烷基丙基琥珀酸酐、3-三乙氧基甲硅烷基丙基琥珀酸酐、3-三苯氧基甲硅烷基丙基琥珀酸酐等。作为上述通式(8)表示的有机硅烷化合物的具体例,可举出3-三甲氧基甲硅烷基丙基环己基二羧酸酐等。作为上述通式(9)表示的有机硅烷化合物的具体例,可举出3-三甲氧基甲硅烷基丙基邻苯二甲酸酐等。
(A)硅氧烷树脂可以为前述的具有自由基聚合性基团的有机硅烷化合物、具有羧基及/或二羧酸酐基的有机硅烷化合物、与其他的有机硅烷化合物的水解缩合物。作为其他的有机硅烷化合物,可举出例如甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三(甲氧基乙氧基)硅烷、甲基三丙氧基硅烷、甲基三异丙氧基硅烷、甲基三丁氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、己基三甲氧基硅烷、十八烷基三甲氧基硅烷、十八烷基三乙氧基硅烷、3-氨基丙基三乙氧基硅烷、N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷、3-氯丙基三甲氧基硅烷、3-(N,N-二缩水甘油基)氨基丙基三甲氧基硅烷、3-环氧丙氧基丙基三甲氧基硅烷、γ-氨基丙基三甲氧基硅烷、γ-氨基丙基三乙氧基硅烷、N-β-(氨基乙基)-γ-氨基丙基三甲氧基硅烷、β-氰基乙基三乙氧基硅烷、环氧丙氧基甲基三甲氧基硅烷、环氧丙氧基甲基三乙氧基硅烷、α-环氧丙氧基乙基三甲氧基硅烷、α-环氧丙氧基乙基三乙氧基硅烷、β-环氧丙氧基乙基三甲氧基硅烷、β-环氧丙氧基乙基三乙氧基硅烷、α-环氧丙氧基丙基三甲氧基硅烷、α-环氧丙氧基丙基三乙氧基硅烷、β-环氧丙氧基丙基三甲氧基硅烷、β-环氧丙氧基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三甲氧基硅烷、γ-环氧丙氧基丙基三乙氧基硅烷、γ-环氧丙氧基丙基三丙氧基硅烷、γ-环氧丙氧基丙基三异丙氧基硅烷、γ-环氧丙氧基丙基三丁氧基硅烷、γ-环氧丙氧基丙基三(甲氧基乙氧基)硅烷、α-环氧丙氧基丁基三甲氧基硅烷、α-环氧丙氧基丁基三乙氧基硅烷、β-环氧丙氧基丁基三甲氧基硅烷、β-环氧丙氧基丁基三乙氧基硅烷、γ-环氧丙氧基丁基三甲氧基硅烷、γ-环氧丙氧基丁基三乙氧基硅烷、δ-环氧丙氧基丁基三甲氧基硅烷、δ-环氧丙氧基丁基三乙氧基硅烷、(3,4-环氧环己基)甲基三甲氧基硅烷、(3,4-环氧环己基)甲基三乙氧基硅烷、2-(3,4-环氧环己基)乙基三丙氧基硅烷、2-(3,4-环氧环己基)乙基三丁氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、2-(3,4-环氧环己基)乙基三乙氧基硅烷、2-(3,4-环氧环己基)乙基三苯氧基硅烷、3-(3,4-环氧环己基)丙基三甲氧基硅烷、3-(3,4-环氧环己基)丙基三乙氧基硅烷、4-(3,4-环氧环己基)丁基三甲氧基硅烷、4-(3,4-环氧环己基)丁基三乙氧基硅烷、二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、γ-环氧丙氧基丙基甲基二甲氧基硅烷、γ-氨基丙基甲基二甲氧基硅烷、γ-氨基丙基甲基二乙氧基硅烷、N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基硅烷、环氧丙氧基甲基二甲氧基硅烷、环氧丙氧基甲基甲基二乙氧基硅烷、α-环氧丙氧基乙基甲基二甲氧基硅烷、α-环氧丙氧基乙基甲基二乙氧基硅烷、β-环氧丙氧基乙基甲基二甲氧基硅烷、β-环氧丙氧基乙基甲基二乙氧基硅烷、α-环氧丙氧基丙基甲基二甲氧基硅烷、α-环氧丙氧基丙基甲基二乙氧基硅烷、β-环氧丙氧基丙基甲基二甲氧基硅烷、β-环氧丙氧基丙基甲基二乙氧基硅烷、γ-环氧丙氧基丙基甲基二甲氧基硅烷、γ-环氧丙氧基丙基甲基二乙氧基硅烷、γ-环氧丙氧基丙基甲基二丙氧基硅烷、β-环氧丙氧基丙基甲基二丁氧基硅烷、γ-环氧丙氧基丙基甲基二(甲氧基乙氧基)硅烷、γ-环氧丙氧基丙基乙基二甲氧基硅烷、γ-环氧丙氧基丙基乙基二乙氧基硅烷、3-氯丙基甲基二甲氧基硅烷、3-氯丙基甲基二乙氧基硅烷、环己基甲基二甲氧基硅烷、十八烷基甲基二甲氧基硅烷、四甲氧基硅烷、四乙氧基硅烷、三氟甲基三甲氧基硅烷、三氟甲基三乙氧基硅烷、三氟丙基三甲氧基硅烷、三氟丙基三乙氧基硅烷、全氟丙基三甲氧基硅烷、全氟丙基三乙氧基硅烷、全氟戊基三甲氧基硅烷、全氟戊基三乙氧基硅烷、十三氟辛基三甲氧基硅烷、十三氟辛基三乙氧基硅烷、十三氟辛基三丙氧基硅烷、十三氟辛基三异丙氧基硅烷、十七氟癸基三甲氧基硅烷、十七氟癸基三乙氧基硅烷、双(三氟甲基)二甲氧基硅烷、双(三氟丙基)二甲氧基硅烷、双(三氟丙基)二乙氧基硅烷、三氟丙基甲基二甲氧基硅烷、三氟丙基甲基二乙氧基硅烷、三氟丙基乙基二甲氧基硅烷、三氟丙基乙基二乙氧基硅烷、十七氟癸基甲基二甲氧基硅烷等。可使用它们中2种以上。这些中,优选三氟丙基三甲氧基硅烷、三氟丙基三乙氧基硅烷、十三氟辛基三甲氧基硅烷、十三氟辛基三乙氧基硅烷等。
(A)硅氧烷树脂可通过将有机硅烷化合物水解缩合而得到。例如,可通过在将有机硅烷化合物水解后,在有机溶剂的存在下或无溶剂下使得到的硅烷醇化合物进行缩合反应而得到。
水解反应的各种条件可以考虑反应规模、反应容器的大小、形状等而适当设定。例如,优选的是,在溶剂中,经1~180分钟向有机硅烷化合物中添加酸催化剂及水,然后,于室温~110℃进行1~180分钟反应。通过在这样的条件下进行水解反应,能抑制急剧的反应。反应温度更优选为30~105℃。
水解反应优选在酸催化剂的存在下进行。作为酸催化剂,优选包含甲酸、乙酸、磷酸的酸性水溶液。相对于水解反应时使用的全部有机硅烷化合物100重量份而言,酸催化剂的添加量优选为0.1~5重量份。通过使酸催化剂的量为上述范围,能更高效地进行水解反应。
在通过有机硅烷化合物的水解反应得到硅烷醇化合物后,优选于50℃以上、溶剂的沸点以下直接对反应液进行1~100小时加热,使其进行缩合反应。另外,为了提高聚硅氧烷的聚合度,可进行再加热或碱催化剂添加。
作为有机硅烷化合物的水解反应及硅烷醇化合物的缩合反应中可使用的有机溶剂,可举出例如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、叔丁醇、戊醇、4-甲基-2-戊醇、3-甲基-2-丁醇、3-甲基-3-甲氧基-1-丁醇、1-叔丁氧基-2-丙醇、二丙酮醇等醇类;乙二醇、丙二醇等二醇类;乙二醇单甲基醚、乙二醇单乙基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单丙基醚、丙二醇单丁基醚、乙二醇二甲基醚、乙二醇二乙基醚、乙二醇二丁基醚、乙醚等醚类;甲基乙基酮、乙酰丙酮、甲基丙基酮、甲基丁基酮、甲基异丁基酮、二异丁基酮、环戊酮、2-庚酮等酮类;二甲基甲酰胺、二甲基乙酰胺等酰胺类;乙酸乙酯、乙酸丙酯、乙酸丁酯、乙酸异丁酯、乙二醇单乙基醚乙酸酯、丙二醇单甲基醚乙酸酯、乙酸3-甲氧基丁酯、乙酸3-甲基-3-甲氧基丁酯、乳酸甲酯、乳酸乙酯、乳酸丁酯等乙酸酯类;甲苯、二甲苯、己烷、环己烷等芳香族或脂肪族烃、γ-丁内酯、N-甲基-2-吡咯烷酮、二甲基亚砜等。从固化膜的透过率、耐破裂性等方面考虑,可优选使用二丙酮醇、丙二醇单甲基醚、丙二醇单甲基醚乙酸酯、丙二醇单乙基醚、丙二醇单叔丁基醚、丙二醇单丙基醚、丙二醇单丁基醚、γ-丁内酯等。
在通过水解反应生成溶剂的情况下,也可在无溶剂下进行水解。还优选在反应结束后,通过进一步添加溶剂从而作为树脂组合物调节至适当的浓度。另外,根据目的,可以在水解后,在加热及/或减压下馏出、除去适量的生成的醇等,然后添加合适的溶剂。
相对于全部有机硅烷化合物100重量份而言,水解反应中使用的溶剂的量优选为80重量份以上、且500重量份以下。通过使溶剂的量为上述范围,能更高效地进行水解反应。
另外,水解反应中使用的水优选为离子交换水。相对于硅烷原子1摩尔而言,水的量优选为1.0~4.0摩尔。
