JP6712589B2 - 透明シロキサン封入剤及び接着剤 - Google Patents
透明シロキサン封入剤及び接着剤 Download PDFInfo
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- JP6712589B2 JP6712589B2 JP2017518605A JP2017518605A JP6712589B2 JP 6712589 B2 JP6712589 B2 JP 6712589B2 JP 2017518605 A JP2017518605 A JP 2017518605A JP 2017518605 A JP2017518605 A JP 2017518605A JP 6712589 B2 JP6712589 B2 JP 6712589B2
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- siloxane
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims description 159
- 239000000853 adhesive Substances 0.000 title claims description 26
- 230000001070 adhesive effect Effects 0.000 title claims description 25
- 239000008393 encapsulating agent Substances 0.000 title claims description 13
- 239000002245 particle Substances 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 109
- 239000000203 mixture Substances 0.000 claims description 97
- 229920000642 polymer Polymers 0.000 claims description 93
- 239000000463 material Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- -1 polyethylene terephthalate Polymers 0.000 claims description 42
- 239000000758 substrate Substances 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 238000006116 polymerization reaction Methods 0.000 claims description 33
- 239000003795 chemical substances by application Substances 0.000 claims description 29
- 238000000151 deposition Methods 0.000 claims description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 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 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 238000001429 visible spectrum Methods 0.000 claims description 13
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 9
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 8
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052719 titanium Inorganic materials 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 8
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 claims description 7
- 229910008051 Si-OH Inorganic materials 0.000 claims description 7
- 229910006358 Si—OH Inorganic materials 0.000 claims description 7
- 238000002834 transmittance Methods 0.000 claims description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000919 ceramic Substances 0.000 claims description 6
- 239000006059 cover glass Substances 0.000 claims description 6
- 239000002105 nanoparticle Substances 0.000 claims description 6
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 claims description 6
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 claims description 6
- 239000012528 membrane Substances 0.000 claims description 5
- 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 claims description 5
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 claims description 5
