WO2009096050A1 - シロキサン系樹脂組成物 - Google Patents
シロキサン系樹脂組成物 Download PDFInfo
- Publication number
- WO2009096050A1 WO2009096050A1 PCT/JP2008/059689 JP2008059689W WO2009096050A1 WO 2009096050 A1 WO2009096050 A1 WO 2009096050A1 JP 2008059689 W JP2008059689 W JP 2008059689W WO 2009096050 A1 WO2009096050 A1 WO 2009096050A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- siloxane
- based resin
- resin composition
- general formula
- Prior art date
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 201
- 239000011342 resin composition Substances 0.000 title claims abstract description 169
- 150000001875 compounds Chemical class 0.000 claims abstract description 178
- 229920005989 resin Polymers 0.000 claims abstract description 47
- 239000011347 resin Substances 0.000 claims abstract description 47
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 8
- -1 aluminum compound Chemical class 0.000 claims description 91
- 239000002245 particle Substances 0.000 claims description 74
- 239000007787 solid Substances 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000000962 organic group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 229910052710 silicon Inorganic materials 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 20
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 238000006482 condensation reaction Methods 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 230000003287 optical effect Effects 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 238000003384 imaging method Methods 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 150000003377 silicon compounds Chemical class 0.000 claims description 5
- 150000003606 tin compounds Chemical class 0.000 claims description 4
- 150000003609 titanium compounds Chemical class 0.000 claims description 4
- 150000003755 zirconium compounds Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 abstract description 4
- 239000010408 film Substances 0.000 description 132
- 239000000243 solution Substances 0.000 description 125
- 238000000034 method Methods 0.000 description 70
- 238000002834 transmittance Methods 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 47
- 229920000642 polymer Polymers 0.000 description 39
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 34
- 238000011156 evaluation Methods 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 30
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- 229910000077 silane Inorganic materials 0.000 description 27
- 238000006460 hydrolysis reaction Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 19
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 18
- 238000000576 coating method Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 15
- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 14
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 14
- 230000007062 hydrolysis Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 229920001296 polysiloxane Polymers 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 239000002612 dispersion medium Substances 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical class [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 6
- QMYDVDBERNLWKB-UHFFFAOYSA-N propane-1,2-diol;hydrate Chemical compound O.CC(O)CO QMYDVDBERNLWKB-UHFFFAOYSA-N 0.000 description 6
- 229910001928 zirconium oxide Inorganic materials 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 5
- 239000011246 composite particle Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000005462 imide group Chemical group 0.000 description 5
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 4
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 4
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 4
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 4
- KSMGAOMUPSQGTB-UHFFFAOYSA-N 9,10-dibutoxyanthracene Chemical compound C1=CC=C2C(OCCCC)=C(C=CC=C3)C3=C(OCCCC)C2=C1 KSMGAOMUPSQGTB-UHFFFAOYSA-N 0.000 description 4
- LBQJFQVDEJMUTF-UHFFFAOYSA-N 9,10-dipropoxyanthracene Chemical compound C1=CC=C2C(OCCC)=C(C=CC=C3)C3=C(OCCC)C2=C1 LBQJFQVDEJMUTF-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- 229940014800 succinic anhydride Drugs 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 4
- RYNQKSJRFHJZTK-UHFFFAOYSA-N (3-methoxy-3-methylbutyl) acetate Chemical compound COC(C)(C)CCOC(C)=O RYNQKSJRFHJZTK-UHFFFAOYSA-N 0.000 description 3
- WVEBRTCXZNCHBT-UHFFFAOYSA-N 1-[4-[(2-methylphenyl)methylsulfanylmethyl]phenyl]ethanone trifluoromethanesulfonic acid Chemical compound FC(S(=O)(=O)[O-])(F)F.CC1=C(C[SH+]CC2=CC=C(C=C2)C(C)=O)C=CC=C1 WVEBRTCXZNCHBT-UHFFFAOYSA-N 0.000 description 3
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- JHEXHONJLZFOFQ-UHFFFAOYSA-N 4-(benzylsulfanylmethyl)phenol trifluoromethanesulfonic acid Chemical compound [O-]S(=O)(=O)C(F)(F)F.Oc1ccc(C[SH+]Cc2ccccc2)cc1 JHEXHONJLZFOFQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004642 Polyimide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 229930188620 butyrolactone Natural products 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229920001721 polyimide Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 229910001887 tin oxide Inorganic materials 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- NJMCHQONLVUNAM-UHFFFAOYSA-N (2-nitrophenyl)methyl n-cyclohexylcarbamate Chemical compound [O-][N+](=O)C1=CC=CC=C1COC(=O)NC1CCCCC1 NJMCHQONLVUNAM-UHFFFAOYSA-N 0.000 description 2
- QAEDNLDMOUKNMI-UHFFFAOYSA-O (4-hydroxyphenyl)-dimethylsulfanium Chemical compound C[S+](C)C1=CC=C(O)C=C1 QAEDNLDMOUKNMI-UHFFFAOYSA-O 0.000 description 2
- 0 *[Si](*)(*)*NC(c1cc(Oc(cc2)cc(C(N*[Si](*)(*)*)=O)c2C(O)=O)ccc1C(O)=O)=O Chemical compound *[Si](*)(*)*NC(c1cc(Oc(cc2)cc(C(N*[Si](*)(*)*)=O)c2C(O)=O)ccc1C(O)=O)=O 0.000 description 2
- KGUMNRYFUFLBGA-UHFFFAOYSA-N 1,4-dihydropyridine-3-carboxamide Chemical compound NC(=O)C1=CNC=CC1 KGUMNRYFUFLBGA-UHFFFAOYSA-N 0.000 description 2
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 2
- NOHNQBSUXAVDOP-UHFFFAOYSA-N 1-[4-[(2-methylphenyl)methylsulfanylmethyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1CSCC1=CC=CC=C1C NOHNQBSUXAVDOP-UHFFFAOYSA-N 0.000 description 2
- PACGLQCRGWFBJH-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1 PACGLQCRGWFBJH-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-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 compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- JIUWLLYCZJHZCZ-UHFFFAOYSA-N 3-propyloxolane-2,5-dione Chemical compound CCCC1CC(=O)OC1=O JIUWLLYCZJHZCZ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- IOSONAGXTXMCDY-UHFFFAOYSA-N 4-(benzylsulfanylmethyl)phenol Chemical compound C1=CC(O)=CC=C1CSCC1=CC=CC=C1 IOSONAGXTXMCDY-UHFFFAOYSA-N 0.000 description 2
- STCQADFDVULNEN-UHFFFAOYSA-N 4-[(2-methylphenyl)methylsulfanylmethyl]phenol Chemical compound CC1=CC=CC=C1CSCC1=CC=C(O)C=C1 STCQADFDVULNEN-UHFFFAOYSA-N 0.000 description 2
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- VOARQMXRPHXHID-UHFFFAOYSA-N methyl-[3-(oxiran-2-ylmethoxy)propyl]-dipropoxysilane Chemical compound CCCO[Si](C)(OCCC)CCCOCC1CO1 VOARQMXRPHXHID-UHFFFAOYSA-N 0.000 description 1
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- LABYRQOOPPZWDG-UHFFFAOYSA-M naphthalene-1-sulfonate;triphenylsulfanium Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 LABYRQOOPPZWDG-UHFFFAOYSA-M 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- FMLYSTGQBVZCGN-UHFFFAOYSA-N oxosilicon(2+) oxygen(2-) titanium(4+) Chemical compound [O-2].[Ti+4].[Si+2]=O.[O-2].[O-2] FMLYSTGQBVZCGN-UHFFFAOYSA-N 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VPLNCHFJAOKWBT-UHFFFAOYSA-N phenyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)C1=CC=CC=C1 VPLNCHFJAOKWBT-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical class C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 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
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 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
- BPCXHCSZMTWUBW-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F BPCXHCSZMTWUBW-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-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
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 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
- 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
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- NLKPPXKQMJDBFO-UHFFFAOYSA-N triethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OCC)(OCC)OCC)CCC2OC21 NLKPPXKQMJDBFO-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- GSUGNQKJVLXBHC-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCOCC1CO1 GSUGNQKJVLXBHC-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
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- FFJVMNHOSKMOSA-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCCC([Si](OC)(OC)OC)OCC1CO1 FFJVMNHOSKMOSA-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- KKFKPRKYSBTUDV-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CC(CC)OCC1CO1 KKFKPRKYSBTUDV-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- DBUFXGVMAMMWSD-UHFFFAOYSA-N trimethoxy-[3-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(CCC[Si](OC)(OC)OC)CCC2OC21 DBUFXGVMAMMWSD-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 description 1
- ZOWVSEMGATXETK-UHFFFAOYSA-N trimethoxy-[4-(7-oxabicyclo[4.1.0]heptan-4-yl)butyl]silane Chemical compound C1C(CCCC[Si](OC)(OC)OC)CCC2OC21 ZOWVSEMGATXETK-UHFFFAOYSA-N 0.000 description 1
- GUKYSRVOOIKHHB-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCOCC1CO1 GUKYSRVOOIKHHB-UHFFFAOYSA-N 0.000 description 1
- PBRKCNMSBIMTKC-UHFFFAOYSA-N triphenyl-(10-triphenylsilylanthracen-9-yl)silane Chemical compound C1=CC=CC=C1[Si](C=1C2=CC=CC=C2C(=C2C=CC=CC2=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PBRKCNMSBIMTKC-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- 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
- C09D183/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
Definitions
- the present invention relates to a siloxane-based resin composition.
- the curable composition for an antireflection film for microlens containing titanium oxide particles coated with a metal element oxide, a curable compound, and a curing catalyst allows the light caused by the refractive index difference between the air medium and the microlens. It has been proposed to suppress reflection (see, for example, Patent Document 1). In addition, a variety of refractive index adjustments have been made to suppress reflection of light caused by refractive index differences between the light receiving unit and the color filter, between the color filter and the microlens, and to flatten the base step. A planarizing film is used.
- a coating material for such a flattened film for example, a siloxane-based resin composition obtained by hydrolyzing and condensing an alkoxysilane compound in the presence of metal compound particles (for example, see Patent Document 2), fluorine A thermosetting resin composition containing a fluorine-containing siloxane polymer containing a silane compound and an epoxy group-containing silane compound as a copolymerization component (for example, see Patent Document 3) is disclosed.
- the coating materials used for flattening film applications not only have the characteristics of completely covering and flattening the base step, but also have sufficient adhesion to the substrate surface, resin surface, and element surface made of base metal and inorganic materials. Sex is required.
- it is known to contain a silane coupling agent in order to improve adhesion (see, for example, Patent Documents 4 to 5).
- a silane coupling agent in order to improve adhesion (see, for example, Patent Documents 4 to 5).
- the silane coupling agents disclosed therein are added to the siloxane-based resin composition, sufficient adhesion cannot be obtained.
- JP 2005-283786 A JP 2007-246877 A JP 2007-119744 A JP 2003-43688 paragraph 0032
- Japanese Patent Laying-Open No. 2005-49791 paragraph 0109
- the present invention has been made based on the above circumstances, and provides a siloxane-based resin composition capable of obtaining a cured film having excellent adhesiveness.
- the present invention is a siloxane-based resin composition containing (a) a siloxane-based resin and (b) an imidosilane compound represented by the following general formula (4).
- the present invention also provides (a) a siloxane-based resin composition containing a siloxane-based resin, wherein the (a) siloxane-based resin is any one of (a-2) the following general formulas (1) to (3):
- a siloxane-based resin which is a reaction product obtained by hydrolyzing one or more alkoxysilane compounds represented by the above formula and an imidosilane compound represented by the following general formula (5) and subjecting the hydrolyzate to a condensation reaction It is a composition.
- R 7 may be the same or different and represents an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, a phenyl group, a phenoxy group, or a substituted product thereof.
- R 10 may be the same or different and each represents a trivalent organic group having 3 to 30 carbon atoms.
- R 11 may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- ⁇ represents an integer of 1 to 3.
- R 1 Si (OR 2 ) 3 (1)
- R 1 represents hydrogen, an alkyl group, an alkenyl group, an aryl group, or a substituted product thereof.
- R 2 may be the same or different and represents a methyl group, an ethyl group, a propyl group, an isopropyl group or a butyl group.
- R 3 and R 4 each represent hydrogen, an alkyl group, an alkenyl group, an aryl group or substituted versions thereof.
- R 5 may be the same or different and each represents a methyl group, an ethyl group, a propyl group, an isopropyl group or a butyl group.
- R 6 may be the same or different and represents a methyl group, an ethyl group, a propyl group, an isopropyl group, or a butyl group.
- R 8 and R 9 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a substituted product thereof.
- R 10 may be the same or different and each represents a trivalent organic group having 3 to 30 carbon atoms.
- R 11 may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- ⁇ represents an integer of 1 to 3, and ⁇ represents an integer of 0 to 2. However, ⁇ + ⁇ ⁇ 4.
- a cured film having excellent adhesiveness can be formed.
- the cured film obtained by using the siloxane-based resin composition of the present invention can be suitably used for optical articles such as a solid-state imaging device and a display optical filter.
- the siloxane-based resin composition of the present invention uses an imidosilane compound having a specific structure and can be classified into the following two types depending on the method of introducing the imidosilane compound.
- the first embodiment is a siloxane-based resin composition containing (a) a siloxane-based resin and (b) an imidosilane compound represented by the general formula (4).
- the imide silane compound as the component (b) described later, the adhesiveness of the obtained cured film can be dramatically improved.
- one or more alkoxysilane compounds represented by any one of the general formulas (1) to (3) and an imidosilane compound represented by the general formula (5) are hydrolyzed, It is a siloxane-based resin composition containing a siloxane-based resin that is a reaction product obtained by a condensation reaction of a hydrolyzate.
- a siloxane resin composition containing a siloxane-based resin that is a reaction product obtained by a condensation reaction of a hydrolyzate.
- the imidosilane compound represented by the general formula (4) or (5) serves as an adhesion improver.
- the siloxane-based resin refers to both a siloxane resin and a particle surface graft polysiloxane described later.
