JPWO2008066116A1 - ポリシロキサン系組成物 - Google Patents
ポリシロキサン系組成物 Download PDFInfo
- Publication number
- JPWO2008066116A1 JPWO2008066116A1 JP2008547031A JP2008547031A JPWO2008066116A1 JP WO2008066116 A1 JPWO2008066116 A1 JP WO2008066116A1 JP 2008547031 A JP2008547031 A JP 2008547031A JP 2008547031 A JP2008547031 A JP 2008547031A JP WO2008066116 A1 JPWO2008066116 A1 JP WO2008066116A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- polysiloxane
- compound
- component
- polyhedral
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 Polysiloxane Polymers 0.000 title claims abstract description 208
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 110
- 239000000203 mixture Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract description 30
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 41
- 125000000524 functional group Chemical group 0.000 claims description 34
- 230000003287 optical effect Effects 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229920000570 polyether Polymers 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 229920002367 Polyisobutene Polymers 0.000 claims description 3
- 229920001281 polyalkylene Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 claims description 2
- 239000010408 film Substances 0.000 description 35
- 125000004429 atom Chemical group 0.000 description 32
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 32
- 239000000463 material Substances 0.000 description 30
- 239000011521 glass Substances 0.000 description 24
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000003700 epoxy group Chemical group 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 15
- 239000000853 adhesive Substances 0.000 description 14
- 230000001070 adhesive effect Effects 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 229910052697 platinum Inorganic materials 0.000 description 11
- 238000002834 transmittance Methods 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 125000000962 organic group Chemical group 0.000 description 10
- 230000001681 protective effect Effects 0.000 description 10
- 235000012239 silicon dioxide Nutrition 0.000 description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 description 10
- VAUMWVVODNTNEA-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenyl)methoxyboronic acid Chemical compound FC1=C(C(=C(C(=C1COB(O)O)F)F)F)F VAUMWVVODNTNEA-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 9
- 238000006482 condensation reaction Methods 0.000 description 9
- 239000000565 sealant Substances 0.000 description 9
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 9