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910052735 hafnium Inorganic materials 0.000 claims description 4
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 4
- 229920006254 polymer film Polymers 0.000 claims description 4
- 229910052715 tantalum Inorganic materials 0.000 claims description 4
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052726 zirconium Inorganic materials 0.000 claims description 4
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 2
- 230000035699 permeability Effects 0.000 claims description 2
- 239000010453 quartz Substances 0.000 claims description 2
- 239000010980 sapphire Substances 0.000 claims description 2
- 229910052594 sapphire Inorganic materials 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims 3
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 claims 2
- 210000002858 crystal cell Anatomy 0.000 claims 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims 2
- 229920000592 inorganic polymer Polymers 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 claims 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims 1
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 1
- 239000005020 polyethylene terephthalate Substances 0.000 claims 1
- 239000004926 polymethyl methacrylate Substances 0.000 claims 1
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims 1
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 claims 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000010410 layer Substances 0.000 description 49
- 238000001723 curing Methods 0.000 description 36
- 239000000945 filler Substances 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 17
- 229910000077 silane Inorganic materials 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 230000008021 deposition Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 15
- 125000003545 alkoxy group Chemical group 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
- 229910052710 silicon Inorganic materials 0.000 description 14
- 239000007822 coupling agent Substances 0.000 description 13
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 13
- 150000004756 silanes Chemical class 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 9
- 239000010949 copper Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229910052709 silver Inorganic materials 0.000 description 9
- 239000004332 silver Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 239000002318 adhesion promoter Substances 0.000 description 8
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- ZLDHYRXZZNDOKU-UHFFFAOYSA-N n,n-diethyl-3-trimethoxysilylpropan-1-amine Chemical compound CCN(CC)CCC[Si](OC)(OC)OC ZLDHYRXZZNDOKU-UHFFFAOYSA-N 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 239000004065 semiconductor Substances 0.000 description 8
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 7
