JP6751100B2 - 高屈折率シロキサンモノマー、それらの重合及び用途 - Google Patents
高屈折率シロキサンモノマー、それらの重合及び用途 Download PDFInfo
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- JP6751100B2 JP6751100B2 JP2017549399A JP2017549399A JP6751100B2 JP 6751100 B2 JP6751100 B2 JP 6751100B2 JP 2017549399 A JP2017549399 A JP 2017549399A JP 2017549399 A JP2017549399 A JP 2017549399A JP 6751100 B2 JP6751100 B2 JP 6751100B2
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- polymerization
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- 239000000178 monomer Substances 0.000 title claims description 50
- 238000006116 polymerization reaction Methods 0.000 title claims description 18
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title description 14
- 229920000642 polymer Polymers 0.000 claims description 66
- -1 hydroxy, acetoxy Chemical group 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000002131 composite material Substances 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 229910008051 Si-OH Inorganic materials 0.000 claims description 4
- 229910006358 Si—OH Inorganic materials 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 229920002379 silicone rubber Polymers 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 238000003618 dip coating Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 238000007650 screen-printing Methods 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 239000004593 Epoxy Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 229910003460 diamond Inorganic materials 0.000 claims description 2
- 239000010432 diamond Substances 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- 239000002073 nanorod Substances 0.000 claims description 2
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229960001716 benzalkonium Drugs 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 230000000379 polymerizing effect Effects 0.000 claims 1
- 150000004756 silanes Chemical group 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 8
- 229910000077 silane Inorganic materials 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000008393 encapsulating agent Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- QBDNNWJCTQXCFX-UHFFFAOYSA-N C=1C=CC=CC=1O[SiH2]C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1O[SiH2]C1=CC=CC=C1 QBDNNWJCTQXCFX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WAPCMSZDGPIUBZ-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=C(C=CC=C1)[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=C(C=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C1=C(C=CC=C1)[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=C(C=CC=C1)OC1=CC=CC=C1 WAPCMSZDGPIUBZ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 3
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 3