- the siloxane-based resin is not particularly limited as long as it is a resin having a continuous siloxane bond as a skeleton.
- (a-1) a reaction product obtained by hydrolyzing one or more alkoxysilane compounds represented by any one of the following general formulas (1) to (3) and subjecting the hydrolyzate to a condensation reaction
- the siloxane resin which is a thing is mentioned.
- R 1 represents hydrogen, an alkyl group, an alkenyl group, an aryl group, or a substituted product thereof.
- the alkyl group and alkenyl group preferably have 1 to 4 carbon atoms, and the aryl group preferably has 6 to 14 carbon atoms.
- Examples of the substituent introduced into the substituent include a halogen-containing group, an epoxy-containing group, an amino-containing group, a (meth) acryloyl-containing group, a cyano-containing group, a fluorene-containing group, and a vinyl group.
- R 2 may be the same or different and represents a methyl group, an ethyl group, a propyl group, an isopropyl group or a butyl group.
- the butyl group is preferably an n-butyl group.
- R 3 and R 4 each represent hydrogen, an alkyl group, an alkenyl group, an aryl group, or a substituted product thereof.
- the alkyl group and alkenyl group preferably have 1 to 4 carbon atoms, and the aryl group preferably has 6 to 14 carbon atoms.
- Examples of the substituent introduced into the substituent include a halogen-containing group, an epoxy-containing group, an amino-containing group, a (meth) acryloyl-containing group, and a vinyl group.
- R 5 may be the same or different and each represents a methyl group, an ethyl group, a propyl group, an isopropyl group or a butyl group.
- the butyl group is preferably an n-butyl group.
- R 6 may be the same or different and represents a methyl group, an ethyl group, a propyl group, an isopropyl group, or a butyl group. A methyl group or an ethyl group is preferred.
- Examples of the trifunctional alkoxysilane compound represented by the general formula (1) include methyltrimethoxysilane, methyltriethoxysilane, methyltripropoxysilane, methyltriisopropoxysilane, methyltributoxysilane, and ethyltrimethoxysilane.
- Ethyltriethoxysilane hexyltrimethoxysilane, octadecyltrimethoxysilane, octadecyltriethoxysilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltriisopropoxysilane, naphthyltrimethoxysilane, naphthyltriethoxysilane, naphthyltriisoiso Propoxysilane, anthracenyltrimethoxysilane, anthracenyltriethoxysilane, anthracenyltriisopropoxysilane, phenanthryltrimethoxy Silane, phenanthryl triethoxysilane, phenanthryl triisopropoxysilane, biphenyltrimethoxysilane, biphenyltriethoxysilane, biphenyltriisopropoxysi
- Examples of the bifunctional alkoxysilane compound represented by the general formula (2) include dimethyldimethoxysilane, dimethyldiethoxysilane, diphenyldimethoxysilane, diphenyldiethoxysilane, methylphenyldimethoxysilane, methylvinyldimethoxysilane, and methylvinyl.
- Examples of the tetrafunctional alkoxysilane compound represented by the general formula (3) include tetramethoxysilane and tetraethoxysilane.
- alkoxysilane compounds represented by any of the general formulas (1) to (3) may be used alone or in combination of two or more.
- the siloxane-based resin is (a-2) one type represented by any one of the general formulas (1) to (3). It is a reaction product obtained by hydrolyzing the above alkoxysilane compound and the imidosilane compound represented by the following general formula (5) and subjecting the hydrolyzate to a condensation reaction. Two or more of the alkoxysilane compounds and imidosilane compounds may be used in combination.
- R 8 and R 9 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a substituted product thereof.
- R 10 may be the same or different and each represents a trivalent organic group having 3 to 30 carbon atoms.
- R 11 may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- ⁇ represents an integer of 1 to 3, and ⁇ represents an integer of 0 to 2. However, ⁇ + ⁇ ⁇ 4.
- the imidosilane compound represented by the general formula (5) has an imide moiety excellent in solvent resistance, adhesiveness, and flexibility.
- the Si— [OR 9 ] ⁇ portion of the imidosilane compound is incorporated into the reaction product by a hydrolysis / condensation reaction with the alkoxysilane compound represented by any one of the general formulas (1) to (3). Thereby, the softness
- the imide silane compound is taken into the siloxane skeleton by the Si— [OR 9 ] ⁇ moiety, the nitrogen atom in the imide group faces outward in the cured film (or the substrate side in the configuration having the cured film on the substrate). It is conceivable that. For this reason, it is considered that the lone pair of nitrogen atoms and the hydroxyl group generally present on the substrate such as silicon efficiently interact with each other by hydrogen bonds and the like, thereby improving the adhesion.
- the imide portion is suppressed from curing shrinkage as compared with a compound having an amic acid structure that is ring-closed by heat, the siloxane-based resin composition of the present invention has excellent planarization characteristics.
- R 8 and R 9 include a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a phenyl group.
- substituents include an alkoxyalkyl group, an alkylphenyl group, and an alkoxyphenyl group.
- ⁇ is preferably 0. Further, from the viewpoint of adhesiveness, ⁇ + ⁇ ⁇ 2 is preferable.
- R 10 may be the same or different and represents a trivalent organic group having 3 to 30 carbon atoms and is a residue of an acid anhydride in an acid anhydride-containing silane compound.
- the acid anhydride constituting R 10 preferably contains an aromatic ring or an aliphatic ring.
- acid anhydrides include maleic anhydride, phthalic anhydride, methyl phthalic anhydride, succinic anhydride, glutaric anhydride, 4-methylcyclohexane-1,2-dicarboxylic anhydride, cis- 4-cyclohexene-1,2-dicarboxylic anhydride, cis-1,2-cyclohexanedicarboxylic anhydride, 1,8-naphthalic anhydride, methyl-5-norbornene-2,3-dicarboxylic anhydride, 5 -Norbornene-2,3-dicarboxylic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, "Licacid (registered trademark)" HNA (trade name, manufactured by Shin Nippon Rika Co., Ltd.), “Ricacid “HNA-100 (trade name, manufactured by Shin Nippon Rika Co., Ltd.) and those obtained by substituting some hydrogen atoms of these acid anhydrides with
- Examples of monovalent organic groups having 1 to 10 carbon atoms include alkyl groups such as methyl, ethyl, n-propyl, n-butyl, and n-pentyl, oxymethyl, oxyethyl, and oxy n-propyl. And oxyalkyl groups such as an oxy n-butyl group and an oxy n-pentyl group. Of these, a methyl group, an ethyl group, an n-propyl group, and an n-butyl group are preferable because they can be easily produced.
- phthalic anhydride succinic anhydride, glutaric anhydride, 4-methylcyclohexane-1,2-dicarboxylic anhydride, 1,8-naphthalic anhydride, 5-norbornene-2,3 -Dicarboxylic anhydrides, methyl phthalic anhydrides, and those substituted with monovalent organic groups having 1 to 10 carbon atoms are preferred.
- phthalic anhydride, succinic anhydride, and glutaric anhydride are more preferable from the viewpoints of transparency and adhesiveness.
- R 11 may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- the organic group include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, t-butyl groups, cyclohexyl groups and other alkyl groups, 2-hydroxyethyl groups and other hydroxyalkyl groups, An aryl group such as a phenyl group, an alkoxyaryl group such as a methoxyphenyl group, an alkoxyl group such as a methoxy group, an ethoxy group, an n-propoxy group, and an isopropoxy group.
- An isopropyl group, a t-butyl group, a cyclohexyl group, a methoxy group or an ethoxy group is preferable because of easy synthesis.
- a hydrogen atom, a hydroxyalkyl group such as a methylol group or an ethylol group, an i-propyl group, a t-butyl group, or a phenyl group that decomposes into a hydrogen atom upon curing is preferable. More preferred are a hydrogen atom, i-propyl group, and t-butyl group.
- imide silane compound represented by the general formula (5) examples include compounds shown below and compounds described later as examples of the imide silane compound represented by the general formula (4).
- the amount of the imidosilane compound represented by the general formula (5) used for the reaction product of (a-2) is the same as that of the alkoxysilane compound represented by any one of the general formulas (1) to (3).
- 5 parts by weight or more is preferable with respect to 100 parts by weight of the total amount of the imidosilane compound represented by the general formula (5), and the adhesiveness, crack resistance and solvent resistance of the cured film are further improved.
- 10 weight part or more is more preferable, a shrinkage
- 50 weight part or less is preferable and can maintain high transparency of a cured film.
- the siloxane-based resin composition of the present invention when (a) the siloxane-based resin is the reaction product of (a-1), silicon compound particles, aluminum compound particles, tin compound particles, titanium compound particles, and zirconium compound particles In the presence of at least one compound particle selected from the group consisting of: one or more alkoxysilane compounds represented by any one of the general formulas (1) to (3), A particle surface graft polysiloxane which is a reaction product obtained by a condensation reaction is preferable. In the case of the reaction product (a-2), in the presence of at least one compound particle selected from the group consisting of silicon compound particles, aluminum compound particles, tin compound particles, titanium compound particles and zirconium compound particles.
- One or more alkoxysilane compounds represented by any one of the general formulas (1) to (3) and an imidosilane compound represented by the general formula (5) are hydrolyzed, and the hydrolyzate is condensed.
- a particle surface grafted polysiloxane, which is a reaction product obtained by reaction, is preferred. By containing these compound particles, the refractive index of the obtained coating film and cured film can be easily adjusted.
- the compound particles include silicon, aluminum, tin, titanium or zirconium oxides, sulfides and hydroxides. What is necessary is just to select a compound particle suitably according to the refractive index of the target coating film and a cured film.
- a compound particle suitably according to the refractive index of the target coating film and a cured film.
- zirconium oxide particles, tin oxide particles, titanium oxide particles, and composite particles thereof are preferably used.
- titanium oxide particles and zirconium oxide particles are preferable because they have a high refractive index improving effect, and titanium oxide particles are more preferable.
- silica particles, aluminum oxide particles, and composite particles thereof are preferably used.
- silica particles are preferable because the refractive index can be further lowered. Two or more kinds of these compound particles may be used. Moreover, in order to make it easy to react with an alkoxysilane compound or an imidosilane compound, the compound particle which has groups, such as a hydroxyl group which can react with an alkoxysilane compound or an imidosilane compound, on the surface is preferable.
- the number average particle diameter of the compound particles is preferably 1 nm or more from the viewpoint of crack resistance of the resulting cured film. Further, when used as a waveguide embedding material, 40 nm or less is preferable from the viewpoint of embedding. In order to achieve both crack resistance, transparency and embedding properties of the cured film, the number average particle diameter is more preferably 1 nm to 30 nm.
- the number average particle size of the compound particles is measured by a gas adsorption method, a dynamic light scattering method, an X-ray small angle scattering method, a method of directly measuring the particle size by a transmission electron microscope or a scanning electron microscope, and the like.
- the number average particle diameter in the present invention refers to a value measured by a dynamic light scattering method.
- the content of the compound particles in the siloxane-based resin composition is preferably 5% by weight or more, and more preferably 10% by weight or more in the reaction product of (a-1) or (a-2). Moreover, 90 weight% or less is preferable and 70 weight% or less is more preferable. Within this range, a cured film with better transmittance and crack resistance can be obtained. Furthermore, in order to reduce the curing shrinkage, it is preferably 20% by weight or more in the reaction product of (a-1) or (a-2).
- metal compound particles include tin oxide-titanium oxide composite particles “OPTRAIK (registered trademark)” TR-502, “OPTRAIK” TR-504, “OPTRAIK” TR. -520, "Optlake” TR-513, “Oplake” TR-503, “Optlake” TR-527, “Optlake” TR-528, “Optlake” TR-529 of silicon oxide-titanium oxide composite particles "Op-tlake” TR-505 (trade name, manufactured by Catalyst Kasei Kogyo Co., Ltd.), zirconium oxide particles (manufactured by Kojundo Chemical Laboratory Co., Ltd.), tin oxide-zirconium oxide composite particles ( Catalyst Chemical Industry Co., Ltd.) and tin oxide particles (manufactured by Kojundo Chemical Laboratory Co., Ltd.).
- IPA-ST having a number average particle diameter of 12 nm using isopropanol as a dispersion medium
- MIBK-ST having a number average particle diameter of 12 nm using methyl isobutyl ketone as a dispersion medium
- propylene glycol monomethyl ether as a dispersion medium.
- PGM-ST having a number average particle diameter of 15 nm (trade name, manufactured by Nissan Chemical Industries, Ltd.), Oscar 101 having a number average particle diameter of 12 nm using ⁇ -butyrolactone as a dispersion medium, and propylene glycol monomethyl ether as a dispersion medium.
- Quartron PL-2L-PGME having a number average particle diameter of 16 nm
- Quartron PL-2L-BL having a number average particle diameter of 17 nm using ⁇ -butyrolactone as a dispersion medium
- Quatron PL having a number average particle diameter of 17 nm using diacetone alcohol as a dispersion medium -2L-DAA
- the number that the dispersion is water examples include Quartron PL-2L and GP-2L (trade names, manufactured by Fuso Chemical Industry Co., Ltd.) having an average particle diameter of 18 to 20 nm.
- (A-1) and (a-2) used in the present invention hydrolyze the alkoxysilane compound and, if necessary, an imidosilane compound (hereinafter collectively referred to as a silane compound), and condense the hydrolyzate. It is a reaction product obtained by reacting. It is preferable to hydrolyze the silane compound in the presence of the compound particles and cause the hydrolyzate to undergo a condensation reaction.
- a silane compound an imidosilane compound
- the hydrolysis reaction is preferably performed with an acid catalyst in a solvent. Specifically, it is preferable to add an acid catalyst and water to the silane compound in a solvent over 1 to 180 minutes, and then react at room temperature to 110 ° C. for 1 to 180 minutes. By performing the hydrolysis reaction under such conditions, a rapid reaction can be suppressed.
- the reaction temperature is more preferably 40 to 105 ° C.
- the condensation reaction by heating the reaction solution at a temperature of 50 ° C. or higher and lower than the boiling point of the solvent for 1 to 100 hours.