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910002601 GaN Inorganic materials 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000011068 loading method Methods 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000005538 encapsulation Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 229910010271 silicon carbide Inorganic materials 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 229910052797 bismuth Inorganic materials 0.000 description 4
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 4
- 229910000085 borane Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 239000013020 final formulation Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002923 metal particle Substances 0.000 description 4
- 229910052752 metalloid Inorganic materials 0.000 description 4
- 150000004767 nitrides Chemical class 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical group CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 229910052582 BN Inorganic materials 0.000 description 3
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- 229910018540 Si C Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 3
- ZXWUGCNBZZSJJN-UHFFFAOYSA-N dihydroxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](O)(O)C(C)C ZXWUGCNBZZSJJN-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002738 metalloids Chemical class 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000002071 nanotube Substances 0.000 description 3
- 239000002070 nanowire Substances 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 238000002161 passivation Methods 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000002096 quantum dot Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 239000012780 transparent material Substances 0.000 description 3
- JCGDCINCKDQXDX-UHFFFAOYSA-N trimethoxy(2-trimethoxysilylethyl)silane Chemical compound CO[Si](OC)(OC)CC[Si](OC)(OC)OC JCGDCINCKDQXDX-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 239000011345 viscous material Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- DDIXHFKHYMZDFP-UHFFFAOYSA-N (4-methylphenyl)silicon Chemical compound CC1=CC=C([Si])C=C1 DDIXHFKHYMZDFP-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
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- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- G—PHYSICS
- G06—COMPUTING; CALCULATING OR COUNTING
- G06F—ELECTRIC DIGITAL DATA PROCESSING
- G06F3/00—Input arrangements for transferring data to be processed into a form capable of being handled by the computer; Output arrangements for transferring data from processing unit to output unit, e.g. interface arrangements
- G06F3/01—Input arrangements or combined input and output arrangements for interaction between user and computer