对于本发明的负型感光性树脂组合物中的(A)硅氧烷树脂的含量而言,从进一步减小固化膜的膜应力、进一步提高密合性的观点考虑,在固态成分中,优选为15重量%以上,更优选为25重量%以上。另一方面,从进一步提高固化膜的硬度及玻璃表面强度的观点考虑,(A)硅氧烷树脂的含量在固态成分中优选为60重量%以下,更优选为40重量%以下。
本发明的负型感光性树脂组合物含有(B)反应性单体。作为(B)反应性单体,优选具有乙烯基、α-甲基乙烯基、烯丙基、苯乙烯基、(甲基)丙烯酰基等自由基聚合性基团的化合物,更优选具有(甲基)丙烯酰基的化合物。从进一步提高固化膜的交联密度、进一步提高玻璃表面强度的观点考虑,优选多官能(甲基)丙烯酸酯。
所谓多官能(甲基)丙烯酸酯,是指具有2个以上的丙烯酸酯基的化合物,例如,作为具有2个丙烯酸酯基的化合物,可举出2,2-[9H-芴-9,9-二基双(1,4-亚苯基)双氧基]二乙醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、二羟甲基三环癸烷二(甲基)丙烯酸酯、乙氧基化双酚A二(甲基)丙烯酸酯、甘油二(甲基)丙烯酸酯、三丙二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,9-壬二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯,作为具有3个以上的丙烯酸酯基的化合物,可举出三(2-羟基乙基)异氰脲酸的丙烯酸酯、甘油三(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、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、乙氧基化季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、三季戊四醇七(甲基)丙烯酸酯、三季戊四醇八(甲基)丙烯酸酯、四季戊四醇九(甲基)丙烯酸酯、四季戊四醇十(甲基)丙烯酸酯、五季戊四醇十一(甲基)丙烯酸酯、五季戊四醇十二(甲基)丙烯酸酯等。可含有它们中的2种以上。
对于本发明的负型感光性树脂组合物中的(B)反应性单体的含量而言,从提高固化膜的硬度及玻璃表面强度的观点考虑,在固态成分中,优选为5重量%以上,更优选为10重量%以上。另一方面,从进一步减小固化膜的膜应力、进一步提高密合性的观点考虑,(B)反应性单体的含量在固态成分中优选为50重量%以下,更优选为30重量%以下。
本发明的负型感光性树脂组合物含有(C)光自由基聚合引发剂。作为(C)光自由基聚合引发剂,可举出例如烷基苯酮系光自由基聚合引发剂、酰基氧化膦系光自由基聚合引发剂、肟酯系光自由基聚合引发剂、二苯甲酮系光自由基聚合引发剂、呫吨酮系光自由基聚合引发剂、咪唑系光自由基聚合引发剂、苯并噻唑系光自由基聚合引发剂、苯并噁唑系光自由基聚合引发剂、咔唑系光自由基聚合引发剂、三嗪系光自由基聚合引发剂、苯甲酸酯系光自由基聚合引发剂、磷系光自由基聚合引发剂、钛酸酯等无机系光自由基聚合引发剂等。可含有它们中的2种以上。
作为烷基苯酮系光自由基聚合引发剂,可举出例如α-氨基烷基苯酮系光自由基聚合引发剂、α-羟基烷基苯酮系光自由基聚合引发剂等。可含有它们中的2种以上。这些中,从提高固化膜的硬度的观点考虑,优选α-氨基烷基苯酮系光自由基聚合引发剂、酰基氧化膦系光自由基聚合引发剂、肟酯系光自由基聚合引发剂、具有氨基的二苯甲酮系光自由基聚合引发剂、具有氨基的苯甲酸酯系光自由基聚合引发剂。这些化合物不仅参与自由基聚合性基团的交联反应,而且在光照射及热固化时,还作为碱或酸参与(A)硅氧烷树脂的交联,因此,固化膜的硬度进一步提高。
作为α-氨基烷基苯酮系光自由基聚合引发剂,可举出例如2-甲基-[4-(甲基硫基)苯基]-2-吗啉代丙烷-1-酮、2-二甲基氨基-2-(4-甲基苄基)-1-(4-吗啉-4-基-苯基)-丁烷-1-酮、2-苄基-2-二甲基氨基-1-(4-吗啉代苯基)-丁酮-1等。作为酰基氧化膦系光自由基聚合引发剂,可举出例如2,4,6-三甲基苯甲酰基苯基氧化膦、双(2,4,6-三甲基苯甲酰基)-苯基氧化膦、双(2,6-二甲氧基苯甲酰基)-(2,4,4-三甲基戊基)-氧化膦等。作为肟酯系光自由基聚合引发剂,可举出例如1-苯基-1,2-丙二酮-2-(邻乙氧基羰基)肟、1,2-辛烷二酮,1-[4-(苯基硫基)-2-(O-苯甲酰基肟)]、1-苯基-1,2-丁二酮-2-(邻甲氧基羰基)肟、1,3-二苯基丙三酮-2-(邻乙氧基羰基)肟、1-[9-乙基-6-(2-甲基苯甲酰基)-9H-咔唑-3-基]乙酮1-(O-乙酰基肟)等。作为具有氨基的二苯甲酮系光自由基聚合引发剂,可举出例如4,4-双(二甲基氨基)二苯甲酮、4,4-双(二乙基氨基)二苯甲酮等。作为具有氨基的苯甲酸酯系光自由基聚合引发剂,可举出例如对二甲基氨基苯甲酸乙酯、对二甲基氨基苯甲酸2-乙基己酯、对二乙基氨基苯甲酸乙酯等。
对于本发明的负型感光性树脂组合物中的(C)光自由基聚合引发剂的含量而言,从使自由基固化充分进行的观点考虑,在负型感光性树脂组合物固态成分中,优选为0.01重量%以上,更优选为0.1重量%以上。另一方面,从抑制光自由基聚合引发剂的残留、提高耐溶剂性的观点考虑,光自由基聚合引发剂的含量优选为20重量%以下,更优选为10重量%以下。
本发明的树脂组合物含有(D)二氧化硅粒子。二氧化硅粒子的平均粒径优选为1~200nm,从进一步提高固化膜的透明性的观点考虑,更优选为1~70nm。此处,(D)二氧化硅粒子的平均粒径可利用动态光散射法求出。具体而言,通过半导体激光器,向(D)二氧化硅粒子浓度为10~30质量%的分散液照射波长为780nm的光,测定散射光后,利用FFT-外差法进行频率分析,由此,能求出平均粒径。
作为二氧化硅粒子,可举出例如sicastar(Corefront Corporation制)、“REOLOSIL”(注册商标)(Tokuyama Corporation制)等。可使用珠磨机等分散机将它们粉碎或分散。作为二氧化硅粒子的分散液,可举出例如IPA-ST、MIBK-ST、IPA-ST-L、IPA-ST-ZL、PGM-ST、PMA-ST(均为日产化学工业株式会社制)、“OSCAR”(注册商标)101、“OSCAR”105、“OSCAR”106、“CATALOID”(注册商标)-S(均为日挥触媒化成株式会社制)、“Quartron”(注册商标)PL-1-IPA、PL-1-TOL,PL-2L-PGME、PL-2L-MEK、PL-2L、GP-2L(均为扶桑化学工业株式会社制)等。可含有它们中的2种以上。
对于本发明的负型感光性树脂组合物中的(D)二氧化硅粒子的含量而言,从进一步提高固化膜的硬度及玻璃表面强度的观点考虑,在固态成分中,优选为10重量%以上,更优选为20重量%以上。另一方面,从进一步减小固化膜的膜应力、进一步提高密合性的观点考虑,对于(D)二氧化硅粒子的含量而言,在固态成分中,优选为50重量%以下,更优选为40重量%以下。
本发明的负型感光性树脂组合物含有(E)具有氧杂环丁基的硅氧烷化合物。作为(E)具有氧杂环丁基的硅氧烷化合物,可举出例如下述通式(10)表示的化合物等。
[化学式6]
上述通式(10)中,R21~R24表示氢原子、烷基、环烷基或下述通式(11)表示的基团。其中,R21~R24中的至少1个为下述通式(11)表示的基团。w表示1~10的整数。从反应性的观点考虑,烷基的碳原子数优选为1~6,环烷基的碳原子数优选为3~6。
[化学式7]
上述通式(11)中,R25~R29表示氢原子、氟原子、碳原子数为1~4的烷基、苯基或碳原子数为1~4的全氟烷基。p表示1~6的整数。
前述通式(10)表示的硅氧烷化合物可通过将具有氧杂环丁基的烷氧基硅烷化合物、根据需要与不具有氧杂环丁基的烷氧基硅烷化合物一同水解而得到。