- reheating or addition of a base catalyst may be performed.
- Examples of the acid catalyst used in the hydrolysis reaction include acid catalysts such as hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polyvalent carboxylic acid or anhydrides thereof, and ion exchange resins.
- acid catalysts such as hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, hydrochloric acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polyvalent carboxylic acid or anhydrides thereof, and ion exchange resins.
- an acidic aqueous solution using formic acid, acetic acid or phosphoric acid is preferred.
- the preferred content of these acid catalysts is preferably 0.05 parts by weight or more, more preferably 0.1 parts by weight or more, preferably 100 parts by weight or more, based on 100 parts by weight of the total silane compounds used during the hydrolysis reaction. It is 10 parts by weight or less, more preferably 5 parts by weight or less.
- the total silane compound amount refers to an amount including all of the silane compound, its hydrolyzate and its condensate, and the same shall apply hereinafter.
- the solvent is not particularly limited, but is appropriately selected in consideration of the stability, wettability, volatility, etc. of the siloxane-based resin composition. Not only one type of solvent but also two or more types of solvents can be used. Examples of the solvent include methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, and 3-methyl-3-methoxy.
- -1-alcohols such as butanol and diacetone alcohol; glycols such as ethylene glycol and propylene glycol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether , Propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ethylene glycol dimethyl ether, ethylene glycol Ethers such as coal diethyl ether, ethylene glycol dibutyl ether, diethyl ether; ketones such as methyl ethyl ketone, acetyl acetone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclopentanone, 2-heptanone; dimethylformamide, Amides such as dimethylacetamide;
- propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether t-Butyl ether, ⁇ -butyrolactone and the like are preferably used.
- concentration as a resin composition by adding a solvent after completion
- the amount of the solvent used in the hydrolysis reaction is preferably 50 parts by weight or more, more preferably 80 parts by weight or more with respect to 100 parts by weight of the total silane compound. Moreover, 500 weight part or less is preferable and 200 weight part or less is more preferable.
- generation of a gel can be suppressed by making the quantity of a solvent into 50 weight part or more. Moreover, a hydrolysis reaction advances rapidly by setting it as 500 parts weight or less.
- the water used for the hydrolysis reaction is preferably ion-exchanged water.
- the amount of water can be arbitrarily selected, but is preferably in the range of 1.0 to 4.0 mol with respect to 1 mol of the silane compound.
- an imidosilane compound represented by the following general formula (4) will be described.
- the adhesiveness of the resulting cured film can be dramatically improved by containing such an imide silane compound.
- the imidosilane compound represented by the general formula (4) has an imide moiety excellent in solvent resistance, adhesiveness, and flexibility.
- the Si- [R 7 ] ⁇ portion reacts with the siloxane matrix formed by the siloxane-based resin of the component (a), and the imide portion is taken into the cured film by organic bonds it is conceivable that. Thereby, the softness
- the imide silane compound is taken into the siloxane matrix by the Si— [R 7 ] ⁇ portion, the nitrogen atoms in the imide group face outward in the cured film (or the substrate side in the configuration having the cured film on the substrate). It is conceivable that. For this reason, it is considered that the lone pair of nitrogen atoms and the hydroxyl group generally present on the substrate such as silicon efficiently interact with each other by hydrogen bonds and the like, thereby improving the adhesion.
- the imide portion is suppressed from curing shrinkage as compared with a compound having an amic acid structure that is ring-closed by heat, the siloxane-based resin composition of the present invention has excellent planarization characteristics. In this invention, you may contain 2 or more types of the imide silane compound of (b) component. Moreover, also in the 2nd aspect of the siloxane-type resin composition of this invention, it is preferable to contain such (b) imidosilane compound.
- R 7 may be the same or different and represents an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, a phenyl group, a phenoxy group, or a substituted product thereof.
- R 10 may be the same or different and each represents a trivalent organic group having 3 to 30 carbon atoms.
- R 11 may be the same or different and each represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- ⁇ represents an integer of 1 to 3.
- specific examples of the alkyl group represented by R 7 include a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.
- a methyl group or an ethyl group is preferable because of ease of synthesis.
- Specific examples of the alkoxyl group include a methoxy group, an ethoxy group, an n-propoxy group, and an isopropoxy group. From the viewpoint of ease of synthesis, a methoxy group or an ethoxy group is preferable.
- substituents include the groups listed as examples of substituents in R 8 to R 9 , alkylphenoxy groups such as 4-methylphenoxy group and 4-ethylphenoxy group, 4-methoxyphenoxy group, Examples include alkoxyphenoxy groups such as 4-ethoxyphenoxy group.
- R 10 and R 11 are as described in the general formula (5). From the viewpoint of adhesiveness, ⁇ ⁇ 2 is preferable.
- Examples of the imidosilane compound represented by the general formula (4) include the following compounds.
- the imidosilane compound represented by the general formula (4) or (5) includes a primary amine compound represented by the following general formula (9) and an acid anhydride-containing silane represented by the general formula (10) or (11) It can be easily obtained from a compound by a known imidization method via amic acid.
- R 11 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms that does not contain a silicon atom.
- R 7 may be the same or different, and represents an alkyl group having 1 to 6 carbon atoms, an alkoxyl group having 1 to 6 carbon atoms, a phenyl group, a phenoxy group, or a substituent thereof.
- R 8 and R 9 may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a substituted product thereof.
- R 10 may be the same or different and each represents a trivalent organic group having 3 to 30 carbon atoms.
- ⁇ represents an integer of 1 to 3.
- ⁇ represents an integer of 1 to 3, and ⁇ represents an integer of 0 to 2. However, ⁇ + ⁇ ⁇ 4.
- the content of the imidosilane compound represented by the general formula (4) is 0.1 weight with respect to 100 parts by weight of the (a) siloxane-based resin.
- Part or more is preferable, and the adhesiveness, crack resistance and solvent resistance of the cured film can be further improved.
- 4 weight part or more is more preferable, a cure shrinkage rate can be reduced and crack resistance can be improved more.
- 20 weight part or less is preferable and can maintain the transparency of a cured film high.
- the content thereof is (a) 100 parts by weight of the siloxane-based resin. 0.1 parts by weight or more is preferable, and the adhesiveness, crack resistance and solvent resistance of the cured film can be further improved. Moreover, 10 weight part or less is preferable and can maintain the transparency of a cured film high.
- the total amount of the residue of the imidosilane compound represented by the general formula (5) and the imidosilane compound represented by the general formula (4) is 1.1 with respect to 100 parts by weight of the (a) siloxane-based resin.
- weight part More than the weight part is preferable and can improve adhesiveness, crack resistance, and solvent resistance more. Furthermore, 5 weight part or more is more preferable, a cure shrinkage rate can be reduced and crack resistance can be improved more. Moreover, 50 weight part or less is preferable and can maintain high transparency of a cured film.
- the siloxane-based resin composition of the present invention preferably contains (c) an acid generator or a base generator.
- a cured film can be formed in a temperature range of 120 ° C. to 200 ° C. Since the curing is completed at a low temperature, the molecular motion in the subsequent high-temperature heat treatment is small, and the curing shrinkage is small. For this reason, thermal stress is reduced and crack resistance is further improved.
- the acid generator includes a compound that generates an acid by light (hereinafter referred to as a photoacid generator) and a compound that generates an acid by heat (hereinafter referred to as a thermal acid generator).
- the base generator includes a compound that generates a base by light (hereinafter referred to as a base generator) and a compound that generates a base by heat (hereinafter referred to as a thermal base generator).
- photoacid generator examples include onium salt compounds, halogen-containing compounds, diazoketone compounds, diazomethane compounds, sulfone compounds, sulfonic acid ester compounds, and sulfonimide compounds. Two or more of these may be used.
- the onium salt compounds include diazonium salts, ammonium salts, iodonium salts, sulfonium salts, phosphonium salts, oxonium salts and the like.
- diphenyliodonium triflate diphenyliodonium pyrenesulfonate, diphenyliodonium dodecylbenzenesulfonate, triphenylsulfonium triflate (trade name “TPS-105” manufactured by Midori Chemical Co., Ltd.), 4-t-butylphenyldiphenylsulfonium triflate ( Trade name “WPAG-339” manufactured by Wako Pure Chemical Industries, Ltd.), 4-methoxyphenyldiphenylsulfonium triflate (trade name “WPAG-370” manufactured by Wako Pure Chemical Industries, Ltd.), triphenylsulfonium nonaflate (product) “TPS-109” manufactured by Midori Chemical
- halogen-containing compounds examples include 1,1-bis (4-chlorophenyl) -2,2,2-trichloroethane, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6. -Bis (trichloromethyl) -s-triazine and the like.
- diazoketone compound examples include esters of 1,2-naphthoquinonediazide-4-sulfonic acid and 2,2,3,4,4′-tetrahydroxybenzophenone, 1,2-naphthoquinonediazide-4-sulfonic acid and 1,1 , Esters with 1-tris (4-hydroxyphenyl) ethane, and the like.
- diazomethane compound examples include diazomethane, methylsulfonyl-p-toluenesulfonyldiazomethane, cyclohexylsulfonyl (1,1-dimethylethylsulfonyl) diazomethane, bis (1,1-dimethylethylsulfonyl) diazomethane, phenylsulfonyl (benzoyl) diazomethane, and the like. It is done.
- sulfone compound examples include benzoin tosylate, pyrogallol trimesylate, nitrobenzyl-9,10-diethoxyanthracene-2-sulfonate, and the like.
- 5-norbornene-2,3-dicarboxyimidyl triflate (trade name “NDI-105” manufactured by Midori Chemical Co., Ltd.), 5-norbornene-2,3-dicarboxyimidyl naphthalimidyl butane sulfonate , 5-norbornene-2,3-dicarboxyimidyl tosylate (trade name “NDI-101” manufactured by Midori Chemical Co., Ltd.), 4-methylphenylsulfonyloxyimino- ⁇ - (4-methoxyphenyl) acetonitrile (trade name) “PAI-101” manufactured by Midori Chemical Co., Ltd.), trifluoromethylsulfonyloxyimino- ⁇ - (4-methoxyphenyl) acetonitrile (trade name “PAI-105” manufactured by Midori Chemical Co., Ltd.), 9-camphorsulfonyloxy Imino ⁇ -4-methoxyphenylacet
- the content of the photoacid generator is usually 1 to 10 parts by weight, more preferably 1 to 7 parts by weight with respect to 100 parts by weight of (a) siloxane-based resin. If it is 1 part by weight or more, the effect of promoting curing can be sufficiently obtained even when a cured film is formed in a temperature range of 120 ° C. to 200 ° C., and crack resistance and solvent resistance are further improved. If it is 10 weight or less, the transparency of a cured film can be kept high.
- these photoacid generators are preferably used in combination with 9,10-disubstituted anthracene compounds as sensitizers. Since the 9,10-disubstituted anthracene-based compound is not colored by the photobleaching reaction, high transparency can be maintained even when it remains in the cured film.
- Examples of 9,10-disubstituted anthracene compounds include 9,10-diphenylanthracene, 9,10-bis (4-methoxyphenyl) anthracene, 9,10-bis (triphenylsilyl) anthracene, and 9,10-dimethoxyanthracene. 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, 9,10-dibutoxyanthracene, 9,10-dipentaoxyanthracene, 2-t-butyl-9,10-dibutoxyanthracene, 9, And 10-bis (trimethylsilylethynyl) anthracene.
- 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 9,10-dipropoxyanthracene, and 9,10-dibutoxyanthracene are particularly preferable. Two or more of these sensitizers may be used.
- the content of the sensitizer is usually 0.05 to 5 parts by weight, more preferably 0.1 to 3 parts by weight, based on 100 parts by weight of (a) siloxane-based resin. If it is 0.05 parts by weight or more, the acid generation efficiency by light is improved, and a sufficient curing promoting effect can be obtained even when a cured film is formed in the temperature range of 120 ° C. to 200 ° C. More improved. If it is 5 parts by weight or less, the transparency of the cured film can be kept high.
- thermal acid generator examples include SI-60, SI-80, SI-100, SI-110, SI-145, SI-150, SI-60L, SI-80L, SI-100L, SI- 110L, SI-145L, SI-150L, SI-160L, SI-180L (all from Sanshin Chemical Industry Co., Ltd.), 4-hydroxyphenyldimethylsulfonium, benzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl -4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-acetylphenylmethylsulfonium, 2-methylbenzyl-4-benzoyloxyphenylmethylsulfonium, their methanesulfonate, trifluoromethanesulfonate, camphorsulfonate P-toluenesulfonate is It is below.
- 4-hydroxyphenyldimethylsulfonium benzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-acetylphenylmethylsulfonium, 2-methylbenzyl-4- Benzoyloxyphenylmethylsulfonium, their trifluoromethanesulfonate, camphorsulfonate, and p-toluenesulfonate.
- the content of the thermal acid generator is usually 0.01 to 10 parts by weight, more preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the (a) siloxane resin. If it is 0.01 parts by weight or more, curing proceeds sufficiently even when a cured film is formed in a temperature range of 120 ° C. to 200 ° C., and crack resistance and solvent resistance are further improved. If it is 10 parts by weight or less, the transparency of the cured film can be kept high.
- Preferred examples of the photobase generator include propionyl acetophenone oxime, propionyl benzophenone oxime, propionyl acetone oxime, butyryl acetophenone oxime, butyryl benzophenone oxime, butyryl acetone oxime, adipoyl acetophenone oxime, adipoyl benzophenone oxime, Poylacetone oxime, acryloylacetophenone oxime, acryloylbenzophenone oxime, acryloylacetone oxime, [[(2-nitrobenzyl) oxy] carbonyl] cyclohexylamine, bis [[(2-nitrobenzyl) oxy] carbonyl] hexamethylene Diamine, bis [[( ⁇ , ⁇ -dimethyl-3,5-dimethoxybenzyl) oxy] carbonyl] hexamethylenediamine, and the like. I can get lost. Two or more of these
- the content of the photobase generator is usually 1 to 10 parts by weight, more preferably 1 to 7 parts by weight with respect to 100 parts by weight of (a) siloxane-based resin.