- G06F3/03—Arrangements for converting the position or the displacement of a member into a coded form
- G06F3/041—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means
- G06F3/044—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means by capacitive means
- G06F3/0445—Digitisers, e.g. for touch screens or touch pads, characterised by the transducing means by capacitive means using two or more layers of sensing electrodes, e.g. using two layers of electrodes separated by a dielectric layer
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- 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
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Description
SiR 1 a R 2 4−a を有する第1の化合物が提供され、
式中、
aは1〜3であり、
R 1 は反応性基であり、
R 2 はアルキル基又はアリール基である。
式中、
R 3 は架橋性官能基であり、
R 4 は反応性基であり、
R 5 はアルキル基又はアリール基であり、
b=1〜2、c=1〜(4−b)である。
SiR 9 f R 10 g
を有し、
式中、
R 9 は反応性基であり、
f=1〜4であり、
R 10 はアルキル又はアリール基であり、
g=4−fである。
式中、
aは1〜3であり、
R 1 は、反応性基であり、
R 2 はアルキル基又はアリール基であり、
第二の化合物は、化学式SiR 3 b R 4 c R 5 4−(b+c) を有し、
式中、
R 3 は架橋性官能基であり、
R 4 は、反応性基であり、
R 5 は、アルキル又はアリール基であり、
b=1〜2、c=1〜(4−b)である。
式中、
R 9 は反応性基であり、
f=1〜4であり、
R 10 はアルキル基又はアリール基であり、
g=4−fである。
R 2 3−a R 1 a SiR 11 SiR 1 b R 2 3−b を有する化学物質、又は1000g/mol未満の分子量を有するそれらのオリゴマーを上述したように、第1、第2及び第3の化合物又はこれらの任意の組み合わせと一緒に重合させることができ、
式中、
aは1〜3であり、
bは1〜3であり、
R 1 は上記のような反応性基であり、
R 2 はアルキル、アルケニル、アルキニル、アルコール、カルボン酸、ジカルボン酸、アリール、ポリアリール、多環式アルキル、ヘテロ環式脂肪族、ヘテロ環式芳香族基であり、
R 11 は、独立して、アルキル基又はアリール基である。これらの化合物の例は、1,2−ビス(ジメチルヒドロキシルシリル)エタン、1,2−ビス(トリメトキシシリル)エタン、1,2−ビス(ジメトキシメチルシリル)エタン、1,2−ビス(メトキシジメチルシリル)エタン、1,2−ビス(トリエトキシシリル)エタン、1,3−ビス(ジメチルヒドロキシルシリル)プロパン、1,3−ビス(トリメトキシシリル)プロパン、1,3−ビス(ジメトキシメチルシリル)プロパン、1,3−ビス(メトキシジメチルシリル)プロパン、1,3−ビス(トリエトキシシリル)プロパン、1,4−ビス(ジメチルヒドロキシルシリル)ブタン、1,4−ビス(トリメトキシシリル)ブタン、1,4−ビス(ジメトキシメチルシリル)ブタン、1,4−ビス(メトキシジメチルシリル)ブタン、1,4−ビス(トリエトキシシリル)ブタン、1,5−ビス(ジメチルヒドロキシルシリル)ペンタン、1,5−ビス(トリメトキシシリル)ペンタン、1,5−ビス(ジメトキシメチルシリル)ペンタン、1,5−ビス(メトキシジメチルシリル)ペンタン、1,5−ビス(トリエトキシシリル)ペンタン、1,6−ビス(ジメチルヒドロキシルシリル)ヘキサン、1,6−ビス(トリメトキシシリル)ヘキサン、1,6−ビス(ジメトキシメチルシリル)ヘキサン、1,6−ビス(メトキシジメチルシリル)ヘキサン、1,6−ビス(トリエトキシシリル)ヘキサン、1,4−ビス(トリメトキシシリル)ベンゼン、ビス(トリメトキシシリル)ナフタレン、ビス(トリメトキシシリル)アントラセン、ビス(トリメトキシシリル)フェナントレン、ビス(トリメトキシシリル)ノルボルネン、1,4−ビス(ジメチルヒドロキシシリル)ベンゼン、1,4−ビス(メトキシジメチルシリル)ベンゼン、及び1,4−ビス(トリエトキシシリル)ベンゼンが挙げられる。
R 5 3−(c+d) R 4 d R 3 c SiR 11 SiR 3 e R 4 f R 5 3−(e+f)
を有する化合物または1000g/mol未満の分子量を有するそれらのオリゴマーを上述したように、第1、第2及び第3の化合物又はこれらの任意の組み合わせと一緒に重合させ、
式中、
R 3 は架橋性官能基であり、
R 4 は反応性基であり、
R 5 はアルキル、アルケニル、アルキニル、アルコール、カルボン酸、ジカルボン酸、アリール、ポリアリール基、多環式アルキル、ヘテロ環式脂肪族、ヘテロ環式脂肪族基であり、
R 12 は独立してアルキル基又はアリール基であり、
c=1〜2、d=1〜(3−c)、e=1〜2及びf=1〜(3−e)である。これらの化合物の例は、1,2−ビス(エテニルジメトキシシリル)エタン、1,2−ビス(エチニルジメトキシシリル)エタン、1,2−ビス(エチニルジメトキシ)エタン、1,2−ビス(3−グリシドキシプロピルジメトキシシリル)エタン、1,2−ビス[2−(3,4−エポキシシクロヘキシル)エチルジメトキシシリル]エタン、1,2−ビス(プロピルメタクリル化メトキシシリル)エタン、1,4−ビス(エテニルジメトキシシリル)ベンゼン、1,4−ビス(エチニルジメトキシシリル)ベンゼン、1,4−ビス(エチニルジメトキシシリル)ベンゼン、1,4−ビス(3−グリシドキシプロピルジメトキシシリル)ベンゼン、1,4−ビス[2−(3,4−エポキシシクロヘキシル)エチルジメトキシシリル]ベンゼン、1,4−ビス(プロピルメタクリル化ジメトキシシリル)ベンゼンである。