作为具有氧杂环丁基的烷氧基硅烷化合物,可举出例如(氧杂环丁烷-3-基)甲基三甲氧基硅烷、(氧杂环丁烷-3-基)甲基三乙氧基硅烷、(氧杂环丁烷-3-基)甲基三正丙基氧基硅烷、(氧杂环丁烷-3-基)甲基三异丙基氧基硅烷、(氧杂环丁烷-3-基)甲基三乙酰氧基硅烷、(氧杂环丁烷-3-基)甲基甲基二甲氧基硅烷、(氧杂环丁烷-3-基)甲基甲基二乙氧基硅烷、(氧杂环丁烷-3-基)甲基甲基二正丙基氧基硅烷、(氧杂环丁烷-3-基)甲基甲基二异丙基氧基硅烷、(氧杂环丁烷-3-基)甲基甲基二乙酰氧基硅烷、(氧杂环丁烷-3-基)甲基乙基二甲氧基硅烷、(氧杂环丁烷-3-基)甲基乙基二乙氧基硅烷、(氧杂环丁烷-3-基)甲基乙基二正丙基氧基硅烷、(氧杂环丁烷-3-基)甲基乙基二异丙基氧基硅烷、(氧杂环丁烷-3-基)甲基乙基二乙酰氧基硅烷、(氧杂环丁烷-3-基)甲基苯基二甲氧基硅烷、(氧杂环丁烷-3-基)甲基苯基二乙氧基硅烷、(氧杂环丁烷-3-基)甲基苯基二正丙基氧基硅烷、(氧杂环丁烷-3-基)甲基苯基二异丙基氧基硅烷、(氧杂环丁烷-3-基)甲基苯基二乙酰氧基硅烷、二(氧杂环丁烷-3-基)甲基二甲氧基硅烷、二(氧杂环丁烷-3-基)甲基二乙氧基硅烷、二(氧杂环丁烷-3-基)甲基二正丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基二异丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基二乙酰氧基硅烷、二(氧杂环丁烷-3-基)甲基甲基甲氧基硅烷、二(氧杂环丁烷-3-基)甲基甲基乙氧基硅烷、二(氧杂环丁烷-3-基)甲基甲基正丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基甲基异丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基甲基乙酰氧基硅烷、二(氧杂环丁烷-3-基)甲基乙基甲氧基硅烷、二(氧杂环丁烷-3-基)甲基乙基乙氧基硅烷、二(氧杂环丁烷-3-基)甲基乙基正丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基乙基异丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基乙基乙酰氧基硅烷、二(氧杂环丁烷-3-基)甲基苯基甲氧基硅烷、二(氧杂环丁烷-3-基)甲基苯基乙氧基硅烷、二(氧杂环丁烷-3-基)甲基苯基正丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基苯基异丙基氧基硅烷、二(氧杂环丁烷-3-基)甲基苯基乙酰氧基硅烷、三(氧杂环丁烷-3-基)甲基甲氧基硅烷、三(氧杂环丁烷-3-基)甲基乙氧基硅烷、三(氧杂环丁烷-3-基)甲基正丙基氧基硅烷、三(氧杂环丁烷-3-基)甲基异丙基氧基硅烷、三(氧杂环丁烷-3-基)甲基乙酰氧基硅烷等。可使用它们中的2种以上。
另外,作为不具有氧杂环丁基的烷氧基硅烷化合物,可举出例如四甲氧基硅烷、四乙氧基硅烷、甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三丙氧基硅烷、甲基三异丙氧基硅烷、乙基三甲氧基硅烷、乙基三乙氧基硅烷、丙基三乙氧基硅烷、丁基三甲氧基硅烷、环己基三甲氧基硅烷、环己基三乙氧基硅烷、苯基三甲氧基硅烷、苯基三乙氧基硅烷、二甲基二乙氧基硅烷、二甲基二乙氧基硅烷、二乙基二甲氧基硅烷、二乙基二乙氧基硅烷、二苯基二甲氧基硅烷、二苯基二乙氧基硅烷、甲基苯基二甲氧基硅烷、甲基苯基二乙氧基硅烷、三甲基硅烷醇、三乙基硅烷醇、三丙基硅烷醇、三丁基硅烷醇、三苯基硅烷醇、三甲基甲氧基硅烷、三甲基乙氧基硅烷、三乙基甲氧基硅烷、三乙基乙氧基硅烷、三丙基甲氧基硅烷、三丙基乙氧基硅烷、乙酸三甲基甲硅烷基酯、苯甲酸三甲基甲硅烷基酯、乙酸三乙基甲硅烷基酯、苯甲酸三乙基甲硅烷基酯、苄基二甲基甲氧基硅烷、苄基二甲基乙氧基硅烷、二苯基甲氧基甲基硅烷、二苯基乙氧基甲基硅烷、乙酰基三苯基硅烷、乙氧基三苯基硅烷、六甲基二硅氧烷、六乙基二甲基二硅氧烷、六丙基二硅氧烷、1,3-二丁基-1,1,3,3-四甲基二硅氧烷、1,3-二苯基-1,1,3,3-四甲基二硅氧烷、1,3一二甲基-1,1,3,3-四苯基二硅氧烷等。可使用它们中的2种以上。
作为(E)具有氧杂环丁基的硅氧烷化合物,可举出例如“ARONE OXETANE”(注册商标)OXT-191(商品名,东亚合成株式会社制)(通式(10)中的R21~R24为(3-乙基-3-氧杂环丁基)甲基,w平均为5)、下述通式(12)或(15)表示的化合物等。可含有它们中的2种以上。
[化学式8]
前述通式(12)中,R30及R32表示氢原子、氟原子、碳原子数为1~6个的烷基、碳原子数为1~6个的氟烷基、碳原子数为6~18的芳基、呋喃基或噻吩基。R31表示下述通式(13)表示的基团。d表示0~3的整数。作为碳原子数为1~6的烷基,可举出例如甲基、乙基、丙基、丁基、戊基、己基等。作为碳原子数为1~6的氟烷基,可举出例如三氟甲基、全氟甲基、全氟乙基、全氟丙基等。作为碳原子数为6~18的芳基,可举出例如苯基、萘基等。
[化学式9]
上述通式(13)中,R33、R35、R36及R38表示碳原子数为1~4的烷基、碳原子数为6~18的芳基,R34及R37表示碳原子数为1~4的烷基、碳原子数为6~18的芳基或下述通式(14)表示的基团。u表示0~200的整数。u为2以上时,多个R34及R37可以相同也可以不同。
[化学式10]
上述通式(14)中,R39~R43表示碳原子数为1~4的烷基或碳原子数为6~18的芳基。Z表示0~100的整数。z为2以上时,多个R39及R43可以相同也可以不同。
[化学式11]
前述通式(15)中,R30表示氢原子、氟原子、碳原子数为1~6个的烷基、碳原子数为1~6个的氟烷基、碳原子数为6~18的芳基、呋喃基或噻吩基,R44表示3~10价的有机基团。可举出例如下述通式(16)~(18)中任意式表示的线状、分支状或笼状的含有聚硅氧烷的基团等。通式(15)中,j表示与R44的价数相等的3~10的整数。
[化学式12]
作为前述通式(18)表示的笼状的(E)具有氧杂环丁基的硅氧烷化合物,可举出例如倍半硅氧烷衍生物OX-SQ TX-100、OX-SQ SI-20(以上为商品名,东亚合成株式会社制)等。
这些中,优选具有多个氧杂环丁基的化合物。通过具有多个氧杂环丁基,从而由氧杂环丁烷环的开环反应带来的缓和固化膜应力的效果提高,能进一步提高与有机膜、无机膜的密合性。
对于本发明的负型感光性树脂组合物中的(E)具有氧杂环丁基的硅氧烷化合物的含量而言,从进一步缓和固化膜的应力、进一步提高密合性的观点考虑,在固态成分中,优选为0.1重量%以上,更优选为1重量%以上,进一步优选为2重量%以上。另一方面,从提高固化膜的硬度及玻璃表面强度的观点考虑,优选为10重量%以下,更优选为6重量%以下,进一步优选为5重量%以下。
本发明的负型感光性树脂组合物优选含有下述通式(19)表示的金属螯合物化合物。金属螯合物化合物作为(A)硅氧烷树脂的硅烷醇缩合反应的催化剂而促进固化,因此,交联密度进一步提高,能提高固化膜的硬度。
[化学式13]
上述通式(19)中,M表示金属原子,R45表示氢、烷基、芳基或链烯基,R46及R47各自独立地表示氢、烷基、芳基、链烯基或烷氧基。其中,烷基、芳基、链烯基或烷氧基可以被取代基取代。e表示金属原子M的原子价,f表示0~e的整数。从反应性的观点考虑,e-f优选为0。
作为金属原子M,从固化膜的透明度的观点考虑,优选钛、锆、铝、锌、钴、钼、镧、钡、锶、镁、钙,从显影时的密合性、固化膜的耐湿热性的观点考虑,更优选锆、铝。