- the amount is 1 part by weight or more, a sufficient curing acceleration effect can be obtained even when a cured film is formed in a temperature range of 120 ° C. to 200 ° C., and crack resistance and solvent resistance are further improved. If it is 10 parts by weight or less, the transparency of the cured film can be kept high.
- the sensitizer of the photoacid generator it is preferable to use a combination of the sensitizers listed above as the sensitizer of the photoacid generator.
- the content of the sensitizer is usually 0.05 to 5 parts by weight, more preferably 0.1 to 3 parts by weight, based on 100 parts by weight of the (a) siloxane-based resin. If it is 0.05 parts by weight or more, a curing acceleration effect can be sufficiently obtained even when a cured film is formed in a temperature range of 120 ° C. to 200 ° C., and crack resistance and solvent resistance are further improved. If it is 5 parts by weight or less, the transparency of the cured film can be kept high.
- thermal base generator examples include carbamate derivatives such as 1-methyl-1- (4-biphenylyl) ethyl carbamate and 1,1-dimethyl-2-cyanoethyl carbamate, urea and N, N-dimethyl- Examples include urea derivatives such as N′-methylurea, dihydropyridine derivatives such as 1,4-dihydronicotinamide, quaternized ammonium salts of organic silane and organic borane, dicyandiamide, and the like. Two or more of these may be used.
- 1-methyl-1- (4-biphenylyl) ethylcarbamate, 1,1-dimethyl-2-cyanoethylcarbamate, N, N-dimethyl-N′-methylurea, 1,4-dihydronicotinamide preferable.
- the content of the thermal base generator is usually 0.01 to 10 parts by weight, more preferably 0.01 to 5 parts by weight, based on 100 parts by weight of the (a) siloxane resin. If it is 0.01 parts by weight or more, a curing acceleration effect can be sufficiently obtained even when a cured film is formed in a temperature range of 120 ° C. to 200 ° C., and crack resistance and solvent resistance are further improved. If it is 10 parts by weight or less, the transparency of the cured film can be kept high.
- the siloxane-based resin composition of the present invention may contain a solvent so that the solid content has an appropriate concentration.
- propylene glycol monomethyl ether propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, diacetone alcohol, ⁇ -butyrolactone, and the like are preferable. .
- the content of the total solvent in the siloxane-based resin composition of the present invention is preferably 100 to 9900 parts by weight, more preferably 100 to 5000 parts by weight with respect to 100 parts by weight of (a) siloxane-based resin.
- the siloxane-based resin composition of the present invention may contain various surfactants in order to improve flowability and film thickness uniformity during coating.
- various surfactants there is no restriction
- a fluorine-type surfactant, a silicone type surfactant, a polyalkylene oxide type surfactant, a poly (meth) acrylate type surfactant etc. can be used. Two or more of these may be contained. From the viewpoint of flowability and film thickness uniformity, a fluorosurfactant is preferred.
- Fluorosurfactants include "Megafac (registered trademark)" F172 (trade name, manufactured by Dainippon Ink & Chemicals, Inc.), BM-1000, BM-1100 (above, trade names, Yusho Co., Ltd.) NBX-15, FTX-218 (trade name, manufactured by Neos Co., Ltd.) are particularly preferable from the viewpoint of flowability and film thickness uniformity.
- silicone surfactants examples include SH28PA, SH7PA, SH21PA, SH30PA, ST94PA (all manufactured by Toray Dow Corning Silicone Co., Ltd.), BYK-333 (manufactured by Big Chemie Japan Co., Ltd.), and the like. It is done.
- surfactants include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene nonyl phenyl ether, polyoxyethylene distearate and the like.
- the surfactant content is usually 0.001 to 10 parts by weight per 100 parts by weight of (a) siloxane-based resin.
- the siloxane-based resin composition of the present invention can contain a viscosity modifier, a stabilizer, a colorant, a vitreous forming agent, and the like as necessary.
- the siloxane-based resin composition of the present invention includes (d) a group represented by the following general formula (6) or (7) that promotes or facilitates curing of the siloxane-based resin composition.
- You may contain the crosslinkable compound which does not have a silicon atom which has, and / or the crosslinkable compound represented by following General formula (8).
- the matrix material (a) siloxane-based resin is firmly bonded, and high heat cycle properties are obtained, and crack resistance is improved.
- a cured film having excellent properties can be formed. Two or more of these may be contained.
- R 12 may be the same or different and represents a hydrogen atom or a monovalent organic group.
- n represents an integer of 1 to 4.
- R 13 and R 14 represent a hydrogen atom or a monovalent organic group.
- Specific examples of R 12 to R 14 include a hydrogen atom, an alkyl group such as a methyl group, an ethyl group, a propyl group, and a butyl group, and an aryl group such as a phenyl group. From the viewpoint of the temporal stability of the resin composition and the reactivity of the crosslinkable compound, a methyl group and an ethyl group are preferred.
- R 15 and R 16 may be the same or different and each represents an alkyl group having 1 to 4 carbon atoms, a phenyl group, or a substituted product thereof. However, at least one of p R 15 and R 16 is a phenyl group or a substituted product thereof.
- the substituent of the alkyl group or phenyl group include CF 3 group, CH 2 CF 3 group, C 2 H 4 CF 3 group, C 6 H 4 CH 3 group, and C 6 H 4 t-Bu group.
- R 15 and R 16 are preferably a methyl group or a phenyl group.
- p represents an integer of 4 or more and 20 or less.
- crosslinkable compound having a group represented by the general formula (6) and having no silicon atom are shown.
- crosslinkable compound having a group represented by the general formula (7) and having no silicon atom are shown.
- “NIKALAC (registered trademark)” MX-280, “NIKACALAC” MX-270 (above, trade name, manufactured by Sanwa Chemical Co., Ltd.) having a group represented by the general formula (7) is a viewpoint of crack resistance.
- NIKALAC registered trademark
- NIKACALAC NIKACALAC
- crosslinkable compound represented by the general formula (8) Specific examples of the crosslinkable compound represented by the general formula (8) are shown below. Since such a crosslinkable compound has a phenyl group, the transmittance can be further improved while keeping the refractive index of the resulting composition high. In addition, by containing such a crosslinkable compound, unlike the case of containing a reaction product obtained by condensation reaction of the compound, the crosslinkable compound undergoes a curing reaction during the heat treatment of the composition, thereby further improving crack resistance. Can be made.
- crosslinkable compounds represented by the general formula (8) when the molar ratio of the alkyl group to the phenyl group in R 15 and R 16 (alkyl group / phenyl group) is 0 to 1, the transmittance and crack resistance Can be further improved. Specifically, S-3, S-4, S-11, S-12, S-13, S-14, and S-15 are preferable.
- the crosslinkable compound having a group represented by the general formula (6) or (7) is an organic compound having no silicon atom, and the effect of improving crack resistance is remarkably exhibited even if the content is small.
- the content of these crosslinkable compounds is preferably 0.1 parts by weight or more, and 0.5 parts by weight or more with respect to 100 parts by weight of the (a) siloxane resin in the siloxane resin composition. More preferred. Moreover, 20 weight part or less is preferable and 10 weight part or less is more preferable. If it is this range, the oxidation deterioration of the crosslinkable compound by heat processing can be suppressed, and the transmittance
- the crosslinkable compound represented by the general formula (8) is a compound having a silicon atom, and is preferably contained in a larger amount than the crosslinkable compound represented by the general formula (6) or (7). .
- 10 parts by weight or more is preferable and 20 parts by weight or more is more preferable with respect to 100 parts by weight of (a) siloxane-based resin in the siloxane-based resin composition.
- the crack resistance can be further improved.
- 30 parts by weight or more is preferable in order to reduce the curing shrinkage rate.
- 50 parts by weight or less is preferable, and 40 parts by weight or less is more preferable.
- the total content thereof is preferably 10 parts by weight or more, more preferably 20 parts by weight or more with respect to 100 parts by weight of the (a) siloxane resin in the siloxane resin composition. . Moreover, 40 weight part or less is more preferable.
- the content of the crosslinkable compound represented by the general formula (6) or (7) is preferably 0.1% by weight or more based on the total solid content in the siloxane-based resin composition. More preferably, it is more than wt%. Moreover, 20 weight% or less is preferable and 10 weight% or less is more preferable.
- the crack resistance can be greatly improved by a synergistic effect thereof.
- siloxane-based resin composition of the present invention By mixing (a) a siloxane-based resin with (b) an imidosilane compound, and (c) an acid generator or base generator, a crosslinkable compound, a surfactant, etc.
- the siloxane-based resin composition of the present invention can be obtained. At this time, it may be diluted with an arbitrary solvent.
- the mixing temperature is not particularly limited, but is preferably in the range of 5 to 50 ° C. for ease of operation.
- the siloxane-based resin composition of the present invention is suitably used as a solid-state image sensor material.
- the refractive index is 1.60 to 1.80, it is suitably used as a waveguide planarizing film material, and when the refractive index is less than 1.6, it is suitably used as a color filter planarizing film material.
- the siloxane-based resin composition of the present invention can be applied on a substrate to obtain a coating film, and then cured to form a cured film. Heating is generally used as a method for curing the coating film, and the coating film may be dried by heating as necessary.
- microgravure coating, spin coating, dip coating, curtain flow coating, roll coating, spray coating, flow coating, and the like can be preferably used.
- the heating and drying conditions are appropriately selected according to the base material and resin composition to be applied, but it is usually preferable to perform the treatment at a temperature of room temperature to 400 ° C. for 0.5 minutes to 240 minutes.
- a particularly preferred curing temperature is 100 to 400 ° C, more preferably 150 to 400 ° C.
- the coating film and the film thickness after curing are not particularly limited, but both are generally in the range of 0.001 to 100 ⁇ m.
- the coating film and the cured film formed from the siloxane-based resin composition of the present invention are suitably used for optical articles such as a solid-state imaging device and a display optical filter such as a liquid crystal display. More specifically, it can be used for a planarization film of a solid-state imaging device or a buried planarization film for a waveguide. Further, it can be used for a low refractive index layer, a high refractive index layer and a hard coat layer such as an antireflection film and an antireflection plate of an optical filter.
- the obtained coating film is subjected to an ultraviolet intensity of about 5 mW / cm 2 (wavelength using an exposure machine (Contact Aligner PLA501F, manufactured by Canon Inc.)). The whole surface was exposed to ultraviolet full-wavelength for 3 minutes (bleaching exposure main wavelengths: 365 nm, 405 nm, 436 nm) at 365 nm. Subsequently, after heating at 250 degreeC for 5 minutes on the hotplate in an air atmosphere, it heated at 300 degreeC for 5 minutes, and obtained the cured film.
- the obtained coating film is heated at 250 ° C. for 5 minutes on a hot plate in an air atmosphere and then heated at 300 ° C. for 5 minutes. Thus, a cured film was obtained.
- Synthesis Example 6 Synthesis of aromatic bisimide oligomer (vi) In a vessel equipped with a stirrer, a reflux condenser, and a nitrogen introduction tube, 32.58 g (220 mmol) of phthalic anhydride, 1.39 g of ⁇ -picoline, N-methyl A solution obtained by adding 130.3 g of -2-pyrrolidone (hereinafter abbreviated as NMP) to which 24.8 g (100 mmol) of 1,3-bis (3-aminopropyl) tetramethyldisiloxane was dissolved in 99.4 g of NMP was added. The solution was added dropwise and stirred for 2 hours under nitrogen and nitrogen atmosphere.
- NMP -2-pyrrolidone
- Synthesis Example 7 Synthesis of Silicone Polyimide Precursor (vii) 35.42 g (160 mmol) of aminopropyltriethoxysilane was added to 40 g of ⁇ -butyrolactone and dissolved by stirring. After adding 24.82 g (80 mmol) of 4,4′-oxydiphthalic dianhydride and stirring at room temperature for 30 minutes, the mixture was stirred at 40 ° C. for 2 hours. The resulting solution was diluted with ⁇ -butyrolactone so that the solid content concentration was 20% by weight to obtain a solution of a silicone polyimide precursor (vii) represented by the following structure.
- Example 1 Methyltrimethoxysilane 20.4 g (0.15 mol), phenyltrimethoxysilane 69.4 g (0.35 mol), number-average particle diameter 15 nm “OPTRAIK” TR-521 (trade name, manufactured by Catalyst Kasei Kogyo Co., Ltd.) Composition: 30% by weight of titanium oxide particles, 70% by weight of ⁇ -butyrolactone) 70.6 g and 44.1 g of ⁇ -butyrolactone were placed in a reaction vessel, and 30.6 g of water and 0.48 g of phosphoric acid were stirred into this solution. However, it was added dropwise so that the reaction temperature did not exceed 40 ° C.
- a siloxane-based resin composition 1 was obtained by adding 10 g of ⁇ -butyrolactone and 2.5 g of a solution of imidosilane compound (i) (0.5 g of solid content) to 10 g of the obtained polymer solution A and dissolving.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 2 “OPTRAIK” TR- with 8.2 g (0.06 mol) of methyltrimethoxysilane, 55.5 g (0.28 mol) of phenyltrimethoxysilane, 7.2 g (0.06 mol) of dimethyldimethoxysilane, and a number average particle diameter of 15 nm 521 71.1 g and ⁇ -butyrolactone 23.9 g were placed in a reaction vessel, and 34.5 g of water and 1.0 g of phosphoric acid were added dropwise to this solution with stirring so that the reaction temperature did not exceed 40 ° C.
- a cured film was prepared using the obtained siloxane-based resin composition 2, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 3 A siloxane-based resin composition 3 was obtained in the same manner as in Example 2 except that Nicalac MX-270 was not used. A cured film was prepared using the obtained siloxane-based resin composition 3, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 4 70.0 g of propylene glycol monomethyl ether acetate dispersion of zirconium oxide particles having a number average particle size of 30 nm (zirconium oxide 30% by weight, propylene glycol monomethyl ether acetate 70% by weight) instead of 71.1 g of “OPTRAIK” TR-521
- a polymer solution C (solid content: 46% by weight) was obtained in the same manner as in Example 2 except that was used.