R 1 a R 2 b R 3 3−(a+b) Si−O−SiR 2 2 −O−SiR 1 a R 2 b R 3 3−(a+b)
を有するシロキサンモノマーを先に言及したシランと重合させるか、又は最終配合物に添加剤として添加し、
式中
R 1 は上で説明したような反応性基であり、
R 2 は、上で説明したようなアルキル又はアリールであり、
R 3 は上で説明したような架橋性官能基であり、
a=0〜3、b=0〜3である。これらの化合物の例は、1,1,5,5−テトラメトキシ−1,5−ジメチル−3,3−ジフェニルトリシロキサン、1,1,5,5−テトラメトキシ−1,3,3,5−テトラフェニルトリシロキサン、1,1、5,5−テトラエトキシ−3,3−ジフェニルトリシロキサン、1,1,5,5−テトラメトキシ−1,5−ジビニル−3,3−ジフェニルトリシロキサン、1,1,5,5−テトラメトキシ−1,5−ジメチル−3,3−ジイソプロピルトリシロキサン、1,1,1,5,5,5−ヘキサメトキシ−3,3−ジフェニルトリシロキサン、1,5−ジメチル−1,5−ジエトキシ−3,3−ジフェニルトリシロキサン、1,5−ビス(メルカプトプロピル)−1,1,5,5−テトラメトキシ−3,3−ジフェニルトリシロキサン、1,5−ジビニル−1,1,5,5−テトラメトキシ−3−フェニル−3−メチルトリシロキサン、1,5−ジビニル−1,1,5,5−テトラメトキシ−3−シクロヘキシル−3−メチルトリシロキサン、1,1,7,7−テトラメトキシ−1,7−ジビニル−3,3,5,5−テトラメチルテトラシロキサン、1,1,5,5−テトラメトキシ−3,3−ジメチルトリシロキサン、1,1,7,7−テトラエトキシ−3,3,5,5−テトラメチルテトラシロキサン、1,1,5,5−テトラエトキシ−3,3−ジメチルトリシロキサン、1,1,5,5−テトラメトキシ−1,5−[2−(3,4−エポキシシクロヘキシル)エチル]−3,3−ジフェニルトリシロキサン、1,1,5,5−テトラメトキシ−1,5−(3−グリシドキシプロピル)−3、3−ジフェニルトリシロキサン、1,5−ジメチル−1,5−ジメトキシ−1,5−[2−(3,4−エポキシシクロヘキシル)エチル]−3,3−ジフェニルトリシロキサン、1,5−ジメチル−1,5−ジメトキシ−1,5−(3−グリシドキシプロピル)−3,3−ジフェニルトリシロキサンを挙げることができる。
R 1 a R 2 b SiR 3 4−(a+b)
を有するシラン化合物であってもよく、
式中、
R 1 はヒドロキシル、アルコキシ又はアセチルオキシのような反応性基であり、
R 2 はアルキル又はアリール基であり、
R 3 はエポキシ、オキセタン、アルケニル、アクリレート又はアルキニル基のような架橋性化合物であり、a=0〜1及びb=0〜1である。このような添加剤の例は、トリ−(3−グリシドキシプロピル)フェニルシラン、トリ−[2−(3,4−エポキシシクロヘキシル)エチル]フェニルシラン、トリ−(3−メタクリロキシプロピル)フェニルシラン、トリ−(3−アクリロキシプロピル)フェニルシラン、テトラ−(3−グリシドキシプロピル)シラン、テトラ−[2−(3,4−エポキシシクロヘキシル)エチル]シラン、テトラ−(3−メタクリロキシプロピル)シラン、テトラ−(3−アクリロキシプロピル)シラン、トリ−(3−グリシドキシプロピル)p−トリルシラン、トリ−[2−(3,4−エポキシシクロヘキシル)エチル]p−トリルシラン、トリ−(3−メタクリロキシプロピル)p−トリルシラン、トリ−(3−アクリロキシプロピル)p−トリルシラン、トリ−(3−グリシドキシプロピル)ヒドロキシルシラン、トリ−[2−(3,4−エポキシシクロヘキシル)エチル]ヒドロキシルシラン、トリ−(3−メタクリロキシプロピル)ヒドロキシルシラン、トリ−(3−アクリロキシプロピル)ヒドロキシルシランである。
R 13 h R 14 i SiR 15 j
を有する任意のシランモノマーとすることができ、
式中、
R 13 は、ハロゲン、ヒドロキシル、アルコキシ、アセチル又はアセチルオキシのような反応性基であり、
R 14 は、アルキル基又はアリール基であり、
R 15 は、エポキシ、無水物、シアノ、オキセタン、アミン、チオール、アリル、アルケニル又はアルキニルを含む官能基であり、
h=0〜4、i=0〜4、j=0〜4、及びh+i+j=4である。カップリング剤は、最終生成物が調製されるときにフィラー、シロキサンポリマー、硬化剤及び添加剤と直接混合されてもよいし、又はそれらが粒子と混合される前にフィラー粒子はカップリング剤で処理してもよい。
本明細書に含まれる適用可能な安定剤又は酸化防止剤の中には、高分子量ヒンダードフェノール及び硫黄とリン含有フェノールなどの多官能性フェノールがある。ヒンダードフェノールは当業者に周知であり、そのフェノール性ヒドロキシル基のすぐ近くに立体的に嵩高い基を有するフェノール化合物として特徴付けることができる。特に、tert−ブチル基は、一般に、フェノール性ヒドロキシル基に対してオルト位の少なくとも1つでベンゼン環に置換されている。これらの立体的に嵩高い置換基がヒドロキシル基の近くに存在すると、その伸長頻度が遅くなり、それに応じてその反応性が低下する。この障害はフェノール化合物にその安定化特性を提供する。代表的なヒンダードフェノールには、1,3,5−トリメチル−2,4,6−トリス−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−ベンゼン;ペンタエリスリチルテトラキス−3(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)−プロピオネート;n−オクタデシル−3(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)−プロピオネート;4,4’−メチレンビス(2,6−tert−ブチル−フェノール);4,4’−チオビス(6−tert−ブチル−o−クレゾール);2,6−ジ−tert−ブチルフェノール;6−(4−ヒドロキシフェノキシ)−2,4−ビス(n−オクチル−チオ)−1,3,5トリアジン;ジ−n−オクチルチオ)エチル 3,5−ジ−tert−ブチル−4−ヒドロキシ−ベンゾエート;ソルビトールヘキサ[3−(3,5−ジ−tert−ブチル−4−ヒドロキシ−フェニル)−プロピオネートが挙げられる。酸化防止剤の市販の例は、例えばBASF社製のIrganox 1035、Irganox 1010、Irganox 1076、Irganox 1098、Irganox 3114、Irganox PS800、Irganox PS802、Irgafos 168である。