作为R45,可举出例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、戊基、己基、庚基、辛基、壬基、癸基、十八烷基、苯基、乙烯基、烯丙基、油烯基等。从金属螯合物化合物的稳定性的观点考虑,优选正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十八烷基或苯基。
作为R46及R47,可举出例如氢、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、苯基、乙烯基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十八烷基、苄基氧基等。从金属螯合物化合物的合成容易性、稳定性的观点考虑,优选甲基、叔丁基、苯基、甲氧基、乙氧基、正十八烷基,从反应性的观点考虑,更优选甲基。
作为金属原子M为锆的锆螯合物化合物,可举出例如四正丙醇锆、四正丁醇锆、四仲丁醇锆、四苯酚锆、四乙酰丙酮锆、四(2,2,6,6-四甲基-3,5-庚烷二酮)锆、四甲基乙酰乙酸锆、四乙酰乙酸乙酯锆、四甲基丙二酸锆、四乙基丙二酸锆、四苯甲酰丙酮锆、四二苯甲酰基甲酸锆、单正丁氧基乙酰丙酮双(乙酰乙酸乙酯)锆、单正丁氧基乙酰乙酸乙酯双(乙酰丙酮)锆、单正丁氧基三(乙酰丙酮)锆、单正丁氧基三(乙酰丙酮)锆、二(正丁氧基)双(乙酰乙酸乙酯)锆、二(正丁氧基)双(乙酰丙酮)锆、二(正丁氧基)双(乙基丙二酸)锆、二(正丁氧基)双(苯甲酰丙酮)锆、二(正丁氧基)双(二苯甲酰基甲酸)锆等。
作为金属原子M为铝的铝螯合物化合物,可举出例如三异丙醇铝、三正丙醇铝、三仲丁醇铝、三正丁醇铝、三苯酚铝、三乙酰丙酮铝、三(2,2,6,6-四甲基-3,5-庚烷二酮)铝、三乙酰乙酸乙酯铝、三甲基乙酰乙酸铝、三甲基丙二酸铝、三乙基丙二酸铝、乙酸乙酯二(异丙醇)铝、乙酰丙酮二(异丙醇)铝、乙酰乙酸甲酯二(异丙醇)铝、乙酰乙酸十八烷基酯二(异丙醇)铝、单乙酰丙酮双(乙酰乙酸乙酯)铝等。
这些中,从在各种溶剂中的溶解性、化合物的稳定性的观点考虑,优选四正丙醇锆、四正丁醇锆、四苯酚锆、四乙酰丙酮锆、四(2,2,6,6-四甲基-3,5-庚烷二酮)锆、四甲基丙二酸锆、四乙基丙二酸锆、四乙酰乙酸乙酯锆、二正丁氧基双(乙酰乙酸乙酯)锆、单正丁氧基乙酰丙酮双(乙酰乙酸乙酯)锆、三乙酰丙酮铝、三(2,2,6,6-四甲基-3,5-庚烷二酮)铝、三乙酰乙酸乙酯铝、三甲基乙酰乙酸酯铝、三甲基丙二酸铝、三乙基丙二酸铝、乙酸乙酯二(异丙醇)铝、乙酰丙酮二(异丙醇)铝、乙酰乙酸甲酯二(异丙醇)铝、乙酰乙酸十八烷基酯二(异丙醇)铝、单乙酰丙酮双(乙酰乙酸乙酯)铝。
本发明的负型感光性树脂组合物优选含有硅烷偶联剂等密合改良剂,能提高涂膜与基底基板的粘接性。作为硅烷偶联剂,可举出具有乙烯基、环氧基、苯乙烯基、甲基丙烯酰氧基、丙烯酰氧基、氨基等官能团的硅烷偶联剂。具体而言,优选3-环氧丙氧基丙基三甲氧基硅烷、3-环氧丙氧基丙基三乙氧基硅烷、3-环氧丙氧基丙基甲基二甲氧基硅烷、3-环氧丙氧基丙基甲基二乙氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、3-氯丙基甲基二甲氧基硅烷、3-氯丙基三甲氧基硅烷、乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三(2-甲氧基乙氧基)硅烷、N-(2-氨基乙基)-3-氨基丙基甲基二甲氧基硅烷、N-(2-氨基乙基)-3-氨基丙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-丙烯酰氧基丙基三甲氧基硅烷、3-氨基丙基三甲氧基硅烷、3-氨基丙基三乙氧基硅烷、3-三乙氧基甲硅烷基-N-(1,3-二甲基-丁叉)丙基胺、3-巯基丙基三甲氧基硅烷、3-脲基丙基三乙氧基硅烷、3-异氰酸酯丙基三乙氧基硅烷、对苯乙烯基三甲氧基硅烷等。
对于本发明的负型感光性树脂组合物中的密合改良剂的含量而言,从进一步提高粘接性的观点考虑,在负型感光性树脂组合物的固态成分中,优选为0.1重量%以上,更优选为1重量%以上。另一方面,从提高基于碱显影的图案分辨率的观点考虑,对于密合改良剂的含量而言,在负型感光性树脂组合物的固态成分中,优选为10重量%以下,更优选为5重量%以下。
本发明的负型感光性树脂组合物可含有各种固化剂,能促进负型感光性树脂组合物的固化或使负型感光性树脂组合物的固化容易进行。作为固化剂,可举出例如含氮有机物、聚硅氧烷树脂固化剂、各种金属醇盐、异氰酸酯化合物及其聚合物、羟甲基化三聚氰胺衍生物、羟甲基化脲衍生物等。可含有它们中的2种以上。其中,从固化剂的稳定性、得到的涂布膜的加工性等考虑,可优选使用金属螯合物化合物、羟甲基化三聚氰胺衍生物、羟甲基化脲衍生物。
由于(A)硅氧烷树脂的固化通过酸而被促进,因此,可在本发明的负型感光性树脂组合物中含有热产酸剂等固化催化剂。作为热产酸剂,可举出例如芳香族重氮盐、锍盐、二芳基碘鎓盐、三芳基锍盐、三芳基硒盐等各种鎓盐系化合物、磺酸酯、卤化合物等。
本发明的负型感光性树脂组合物可含有阻聚剂。通过含有阻聚剂,能提高负型感光性树脂组合物的保存稳定性及分辨率。作为阻聚剂,可举出例如苯酚、邻苯二酚、间苯二酚、对苯二酚、4-叔丁基邻苯二酚、2,6-二(叔丁基)-对甲酚、吩噻嗪、4-甲氧基苯酚等。
对于本发明的负型感光性树脂组合物中的阻聚剂的含量而言,在负型感光性树脂组合物的固态成分100重量%中,优选为0.01重量%以上,更优选为0.1重量%以上。另一方面,从提高固化膜的硬度的观点考虑,阻聚剂的含量优选为5重量%以下,更优选为1重量%以下。
本发明的负型感光性树脂组合物可含有紫外线吸收剂。通过含有紫外线吸收剂,能提高负型感光性树脂组合物的分辨率及固化膜的耐光性。作为紫外线吸收剂,从透明性、非着色性的方面考虑,可优选使用苯并三唑系化合物、二苯甲酮系化合物、三嗪系化合物。
作为苯并三唑系化合物,可举出例如2-(2H苯并三唑-2-基)苯酚、2-(2H-苯并三唑-2-基)-4,6-叔戊基苯酚、2-(2H苯并三唑-2-基)-4-(1,1,3,3-四甲基丁基)苯酚、2(2H-苯并三唑-2-基)-6-十二烷基-4-甲基苯酚、2-(2’-羟基-5’-甲基丙烯酰氧基乙基苯基)-2H-苯并三唑等。
作为二苯甲酮系化合物,可举出例如2-羟基-4-甲氧基二苯甲酮等。
作为三嗪系化合物,可举出例如2-(4,6-二苯基-1,3,5三嗪-2-基)-5-[(己基)氧基]-苯酚等。
对于本发明的负型感光性树脂组合物中的紫外线吸收剂的含量而言,从提高与成为固化膜的基底的玻璃等基材的密合性的观点考虑,优选为10重量%以下,更优选为5重量%以下。
本发明的负型感光性树脂组合物可含有溶剂。通过含有溶剂,能将各成分均匀溶解。作为溶剂,可举出例如脂肪族烃、羧酸酯、酮、醚、醇类等。可含有它们中的2种以上。从将各成分均匀溶解、提高得到的涂布膜的透明性的观点考虑,优选具有醇式羟基的化合物、具有羰基的环状化合物。
作为具有醇式羟基的化合物,可举出例如丙酮醇、3-羟基-3-甲基-2-丁酮、4-羟基-3-甲基-2-丁酮、5-羟基-2-戊酮、4-羟基-4-甲基-2-戊酮(二丙酮醇)、乳酸乙酯、乳酸丁酯、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单正丙基醚、丙二醇单正丁基醚、丙二醇单叔丁基醚、3-甲氧基-1-丁醇、3-甲基-3-甲氧基-1-丁醇等。这些中,从保存稳定性的观点考虑,优选二丙酮醇、3-甲基-3-甲氧基-1-丁醇。
作为具有羰基的环状化合物的具体例,可举出γ-丁内酯、γ-戊内酯、δ-戊内酯、碳酸亚丙酯、N-甲基吡咯烷酮、环己酮、环庚酮等。这些中,特别优选使用γ-丁内酯。
作为脂肪族烃,可举出例如二甲苯、乙基苯、溶剂石脑油(solvent naphtha)等。
作为羧酸酯,可举出例如乙酸苄酯、苯甲酸乙酯、γ-丁内酯、苯甲酸甲酯、丙二酸二乙酯、乙酸2-乙基己酯、乙酸2-丁氧基乙酯、乙酸3-甲氧基-3-甲基丁酯、草酸二乙酯、乙酰乙酸乙酯、乙酸环己酯、乙酸3-甲氧基丁酯、乙酰乙酸甲酯、3-乙氧基丙酸乙酯、乙酸2-乙基丁酯、丙酸异戊酯、丙二醇单甲基醚丙酸酯、丙二醇单乙基醚乙酸酯、乙酸乙酯、乙酸丁酯、乙酸异戊酯、乙酸戊酯、丙二醇单甲基醚乙酸酯等。