- To 10 g of the resulting polymer solution C 15 g of propylene glycol monomethyl ether acetate and 2.05 g (solid content 0.41 g) of the imidosilane compound (i) were added and dissolved to obtain a siloxane-based resin composition 4.
- a cured film was prepared using the obtained siloxane-based resin composition 4, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 5 "OPTRAIK" TR-521 75.0g instead of propylene glycol monomethyl ether acetate dispersion of aluminum oxide particles with a number average particle size of 30nm (30% aluminum oxide, 70% propylene glycol monomethyl ether acetate) 45.0g The same operation as in Example 2 was performed except that was used to obtain a polymer solution D (solid content: 40% by weight).
- a siloxane-based resin composition 5 was obtained by adding 1.8 g of the above solution (solid content: 0.36 g) and dissolving.
- a cured film was prepared using the obtained siloxane-based resin composition 5 and evaluated for refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 6 A siloxane-based resin composition 6 was obtained in the same manner as in Example 5 except that BHPMT was not used. A cured film was prepared using the obtained siloxane-based resin composition 6 and evaluated for refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 7 8.2 g (0.06 mol) of methyltrimethoxysilane, 55.5 g (0.28 mol) of phenyltrimethoxysilane, 5.4 g (0.026 mol) of tetraethoxysilane, 52.4 g of “Optlake” TR-521, ⁇ -20.5 g of butyrolactone was placed in a reaction vessel, and 34.5 g of water and 1.0 g of phosphoric acid were added dropwise to this solution with stirring so that the reaction temperature did not exceed 40 ° C. After the dropwise addition, a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C.
- a cured film was prepared using the obtained siloxane-based resin composition 7, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 8 A siloxane-based resin composition 8 was obtained in the same manner as in Example 7 except that NDI-101 and DBA were not used. A cured film was prepared using the obtained siloxane-based resin composition 8, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 9 Methyltrimethoxysilane 12.3 g (0.15 mol), phenyltrimethoxysilane 41.6 g (0.35 mol), “OPTRAIK” TR-527 (trade name, manufactured by Catalyst Kasei Kogyo Co., Ltd.) having a number average particle size of 15 nm
- Composition 193 g of titanium oxide particles 20 wt%, methanol 80 wt%) and 94.0 g of propylene glycol monomethyl ether acetate were put in a reaction vessel, and 16.2 g of water and 0.27 g of phosphoric acid were added to this solution while stirring. The reaction was dropwise added so that the reaction temperature did not exceed 40 ° C.
- a cured film was prepared using the obtained siloxane-based resin composition 9, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 10 A siloxane-based resin composition 8 was obtained in the same manner as in Example 9 except that NCA and DPA were not used. A cured film was prepared using the obtained siloxane-based resin composition 10 and evaluated for refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 11 To 20 g of the polymer solution F used in Example 9, 25 g of propylene glycol monomethyl ether acetate, 1.76 g of a solution of imidosilane compound (iii) (solid content 0.352 g), and 2,2-dimethoxymethyl-4 which is a crosslinkable compound 0.264 g of t-butylphenol (trade name, DMOM-PTBP, manufactured by Honshu Chemical Industry Co., Ltd.) and 2-methylbenzyl-4-acetylphenylmethylsulfonium trifluoromethanesulfonate (MBAPMT) 0 which is a thermal acid generator 0.088 g was added and dissolved to obtain a siloxane-based resin composition 11.
- imidosilane compound (iii) solid content 0.352 g
- 2,2-dimethoxymethyl-4 which is a crosslinkable compound 0.264 g of t-butylphenol (trade name, DMOM-PTBP, manufactured by Honshu Chemical Industry Co., Ltd.)
- a cured film was prepared using the obtained siloxane-based resin composition 11, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 12 A siloxane-based resin composition 12 was obtained in the same manner as in Example 11 except that DMOM-PTBP and MBAPMT were not used. A cured film was prepared using the obtained siloxane-based resin composition 12, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 13 20 g of the polymer solution F used in Example 9, 25 g of propylene glycol monomethyl ether acetate, 1.76 g of a solution of imidosilane compound (iii) (solid content 0.352 g), 2.64 g of S-3 as a crosslinkable compound, and thermal acid 0.0176 g of benzyl-4-hydroxyphenylmethylsulfonium trifluoromethanesulfonate (BHPMT) as a generator was added and dissolved to obtain a siloxane-based resin composition 13.
- BHPMT benzyl-4-hydroxyphenylmethylsulfonium trifluoromethanesulfonate
- a cured film was prepared using the obtained siloxane-based resin composition 13, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 14 A siloxane-based resin composition 14 was obtained in the same manner as in Example 13 except that S-3 was not used. A cured film was prepared using the obtained siloxane-based resin composition 14, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 15 20 g of the polymer solution F used in Example 9, 25 g of propylene glycol monomethyl ether acetate, 1.76 g of a solution of imidosilane compound (iii) (solid content: 0.352 g), “Nicalak” MX-270 (Sanwa) as a crosslinkable compound Chemical Co., Ltd. (0.88 g) and thermal base generator 1-methyl-1- (4-biphenylyl) ethylcarbamate (MBEC) 0.176 g were added and dissolved to obtain siloxane-based resin composition 15. It was.
- a cured film was prepared using the obtained siloxane-based resin composition 15 and evaluated for refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 16 A siloxane-based resin composition 16 was obtained in the same manner as in Example 15 except that MBEC was not used. A cured film was prepared using the obtained siloxane-based resin composition 16 and evaluated for refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 17 20 g of the polymer solution F used in Example 9, 25 g of propylene glycol monomethyl ether acetate, 1.76 g of a solution of imidosilane compound (iii) (solid content: 0.352 g), TML-BPA (Honshu Chemical Co., Ltd.) 1) 1.32 g and 0.44 g of thermal acid generator benzyl-4-hydroxyphenylmethylsulfonium trifluoromethanesulfonate (BHPMT) were added and dissolved to obtain a siloxane-based resin composition 17.
- imidosilane compound (iii) solid content: 0.352 g
- TML-BPA Hyshu Chemical Co., Ltd.
- BHPMT thermal acid generator benzyl-4-hydroxyphenylmethylsulfonium trifluoromethanesulfonate
- a cured film was prepared using the obtained siloxane-based resin composition 17, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 18 24.5 g (0.18 mol) of methyltrimethoxysilane, 83.3 g (0.42 mol) of phenyltrimethoxysilane and 124.0 g of ⁇ -butyrolactone were placed in a reaction vessel, and while stirring, 38 g of water and 0.57 g of phosphoric acid was added dropwise so that the reaction temperature did not exceed 30 ° C. After the dropwise addition, a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C. for 2.5 hours, and reacted while distilling off methanol produced by hydrolysis. Thereafter, the solution was further heated and stirred at a bath temperature of 130 ° C.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 19 A siloxane-based resin composition 19 was obtained in the same manner as in Example 18 except that the solution of the imidosilane compound (i) was changed to 0.32 g (solid content: 0.064 g). A cured film was prepared using the obtained siloxane-based resin composition 19, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 20 Methyltrimethoxysilane 12.3 g (0.15 mol), phenyltrimethoxysilane 41.6 g (0.35 mol), number average particle diameter 20 nm silica particle diacetone alcohol solvent dispersion “Quartron” PL-2L-DAA (product) Name, Fuso Chemical Industries Co., Ltd .: solid content 26.4 wt%) 146.21 g and propylene glycol monomethyl ether acetate 94.0 g were put in a reaction vessel. To this solution, water 16.2 g and phosphoric acid 0. 27 g was added dropwise with stirring so that the reaction temperature did not exceed 40 ° C.
- a cured film was prepared using the obtained siloxane-based resin composition 20, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 21 A siloxane-based resin composition 21 was obtained in the same manner as in Example 20 except that S-11 was not used. A cured film was prepared using the obtained siloxane-based resin composition 21, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 22 152.67 g (0.7 mol) of trifluoropropyltrimethoxysilane and 70.89 g (0.3 mol) of ⁇ -glycidoxypropyltrimethoxysilane were dissolved in 280.22 g of propylene glycol monobutyl ether (boiling point 170 ° C.). To this, 54.0 g of water and 1.12 g of phosphoric acid were added with stirring. The obtained solution was heated at a bath temperature of 105 ° C. for 2 hours, the internal temperature was raised to 90 ° C., and a component mainly composed of methanol produced as a by-product was distilled off. Subsequently, the bath temperature is heated at 130 ° C.
- the internal temperature is increased to 118 ° C., and a component mainly composed of water and propylene glycol monobutyl ether is distilled off, followed by cooling to room temperature and the polymer solution I (solid content) A concentration of 45% by weight) was obtained.
- 20 g of the obtained polymer solution I was taken, 0.9 g of the imidosilane compound (i) solution (solid content 0.18 g), 2-methylbenzyl-4-acetylphenylmethylsulfonium trifluoromethanesulfonate as a thermal acid generator (MBAPMT) 0.18 g and propylene glycol monomethyl ether acetate 20 g were added and dissolved to obtain a siloxane-based resin composition 22.
- MBAPMT thermal acid generator
- a cured film was prepared using the obtained siloxane-based resin composition 22, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 23 A siloxane-based resin composition 23 was obtained in the same manner as in Example 22 except that MBAPMT was not used. A cured film was prepared using the obtained siloxane-based resin composition 23, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 24 234.05 g (0.5 mol) of tridecafluorooctyltrimethoxysilane and 123.2 g (0.5 mol) of ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane (propylene glycol monomethyl ether (boiling point 121 ° C.)) It melt
- the mixture was heated at a bath temperature of 115 ° C. for 4.0 hours, the internal temperature was raised to 118 ° C., and a component mainly composed of water and propylene glycol monomethyl ether was distilled off, followed by cooling to room temperature and the polymer solution J (solid content A concentration of 43% by weight) was obtained.
- a cured film was prepared using the obtained siloxane-based resin composition 24, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 25 Trifluoropropyltrimethoxysilane 32.72 g (0.15 mol), ⁇ -glycidoxypropyltrimethoxysilane 82.71 g (0.35 mol), silica particle diacetone alcohol solvent dispersion “Quartron” PL-2L-DAA 146.21 g and 94.0 g of propylene glycol monomethyl ether acetate were placed in a reaction vessel, and 16.2 g of water and 0.27 g of phosphoric acid were added dropwise to this solution with stirring so that the reaction temperature did not exceed 40 ° C. .
- a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C. for 2.5 hours, and reacted while distilling off methanol produced by hydrolysis. Thereafter, the solution was further heated and stirred at a bath temperature of 115 ° C. for 2 hours, and then cooled to room temperature to obtain a polymer solution K (solid content: 44% by weight). 20 g of the resulting polymer solution K was taken, 0.88 g of the imidosilane compound (i) solution (solid content 0.176 g), ⁇ -4-methoxyphenylacetonitrile (trade name, PAI-106, Midori) as a photoacid generator Chemical Co., Ltd. (0.176 g) and propylene glycol monomethyl ether acetate (20 g) were added and dissolved to obtain a siloxane-based resin composition 25.
- the imidosilane compound (i) solution solid content 0.176 g
- a cured film was prepared using the obtained siloxane-based resin composition 25, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 26 A siloxane-based resin composition 26 was obtained in the same manner as in Example 25 except that PAI-106 was not used. A cured film was prepared using the obtained siloxane-based resin composition 26, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 27 A siloxane-based resin composition 27 was obtained in the same manner as in Example 12 except that the solution of the imidosilane compound (iii) was changed to 9.7 g (solid content: 1.94 g). A cured film was prepared using the obtained siloxane-based resin composition 27, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 28 A siloxane-based resin composition 28 was obtained in the same manner as in Example 18 except that the solution of the imidosilane compound (i) was changed to 4.0 g (solid content 0.8 g). A cured film was prepared using the obtained siloxane-based resin composition 28, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 29 A siloxane-based resin composition 29 was obtained in the same manner as in Example 23 except that the solution of the imidosilane compound (i) was changed to 0.036 g (solid content: 0.0072 g). A cured film was prepared using the obtained siloxane-based resin composition 29, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 30 Methyltrimethoxysilane 20.4 g (0.15 mol), phenyltrimethoxysilane 39.66 g (0.20 mol), imide silane compound (i) solution 238.09 g (solid content 47.62 g, 0.15 mol), number average 70.6 g of “Optlake” TR-521 having a particle diameter of 15 nm and 44.1 g of ⁇ -butyrolactone were placed in a reaction vessel. To this solution, 30.6 g of water and 0.48 g of phosphoric acid were stirred while the reaction temperature was changed. The solution was added dropwise so as not to exceed 40 ° C.
- a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C. for 2.5 hours, and reacted while distilling off methanol produced by hydrolysis. Thereafter, the solution was further heated and stirred at a bath temperature of 130 ° C. for 2 hours and then cooled to room temperature to obtain a polymer solution L (solid content: 55% by weight).
- a polymer solution L solid content: 55% by weight.
- 10 g of the obtained polymer solution L 10 g of ⁇ -butyrolactone was added and dissolved to obtain a siloxane-based resin composition 30.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 31 To 10 g of the polymer solution L used in Example 30, 10 g of ⁇ -butyrolactone and 2.5 g of the imidosilane compound (i) solution (solid content 0.5 g) were added and dissolved to obtain a siloxane-based resin composition 31.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 32 24.5 g (0.18 mol) of methyltrimethoxysilane, 43.63 g (0.22 mol) of phenyltrimethoxysilane, 339.42 g of a solution of imidosilane compound (ii) (solid content 67.88 g, 0.20 mol), ⁇ - 124.0 g of butyrolactone was placed in a reaction vessel, and 38 g of water and 0.57 g of phosphoric acid were added dropwise with stirring so that the reaction temperature did not exceed 30 ° C. After the dropwise addition, a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 33 24.5 g (0.18 mol) of methyltrimethoxysilane, 43.63 g (0.22 mol) of phenyltrimethoxysilane, 339.42 g of a solution of imidosilane compound (ii) (solid content 67.88 g) (0.20 mol), ⁇ -124.0 g of butyrolactone was placed in a reaction vessel, and 38 g of water and 0.57 g of phosphoric acid were added dropwise with stirring so that the reaction temperature did not exceed 30 ° C. After the dropwise addition, a distillation apparatus was attached to the flask, and the resulting solution was heated and stirred at a bath temperature of 105 ° C.