撹拌棒及び還流冷却器を備えた500mL丸底フラスコに、ジフェニルシランジオール(60g、45mol%)、2−(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(55.67g、36.7mol%)及びテトラメトキシシラン(17.20g、18.3mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、メタノール1mLに溶解した水酸化バリウム一水和物0.08gをシランの混合物に滴下した。ジフェニルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは1000mPasの粘度及び1100のMwを有していた。
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジフェニルシランジオール(30g、45mol%)、2−(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(28.1g、37mol%)及びジメチルジメトキシシラン(6.67g、18mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、メタノール1mLに溶解した水酸化バリウム一水和物0.035gをシランの混合物に滴下した。ジフェニルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは2750mPasの粘度及び896のMwを有していた。
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジフェニルシランジオール(24.5g、50mol%)、2−(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(18.64g、33.4mol%)及びテトラメトキシシラン(5.75g、16.7mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、メタノール1mLに溶解した水酸化バリウム一水和物0.026gをシランの混合物に滴下した。ジフェニルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。このシロキサンポリマーは7313mPasの粘度及び1328のMwを有していた。
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジフェニルシランジオール(15g、50mol%)、2−(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(13.29g、38.9mol%)及びビス(トリメトキシシリル)エタン(4.17g、11.1mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、メタノール1mLに溶解した水酸化バリウム一水和物0.0175gをシランの混合物に滴下した。ジフェニルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは、1788mPasの粘度及び1590のMwを有していた。
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジフェニルシランジオール(15g、45mol%)、2−(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(13.29g、35mol%)及びビニルトリメトキシシラン(4.57g、20mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、メタノール1mLに溶解した水酸化バリウム一水和物0.018gをシランの混合物に滴下した。ジフェニルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは、1087mPas及び1004のMwの粘度を有していた。
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジイソプロピルシランジオール(20.05g、55.55mol%)、2−(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(20.0g、33.33mol%)及びビス(トリメトキシシリル)エタン(7.3g、11,11mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、1mLのメタノールに溶解した0.025gの水酸化バリウム一水和物をシランの混合物に滴下した。ジイソプロピルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは150mPasの粘度及び781のMwを有していた。
シロキサンポリマーvii:
撹拌棒及び還流冷却器を備えた250mL丸底フラスコに、ジイソブチルシランジオール(18.6g、60mol%)及び2−(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(17.32g、40mol%)を充填した。フラスコを窒素雰囲気下で80℃に加熱し、1mLのメタノールに溶解した0.019gの水酸化バリウム一水和物をシランの混合物に滴下した。ジイソブチルシランジオールがアルコキシシランと反応した間、シラン混合物を80℃で30分間撹拌した。30分後、形成されたメタノールを真空下で蒸発させた。シロキサンポリマーは75mPasの粘度及び710のMwを有していた。
メタノール中のジフェニルシランジオール(100.0g、0.46mol)、3−(トリメトキシシリル)プロピルメタクリレート(62.6g、0.25mol)、メチルトリメトキシシラン(17.2g、0.13mol)及びBaO(0.1g)を500mLフラスコに入れ、1時間還流した。揮発性物質を減圧下で蒸発させ、透明な樹脂を得た。