作为酮,可举出例如环戊酮、环己酮等。
作为醚,可举出例如丙二醇单甲基醚、丙二醇单乙基醚、丙二醇叔丁基醚、二丙二醇单甲基醚等丙二醇衍生物等脂肪族醚类等。
从适度地调节将本发明的负型感光性树脂组合物涂布于玻璃基板时的挥发性及干燥特性、提高涂布性的观点考虑,优选含有大气压下的沸点为150℃以上且250℃以下的有机溶剂、和大气压下的沸点低于150℃的有机溶剂。大气压下的沸点为150℃以上且250℃以下的有机溶剂的沸点更优选为150℃以上且200℃以下。
作为大气压下的沸点为150℃以上且250℃以下的有机溶剂,可举出例如4-羟基-4-甲基-2-戊酮(二丙酮醇)、乳酸乙酯、乳酸丁酯、丙二醇单叔丁基醚、3-甲氧基-1-丁醇、3-甲基-3-甲氧基-1-丁醇、乙酸苄酯、苯甲酸乙酯、苯甲酸甲酯、丙二酸二乙酯、乙酸2-乙基己酯、乙酸2-丁氧基乙酯、乙酸3-甲氧基-3-甲基丁酯、草酸二乙酯、乙酰乙酸乙酯、乙酸环己酯、乙酸3-甲氧基丁酯、乙酰乙酸甲酯、3-乙氧基丙酸乙酯、丙酸异戊酯、丙二醇单甲基醚丙酸酯、γ-丁内酯、γ-戊内酯、δ-戊内酯、碳酸亚丙酯、N-甲基吡咯烷酮、环己酮、环庚酮等。这些中,特别优选使用4-羟基-4-甲基-2-戊酮(二丙酮醇)、3-甲基-3-甲氧基-1-丁醇、乙酸3-甲氧基-3-甲基丁酯、乙酸3-甲氧基丁酯、γ-丁内酯。
作为大气压下的沸点低于150℃的有机溶剂,可举出例如乙酸甲酯、乙酸乙酯、乙酸异丙酯、乙酸正丙酯、乙酸丁酯、乙二醇单甲基醚乙酸酯、丙二醇单甲基醚乙酸酯、丙二醇单甲基醚、丙二醇单乙基醚、乙二醇乙基醚、乙二醇甲基醚、丁醇、异丁醇、正丙醇、乙酸乙酯等。这些中,特别优选使用丙二醇单甲基醚乙酸酯、丙二醇单甲基醚。
本发明的负型感光性树脂组合物可含有表面活性剂。通过含有表面活性剂,能提高涂布时的流动性。作为表面活性剂,可举出例如氟系表面活性剂;聚硅氧烷系表面活性剂;含氟热分解性表面活性剂;聚醚改性硅氧烷系表面活性剂;聚环氧烷系表面活性剂;聚(甲基)丙烯酸酯系表面活性剂;月桂基硫酸铵、聚氧乙烯烷基醚硫酸三乙醇胺等阴离子表面活性剂;硬脂基胺乙酸酯、月桂基三甲基氯化铵等阳离子表面活性剂;月桂基二甲基胺氧化物、月桂基羧甲基羟基乙基咪唑鎓甜菜碱等两性表面活性剂;聚氧乙烯月桂基醚、聚氧乙烯硬脂基醚、山梨糖醇酐单硬脂酸酯等非离子表面活性剂等。可含有它们中的2种以上。
这些中,从在抑制缩孔(cissing)等涂布性不良的同时、降低表面张力、抑制涂膜干燥时的不均的观点考虑,优选氟系表面活性剂、聚硅氧烷系表面活性剂、含氟热分解性表面活性剂、聚醚改性硅氧烷系表面活性剂,更优选含氟热分解性表面活性剂。
作为氟系表面活性剂的市售品,可举出例如“MEGAFAC”(注册商标)F142D、MEGAFACF172、MEGAFAC F173、MEGAFAC F183、MEGAFAC F445、MEGAFAC F470、MEGAFAC F475、MEGAFACF477(以上为DIC株式会社制)、NBX-15、FTX-218(NEOS COMPANY LIMITED制)等。作为聚硅氧烷系表面活性剂的市售品,可举出例如“BYK”(注册商标)-333、BYK-301、BYK-331、BYK-345、BYK-307(BYK-Chemie Japan Co.,Ltd.制)等。作为含氟热分解性表面活性剂的市售品,可举出例如“MEGAFAC”(注册商标)DS-21(DIC株式会社制)等。作为聚醚改性硅氧烷系表面活性剂的市售品,可举出例如“BYK”(注册商标)-345、BYK-346、BYK-347、BYK-348、BYK-349(以上为BYK-Chemie Japan Co.,Ltd.制)、“Silface”(注册商标)SAG002、Silface SAG005、Silface SAG0503A、Silface SAG008(以上为日信化学工业株式会社制)等。
本发明的负型感光性树脂组合物可含有分散剂。作为分散剂,可举出例如聚丙烯酸系分散剂、聚羧酸系分散剂、磷酸系分散剂、聚硅氧烷系分散剂等。
本发明的负型感光性树脂组合物可含有(A)硅氧烷树脂以外的树脂,例如,可含有(A)硅氧烷树脂以外的硅氧烷树脂。
接下来,对本发明的负型感光性树脂组合物的制造方法进行说明。作为本发明的负型感光性树脂组合物的制造方法,通常为下述方法:对(A)硅氧烷树脂、(B)反应性单体、(C)光自由基聚合引发剂、(D)二氧化硅粒子、(E)具有氧杂环丁基的硅氧烷化合物及根据需要的其他成分进行搅拌·混合。
通过使本发明的负型感光性树脂组合物固化,能得到本发明的固化膜。
从进一步提高玻璃表面强度的观点考虑,固化膜的膜厚优选为1μm以上。另一方面,从进一步提高与有机膜、无机膜的密合性的观点考虑,固化膜的膜厚优选为10μm以下,更优选为7μm以下,进一步优选为5μm以下。
接下来,举例对由本发明的负型感光性树脂组合物形成固化膜的方法进行说明。
将负型感光性树脂组合物涂布于玻璃基板上,得到涂膜。作为玻璃基板,可举出例如钠钙玻璃、无碱玻璃、石英玻璃、铝硅酸盐玻璃、及使用了这些玻璃的化学强化玻璃等。作为涂布方法,可举出例如使用了旋转器的旋转涂布、喷雾涂布、喷墨涂布、模涂、辊涂等。涂膜的膜厚可根据涂布方法等适当选择。通常,使干燥后的膜厚为1~150μm。
将得到的涂膜干燥,得到干燥膜。作为干燥方法,可举出例如加热干燥、空气干燥、减压干燥、红外线照射等。作为加热干燥装置,可举出例如烘箱、加热板等。干燥温度优选为50~150℃,干燥时间优选为1分钟~数小时。
隔着具有所期望的图案的掩模向得到的干燥膜照射化学射线,得到曝光膜。作为照射的化学射线,可举出例如紫外线、可见光线、电子束、X射线等。优选向本发明的着色树脂组合物照射汞灯的i射线(365nm)、h射线(405nm)、g射线(436nm)。
通过使用碱性显影液等对得到的曝光膜进行显影,从而将未曝光部除去,得到图案。作为可用于碱性显影液的碱性化合物,可举出例如氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、硅酸钠、偏硅酸钠、氨水等无机碱类;乙基胺、正丙基胺等伯胺类;二乙基胺、二正丙基胺等仲胺类;三乙基胺、甲基二乙基胺等叔胺类;四甲基氢氧化铵(TMAH)等四烷基氢氧化铵类、胆碱等季铵盐;三乙醇胺、二乙醇胺、单乙醇胺、二甲基氨基乙醇、二乙基氨基乙醇等醇胺类;吡咯、哌啶、1,8-二氮杂双环[5,4,0]-7-十一碳烯、1,5-二氮杂双环[4,3,0]-5-壬烷、吗啉等环状胺类等有机碱类。
碱性显影液中的碱性化合物的浓度通常为0.01~50质量%,优选为0.02~1质量%。另外,为了使显影后的图案形状更良好,也可添加0.1~5质量%非离子系表面活性剂等表面活性剂。此外,显影液为碱水溶液的情况下,也可向显影液中添加乙醇、γ-丁内酯、二甲基甲酰胺、N-甲基-2-吡咯烷酮等水溶性有机溶剂。
作为显影方法,可举出例如浸渍法、喷雾法、旋覆浸没法等。也可使用纯水等对得到的图案进行漂洗。
通过对得到的图案进行加热处理(后烘烤),能得到经图案化的固化膜。加热处理可在空气中、氮气氛下、真空状态的任意中进行。加热温度优选为150~300℃,加热时间优选为0.25~5小时。可使加热温度连续地变化,也可使加热温度阶段性地变化。
在不需要使固化膜图案化的情况下,也优选对干燥膜整面进行曝光,使固化膜光固化,然后进行加热处理。通过在加热处理前进行光固化,能抑制加热处理中的急剧的膜收缩,能进一步提高固化膜与玻璃基板的密合性。
本发明的负型感光性树脂组合物可合适地用于形成向智能手机、平板PC等的显示装置、车载显示器、仪表盘的前表面所赋予的覆盖玻璃的玻璃强化树脂层。
通过使本发明的负型感光性树脂组合物固化,能得到本发明的玻璃强化树脂层。玻璃强化树脂层起着降低玻璃的易破裂性的增强层的作用。通过在玻璃基板上形成玻璃强化树脂层,能进一步提高玻璃的表面强度。