- the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 34 152.67 g (0.7 mol) of trifluoropropyltrimethoxysilane, 47.26 g (0.2 mol) of ⁇ -glycidoxypropyltrimethoxysilane, and 139.71 g of a solution of imidosilane compound (ii) (solid content 33.33 g). 94 g, 0.1 mol) was dissolved in 280.22 g of propylene glycol monobutyl ether (boiling point: 170 ° C.), and 54.0 g of water and 1.12 g of phosphoric acid were added thereto with stirring. The obtained solution was heated at a bath temperature of 105 ° C.
- the internal temperature was raised to 90 ° C., and a component mainly composed of methanol produced as a by-product was distilled off. Subsequently, the bath temperature is heated at 130 ° C. for 4.0 hours, the internal temperature is increased to 118 ° C., and a component mainly composed of water and propylene glycol monobutyl ether is distilled off, followed by cooling to room temperature, and the polymer solution N (solid content) A concentration of 45% by weight) was obtained.
- a cured film was prepared using the obtained siloxane-based resin composition 34, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 35 To 10 g of the polymer solution A obtained in Example 1, 10 g of ⁇ -butyrolactone and 2.5 g of a solution of imidosilane compound (viii) (solid content 0.5 g) were added and dissolved to obtain a siloxane-based resin composition 35. It was. Using the obtained siloxane-based resin composition 35, the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 36 A siloxane-based resin composition 36 was obtained in the same manner as in Example 35 except that the imidosilane compound (viii) was changed to the imidosilane compound (ix). Using the obtained siloxane-based resin composition 36, the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 37 A siloxane-based resin composition 37 was obtained in the same manner as in Example 35 except that the imidosilane compound (viii) was changed to the imidosilane compound (x). Using the obtained siloxane-based resin composition 37, the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above-described methods.
- Example 38 10.0 g of the polymer solution M used in Example 33 was added, and 1.92 g of the imidosilane compound (viii) solution (solid content: 0.384 g) and propylene glycol monomethyl ether acetate were added and stirred, and the siloxane system A resin composition 38 was obtained. Using the obtained siloxane-based resin composition 38, the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 39 10.0 g of the polymer solution M used in Example 33 was added, and 1.92 g of the imidosilane compound (x) solution (solid content: 0.384 g) and propylene glycol monomethyl ether acetate were added thereto and stirred. A resin composition 39 was obtained. Using the obtained siloxane-based resin composition 39, the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Example 1 A siloxane-based resin composition A1 was obtained in the same manner as in Example 1 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A1, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 2 A siloxane-based resin composition A2 was obtained in the same manner as in Example 4 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A2, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 3 A siloxane-based resin composition A3 was obtained in the same manner as in Example 5 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A3, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 4 A siloxane-based resin composition A4 was obtained in the same manner as in Example 7 except that the imidosilane compound (ii) was not used. A cured film was prepared using the obtained siloxane-based resin composition A4, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 5 A siloxane-based resin composition A5 was obtained in the same manner as in Example 15 except that the imidosilane compound (iii) was not used. A cured film was prepared using the obtained siloxane-based resin composition A5, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 6 A siloxane-based resin composition A6 was obtained in the same manner as in Example 18 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A6, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 7 A siloxane-based resin composition A7 was obtained in the same manner as in Example 22 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A7, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 8 A siloxane-based resin composition A8 was obtained in the same manner as in Example 24 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A8, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 9 A siloxane-based resin composition A9 was obtained in the same manner as in Example 25 except that the imidosilane compound (i) was not used. A cured film was prepared using the obtained siloxane-based resin composition A9, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 10 A siloxane-based resin composition A10 was obtained in the same manner as in Example 1 except that the imidosilane compound (i) was changed to imidosilane (iv). A cured film was prepared using the obtained siloxane-based resin composition A10, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Example 11 A siloxane-based resin composition A11 was obtained in the same manner as in Example 11 except that the imidosilane compound (iii) was changed to imidosilane (v). A cured film was prepared using the obtained siloxane-based resin composition A11, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 12 A siloxane-based resin composition A12 was obtained in the same manner as in Example 18 except that the imidosilane compound (i) was changed to the aromatic bisimide oligomer (vi). A cured film was prepared using the obtained siloxane-based resin composition A12, and evaluation was performed with respect to a refractive index, a transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 13 A siloxane-based resin composition A13 was obtained in the same manner as in Example 25 except that the imidosilane compound (i) was changed to the silicone polyimide precursor (vii). A cured film was prepared using the obtained siloxane-based resin composition A13, and evaluation was performed on the refractive index, transmittance, crack resistance, adhesion, and planarization performance by the above-described methods.
- Comparative Example 14 In a 2 L separable flask equipped with a condenser and a stirrer, 172.8 g (1.6 mol) of m-cresol, 36.6 g (0.3 mol) of 2.3-dimethylphenol, 3.4-dimethylphenol 12 0.2 g (0.1 mol), 37 wt% formaldehyde aqueous solution 12.6 g (formaldehyde: 1.5 mol), oxalic acid dihydrate 12.6 g (0.1 mol) and methyl isobutyl ketone 554 g were added and stirred for 30 minutes. Then, it was left still for 1 hour.
- HPE resin solution solid content: 43% by weight
- 20 g of the resulting novolak resin solution was taken, 0.77 g of imidosilane compound (i), ⁇ -4-methoxyphenylacetonitrile (trade name, PAI-106, manufactured by Midori Chemical Co., Ltd.) 0.172 g as a photoacid generator.
- 20 g of propylene glycol monomethyl ether acetate was added and dissolved to obtain a novolac resin composition B1.
- a cured film was prepared using the obtained novolac resin composition B1, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- Comparative Example 15 A 500 mL three-necked flask was charged with 5 g of 2,2′-azobis (2,4-dimethylvaleronitrile) and 200 g of diethylene glycol ethyl methyl ether (EDM). Subsequently, 25 g of styrene, 20 g of methacrylic acid, 45 g of glycidyl methacrylate and 10 g of tricyclo [5.2.1.02,6] decan-8-yl methacrylate were charged and stirred at room temperature for 30 minutes, and then the atmosphere in the flask was replaced with nitrogen. Thereafter, the flask was immersed in an oil bath at 70 ° C. and heated and stirred for 5 hours.
- EDM diethylene glycol ethyl methyl ether
- EDM was further added to the obtained EDM resin solution to obtain an acrylic resin solution (solid content: 43% by weight).
- the weight average molecular weight (Mw) of the obtained acrylic polymer was 15000.
- 20 g of the resulting acrylic resin solution was taken and 0.77 g of imidosilane compound (ii), 0.258 g of crosslinkable compound “Nicalac” MX-270 and 20 g of propylene glycol monomethyl ether acetate were added and dissolved to obtain an acrylic resin composition B2 was obtained.
- a cured film was prepared using the obtained acrylic resin composition B2, and the refractive index, transmittance, crack resistance, adhesion, and planarization performance were evaluated by the above methods.
- compositions of Examples 1 to 39 and Comparative Examples 1 to 15 are shown in Tables 1 to 4, and the evaluation results are shown in Tables 5 to 6.
- the cured film formed from the siloxane-based resin composition of the present invention is suitably used for optical articles such as solid-state imaging devices and optical filters for displays such as liquid crystal displays. More specifically, it can be used for a planarization film of a solid-state imaging device or a buried planarization film for a waveguide. Further, it can be used for a low refractive index layer, a high refractive index layer and a hard coat layer such as an antireflection film and an antireflection plate of an optical filter.
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Abstract
Description
一般式(1)中、R1は水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R2は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。