- LCOUXOWOYGPJPD-UHFFFAOYSA-N trimethyl-[3-phenoxysilyl-2,6-bis(trimethylsilyloxy)phenoxy]silane Chemical compound C[Si](OC1=C(C(=C(C=C1)[SiH2]OC1=CC=CC=C1)O[Si](C)(C)C)O[Si](C)(C)C)(C)C LCOUXOWOYGPJPD-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FVPYDHRIRRMYPA-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=C(C=CC=C1)[Si](OC)(OC)C1=C(C=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C1=C(C=CC=C1)[Si](OC)(OC)C1=C(C=CC=C1)OC1=CC=CC=C1 FVPYDHRIRRMYPA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QTEONXCRDRLVKU-UHFFFAOYSA-N diphenoxy(phenyl)silane Chemical compound O([SiH](Oc1ccccc1)c1ccccc1)c1ccccc1 QTEONXCRDRLVKU-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SGSRWJWKEQYEGG-UHFFFAOYSA-N 1-bromo-3-(3-bromo-2-phenylphenoxy)-2-phenylbenzene Chemical compound C=1C=CC=CC=1C=1C(Br)=CC=CC=1OC1=CC=CC(Br)=C1C1=CC=CC=C1 SGSRWJWKEQYEGG-UHFFFAOYSA-N 0.000 description 1
- CCDYIFRQRAVVBL-UHFFFAOYSA-N 1-bromo-4-(2-phenoxyphenoxy)benzene Chemical compound O(C1=CC=CC=C1)C1=C(OC2=CC=C(C=C2)Br)C=CC=C1 CCDYIFRQRAVVBL-UHFFFAOYSA-N 0.000 description 1
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 C(C*=CC1)C1OC1[C@]2C=CC=CC12 Chemical compound C(C*=CC1)C1OC1[C@]2C=CC=CC12 0.000 description 1
- SSTNIXFHCIOCJI-UHFFFAOYSA-N Cc(cc1)ccc1Oc1ccccc1 Chemical compound Cc(cc1)ccc1Oc1ccccc1 SSTNIXFHCIOCJI-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- WFMHSHHHQYVLNU-UHFFFAOYSA-N N,N,2,3,4,5,6-heptafluoroaniline trifluoromethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)F.FN(F)c1c(F)c(F)c(F)c(F)c1F WFMHSHHHQYVLNU-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DSGOMNQKHAQJAJ-UHFFFAOYSA-N O(C1=CC=CC=C1)C(O[Si](OC)(OC)C1=CC=CC=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C(O[Si](OC)(OC)C1=CC=CC=C1)OC1=CC=CC=C1 DSGOMNQKHAQJAJ-UHFFFAOYSA-N 0.000 description 1
- HPYDEVNPIXILOL-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](O)(O)C1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](O)(O)C1=CC=C(C=C1)OC1=CC=CC=C1 HPYDEVNPIXILOL-UHFFFAOYSA-N 0.000 description 1
- BZDVVPNZDKAOCZ-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](O)(O)O Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](O)(O)O BZDVVPNZDKAOCZ-UHFFFAOYSA-N 0.000 description 1
- CONHFVHVOKKYBN-UHFFFAOYSA-N O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](OC)(OC)C1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](OC)(OC)C1=CC=C(C=C1)OC1=CC=CC=C1 CONHFVHVOKKYBN-UHFFFAOYSA-N 0.000 description 1
- HSQFHYSCYQKFEX-UHFFFAOYSA-N O(C1=CC=CC=C1)O[Si](O)(O)C1=CC=CC=C1 Chemical group O(C1=CC=CC=C1)O[Si](O)(O)C1=CC=CC=C1 HSQFHYSCYQKFEX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 1