从进一步提高玻璃表面强度的观点考虑,玻璃强化树脂层的厚度优选为1μm以上。另一方面,从进一步提高与有机膜、无机膜的密合性的观点考虑,玻璃强化树脂层的厚度优选为10μm以下,更优选为7μm以下,进一步优选为5μm以下。
本发明的强化玻璃在玻璃基板上具有本发明的玻璃强化树脂层。
实施例
以下,使用实施例及比较例,进一步详细地说明本发明,但本发明不受以下的实施例的限制。
<评价方法>
“透过率”
对于通过各实施例及比较例得到的5cm见方的TEMPAX玻璃基板上的固化膜,使用紫外-可见分光光度计UV-2600(株式会社岛津制作所制),测定波长400nm处的透过率。
“膜应力”
对于通过各实施例及比较例得到的4英寸硅晶圆上的固化膜,使用薄膜应力测定装置(Toho Technology Corporation制),测定室温23℃时的膜应力。
“维氏硬度”
对于通过各实施例及比较例得到的5cm见方的TEMPAX玻璃基板上的固化膜,使用超微小硬度试验装置(Fischer Instruments公司制),按照ISO-14577-1,测定载荷除去速度为0.5mN、室温为23℃时的维氏硬度。
“玻璃表面强度”
将通过各实施例及比较例得到的后烘烤膜放置于支承环上,在以10mm/min的速度按压承载环/>时,利用静态试验装置AG-Xplus(株式会社岛津制作所制)测定玻璃断裂的强度,基于以下的基准判定玻璃表面强度。从工业利用的观点考虑,将A+、A及B作为合格。需要说明的是,无固化膜的仅玻璃时的玻璃表面强度为800MPa。
A+:玻璃表面强度为1200MPa以上。
A:玻璃表面强度为1000MPa以上。
B:玻璃表面强度为900MPa以上且低于100MPa。
C:玻璃表面强度为800以上且低于900MPa。
D:玻璃表面强度低于800MPa。
“与有机膜的密合性”
使用丝网印刷机,以干燥后膜厚成为8μm的方式,在通过各实施例及比较例得到的后烘烤膜上涂布黑色油墨(Teikoku Printing Inks Mfg.Co.,Ltd.制,GLS-HF979),利用热风烘箱,于160℃加热1小时,进行热固化。将层叠有固化膜及黑色膜的玻璃基板在沸腾的纯水中浸渍10分钟,进行干燥,然后按照JIS“K5400”8.5.2(1990)棋盘格胶带法,对固化膜与黑色膜的密合性进行评价。即,在玻璃基板上的固化膜与黑色油墨的层叠膜表面,使用切割刀以到达玻璃板的基底的方式,以1mm的间隔划出正交的纵横各11条平行的直线,制作100个1mm×1mm的方格。在经切割的ITO表面上贴合透明胶带(宽度=18mm,粘合力=3.7N/10mm),用橡皮擦(JIS S6050合格品)摩擦,使其密合,把持胶带的一端,保持与板垂直,瞬间剥离,通过目视对此时的方格的残留数进行计数。通过方格的剥离面积,按照以下的方式进行判断,将4B以上设为合格。
5B:剥离面积为0%
4B:剥离面积为大于0%且小于5%
3B:剥离面积为5%以上且小于15%
2B:剥离面积为15%以上且小于35%
1B:剥离面积为35%以上且小于65%
0B:剥离面积为65%以上且小于100%。
“与无机膜的密合性”
在通过各实施例及比较例得到的后烘烤膜上,以膜厚成为100nm的方式,于90℃蒸镀SiO2,进而,以膜厚成为100nm的方式,于90℃蒸镀Nb2O5。将层叠有固化膜、SiO2膜及Nb2O5膜的玻璃基板在沸腾的纯水中浸渍10分钟,进行干燥,然后按照JIS“K5400”8.5.2(1990)棋盘格胶带法,对固化膜与无机膜的密合性进行评价。即,在玻璃基板上的固化膜与无机膜的层叠膜表面,使用切割刀以到达玻璃板的基底的方式,以1mm的间隔划出正交的纵横各11条平行的直线,制作100个1mm×1mm的方格。在经切割的ITO表面上贴合透明胶带(宽度=18mm,粘合力=3.7N/10mm),用橡皮擦(JIS S6050合格品)摩擦,使其密合,把持胶带的一端,保持与板垂直,瞬间剥离,通过目视对此时的方格的残留数进行计数。通过方格的剥离面积,按照以下的方式进行判断,将4B以上设为合格。
5B:剥离面积为0%
4B:剥离面积为大于0%且小于5%
3B:剥离面积为5%以上且小于15%
2B:剥离面积为15%以上且小于35%
1B:剥离面积为35%以上且小于65%
0B:剥离面积为65%以上且小于100%。
〔合成例1〕
在500mL的三颈瓶中装入甲基三甲氧基硅烷47.67g(0.35mol)、苯基三甲氧基硅烷39.66g(0.20mol)、3-三甲氧基甲硅烷基丙基琥珀酸26.23g(0.10mol)、γ-丙烯酰基丙基三甲氧基硅烷82.04g(0.35mol)、二丙酮醇(以下,记为“DAA”)180.56g,浸渍于40℃的油浴,一边搅拌,一边用滴液漏斗经10分钟添加在水55.8g中溶解磷酸0.401g(相对于装入单体而言为0.2质量份)而成的磷酸水溶液。于40℃进行1小时搅拌,然后,将油浴温度设定为70℃,进行1小时搅拌,进一步经30分钟将油浴升温至115℃。升温开始1小时后,溶液的内温达到100℃,从此时开始进行2小时加热搅拌(内温为100~110℃)。反应中,作为副产物的甲醇及水合计馏出120g。以聚合物浓度成为40质量%的方式,向得到的聚硅氧烷的DAA溶液中添加DAA,得到聚硅氧烷溶液(PS-1)。需要说明的是,利用GPC对得到的聚合物的重均分子量(以下,记为“Mw”)进行测定,结果为5000(聚苯乙烯换算)。
〔合成例2〕
在500mL的三颈瓶中装入甲基三甲氧基硅烷40.86g(0.30mol)、苯基三甲氧基硅烷29.75g(0.15mol)、3-三甲氧基甲硅烷基丙基琥珀酸13.12g(0.05mol)、γ-丙烯酰基丙基三甲氧基硅烷117.20g(0.50mol)、DAA 180.56g,浸渍于40℃的油浴,一边搅拌,一边用滴液漏斗经10分钟添加在水55.8g中溶解磷酸0.401g(相对于装入单体而言为0.2质量份)而成的磷酸水溶液。于40℃进行1小时搅拌,然后,将油浴温度设定为70℃,进行1小时搅拌,进一步经30分钟将油浴升温至115℃。升温开始1小时后,溶液的内温达到100℃,从此时开始进行2小时加热搅拌(内温为100~110℃)。反应中,作为副产物的甲醇及水合计馏出120g。以聚合物浓度成为40质量%的方式,向得到的聚硅氧烷的DAA溶液中添加DAA,得到聚硅氧烷溶液(PS-2)。需要说明的是,利用GPC对得到的聚合物的Mw进行测定,结果为5000(聚苯乙烯换算)。
〔合成例3〕
在500mL的三颈瓶中装入甲基三甲氧基硅烷47.67g(0.35mol)、苯基三甲氧基硅烷49.58g(0.25mol)、3-三甲氧基甲硅烷基丙基琥珀酸52.46g(0.20mol)、γ-丙烯酰基丙基三甲氧基硅烷46.88g(0.20mol),DAA)180.56g,浸渍于40℃的油浴,一边搅拌,一边用滴液漏斗经10分钟添加在水55.8g中溶解磷酸0.401g(相对于装入单体而言为0.2质量份)而成的磷酸水溶液。于40℃进行1小时搅拌,然后,将油浴温度设定为70℃,进行1小时搅拌,进一步经30分钟将油浴升温至115℃。升温开始1小时后,溶液的内温达到100℃,从此时开始进行2小时加热搅拌(内温为100~110℃)。反应中,作为副产物的甲醇及水合计馏出120g。以聚合物浓度成为40质量%的方式,向得到的聚硅氧烷的DAA溶液中添加DAA,得到聚硅氧烷溶液(PS-3)。需要说明的是,利用GPC对得到的聚合物的Mw进行测定,结果为5000(聚苯乙烯换算)。
〔合成例4〕
在500ml的烧瓶中装入2,2’-偶氮双(异丁腈)3g、PGMEA丙二醇甲基醚乙酸酯(以下,记为“PGMEA”)50g。然后,装入甲基丙烯酸30g、甲基丙烯酸苄酯35g、甲基丙烯酸三环[5.2.1.02,6]癸烷-8-基酯35g,在室温下短暂搅拌,对烧瓶内进行氮气置换,然后,于70℃进行5小时加热搅拌。接下来,向得到的溶液中添加甲基丙烯酸缩水甘油酯15g、二甲基苄基胺1g、对甲氧基苯酚0.2g、PGMEA 100g,于90℃进行4小时加热搅拌,得到丙烯酸树脂溶液(PA-1)。以固态成分浓度成为40重量%的方式,向得到的丙烯酸树脂溶液(PA-1)中添加PGMEA。丙烯酸树脂的Mw为10000,酸值为118mgKOH/g。