一般式(2)中、R3およびR4は、それぞれ水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R5は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。
一般式(3)中、R6は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。
一般式(1)中、R1は水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。アルキル基およびアルケニル基の炭素数は1~4が好ましく、アリール基の炭素数は6~14が好ましい。また、置換体に導入される置換基としては、ハロゲン含有基、エポキシ含有基、アミノ含有基、(メタ)アクリロイル含有基、シアノ含有基、フルオレン含有基、ビニル基などが挙げられる。R2は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。ブチル基はn-ブチル基が好ましい。
一般式(2)中、R3およびR4は、それぞれ水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。アルキル基およびアルケニル基の炭素数は1~4が好ましく、アリール基の炭素数は6~14が好ましい。また、置換体に導入される置換基としては、ハロゲン含有基、エポキシ含有基、アミノ含有基、(メタ)アクリロイル含有基、ビニル基などが挙げられる。R5は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。ブチル基はn-ブチル基が好ましい。
一般式(3)中、R6は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。メチル基またはエチル基が好ましい。
6インチシリコンウエハ上または40mm角ガラス基板上に、シロキサン系樹脂組成物をスピンコーター(ミカサ(株)製1H-360S)を用いて任意の回転数で塗布し、ついでホットプレート(大日本スクリーン製造(株)製SCW-636)を用いて、空気雰囲気下で120℃で3分プリベークすることにより、膜厚2μmの塗布膜を得た。
前記(1)に記載の方法で作製した6インチシリコンウエハ上の硬化膜について、プリズムカプラーMODEL2010(Metricon(株)製)を用いて、23℃での633nm(He-Neレーザー使用)における膜面に対して垂直方向の屈折率(TE)および膜厚を測定した。
前記(1)に記載の方法で40mm角ガラス基板上に作製した硬化膜について、紫外-可視分光光度計UV-260(島津製作所(株)製)を用いて、400nmの透過率を測定し、膜厚1.0μmに換算して透過率を算出した。
前記(1)に記載の方法で6インチシリコンウエハ上に作製した硬化膜について、以下の温度履歴でヒートサイクル試験を行い、各温度において光学顕微鏡でクラックの有無を観察した。加熱は空気雰囲気下のホットプレート上で行った。
ヒートサイクル試験の温度履歴
250℃5分→室温(23℃)5分→280℃5分→室温(23℃)5分→300℃5分→室温(23℃)5分→320℃5分→室温(23℃)5分→340℃5分→室温(23℃)5分→360℃5分→室温(23℃)5分→380℃5分→室温(23℃)5分→400℃5分→室温(23℃)5分→420℃5分→室温(23℃)5分→440℃5分→室温(23℃)5分→460℃5分→室温(23℃)5分。
前記(1)に記載の方法で40mm角ガラス基板上に作製した硬化膜について、JIS K5400 8.5.2(1990)碁盤目テープ法に準じて接着性を評価した。すなわち、硬化膜つき40mm角ガラス基板上の薄膜表面に、カッターナイフでガラス板の素地に到達するように、直交する縦横11本ずつの平行な直線を1mm間隔で引いて、1mm×1mmのマス目を100個作製した。切られた薄膜表面にセロハン粘着テープ(幅=18mm、粘着力=3.7N/10mm)を張り付け、消しゴム(JIS S6050合格品)で擦って密着させ、テープの一端を持ち、板に直角に保ち瞬間的に剥離した際のマス目の残存数を目視によって評価した。
前記(1)記載の方法でシリコンウエハ上に作製した硬化膜について、キュア前後の硬化収縮率を算出した。この値が0~15%の場合、平坦化性能は良好といえる。硬化収縮率は以下の式に従って算出した。
硬化収縮率(%)=(1-キュアで得られた硬化膜の膜厚÷塗布膜の膜厚)×100 。
プロピレングリコールモノメチルエーテル400gに3-トリメトキシシリルプロピルコハク酸無水物41.97g(160mmol)とt-ブチルアミン11.70g(160mmol)を加えて室温にて30分撹拌した後、60℃にて2時間撹拌した。その後、140℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(i)の溶液を得た。
ジアセトンアルコール400gに2-トリメトキシシリルエチルフタル酸無水物23.71g(80mmol)とモノエタノールアミン4.89g(80mmol)を加えて室温にて30分間撹拌した後、60℃にて2時間撹拌した。その後、140℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(ii)の溶液を得た。
プロピレングリコールモノメチルエーテルアセテート400gに3-トリメトキシシリルプロピルコハク酸無水物20.99g(80mmol)とアニリン7.45g(80mmol)を加えて室温にて30分間撹拌した後、60℃にて2時間撹拌した。その後、160℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(iii)の溶液を得た。
γ-ブチロラクトン40gにイソシアネートプロピルトリメトキシシラン32.84g(160mmol)を加えて撹拌し溶解させた。フタル酸無水物23.70g(160mmol)を加えて室温にて30分間撹拌した後、140℃にて2時間撹拌した。得られた溶液を固形分濃度が20%重量になるようにγ-ブチロラクトンで希釈して、下記構造で表されるイミドシラン化合物(iv)の溶液を得た。
ジアセトンアルコール400gにアミノプロピルトリエトキシシラン35.42g(160mmol)と、無水コハク酸16.01g(160mmol)を加えて室温にて30分間撹拌した後、60℃にて2時間撹拌した。その後、160℃まで昇温し、ジアセトンアルコールと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(v)の溶液を得た。
撹拌機、還流冷却管、および窒素導入管を備えた容器に、無水フタル酸32.58g(220mmol)、γ-ピコリン1.39g、N-メチル-2-ピロリドン(以下NMPと略す)130.3gを添加し、ここに、1,3-ビス(3-アミノプロピル)テトラメチルジシロキサン24.8g(100mmol)をNMP99.4gに溶解したものを滴下し、窒素、窒素雰囲気下で2時間撹拌した。その後、無水酢酸40.8g(400mmol)を添加し、窒素雰囲気下で撹拌しながら70℃まで加熱昇温し70℃で4時間反応させた。反応終了後室温まで冷却し、2000mlの水に投入し、ビスイミド粉43.24gを得た。このビスイミド粉の赤外吸収スペクトルを測定したところ、1720cm-1、1780cm-1にイミド環の特性吸収が確認された。得られたビスイミド粉を、固形分濃度が20重量%になるようにγ-ブチロラクトンに溶解して、下記構造で表される芳香族ビスイミドオリゴマー(vi)の溶液を得た。
γ-ブチロラクトン40gにアミノプロピルトリエトキシシラン35.42g(160mmol)を加えて撹拌し溶解させた。4,4’-オキシジフタル酸二無水物24.82g(80mmol)を加えて室温にて30分間撹拌した後、40℃にて2時間撹拌した。得られた溶液を固形分濃度が20重量%になるようにγ-ブチロラクトンで希釈して、下記構造で表されるシリコーンポリイミド前駆体(vii)の溶液を得た。
プロピレングリコールモノメチルエーテル400gにジメトキシシリル-3,3’-ビス(プロピルコハク酸無水物)29.80g(80mmol)とt-ブチルアミン11.70g(160mmol)を加えて室温にて30分撹拌した後、60℃にて2時間撹拌した。その後、140℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(viii)の溶液を得た。
ジアセトンアルコール400gにジメトキシシリル-2,2’-ビス(エチルフタル酸無水物)35.24g(80mmol)とモノエタノールアミン9.78g(160mmol)を加えて室温にて30分間撹拌した後、60℃にて2時間撹拌した。その後、140℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(ix)の溶液を得た。
プロピレングリコールモノメチルエーテル400gにメトキシシリル-3,3’,3”-トリス(プロピルコハク酸無水物)24.13g(50mmol)とi-プロピルアミン8.87g(150mmol)を加えて室温にて30分撹拌した後、60℃にて2時間撹拌した。その後、140℃まで昇温し、プロピレングリコールモノメチルエーテルと水を共沸させながら、6時間反応させた。得られた溶液を固形分濃度が20重量%になるようにジアセトンアルコールで希釈して、下記構造で表されるイミドシラン化合物(x)の溶液を得た。
メチルトリメトキシシラン 20.4g(0.15mol)、フェニルトリメトキシシラン 69.4g(0.35mol)、数平均粒子径15nmの“オプトレイク”TR-521(商品名、触媒化成工業(株)製 組成:酸化チタン粒子30重量%、γ-ブチロラクトン70重量%)70.6g、γ-ブチロラクトン 44.1gを反応容器に入れ、この溶液に、水30.6gおよびリン酸0.48gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液A(固形分55重量%)を得た。得られたポリマー溶液A10gに、γ-ブチロラクトン10gおよびイミドシラン化合物(i)の溶液2.5g(固形分0.5gを加えて溶解し、シロキサン系樹脂組成物1を得た。
メチルトリメトキシシラン 8.2g(0.06mol)、フェニルトリメトキシシラン 55.5g(0.28mol)、ジメチルジメトキシシラン 7.2g(0.06mol)、数平均粒子径15nmの“オプトレイク”TR-521 71.1g、γ-ブチロラクトン 23.9gを反応容器に入れ、この溶液に、水34.5gおよびリン酸1.0gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液B(固形分48重量%)を得た。得られたポリマー溶液B10gに、γ-ブチロラクトン10g、架橋性化合物である“ニカラック”MX-270(三和ケミカル(株)製)0.24gおよびイミドシラン化合物(ii)の溶液3.6g(固形分0.72g)を加えて溶解し、シロキサン系樹脂組成物2を得た。
ニカラックMX-270を用いなかった他は実施例2と同様にしてシロキサン系樹脂組成物3を得た。得られたシロキサン系樹脂組成物3を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
“オプトレイク”TR-521 71.1gの替わりに、数平均粒子径30nmの酸化ジルコニウム粒子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(酸化ジルコニウム30重量%、プロピレングリコールモノメチルエーテルアセテート70重量%)70.0gを用いた以外は実施例2と同様の操作を行い、ポリマー溶液C(固形分46重量%)を得た。得られたポリマー溶液C10gにプロピレングリコールモノメチルエーテルアセテート15gおよびイミドシラン化合物(i)の溶液2.05g(固形分0.41g)を加えて溶解し、シロキサン系樹脂組成物4を得た。
“オプトレイク”TR-521 71.1gの替わりに、数平均粒子径30nmの酸化アルミニウム粒子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(酸化アルミニウム30重量%、プロピレングリコールモノメチルエーテルアセテート70重量%)45.0gを用いた以外は実施例2と同様の操作を行い、ポリマー溶液D(固形分40%重量%)を得た。得られたポリマー溶液D10gに、3-メチル-3-メトキシブチルアセテート20g、熱酸発生剤であるベンジル-4-ヒドロキシフェニルメチルスルホニウムトリフルオロメタンスルフォネート(BHPMT)0.12gおよびイミドシラン化合物(i)の溶液1.8g(固形分0.36g)を加えて溶解し、シロキサン系樹脂組成物5を得た。
BHPMTを用いなかった他は実施例5と同様にしてシロキサン系樹脂組成物6を得た。得られたシロキサン系樹脂組成物6を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
メチルトリメトキシシラン 8.2g(0.06mol)、フェニルトリメトキシシラン 55.5g(0.28mol)、テトラエトキシシラン 5.4g(0.026mol)、“オプトレイク”TR-521 52.4g、γ-ブチロラクトン20.5gを反応容器に入れ、この溶液に、水34.5gおよびリン酸1.0gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールおよびエタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液E(固形分60重量%)を得た。得られたポリマー溶液E20gに、γ-ブチロラクトン40g、光酸発生剤である5-ノルボルネン-2,3-ジカルボキシイミジルトシレート(商品名NDI-101、みどり化学(株)製)0.48g、増感剤である9,10-ジブトキシアントラセン(DBA)0.036gおよびイミドシラン化合物(ii)の溶液0.12g(固形分0.024g)を加えて溶解し、シロキサン系樹脂組成物7を得た。
NDI-101およびDBAを用いなかった他は実施例7と同様にしてシロキサン系樹脂組成物8を得た。得られたシロキサン系樹脂組成物8を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
メチルトリメトキシシラン 12.3g(0.15mol)、フェニルトリメトキシシラン 41.6g(0.35mol)、数平均粒子径15nmの“オプトレイク”TR-527(商品名、触媒化成工業(株)製 組成:酸化チタン粒子20重量%、メタノール80重量%)193g、プロピレングリコールモノメチルエーテルアセテート94.0gを反応容器に入れ、この溶液に、水16.2gおよびリン酸0.27gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温115℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液F(固形分44重量%)を得た。得られたポリマー溶液Fを20g取り、光塩基発生剤である[[(2-ニトロベンジル)オキシ]カルボニル]シクロヘキシルアミン(NCA)0.352g、イミドシラン化合物(i)の溶液3.96g(固形分0.792g)、イミドシラン化合物(iii)の溶液3.96g(固形分0.792g)、増感剤である9,10-ジプロポキシアントラセン(DPA)0.044gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物9を得た。
NCAおよびDPAを用いなかった他は実施例9と同様にしてシロキサン系樹脂組成物8を得た。得られたシロキサン系樹脂組成物10を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例9で用いたポリマー溶液F20gに、プロピレングリコールモノメチルエーテルアセテート25g、イミドシラン化合物(iii)の溶液1.76g(固形分0.352g)、および架橋性化合物である2,2-ジメトキシメチル-4-t-ブチルフェノール(商品名、DMOM-PTBP、本州化学工業(株)製)0.264gおよび熱酸発生剤である2-メチルベンジル-4-アセチルフェニルメチルスルホニウムトリフルオロメタンスルフォネート(MBAPMT)0.088gを加えて溶解し、シロキサン系樹脂組成物11を得た。
DMOM-PTBPおよびMBAPMTを用いなかった他は実施例11と同様してシロキサン系樹脂組成物12を得た。得られたシロキサン系樹脂組成物12を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例9で用いたポリマー溶液F20gに、プロピレングリコールモノメチルエーテルアセテート25g、イミドシラン化合物(iii)の溶液1.76g(固形分0.352g)、架橋性化合物であるS-3 2.64gおよび熱酸発生剤であるベンジル-4-ヒドロキシフェニルメチルスルホニウムトリフルオロメタンスルフォネート(BHPMT)0.0176gを加えて溶解し、シロキサン系樹脂組成物13を得た。
S-3を用いなかった他は実施例13と同様にしてシロキサン系樹脂組成物14を得た。得られたシロキサン系樹脂組成物14を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例9で用いたポリマー溶液F20gに、プロピレングリコールモノメチルエーテルアセテート25g、イミドシラン化合物(iii)の溶液1.76g(固形分0.352g)、架橋性化合物である“ニカラック”MX-270(三和ケミカル(株)製)0.88gおよび熱塩基発生剤である1-メチル-1-(4-ビフェニルイル)エチルカルバメート(MBEC)0.176gを加えて溶解し、シロキサン系樹脂組成物15を得た。
MBECを用いなかった他は実施例15と同様にしてシロキサン系樹脂組成物16を得た。得られたシロキサン系樹脂組成物16を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例9で用いたポリマー溶液F20gに、プロピレングリコールモノメチルエーテルアセテート25g、イミドシラン化合物(iii)の溶液1.76g(固形分0.352g)、架橋性化合物であるTML-BPA(本州化学工業(株)製)1.32gおよび熱酸発生剤であるベンジル-4-ヒドロキシフェニルメチルスルホニウムトリフルオロメタンスルフォネート(BHPMT)0.44gを加えて溶解し、シロキサン系樹脂組成物17を得た。
メチルトリメトキシシラン 24.5g(0.18mol)、フェニルトリメトキシシラン 83.3g(0.42mol)、γ-ブチロラクトン124.0gを反応容器に入れ、撹拌しながら、水38gおよびリン酸0.57gを反応温度が30℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液G(固形分32重量%)を得た。得られたポリマー溶液Gを10.0gとり、これにイミドシラン化合物(i)の溶液1.92g(固形分0.384g)、およびプロピレングリコールモノメチルエーテルアセテートを添加して撹拌し、シロキサン系樹脂組成物18を得た。
イミドシラン化合物(i)の溶液を0.32g(固形分0.064g)に変更した他は実施例18と同様にしてシロキサン系樹脂組成物19を得た。得られたシロキサン系樹脂組成物19を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
メチルトリメトキシシラン 12.3g(0.15mol)、フェニルトリメトキシシラン 41.6g(0.35mol)、数平均粒子径20nmの シリカ粒子ジアセトンアルコール溶剤分散液“クォートロン”PL-2L-DAA(商品名、扶桑化学工業(株)製:固形分26.4重量%)を146.21g、プロピレングリコールモノメチルエーテルアセテート94.0gを反応容器に入れ、この溶液に、水16.2gおよびリン酸0.27gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温115℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液H(固形分44重量%)を得た。得られたポリマー溶液Hを20g取り、架橋性化合物であるS-11(商品名、PDS-9931(ゲレスト(株)製))3.52g、イミドシラン化合物(iii)の溶液2.2g(固形分0.44g)、およびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物20を得た。
S-11を用いなかった他は実施例20と同様にしてシロキサン系樹脂組成物21を得た。得られたシロキサン系樹脂組成物21を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
トリフルオロプロピルトリメトキシシラン 152.67g(0.7モル)、γ-グリシドキシプロピルトリメトキシシラン 70.89g(0.3モル)をプロピレングリコールモノブチルエーテル(沸点170℃)280.22gに溶解し、これに、水54.0g、リン酸1.12gを撹拌しながら加えた。得られた溶液をバス温105℃で2時間加熱し、内温を90℃まで上げて、主として副生するメタノールからなる成分を留出せしめた。次いでバス温130℃で4.0時間加熱し、内温を118℃まで上げて、主として水とプロピレングリコールモノブチルエーテルからなる成分を留出せしめた後、室温まで冷却し、ポリマー溶液I(固形分濃度45重量%)を得た。得られたポリマー溶液Iを20g取り、イミドシラン化合物(i)の溶液0.9g(固形分0.18g)、熱酸発生剤である2-メチルベンジル-4-アセチルフェニルメチルスルホニウムトリフルオロメタンスルフォネート(MBAPMT)0.18gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物22を得た。