- 230000002194 synthesizing effect Effects 0.000 description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000003944 tolyl group Chemical group 0.000 description 7
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 6
- HFKJQIJFRMRSKM-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenoxy]boronic acid Chemical compound OB(O)OC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 HFKJQIJFRMRSKM-UHFFFAOYSA-N 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 125000006038 hexenyl group Chemical group 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000002161 passivation Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 230000002093 peripheral effect Effects 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 description 4
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229910000077 silane Inorganic materials 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000012955 diaryliodonium Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 3
- 239000002657 fibrous material Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000010903 husk Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- POPVULPQMGGUMJ-UHFFFAOYSA-N octasilsesquioxane cage Chemical compound O1[SiH](O[SiH](O2)O[SiH](O3)O4)O[SiH]4O[SiH]4O[SiH]1O[SiH]2O[SiH]3O4 POPVULPQMGGUMJ-UHFFFAOYSA-N 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- VQVGJEIVVJBMCV-UHFFFAOYSA-N (4-octoxyphenyl)-phenyliodanium Chemical compound C1=CC(OCCCCCCCC)=CC=C1[I+]C1=CC=CC=C1 VQVGJEIVVJBMCV-UHFFFAOYSA-N 0.000 description 2
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- 102100033806 Alpha-protein kinase 3 Human genes 0.000 description 2
- 101710082399 Alpha-protein kinase 3 Proteins 0.000 description 2
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- 101150003085 Pdcl gene Proteins 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 2
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- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 239000005340 laminated glass Substances 0.000 description 1
- 229940093474 manganese carbonate Drugs 0.000 description 1
- 239000011656 manganese carbonate Substances 0.000 description 1
- 235000006748 manganese carbonate Nutrition 0.000 description 1
- 229910000016 manganese(II) carbonate Inorganic materials 0.000 description 1
- XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 description 1