〔实施例1〕
在黄色灯下,将苯基双(2,4,6-三甲基苯甲酰基)氧化膦(商品名“‘Irgacure’(注册商标)819”Ciba Specialty Chemicals Inc.制)1.52g、四乙酰丙酮锆(商品名“ORGATIXZC-150”Matsumoto Fine Chemical Co.Ltd.制)1.30g溶解于DAA(沸点=160℃)23.96g、PGMEA(沸点=146℃)1.53g、3-甲基-3-甲氧基-1-丁醇(沸点=174℃,以下记为“MMB”)14.80g的混合溶剂中,添加具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”0.98g、三(2-羟基乙基)异氰脲酸的丙烯酸酯(商品名“‘ARONIX’(注册商标)M-315”东亚合成株式会社制)4.35g、3-氨基丙基三甲氧基硅烷(商品名“KBM-903”信越化学工业株式会社制)0.43g、聚硅氧烷溶液(PS-1)21.74g、二氧化硅粒子的PGMEA30重量%分散液(平均粒径=20~30nm,商品名“PMA-ST”日产化学工业株式会社制)28.99g和含氟热分解性表面活性剂(商品名“DS-21”DIC株式会社制)的PGMEA5重量%溶液0.40g(相当于浓度为200ppm),进行搅拌。接下来,用1.00μm的过滤器进行过滤,制备固态成分浓度为26重量%的负型感光性树脂组合物C-1。
使用旋涂机(MIKASA株式会社制MS-A150),在膜厚为0.7μm的无碱玻璃(Corning制“1737”材料)基板上、4英寸硅晶圆上、5cm见方的TEMPAX玻璃基板(AGC TECHNO GLASS Co.,Ltd.制)上,分别旋涂得到的负型感光性树脂组合物C-1,然后,用90℃的加热板进行2分钟预烘烤,得到预烘烤膜。然后,使用DAINIPPON SCREEN MFG.CO.,LTD.制曝光机“XG-5000”,以500mJ/cm2进行曝光,用180℃的热风烘箱进行30分钟熟化。如上所述地操作,制作厚度为1.5μm的固化膜A-1,将评价的结果示于表2。
〔实施例2〕
代替具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,添加具有氧杂环丁基的硅氧烷化合物“OX-SQ TX-100”,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-2。使用负型感光性树脂组合物C-2,与实施例1同样地操作,制作固化膜A-2,将评价的结果示于表2。
〔实施例3〕
代替具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,添加具有氧杂环丁基的硅氧烷化合物“OX-SQ SI-20”,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-3。使用负型感光性树脂组合物C-3,与实施例1同样地操作,制作固化膜A-3,将评价的结果示于表2。
〔实施例4〕
使聚硅氧烷溶液(PS-1)的添加量为17.39g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为34.78g,使PGMEA的添加量为6.35g,使DAA的添加量为17.68g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-4。使用负型感光性树脂组合物C-4,与实施例1同样地操作,制作固化膜A-4,将评价的结果示于表2。
〔实施例5〕
使聚硅氧烷溶液(PS-1)的添加量为10.87g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为43.48g,使PGMEA的添加量为0.26g,使DAA的添加量为21.60g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-5。使用负型感光性树脂组合物C-5,与实施例1同样地操作,制作固化膜A-5,将评价的结果示于表2。
〔实施例6〕
使聚硅氧烷溶液(PS-1)的添加量为30.44g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为17.39g,使PGMEA的添加量为9.65g,使DAA的添加量为18.74g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-6。使用负型感光性树脂组合物C-6,与实施例1同样地操作,制作固化膜A-6,将评价的结果示于表2。
〔实施例7〕
使聚硅氧烷溶液(PS-1)的添加量为36.96g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为8.70g,使PGMEA的添加量为15.73g,使DAA的添加量为14.82g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-7。使用负型感光性树脂组合物C-7,与实施例1同样地操作,制作固化膜A-7,将评价的结果示于表2。
〔实施例8〕
使苯基双(2,4,6-三甲基苯甲酰基)氧化膦“‘Irgacure’(注册商标)819”的添加量为1.45g,使四乙酰丙酮锆“ORGATIX ZC-150”的添加量为1.25g,使聚硅氧烷溶液(PS-1)的添加量为20.78g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为27.71g,使具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”的添加量为2.08g,使三(2-羟基乙基)异氰脲酸的丙烯酸酯“‘ARONIX’(注册商标)M-315”的添加量为4.16g,使3-氨基丙基三甲氧基硅烷“KBM-903”的添加量为0.42g,使PGMEA的添加量为2.42g,使DAA的添加量为24.53g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-8。使用负型感光性树脂组合物C-8,与实施例1同样地操作,制作固化被膜A-8,将评价的结果示于表2。
〔实施例9〕
使苯基双(2,4,6-三甲基苯甲酰基)氧化膦“‘Irgacure’(注册商标)819”的添加量为1.57g,使四乙酰丙酮锆“ORGATIX ZC-150”的添加量为1.34g,使聚硅氧烷溶液(PS-1)的添加量为22.40g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为29.86g,使具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”的添加量为0.22g,使三(2-羟基乙基)异氰脲酸的丙烯酸酯“‘ARONIX’(注册商标)M-315”的添加量为4.48g,使3-氨基丙基三甲氧基硅烷“KBM-903”的添加量为0.45g,使PGMEA的添加量为0.92g,使DAA的添加量为23.56g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-9。使用负型感光性树脂组合物C-9,与实施例1同样地操作,制作固化膜A-9,将评价的结果示于表2。
〔实施例10〕
代替聚硅氧烷溶液(PS-1),添加聚硅氧烷溶液(PS-2),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-10。使用负型感光性树脂组合物C-10,与实施例1同样地操作,制作固化膜A-10,将评价的结果示于表2。