MBAPMTを用いなかった他は実施例22と同様にしてシロキサン系樹脂組成物23を得た。得られたシロキサン系樹脂組成物23を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
トリデカフルオロオクチルトリメトキシシラン 234.05g(0.5モル)、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 123.2g(0.5モル)をプロピレングリコールモノメチルエーテル(沸点121℃)471.09gに溶解し、これに、水63.0g、リン酸1.79gを撹拌しながら加えた。得られた溶液をバス温105℃で2時間加熱し、内温を90℃まで上げて、主として副生するメタノールからなる成分を留出せしめた。次いでバス温115℃で4.0時間加熱し、内温を118℃まで上げて、主として水とプロピレングリコールモノメチルエーテルからなる成分を留出せしめた後、室温まで冷却し、ポリマー溶液J(固形分濃度43重量%)を得た。得られたポリマー溶液Jを20g取り、イミドシラン化合物(i)の溶液0.9g(固形分0.18g)、架橋性化合物である“ニカラック”MX-280(三和ケミカル(株)製)0.18gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物24を得た。
トリフルオロプロピルトリメトキシシラン 32.72g(0.15mol)、γ-グリシドキシプロピルトリメトキシシラン 82.71g(0.35mol)、シリカ粒子ジアセトンアルコール溶剤分散液“クォートロン”PL-2L-DAAを146.21g、プロピレングリコールモノメチルエーテルアセテート94.0gを反応容器に入れ、この溶液に、水16.2gおよびリン酸0.27gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温115℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液K(固形分44重量%)を得た。得られたポリマー溶液Kを20g取り、イミドシラン化合物(i)の溶液0.88g(固形分0.176g)、光酸発生剤であるα-4-メトキシフェニルアセトニトリル(商品名、PAI-106、みどり化学(株)製)0.176gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物25を得た。
PAI-106を用いなかった他は実施例25と同様してシロキサン系樹脂組成物26を得た。得られたシロキサン系樹脂組成物26を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(iii)の溶液を9.7g(固形分1.94g)に変更した他は実施例12と同様にしてシロキサン系樹脂組成物27を得た。得られたシロキサン系樹脂組成物27を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)の溶液を4.0g(固形分0.8g)に変更した他は実施例18と同様にしてシロキサン系樹脂組成物28を得た。得られたシロキサン系樹脂組成物28を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)の溶液を0.036g(固形分0.0072g)に変更した他は実施例23と同様にしてシロキサン系樹脂組成物29を得た。得られたシロキサン系樹脂組成物29を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
メチルトリメトキシシラン 20.4g(0.15mol)、フェニルトリメトキシシラン 39.66g(0.20mol)、イミドシラン化合物(i)の溶液238.09g(固形分47.62g、0.15mol)、数平均粒子径15nmの“オプトレイク”TR-521 70.6g、γ-ブチロラクトン 44.1gを反応容器に入れ、この溶液に、水30.6gおよびリン酸0.48gを、撹拌しながら、反応温度が40℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液L(固形分55重量%)を得た。得られたポリマー溶液L 10gに、γ-ブチロラクトン10gを加えて溶解し、シロキサン系樹脂組成物30を得た。
実施例30で用いたポリマー溶液L 10gに、γ-ブチロラクトン10gおよびイミドシラン化合物(i)の溶液2.5g(固形分0.5g)を加えて溶解し、シロキサン系樹脂組成物31を得た。
メチルトリメトキシシラン 24.5g(0.18mol)、フェニルトリメトキシシラン 43.63g(0.22mol)、イミドシラン化合物(ii)の溶液339.42g(固形分67.88g、0.20mol)、γ-ブチロラクトン124.0gを反応容器に入れ、撹拌しながら、水38gおよびリン酸0.57gを反応温度が30℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液M(固形分32重量%)を得た。得られたポリマー溶液Mを10.0gとり、これにプロピレングリコールモノメチルエーテルアセテートを添加して撹拌し、シロキサン系樹脂組成物32を得た。
メチルトリメトキシシラン 24.5g(0.18mol)、フェニルトリメトキシシラン 43.63g(0.22mol)、イミドシラン化合物(ii)の溶液339.42g(固形分67.88g)(0.20mol)、γ-ブチロラクトン124.0gを反応容器に入れ、撹拌しながら、水38gおよびリン酸0.57gを反応温度が30℃を越えないように滴下した。滴下後、フラスコに蒸留装置を取り付け、得られた溶液をバス温105℃で2.5時間加熱撹拌して加水分解により生成したメタノールを留去しつつ反応させた。その後、溶液をバス温130℃でさらに2時間加熱撹拌した後、室温まで冷却し、ポリマー溶液M(固形分32重量%)を得た。得られたポリマー溶液Mを10.0gとり、これにイミドシラン化合物(i)の溶液1.92g(固形分0.384g)およびプロピレングリコールモノメチルエーテルアセテートを添加して撹拌し、シロキサン系樹脂組成物33を得た。
トリフルオロプロピルトリメトキシシラン 152.67g(0.7モル)、γ-グリシドキシプロピルトリメトキシシラン 47.26g(0.2モル)、イミドシラン化合物(ii)の溶液139.71g(固形分33.94g、0.1mol)をプロピレングリコールモノブチルエーテル(沸点170℃)280.22gに溶解し、これに、水54.0g、リン酸1.12gを撹拌しながら加えた。得られた溶液をバス温105℃で2時間加熱し、内温を90℃まで上げて、主として副生するメタノールからなる成分を留出せしめた。次いでバス温130℃で4.0時間加熱し、内温を118℃まで上げて、主として水とプロピレングリコールモノブチルエーテルからなる成分を留出せしめた後、室温まで冷却し、ポリマー溶液N(固形分濃度45重量%)を得た。得られたポリマー溶液Nを20g取り、イミドシラン化合物(i)の溶液0.9g(固形分0.18g)、熱酸発生剤である2-メチルベンジル-4-アセチルフェニルメチルスルホニウムトリフルオロメタンスルフォネート(MBAPMT)0.18gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、シロキサン系樹脂組成物34を得た。
実施例1で用いた得られたポリマー溶液A10gに、γ-ブチロラクトン10gおよびイミドシラン化合物(viii)の溶液2.5g(固形分0.5g)を加えて溶解し、シロキサン系樹脂組成物35を得た。得られたシロキサン系樹脂組成物35を用い、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(viii)をイミドシラン化合物(ix)に変更した以外は実施例35と同様にしてシロキサン系樹脂組成物36を得た。得られたシロキサン系樹脂組成物36を用い、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(viii)をイミドシラン化合物(x)に変更した以外は実施例35と同様にしてシロキサン系樹脂組成物37を得た。得られたシロキサン系樹脂組成物37を用い、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例33で用いたポリマー溶液Mを10.0gとり、これにイミドシラン化合物(viii)の溶液1.92g(固形分0.384g)、およびプロピレングリコールモノメチルエーテルアセテートを添加して撹拌し、シロキサン系樹脂組成物38を得た。得られたシロキサン系樹脂組成物38を用い、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
実施例33で用いたポリマー溶液Mを10.0gとり、これにイミドシラン化合物(x)の溶液1.92g(固形分0.384g)、およびプロピレングリコールモノメチルエーテルアセテートを添加して撹拌し、シロキサン系樹脂組成物39を得た。得られたシロキサン系樹脂組成物39を用い、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例1と同様にしてシロキサン系樹脂組成物A1を得た。得られたシロキサン系樹脂組成物A1を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例4と同様にしてシロキサン系樹脂組成物A2を得た。得られたシロキサン系樹脂組成物A2を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例5と同様にしてシロキサン系樹脂組成物A3を得た。得られたシロキサン系樹脂組成物A3を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(ii)を用いなかった他は実施例7と同様してシロキサン系樹脂組成物A4を得た。得られたシロキサン系樹脂組成物A4を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(iii)を用いなかった他は実施例15と同様にしてシロキサン系樹脂組成物A5を得た。得られたシロキサン系樹脂組成物A5を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例18と同様にしてシロキサン系樹脂組成物A6を得た。得られたシロキサン系樹脂組成物A6を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例22と同様にしてシロキサン系樹脂組成物A7を得た。得られたシロキサン系樹脂組成物A7を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例24と同様にしてシロキサン系樹脂組成物A8を得た。得られたシロキサン系樹脂組成物A8を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を用いなかった他は実施例25と同様にしてシロキサン系樹脂組成物A9を得た。得られたシロキサン系樹脂組成物A9を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)をイミドシラン(iv)に変更した他は実施例1と同様にしてシロキサン系樹脂組成物A10を得た。得られたシロキサン系樹脂組成物A10を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(iii)をイミドシラン(v)に変更した他は実施例11と同様にしてシロキサン系樹脂組成物A11を得た。得られたシロキサン系樹脂組成物A11を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)を芳香族ビスイミドオリゴマー(vi)に変更した他は実施例18と同様にしてシロキサン系樹脂組成物A12を得た。得られたシロキサン系樹脂組成物A12を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
イミドシラン化合物(i)をシリコーンポリイミド前駆体(vii)に変更した他は実施例25と同様にしてシロキサン系樹脂組成物A13を得た。得られたシロキサン系樹脂組成物A13を用いて硬化膜を作製し、前記方法で屈折率、透過率、耐クラック性、接着性、平坦化性能について評価を行った。
冷却管と撹拌装置を装着した2Lのセパラブルフラスコに、m-クレゾール172.8g(1.6mol)、2.3-ジメチルフェノール36.6g(0.3モル)、3.4-ジメチルフェノール12.2g(0.1mol)、37重量%ホルムアルデヒド水溶液12.6g(ホルムアルデヒド:1.5mol)、シュウ酸2水和物12.6g(0.1mol)及びメチルイソブチルケトン554gを加え、30分撹拌した後、1時間静置した。2層に分離した上層をデカンテーションによって除去し、2-ヒドロキシプロピオン酸エチル(HPE)を加え、残存メチルイソブチルケトン、水を減圧濃縮によって除去し、HPE樹脂溶液を得た。得られたHPE樹脂溶液にさらにHPEを加えてノボラック樹脂溶液(固形分43重量%)を得た。得られたノボラック樹脂溶液を20g取り、イミドシラン化合物(i)0.77g、光酸発生剤であるα-4-メトキシフェニルアセトニトリル(商品名、PAI-106、みどり化学(株)製)0.172gおよびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、ノボラック系樹脂組成物B1を得た。
2,2’-アゾビス(2,4-ジメチルバレロニトリル)5g、ジエチレングリコールエチルメチルエーテル(EDM)200gを500mLの三口フラスコに仕込んだ。引き続きスチレン25g、メタクリル酸20g、メタクリル酸グリシジル45g、トリシクロ[5.2.1.02,6]デカン-8-イルメタクリレート10gを仕込み、室温で30分間撹拌した後、フラスコ内を窒素置換した。その後、フラスコを70℃のオイルバスに浸けて、5時間加熱撹拌した。得られたEDM樹脂溶液に、さらにEDMを加えてアクリル樹脂溶液(固形分43重量%)を得た。なお、得られたアクリルポリマーの重量平均分子量(Mw)は15000であった。得られたアクリル樹脂溶液を20g取り、イミドシラン化合物(ii)0.77g、架橋性化合物“ニカラック”MX-270 0.258g、およびプロピレングリコールモノメチルエーテルアセテート20gを加えて溶解し、アクリル系樹脂組成物B2を得た。
Claims (13)
- 前記(a)シロキサン系樹脂が、(a-1)下記一般式(1)~(3)のいずれかで表される1種以上のアルコキシシラン化合物を加水分解し、該加水分解物を縮合反応させて得られる反応生成物である請求項1記載のシロキサン系樹脂組成物。
R1Si(OR2)3 (1)
(一般式(1)中、R1は水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R2は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。)
R3R4Si(OR5)2 (2)
(一般式(2)中、R3およびR4は、それぞれ水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R5は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。)
Si(OR6)4 (3)
(一般式(3)中、R6は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。) - 前記(a-1)の反応生成物が、シリコン化合物粒子、アルミニウム化合物粒子、スズ化合物粒子、チタン化合物粒子およびジルコニウム化合物粒子からなる群より選ばれる少なくとも1種の化合物粒子の存在下、前記一般式(1)~(3)のいずれかで表される1種以上のアルコキシシラン化合物を加水分解し、該加水分解物を縮合反応させて得られる反応生成物である請求項2記載のシロキサン系樹脂組成物。
- (a)シロキサン系樹脂を含有するシロキサン系樹脂組成物であって、前記(a)シロキサン系樹脂が、(a-2)下記一般式(1)~(3)のいずれかで表される1種以上のアルコキシシラン化合物と下記一般式(5)で表されるイミドシラン化合物とを加水分解し、該加水分解物を縮合反応させて得られる反応生成物であるシロキサン系樹脂組成物。
R1Si(OR2)3 (1)
(一般式(1)中、R1は水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R2は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。)
R3R4Si(OR5)2 (2)
(一般式(2)中、R3およびR4は、それぞれ水素、アルキル基、アルケニル基、アリール基またはそれらの置換体を表す。R5は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。)
Si(OR6)4 (3)
(一般式(3)中、R6は同じでも異なってもよく、メチル基、エチル基、プロピル基、イソプロピル基またはブチル基を表す。) - 前記(a-2)の反応生成物が、シリコン化合物粒子、アルミニウム化合物粒子、スズ化合物粒子、チタン化合物粒子およびジルコニウム化合物粒子からなる群より選ばれる少なくとも1種の化合物粒子の存在下、前記一般式(1)~(3)のいずれかで表される1種以上のアルコキシシラン化合物と前記一般式(5)で表されるイミドシラン化合物とを加水分解し、該加水分解物を縮合反応させて得られる反応生成物である請求項4記載のシロキサン系樹脂組成物。
- 前記(a)シロキサン系樹脂がフッ素を含有する請求項1~5いずれか記載のシロキサン系樹脂組成物。
- さらに(c)酸発生剤または塩基発生剤を含有する請求項1~6いずれか記載のシロキサン系樹脂組成物。
- さらに(d)下記一般式(6)または(7)で表される基を有する、ケイ素原子を有さない架橋性化合物、および/または下記一般式(8)で表される架橋性化合物を含有する請求項1~7いずれかに記載のシロキサン系樹脂組成物。
- 請求項1~8いずれか記載のシロキサン系樹脂組成物を含む固体撮像素子用材料。
- 請求項1~9いずれか記載のシロキサン系樹脂組成物を硬化させてなる硬化膜。
- 請求項10記載の硬化膜を有する光学物品。
- 請求項10記載の硬化膜を有する固体撮像素子。
- 下記一般式(4)または一般式(5)で表されるイミドシラン化合物を含有する接着改良剤。
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Cited By (13)
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WO2011114995A1 (ja) * | 2010-03-17 | 2011-09-22 | 東レ株式会社 | シランカップリング剤、ネガ型感光性樹脂組成物、硬化膜、およびタッチパネル用部材 |
CN102803274A (zh) * | 2010-03-17 | 2012-11-28 | 东丽株式会社 | 硅烷偶联剂、负型感光性树脂组合物、固化膜、及触控面板用构件 |
JP5459315B2 (ja) * | 2010-03-17 | 2014-04-02 | 東レ株式会社 | シランカップリング剤、ネガ型感光性樹脂組成物、硬化膜、およびタッチパネル用部材 |
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Also Published As
Publication number | Publication date |
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JPWO2009096050A1 (ja) | 2011-05-26 |
US20100316953A1 (en) | 2010-12-16 |
KR20100117581A (ko) | 2010-11-03 |
JP5375094B2 (ja) | 2013-12-25 |
EP2239301A4 (en) | 2013-11-06 |
US8389649B2 (en) | 2013-03-05 |
CN101910318A (zh) | 2010-12-08 |
EP2239301B1 (en) | 2016-04-27 |
TWI437029B (zh) | 2014-05-11 |
EP2239301A1 (en) | 2010-10-13 |
KR101471234B1 (ko) | 2014-12-09 |
TW200932791A (en) | 2009-08-01 |
CN101910318B (zh) | 2012-10-24 |
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