- IMXBRVLCKXGWSS-UHFFFAOYSA-N methyl 2-cyclohexylacetate Chemical compound COC(=O)CC1CCCCC1 IMXBRVLCKXGWSS-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- BJMDYNHSWAKAMX-UHFFFAOYSA-N methyl(diphenyl)sulfanium Chemical compound C=1C=CC=CC=1[S+](C)C1=CC=CC=C1 BJMDYNHSWAKAMX-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000005048 methyldichlorosilane Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000001393 microlithography Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- GXOHBWLPQHTYPF-UHFFFAOYSA-N pentyl 2-hydroxypropanoate Chemical compound CCCCCOC(=O)C(C)O GXOHBWLPQHTYPF-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- KTNLYTNKBOKXRW-UHFFFAOYSA-N phenyliodanium Chemical compound [IH+]C1=CC=CC=C1 KTNLYTNKBOKXRW-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- RXHUEMZQJRTCIA-UHFFFAOYSA-N pyrrolidine-2,5-dione;trifluoromethanesulfonic acid Chemical compound O=C1CCC(=O)N1.OS(=O)(=O)C(F)(F)F RXHUEMZQJRTCIA-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BRGJIIMZXMWMCC-UHFFFAOYSA-N tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(C)O BRGJIIMZXMWMCC-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- FNZBSNUICNVAAM-UHFFFAOYSA-N trimethyl-[methyl-[methyl-(methyl-phenyl-trimethylsilyloxysilyl)oxy-phenylsilyl]oxy-phenylsilyl]oxysilane Chemical compound C=1C=CC=CC=1[Si](C)(O[Si](C)(C)C)O[Si](C)(C=1C=CC=CC=1)O[Si](C)(O[Si](C)(C)C)C1=CC=CC=C1 FNZBSNUICNVAAM-UHFFFAOYSA-N 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Chemical compound CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
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- 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
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- 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
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- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
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Abstract
Description
1). (A)多面体骨格を有するポリシロキサン化合物であって、多面体骨格を形成するSi原子上に、少なくとも1つの、加水分解性シリル基を含有する基を有することを特徴とするポリシロキサン、
(B)光酸発生剤、
とからなるポリシロキサン系組成物。
(1)上記の(A)成分と反応可能な官能基を1つ有し、さらに加水分解性シリル基を1つ以上有する化合物、
(2)上記の(A)成分と反応可能な官能基を2つ以上有する化合物、
これら化合物を反応させて得られることを特徴とする1)〜5)いずれか1項に記載のポリシロキサン系組成物。
本発明は、(A)多面体骨格を有するポリシロキサン化合物であって、多面体骨格を形成するSi原子上に、少なくとも1つの、加水分解性シリル基を含有する基をすることを特徴とするポリシロキサン、および、(B)光酸発生剤、とからなるポリシロキサン系組成物および該組成物を用いた光学部材に関する。
本発明における(A)成分は、多面体骨格を形成するSi原子上に、少なくとも1つの、加水分解性シリル基を含有する基を有することを特徴とするポリシロキサンである。また、分子中にSi原子を6〜24個から形成される多面体骨格を有するポリシロキサン化合物が好ましい。
本発明において使用されるアルケニル基を有するポリシロキサン(化合物I)は、多面体骨格に含有されるSi原子の数は6〜24であることが好ましく、具体的に、例えば、以下の構造で示される多面体構造を有するシルセスキオキサンが例示される(ここでは、Si原子数=8を代表例として例示する)。
本発明において使用されるヒドロシリル基を有するポリシロキサン(化合物III)は、多面体骨格に含有されるSi原子の数は6〜24であることが好ましく、具体的に、例えば、以下の構造で示される多面体構造を有するシルセスキオキサンが例示される(ここでは、Si原子数=8を代表例として例示する)。
本発明における加水分解性シリル基を有するアルケニル化合物(化合物IV)としては、分子中に、加水分解可能なシリル基とアルケニル基を含有していれば、特に制限はない。