〔实施例11〕
代替聚硅氧烷溶液(PS-1),添加聚硅氧烷溶液(PS-3),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-11。使用负型感光性树脂组合物C-11,与实施例1同样地操作,制作固化膜A-11,将评价的结果示于表2。
〔实施例12〕
未添加四乙酰丙酮锆“ORGATIX ZC-150”,使苯基双(2,4,6-三甲基苯甲酰基)氧化膦“‘Irgacure’(注册商标)819”的添加量为1.60g,使聚硅氧烷溶液(PS-1)的添加量为22.89g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为30.52g,使具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”的添加量为1.03g,使三(2-羟基乙基)异氰脲酸的丙烯酸酯“‘ARONIX’(注册商标)M-315”的添加量为4.58g,使3-氨基丙基三甲氧基硅烷“KBM-903”为0.46g,使PGMEA的添加量为0.46g,使DAA的添加量为23.27g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-12。使用负型感光性树脂组合物C-12,与实施例1同样地操作,制作固化膜A-12,将评价的结果示于表2。
〔实施例13〕
使用负型感光性树脂组合物C-1,与实施例1同样地操作,制作0.5μm的固化膜A-13,将评价的结果示于表2。
〔实施例14〕
使用负型感光性树脂组合物C-1,与实施例1同样地操作,制作3μm的固化膜A-14,将评价的结果示于表2。
〔实施例15〕
使用负型感光性树脂组合物C-1,与实施例1同样地操作,制作5μm的固化膜A-15,将评价的结果示于表2。
〔实施例16〕
使用负型感光性树脂组合物C-1,与实施例1同样地操作,制作7μm的固化膜A-16,将评价的结果示于表2。
〔实施例17〕
使用负型感光性树脂组合物C-1,与实施例1同样地操作,制作10μm的固化膜A-17,将评价的结果示于表2。
〔比较例1〕
代替具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,添加不具有硅氧烷键的具有氧杂环丁基的化合物(商品名“‘ARONE OXETANE’(注册商标)OXT-101”东亚合成株式会社制),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-13。使用负型感光性树脂组合物C-13,与实施例1同样地操作,制作固化膜A-18,将评价的结果示于表2。
〔比较例2〕
代替具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,添加不具有硅氧烷键的具有氧杂环丁基的化合物(商品名“‘ARONE OXETANE’(注册商标)OXT-121”东亚合成株式会社制),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-14。使用负型感光性树脂组合物C-14,与实施例1同样地操作,制作固化膜A-19,将评价的结果示于表2。
〔比较例3〕
代替具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,添加不具有硅氧烷键的具有氧杂环丁基的化合物(商品名“‘ARONE OXETANE’(注册商标)OXT-221”东亚合成株式会社制),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-15。使用负型感光性树脂组合物C-15,与实施例1同样地操作,制作固化膜A-20,将评价的结果示于表2。
〔比较例4〕
未添加二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”,使聚硅氧烷溶液(PS-1)的添加量为43.48g,使PGMEA的添加量为21.82g,使DAA的添加量为10.91g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-16。使用负型感光性树脂组合物C-16,与实施例1同样地操作,制作固化膜A-21,将评价的结果示于表2。
〔比较例5〕
未添加具有氧杂环丁基的硅氧烷化合物“‘ARONE OXETANE’(注册商标)OXT-191”,使苯基双(2,4,6-三甲基苯甲酰基)氧化膦“‘Irgacure’(注册商标)819”的添加量为1.58g,使聚硅氧烷溶液(PS-1)的添加量为22.59g,使二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”的添加量为30.12g,使三(2-羟基乙基)异氰脲酸的丙烯酸酯“‘ARONIX’(注册商标)M-315”的添加量为4.52g,使3-氨基丙基三甲氧基硅烷“KBM-903”为0.45g,使PGMEA的添加量为0.73g,使DAA的添加量为23.45g,除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-17。使用负型感光性树脂组合物C-17,与实施例1同样地操作,制作固化膜A-22,将评价的结果示于表2。
〔比较例6〕
代替二氧化硅粒子的PGMEA30重量%分散液“PMA-ST”,添加氧化锆粒子的PGMEA30重量%分散液(商品名“ZRPMA”,CIK Nanotec Co.,Ltd.制),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-18。使用负型感光性树脂组合物C-18,与实施例1同样地操作,制作固化膜A-23,将评价的结果示于表2。
〔比较例7〕
代替聚硅氧烷溶液(PS-1),添加丙烯酸树脂溶液(PA-1),除此之外,与实施例1同样地操作,制备负型感光性树脂组合物C-19。使用负型感光性树脂组合物C-19,与实施例1同样地操作,制作固化膜A-24,将评价的结果示于表2。
将各实施例及比较例中的负型感光性树脂组合物的组成(不包括溶剂)示于表1,将评价结果示于表2。
[表1]
[表2]
[表2]
对于实施例中制作的负型感光性树脂组合物而言,可知形成固化膜时的玻璃表面强度高,且与无机膜、有机膜的密合性优异。
产业上的可利用性
对于本发明的感光性负型感光性树脂组合物而言,由于能形成玻璃表面强度高、且与无机膜、有机膜的密合性优异的固化膜,因而,能形成适用于智能手机等显示装置的可靠性优异的覆盖玻璃。
Claims (6)
1.负型感光性树脂组合物,其含有:(A)具有自由基聚合性基团、和羧基及/或二羧酸酐基的硅氧烷树脂、(B)反应性单体、(C)光自由基聚合引发剂、(D)二氧化硅粒子、(E)具有氧杂环丁基的硅氧烷化合物、及下述通式(19)表示的金属螯合物化合物,其中,在所述负型感光性树脂组合物的固态成分中含有20~40重量%的所述(D)二氧化硅粒子
[化学式1]
所述通式(19)中,M表示金属原子,R45表示氢、烷基、芳基或链烯基,R46及R47各自独立地表示氢、烷基、芳基、链烯基或烷氧基,e表示金属原子M的原子价,f表示0~e的整数。
2.固化膜,其是由权利要求1所述的负型感光性树脂组合物的固化物形成的。
3.如权利要求1所述的负型感光性树脂组合物,其用于形成玻璃强化树脂层。
4.玻璃强化树脂层,其是由权利要求1所述的负型感光性树脂组合物的固化物形成的。
5.如权利要求4所述的玻璃强化树脂层,其厚度为10μm以下。
6.强化玻璃,其中,在玻璃基板上具有权利要求4或5所述的玻璃强化树脂层。
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