例1から得られたポリマー樹脂25gをアセトン50gに溶解した。溶液が濁るまで0.01M HClを添加した。撹拌を室温で8時間続けた。過剰の水を加えてポリマーを沈殿させ、その後、得られたポリマーを分離し、乾燥させた。ポリマーを30gのメチルtert−ブチルエーテル(MTBE)に溶解し、5gのヘキサメチルジシラザンを添加し、続いて0.05gのピリジン塩酸塩を添加した。撹拌を室温で24時間続けた。未反応成分を減圧留去し、得られた樹脂をMTBE−水抽出法で洗浄した。溶媒を減圧下で蒸発させ、透明な樹脂(22.9g)を得た。
以下の組成物の例は、例示のために与えられたものであり、本発明を限定するものではない。
架橋性官能基としてエポキシを有するシロキサンポリマー(18.3g、18.3%)、4μmの平均サイズ(D50)を有する銀フレーク(81g、81%)、3−メタクリレートプロピルトリメトキシシラン(0.5g、0.5%)及びKing Industries K−PURE CXC−1612熱酸発生剤(0.2%)を高せん断ミキサーを用いて混合した。この組成物の粘度は15,000mPasである。
架橋性官能基としてエポキシを有するシロキサンポリマー(44.55g、44.45%)、0.9μmの平均サイズ(D50)を有する酸化アルミニウム(53g、53%)、3−メタクリレートプロピルトリメトキシシラン(1g、1%)、Irganox 1173、(1g、1%)、及びKing Industries K−PURE CXC−1612熱酸発生剤(0.45g、0.45%)を、3本のロールミルを用いて一緒に混合した。この組成物は、20,000mPasの粘度を有する。
官能基としてメタクリレートを有するシロキサンポリマー(89g、89%)、0.007μmの平均サイズ(D50)を有するヒュームドシリカ(5g、5%)、Irganox 1173(2g、2%)及びIrgacure 917光開始剤(4g、4%)を、3本のロールミルを用いて混合した。この組成物の粘度は25,000mPasである。
メタノール中のジフェニルシランジオール(20.0g、92mmol)、9−フェナントレニルトリメトキシシラン(16.6g、56mmol)、3−メタクリロキシプロピルトリメトキシシラン(9.2g、37mmol)及びBaO(25mg)を100mLフラスコに入れ、1時間還流した。揮発性物質を減圧下で蒸発させた。透明ポリマー樹脂(37g)が得られた。
組成物例6、高屈折率材料:
例1に記載したように調製した高屈折率を有するポリマー樹脂8.6gを、50%の固形含有量を有する、1,2−プロパンジオールモノメチルエーテルアセテート(PGMEA)中のZrO2ナノ粒子溶液5.7gとブレンドした。この溶液に、光開始剤(Darocur 1173、BASF製)0.26g、接着促進剤としてオリゴマーの3−メタクリロキシプロピルトリメトキシシラン0.4gおよび界面活性剤(BYK−307、BYK Chemie製)20gを加えた。得られた材料を100mmのシリコンウェハ上に2000rpmでスピンコートした。この膜をホットプレート上で80℃5分で焼き付け、3000mJ/cm2の線量でUV硬化させた。屈折率は、ポリマー樹脂とZrO2ナノ粒子の重量比を変えることによって調整した。
Claims (15)
- 接着剤又は封入剤用組成物であって、
300〜150,000g/molの分子量を有し、25℃で5rpm粘度計で1000〜100,000mPa・secの粘度を有するシロキサンポリマーと、
紫外光の適用時に前記シロキサンポリマーの硬化を促進する硬化剤と
を含み、
前記組成物は、1〜50ミクロンの厚さで可視スペクトルにおいて光透過率が95%以上である可視光に対する透過性を有し、
前記シロキサンポリマーは、ヒドロシリル化なしで形成された材料であり、その中にSiに結合した全ての基に対して5mol%未満のSi−OH基を有し、Si−H結合を実質的に有さない材料であり、
1ミクロン以下の平均粒子径を有する粒子をさらに含み、
前記シロキサンポリマーが、少なくとも第1の化合物と第2の化合物と第3の化合物との重合生成物、または少なくとも第1の化合物と第2の化合物と第4の化合物との重合生成物であり、
前記第1の化合物が、化学式:
SiR 1 a R 2 4−a
を有し、
式中、
aは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり;
前記第2の化合物が、2−(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、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、3−(トリメトキシシリル)プロピルメタクリレート、3−(トリメトキシシリル)プロピルアクリレート、(3−グリシドキシプロピル)トリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシランおよび3−アクリロキシプロピルトリメトキシシランからなる群より選択され;
前記第3の化合物が、化学式:
SiR 9 f R 10 g
を有し、
式中、
R 9 は、反応性基であり、
f=1〜4であり、
R 10 は、アルキル基またはアリール基であり、
g=4−fであり;
前記第4の化合物が、化学式:
R 2 3−a R 1 a SiR 11 SiR 1 b R 2 3−b
を有し、
式中、
aは、1〜3であり、
bは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり、
R 11 は、アルキル基またはアリール基である、組成物。 - 前記平均粒子径が100nm未満である、請求項1に記載の組成物。
- 前記硬化剤が光開始剤である、請求項1または2に記載の組成物。
- 前記シロキサンポリマーがSi−H基を実質的に有さない、前請求項のいずれか一項に記載の組成物。
- 波長632.8nmで1.55〜1.95の屈折率を有する、前請求項のいずれか一項に記載の組成物。
- 基板上に形成されたシロキサンポリマー膜であって、
基板上に保持されたUV硬化シロキサンポリマー膜を含み、該膜は、1〜50ミクロンの厚さで可視スペクトルにおいて光透過率が95%以上である可視光に対する透過性を有し、前記シロキサンポリマーは、その中にSiに結合した全ての基に対して5mol%未満のSi−OH基を有し、Si−H結合を実質的に有さず、