- WYUIWUCVZCRTRH-UHFFFAOYSA-N [[[ethenyl(dimethyl)silyl]amino]-dimethylsilyl]ethene Chemical compound C=C[Si](C)(C)N[Si](C)(C)C=C WYUIWUCVZCRTRH-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- JNDMLEXHDPKVFC-UHFFFAOYSA-N aluminum;oxygen(2-);yttrium(3+) Chemical compound [O-2].[O-2].[O-2].[Al+3].[Y+3] JNDMLEXHDPKVFC-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004759 cyclic silanes Chemical class 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- OLRKVHLFNGKQNH-UHFFFAOYSA-N dihydroxy-bis(2-phenoxyphenyl)silane Chemical compound O(C1=CC=CC=C1)C1=C(C=CC=C1)[Si](O)(O)C1=C(C=CC=C1)OC1=CC=CC=C1 OLRKVHLFNGKQNH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- FWBAMGQNMFKCOL-UHFFFAOYSA-N dimethoxy-(phenoxymethoxy)-(4-phenoxyphenyl)silane Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=C1)[Si](OCOC1=CC=CC=C1)(OC)OC FWBAMGQNMFKCOL-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- NOKUWSXLHXMAOM-UHFFFAOYSA-N hydroxy(phenyl)silicon Chemical class O[Si]C1=CC=CC=C1 NOKUWSXLHXMAOM-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002113 nanodiamond Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KQJXTMMJADHCBV-UHFFFAOYSA-N phenoxybenzene silane Chemical class [SiH4].C1(=CC=CC=C1)OC1=CC=CC=C1 KQJXTMMJADHCBV-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical class [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004032 superbase Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910019655 synthetic inorganic crystalline material Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910019901 yttrium aluminum garnet Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Description
この屈折率の不一致は内部反射を生じ、この内部反射は装置の光出力及び効率を低下させる。
PDMSをより高屈折率のフェニルシリコーン類(RI=1.50〜1.55)に置き換える事は状況をいくらか改善するが、依然として黄変無しでLED内部の条件に耐えることができ、LED製造に適しているより高屈折率材料の需要がある。
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、ヒドロキシ基または-OSiMe3を任意に含有することができる。
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、ヒドロキシ基または-OSiMe3を任意に含有し、yは1あるいは2である。
したがって、例えば従来の加水分解および重合手順により、フェノキシフェニルシランおよび/またはビス - フェノキシフェニルシランから誘導されるポリマーは、フェニルシロキサンまたはフェニルシリコーンよりも高い屈折率を有する。
これらのポリマーは、UV-Aおよび青色光に対して耐性があり、高い熱安定性を有する。
一般的に、本発明のポリマーは酸素透過率(OTR)および水蒸気透過率(WVTR)がフェニルシリコーンエラストマーのOTRおよびWVTRのそれぞれ50%未満である。
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、ヒドロキシ基または-OSiMe3を任意に含有することができる。
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、ヒドロキシ基または-OSiMe3を任意に含有することができる。
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、ヒドロキシ基または-OSiMe3を任意に含有することができる。
PhOPhOPh-Si(X)4-k … IIc
ここで、各Xは、それぞれ独立に水素および低級アルコキシ基から選択される加水分解性基であり、アルコキシ置換基、ハロゲン原子、アセトキシ、ヒドロキシ基または-OSiMe3を任意に含有することができ、kは1〜3の整数である。
そのようなアルコキシ基の例としては、メトキシ(-OMe)エトキシ(-OEt)、n-およびi-プロポキシ(-OPr)、n-、i-およびt-ブトキシ(-OBu)を含む。さらなる例として-OCH2CH2O-CH のようなアルコキシエーテルを含む。
ビス(フェノキシフェニル)-ジメトキシシラン;
ビス(フェノキシフェニル)-ジヒドロキシシラン;
ビス(フェノキシフェニル)-ビス(トリメチルシロキシ)シラン;
p-フェノキシフェニルトリヒドロキシシラン;および
p-フェノキシフェノキシフェニルトリメトキシシランである。
したがって、式Iあるいは式IIa〜式IIcのいずれかのモノマーは、ホモポリマー化されていても良く、または他の式(IIa〜IIcまたはI)のモノマーと共重合されていても良い。
- LEDデバイス、
- CMOSイメージセンサー、
- LCDディスプレイおよびOLEDデバイス、および
- 光学アプリケーション。
サンプルのGC / MSは、トリス(トリメチルシロキシ)-フェノキシフェニルシランに対応するm / z = 464(図)に1つのピークを与えた。これは、白色粉末が、フェノキシフェニルトリヒドロキシシランPhOPhSi(OH)3であることを示している。それは464.85の分子量を有する。