(1)、(2)と反応可能な官能基を有する多面体構造ポリシロキサン化合物は、具体的に説明すると、(1)および(2)成分と反応可能な官能基を含有する基が、Si原子から形成される多面体構造、好ましくは6〜24個のSi原子から形成される多面体構造ポリシロキサンのSi原子上に存在する化合物である。
本発明の(1)成分は、上記(1)、(2)と反応可能な官能基を有する多面体構造ポリシロキサン化合物と反応可能な官能基を1つ有し、さらに加水分解性シリル基を1つ以上有する(A)成分、(2)成分とは異なる化合物である。
−Si(OR33)mR34 3-m
(R33は炭素数1〜6のアルキル基、R34は炭素数1〜6のアルキル基またはアリール基である。R33とR34は同一の基でも良いし異なった基でも良い。mは1〜3の整数である。)で表されるアルコキシシリル基が好ましい。
HSi(OR35)mR36 3-m
(R35は炭素数1〜6のアルキル基、R36は炭素数1〜6のアルキル基またはアリール基である。R35とR36は同一の基でも良いし異なった基でも良い。mは1〜3の整数である)の構造式の化合物を用いることが好ましい。
ASi(OR37)mR38 3-m
(Aはアルケニル基、R37は炭素数1〜6のアルキル基、R38は炭素数1〜6のアルキル基またはアリール基である。R37とR38は同一の基でも良いし異なった基でも良い。mは1〜3の整数である)の構造式の化合物を用いることが好ましい。
本発明の(2)成分は、(A)成分と反応可能な官能基を2つ以上有する化合物であり、前記(A)成分、(1)成分とは異なる化合物である。(A)成分と反応可能な官能基としては、例えばビニル基、アリル基、プロペニル基等のアルケニル基;ヒドロシリル基;(メタ)アクリロイル基;エポキシ基;メルカプト基;ハロゲン基等を含有する有機基が挙げられ、耐熱性・耐光性の観点よりアルケニル基またはヒドロシリル基が好ましい。
(2)成分は本化合物100重量部に対して1〜200重量部用いることが好ましく、さらには5〜100重量部用いることが好ましい。
視光、紫外線、赤外線、X線、α線、β線、γ線等の活性エネルギー線を照射することにより、架橋性シリル基を架橋させることができる酸性活性物質を放出することができる化合物である。
本発明においては、本発明の組成物は、活性エネルギー線照射により硬化し、硬化速度が非常に速く、また、熱履歴を抑えることができる。前記活性エネルギー線源としては、紫外線、電子線等が例示される。活性エネルギー線の強度、照射時間は、用途や生産工程に合わせて、任意に設定されるが、活性エネルギー線照射のみで硬化が不十分な場合は、その後のアニールにより、さらに硬化を進行させてもよい。
液晶表示装置周辺材料における基板材料、カラーフィルター、ブラックマトリックス、導光板、プリズムシート、偏向板、位相差板、視野角補正フィルム、接着剤、パッシベーション膜、偏光子保護フィルム。
。
メチルジメトキシシラン3g、トルエン6g の混合溶液に、多面体骨格を有するアルケニル基含有ポリシロキサンであるオクタ(ビニルジメチルシロキシ)オクタシルセスキオキサン3g、トルエン9g、白金ビニルシロキサン錯体(3%白金、キシレン溶液)15μLの混合溶液をゆっくりと滴下した。滴下終了後、室温で1時間反応させた後、溶媒を留去することにより、オクタ[(ジメトキシメチルシリル)エチルジメチルシロキシ]オクタシルセスキオキサン4g(化合物A)を得た。
製造例1で得た化合物A2gにRHODORSIL−PI2074(光酸発生剤、ローディア製)の2−アセトキシ−1−メトキシプロパン50wt%溶液を0.02gを加えた。このようにして得られた組成物を、ガラス基板上の塗布し、放射線照射装置(アイグラフィックス製、照射距離80mm、3000Wメタルハライドランプ使用)により、50秒照射した。このようにして、ガラス基板上に厚み100μmのポリシロキサン系膜を得た。得られたポリシロキサン系膜は透明性に優れており、紫外可視分光光度計(日本分光株式会社製V−560)でガラス試験片の光線透過率を測定したところ、可視域全域(400〜800nm)で90%以上の透過率を有していた。
製造例1で得た化合物A2gにオプトマーSP−172(光酸発生剤、旭電化工業(株)製)0.03gを加えた。このようにして得られた組成物を、ガラス基板上の塗布し、放射線照射装置(アイグラフィックス製、照射距離80mm、3000Wメタルハライドランプ使用)により、50秒照射した。このようにして、ガラス基板上に厚み95μmのポリシロキサン系膜を得た。得られたポリシロキサン系膜は透明性に優れていることを目視にて確認した。得られたポリシロキサン系膜は透明性に優れており、紫外可視分光光度計(日本分光株式会社製V−560)でガラス試験片の光線透過率を測定したところ、可視域全域(400〜800nm)で90%以上の透過率を有していた。
メチルジメトキシシラン2.4g、H末端ポリジメチルシロキサン(DMS−H03、Gelest製)2.3g、H末端ポリジメチルシロキサン(DMS−H21、Gelest製)1.7g、トルエン15g の混合溶液に、オクタ(ビニルジメチルシロキシ)オクタシルセスキオキサン5g、トルエン15g、白金ビニルシロキサン錯体(エヌ・イー・ケムキャット製、Pt−VTSC−3.0X)2μLの混合溶液をゆっくりと滴下した。滴下終了後、室温で1時間反応させた後、溶媒を留去することにより、化合物Aを10.4g得た。
製造例2で得た化合物A2gにRHODORSIL−PI2074(ジアリールヨードニウム塩)(光酸発生剤、ローディア製)の酢酸プロピレングリコールモノメチルエーテル(PGMEA)10wt%溶液を0.1g、トルエン2gを加えてポリシロキサン組成物を得た。この組成物を、ガラス基板上に4000rpmで60秒間スピンコート塗布し、放射線照射装置(フュージョン製LC−6B、照射距離53.3mm、積算光量240mJ/cm2)により紫外線を照射した。