1ミクロン未満の平均粒子径を有する前記シロキサンポリマー膜内の粒子をさらに含み、
前記シロキサンポリマーが、少なくとも第1の化合物と第2の化合物と第3の化合物との重合生成物、または少なくとも第1の化合物と第2の化合物と第4の化合物との重合生成物であり、
前記第1の化合物が、化学式:
SiR 1 a R 2 4−a
を有し、
式中、
aは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり;
前記第2の化合物が、2−(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、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、3−(トリメトキシシリル)プロピルメタクリレート、3−(トリメトキシシリル)プロピルアクリレート、(3−グリシドキシプロピル)トリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシランおよび3−アクリロキシプロピルトリメトキシシランからなる群より選択され;
前記第3の化合物が、化学式:
SiR 9 f R 10 g
を有し、
式中、
R 9 は、反応性基であり、
f=1〜4であり、
R 10 は、アルキル基またはアリール基であり、
g=4−fであり;
前記第4の化合物が、化学式:
R 2 3−a R 1 a SiR 11 SiR 1 b R 2 3−b
を有し、
式中、
aは、1〜3であり、
bは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり、
R 11 は、アルキル基またはアリール基である、膜。 - 波長632.8nmで1.58〜1.9545の屈折率を有する、請求項6に記載の膜。
- 前記粒子がセラミック粒子であり、特に、前記セラミック粒子が酸化物粒子である、請求項6または7に記載の膜。
- 前記粒子が、400nm未満の平均粒子径を有するナノ粒子であり、前記ナノ粒子が、チタン、タンタル、アルミニウム、ジルコニウム、ハフニウム又はセレンの酸化物であるか、または前記粒子が、シリカ、中空シリカ、ZrO2、ZrO、TiO2、Ta2O5、アンチモンスズ酸化物、又はSnO2であるか、または前記粒子が、シリカ、中空シリカ、ZrO2、ZrO、TiO2である、請求項6〜8のいずれか一項に記載の膜。
- 前記基板が、ガラス、石英、サファイア、有機ポリマー又はハイブリッド有機−無機ポリマーを含むか、または前記基板が、ポリエチレンテレフタレート又はポリメチルメタクリレートを含むか、または前記基板が可撓性基板である、請求項6〜9のいずれか一項に記載の膜。
- ディスプレイの一部であり、タッチスクリーンディスプレイの一部であり、OLEDデバイスの一部であり、またはLCDディスプレイの一部である、請求項6〜9のいずれか一項に記載の膜。
- 前記基板をディスプレイ内の別の基板に接着する接着剤である、請求項6〜11のいずれか一項に記載の膜。
- LEDランプの接着剤又は封入剤である、請求項6〜11のいずれか一項に記載の膜。
- 前記基板が、その上に容量性タッチ感応性デバイスを有する基板であり、前記別の基板がカバーガラスであるか、または前記基板は、その上に形成されたタッチ感応性容量性アレイを有するカバーガラスであり、前記別の基板は、液晶セル及びカラーフィルタのアレイを含む基板であるか、または前記基板は、液晶セル及びカラーフィルタのアレイを含む基板であり、前記別の基板は、その上に形成されたタッチ感応性容量性又は抵抗性アレイを有する基板である、請求項6〜13のいずれか一項に記載の膜。
- シロキサン粒子膜の製造方法であって、
ヒドロシリル化なしに形成された、その中にSi−OH基を実質的に有さず、その中にSi−H基を実質的に有さないシロキサンポリマーを含むシロキサン組成物を基板上に堆積させることを含み、前記シロキサン組成物は、紫外光照射時に前記シロキサンポリマーの硬化を促進する硬化剤を含み、
前記シロキサン組成物は300〜150,000g/molの分子量及び25℃で5rpm粘度計で1000〜100,000mPa・secの粘度を有し、
前記方法はさらに、
堆積したシロキサン組成物に紫外光を照射して組成物を硬化させて硬化膜を形成することを含み、
前記硬化膜は、1〜50ミクロンの厚さで可視スペクトルにおける光透過率が95%以上である可視光に対する透過性を有し、
1ミクロン未満の平均粒子径を有する粒子をさらに含み、
前記シロキサンポリマーが、少なくとも第1の化合物と第2の化合物と第3の化合物との重合生成物、または少なくとも第1の化合物と第2の化合物と第4の化合物との重合生成物であり、
前記第1の化合物が、化学式:
SiR 1 a R 2 4−a
を有し、
式中、
aは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり;
前記第2の化合物が、2−(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、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、3−(トリメトキシシリル)プロピルメタクリレート、3−(トリメトキシシリル)プロピルアクリレート、(3−グリシドキシプロピル)トリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−メタクリロキシプロピルトリメトキシシランおよび3−アクリロキシプロピルトリメトキシシランからなる群より選択され;
前記第3の化合物が、化学式:
SiR 9 f R 10 g
を有し、
式中、
R 9 は、反応性基であり、
f=1〜4であり、
R 10 は、アルキル基またはアリール基であり、
g=4−fであり;
前記第4の化合物が、化学式:
R 2 3−a R 1 a SiR 11 SiR 1 b R 2 3−b
を有し、
式中、
aは、1〜3であり、
bは、1〜3であり、
R 1 は、反応性基であり、
R 2 は、アルキル基またはアリール基であり、
R 11 は、アルキル基またはアリール基である、方法。
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