オリゴマーとポリマー留分(GPCによりMw / Mn = 2325/1924)の混合物を得るためにPhOPhOPhTMOS(3g)を、希釈したHCl(1g)によりアセトン(3g)中で加水分解し、重合させ、スピンコーティングおよび250℃での硬化によって無色のフィルムを得た。このフィルムは高屈折率(633nmでRI = 1.612)を有していた。
実施例2の粗Bis(PhOPh)Si(OH)2、PhOPhTMOS(5g)、メタクリルオキシメチルトリメトキシシラン(2g)およびメタノール中5%Ba(OH)20.2gの全てをフラスコに入れた。フラスコを1時間攪拌しながら80℃に加熱した。反応物を室温に冷却した後、水酸化バリウムを過剰のHClで中和し、DCM溶液中DIWで中性に洗浄した。95℃ / 1mbarで乾燥させると、Mw/ Mn = 1389/884および1.60171の屈折率を有する13.8gのポリマーが得られた。Ciba社のDarocur(登録商標)1173(2%)を用いて配合し、365nm(6J / cm2,30秒)の水銀灯で硬化させた。柔軟で無色のフィルムが得られた。
PhOPhTMOS(6.5g)および3-メタクリルオキシプロピルトリメトキシシラン(MAPTMOS、4.5g)を、0.5mLのBa(OH)2/メタノール溶液(5%)と共に100mL丸底フラスコに入れた。フラスコを70℃に加熱し、温度を80℃に上げる間に、Bis(PhOPh)Si(OH)2(10g)とPhOPhSi(OH)3(2.15g)を徐々に加えた。2時間の反応後、ポリマーを0.1MのHIおよびDIWを用いてトルエン中で中性に洗浄し、メタノールから2回沈殿させた。乾燥後、Mw / Mn = 2147/1265およびRI = 1.59408を有する透明なポリマーが得られた。Ciba社のDarocur(登録商標)1173(2%)を用いて配合し、365nm(6J/cm2、30秒)の水銀灯で硬化させた。柔軟で無色のフィルムが得られた。
PhOPhTMOS(15g)およびBis(PhOPh)DMOS(5g)を、0.5mLのBa(OH)2/メタノール溶液(5%)を含む50mL 丸底フラスコに入れた。フラスコを85℃に加熱し、Bis(PhOPh)Si(OH)2(25g)を徐々に加えた。温度は90℃に上昇した。1時間反応させた後、ポリマーを0.1MHIおよびDIWを用いてトルエン中で中性に洗浄し、メタノールから2回沈殿させた。乾燥後、Mw / Mn = 2325/1580の透明なポリマー(42g)が得られた。ポリマーをアセトン(80g)に溶解し、5滴の濃塩酸を添加し、続いてDIW(〜100mL)をゆっくり添加した。このようにして、末端Si-OMe基はSi-OH基に加水分解された。
Claims (13)
- 第1のモノマーを、1つまたは2つの第2のモノマーとともに加水分解および重合する事によって得られるポリマーであって、
前記第1のモノマーは、
式IIb:p-PhOPhOPh-Si(X) 3 を有し、
ここで、各Xは、水素および1〜6個の炭素原子を有するアルコキシ基からなる群から独立して選択される加水分解性基であり、前記アルコキシ基は、アルコキシ、ハロ、ヒドロキシ、アセトキシ、および-OSiMe 3 からなる群から選択される置換基を任意に含むものであり、
前記1つまたは2つの第2のモノマーは、
式I:(p-Ph-O-Ph) 2 Si(X) 2 を有し、
ここで、各Xは、水素および1〜6個の炭素原子を有するアルコキシ基からなる群から独立して選択される加水分解性基であり、前記アルコキシ基は、アルコキシ、ハロ、ヒドロキシ、アセトキシ、および-OSiMe 3 からなる群から選択される置換基を任意に含む、
または、
式IIa:p-PhOPh-Si(X) 3 を有し、
ここで、各Xは、水素および1〜6個の炭素原子を有するアルコキシ基からなる群から独立して選択される加水分解性基であり、前記アルコキシ基は、アルコキシ、ハロ、ヒドロキシ、アセトキシ、および-OSiMe 3 からなる群から選択される置換基を任意に含む
ものである、ポリマー。 - シラン、ゲルマニウムおよびジルコニウムアルコキシドおよびそれらの組み合わせからなる群から選択されるモノマー部分をさらに含み、式I、IIa、およびIIbのモノマーの合計モル%が、ポリマー合成に使用される総モノマー量の少なくとも10モル%である請求項1に記載のポリマー。
- 塩基性触媒、酸性触媒、ジルコニウムアルコキシド、およびチタンアルコキシドからなる群から選択される触媒の存在下で重合することによって得られる、請求項1または2に記載のポリマー。
- 任意に触媒を添加しないで、加熱下で加水分解および重合して得られる、請求項1〜3のいずれかに記載のポリマー。
- 水の存在下または非存在下での加水分解および重合によって得られる、請求項4に記載のポリマー。
- Si-OH、Si-OMe、Si-OEt、Si-H、ビニル、アクリル、メタクリル、エポキシ、アセトキシおよびメルカプト基からなる群から選択される少なくとも1種の架橋可能な官能基によって架橋された請求項1〜5のいずれかに記載のポリマー。
- 酸素透過率(OTR)および水蒸気透過率(WVTR)がフェニルシリコーンエラストマーのOTRおよびWVTRのそれぞれ50%未満である、請求項6に記載のポリマー。
- 請求項1〜7のいずれかに記載のポリマーから、金属、酸化ケイ素、金属酸化物およびダイヤモンドからなる群から選択される材料と組み合わせて製造されたポリマー複合体であって、前記材料は、粒子、フレーク、ナノ粒子およびナノロッドなる群から選択される部材を含む複合体。
- 請求項1〜7のいずれかに記載のポリマーから製造されたフィルムであって、スピンオン、スプレー、ディップコーティング、スリットコーティングまたはスクリーン印刷し、その後、任意の湿気、熱あるいは紫外線による硬化および乾燥により製造されたフィルム。
- 請求項8に記載のポリマー複合体から製造されたフィルムであって、スピンオン、スプレー、ディップコーティング、スリットコーティングまたはスクリーン印刷し、その後、任意の湿気、熱あるいは紫外線による硬化および乾燥により製造されたフィルム。
- 請求項1〜7のいずれかに記載のポリマーのフィルムを含むLEDデバイス。
- 前記フィルムが0.01μm〜3.0mmの範囲の厚さを有する、請求項11に記載のLEDデバイス。
- 前記フィルムが0.05〜500μmの範囲の厚さを有する、請求項12に記載のLEDデバイス。
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