オキセタン化合物(東亞合成製、アロンオキセタンOXT−121)2gにRHODORSIL−PI2074(ジアリールヨードニウム塩)(光酸発生剤、ローディア製)のPGMEA10wt%溶液を0.1g加えて組成物を得た。この組成物をガラス基板上に3000rpmで60秒間スピンコート塗布し、放射線照射装置(フュージョン製LC−6B、照射距離53.3mm、積算光量240mJ/cm2)により紫外線を照射した。このようにして、ガラス基板上に厚み8μmの硬化物膜を得た。得られた膜は、可視域全域で90%以上、波長400nmにおいて94%の透過率を有していた。この膜を350℃の窒素フロー雰囲気に1時間置くと、膜は褐色に着色した。透過率は可視域全域で65%以下で、波長400nmにおいては10%であった。
脂環エポキシ化合物(ダイセル化学製、セロキサイド2021P)2gにRHODORSIL−PI2074(ジアリールヨードニウム塩)(光酸発生剤、ローディア製)のPGMEA10wt%溶液を0.1g加えて組成物を得た。この組成物をガラス基板上に3000rpmで60秒間スピンコート塗布し、放射線照射装置(フュージョン製LC−6B、照射距離53.3mm、積算光量240mJ/cm2)により紫外線を照射した。このようにして、ガラス基板上に厚み10μmの硬化物膜を得た。得られた膜は、可視域全域で90%以上、波長400nmにおいて96%の透過率を有していた。この膜を350℃の窒素フロー雰囲気に1時間置くと、膜は濃褐色に着色した。透過率は可視域全域で35%以下で、波長400nmにおける透過率は14%であった。
Claims (14)
- (A)多面体骨格を有するポリシロキサン化合物であって、多面体骨格を形成するSi原子上に、少なくとも1つの、加水分解性シリル基を含有する基を有することを特徴とするポリシロキサン、
(B)光酸発生剤、
とからなるポリシロキサン系組成物。 - (A)多面体骨格を有するポリシロキサン化合物が、分子中にSi原子を6〜24個から形成される多面体骨格を有するポリシロキサン化合物であることを特徴とする請求項1記載のポリシロキサン系組成物。
- (A)成分における加水分解性シリル基がアルコキシシリル基であることを特徴とする請求項1または2に記載のポリシロキサン系組成物。
- (A)成分におけるアルコキシシリル基を含有する基が、アルコキシシリルエチル基またはアルコキシシリルプロピル基であることを特徴とする、請求項1〜3いずれか1項に記載のポリシロキサン系組成物。
- (A)成分において、アルコキシシリル基を含有する基が、(アルコキシシリルエチル)ジメチルシリル基、(アルコキシシリルエチル)ジフェニルシリル基、(アルコキシシリルプロピル)ジメチルシリル基、(アルコキシシリルプロピル)ジフェニル基、からなる群において選ばれる少なくとも1つのアルコキシシリル基を含有する基であることを特徴とする請求項1〜4いずれか1項に記載のポリシロキサン系組成物。
- 多面体骨格を有するポリシロキサン化合物(A)が、下記の(1)および(2)成分と反応可能な官能基を有する多面体構造ポリシロキサン化合物であって、
(1)上記の(A)成分と反応可能な官能基を1つ有し、さらに加水分解性シリル基を1つ以上有する化合物、
(2)上記の(A)成分と反応可能な官能基を2つ以上有する化合物、
これら化合物を反応させて得られることを特徴とする請求項1〜5いずれか1項に記載のポリシロキサン系組成物。 - (A)成分における、多面体構造ポリシロキサン化合物が、多面体構造シリル化ケイ酸化合物であることを特徴とする、請求項1〜6いずれか1項に記載のポリシロキサン系組成物。
- (A)成分における、(1)および(2)成分と反応可能な官能基が、アルケニル基またはヒドロシリル基であることを特徴とする、請求項1〜7いずれか1項に記載のポリシロキサン系組成物。
- (1)成分における、加水分解性シリル基が、アルコキシシリル基であることを特徴とする、請求項1〜8のいずれか1項に記載のポリシロキサン系組成物。
- (2)成分における、(A)成分と反応可能な官能基が化合物の両末端に結合していることを特徴とする、請求項1〜9のいずれか1項に記載のポリシロキサン系組成物。
- (2)成分が、ポリアルキレン、ポリイソブチレン、ポリエステル、ポリアクリル酸ブチル、ポリエーテル、ポリアミド、ポリイミド、ポリシロキサンからなる群において選ばれる少なくとも1つであることを特徴とする、請求項1〜10のいずれか1項に記載のポリシロキサン系組成物。
- (A)成分と、(1)および(2)成分との反応がヒドロシリル化反応によって行われることを特徴とする、請求項1〜11のいずれか1項に記載のポリシロキサン系組成物。
- 光酸発生剤が、オニウム塩類である、請求項1〜12のいずれか1項に記載のポリシロキサン系組成物。
- 請求項1〜13のいずれか1項に記載のポリシロキサン系組成物を用いた光学部材。
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JP2007293160A (ja) * | 2006-04-27 | 2007-11-08 | Asahi Kasei Corp | 感光性かご状シルセスキオキサン化合物 |
WO2008133138A1 (ja) * | 2007-04-17 | 2008-11-06 | Kaneka Corporation | 多面体構造ポリシロキサン変性体および該変性体を用いた組成物 |
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US20100063221A1 (en) | 2010-03-11 |
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US8809458B2 (en) | 2014-08-19 |
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