TWI635152B - 聚矽氧接著劑組成物及固體攝影裝置 - Google Patents
聚矽氧接著劑組成物及固體攝影裝置 Download PDFInfo
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- TWI635152B TWI635152B TW103139049A TW103139049A TWI635152B TW I635152 B TWI635152 B TW I635152B TW 103139049 A TW103139049 A TW 103139049A TW 103139049 A TW103139049 A TW 103139049A TW I635152 B TWI635152 B TW I635152B
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- polysiloxane
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- -1 Polysiloxane Polymers 0.000 title claims abstract description 124
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 105
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 74
- 239000000853 adhesive Substances 0.000 title claims abstract description 73
- 239000000203 mixture Substances 0.000 title claims abstract description 71
- 238000003384 imaging method Methods 0.000 title claims description 14
- 239000000758 substrate Substances 0.000 claims abstract description 67
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 34
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 39
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 29
- 229910052710 silicon Inorganic materials 0.000 claims description 29
- 239000010703 silicon Substances 0.000 claims description 29
- 239000011521 glass Substances 0.000 claims description 21
- 125000000962 organic group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000001681 protective effect Effects 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 239000003963 antioxidant agent Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000000919 ceramic Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 2
- 238000006884 silylation reaction Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 22
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 238000013007 heat curing Methods 0.000 abstract description 7
- 238000005498 polishing Methods 0.000 abstract description 7
- 229920000642 polymer Polymers 0.000 abstract description 7
- 238000011161 development Methods 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 19
- 239000010408 film Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 10
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 10
- 238000005227 gel permeation chromatography Methods 0.000 description 9
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 9
- 238000002834 transmittance Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000005856 abnormality Effects 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 8
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 8
- 125000005372 silanol group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 230000009467 reduction Effects 0.000 description 7
- 239000004793 Polystyrene Substances 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 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 6
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000011342 resin composition Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000208340 Araliaceae Species 0.000 description 5
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 5
- 235000003140 Panax quinquefolius Nutrition 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 235000008434 ginseng Nutrition 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000005304 joining Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 239000005051 trimethylchlorosilane Substances 0.000 description 5
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 4
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 4
- SGVYKUFIHHTIFL-UHFFFAOYSA-N Isobutylhexyl Natural products CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 4
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 150000002898 organic sulfur compounds Chemical class 0.000 description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 description 4
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000001029 thermal curing Methods 0.000 description 4
- LFXJGGDONSCPOF-UHFFFAOYSA-N trichloro(hexyl)silane Chemical compound CCCCCC[Si](Cl)(Cl)Cl LFXJGGDONSCPOF-UHFFFAOYSA-N 0.000 description 4
- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 3
- RLHGFJMGWQXPBW-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzamide Chemical compound NC(=O)C1=CC=CC(CC=2NC=NC=2)=C1O RLHGFJMGWQXPBW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229920001214 Polysorbate 60 Polymers 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 2
- GJDRKHHGPHLVNI-UHFFFAOYSA-N 2,6-ditert-butyl-4-(diethoxyphosphorylmethyl)phenol Chemical compound CCOP(=O)(OCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 GJDRKHHGPHLVNI-UHFFFAOYSA-N 0.000 description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- OUBMGJOQLXMSNT-UHFFFAOYSA-N N-isopropyl-N'-phenyl-p-phenylenediamine Chemical compound C1=CC(NC(C)C)=CC=C1NC1=CC=CC=C1 OUBMGJOQLXMSNT-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000007809 chemical reaction catalyst Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- OSXYHAQZDCICNX-UHFFFAOYSA-N dichloro(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](Cl)(Cl)C1=CC=CC=C1 OSXYHAQZDCICNX-UHFFFAOYSA-N 0.000 description 2
- YLJJAVFOBDSYAN-UHFFFAOYSA-N dichloro-ethenyl-methylsilane Chemical compound C[Si](Cl)(Cl)C=C YLJJAVFOBDSYAN-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- VKPSKYDESGTTFR-UHFFFAOYSA-N isododecane Natural products CC(C)(C)CC(C)CC(C)(C)C VKPSKYDESGTTFR-UHFFFAOYSA-N 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 239000005054 phenyltrichlorosilane Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 2
- SIPHWXREAZVVNS-UHFFFAOYSA-N trichloro(cyclohexyl)silane Chemical compound Cl[Si](Cl)(Cl)C1CCCCC1 SIPHWXREAZVVNS-UHFFFAOYSA-N 0.000 description 2
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- FGHOOJSIEHYJFQ-UHFFFAOYSA-N (2,4-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=C(OP(O)O)C(C(C)(C)C)=C1 FGHOOJSIEHYJFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
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- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical compound CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 description 1
- BNCXNUWGWUZTCN-UHFFFAOYSA-N trichloro(dodecyl)silane Chemical compound CCCCCCCCCCCC[Si](Cl)(Cl)Cl BNCXNUWGWUZTCN-UHFFFAOYSA-N 0.000 description 1
- SSBOTKQTCWQWMG-UHFFFAOYSA-N trichloro(nonyl)silane Chemical compound CCCCCCCCC[Si](Cl)(Cl)Cl SSBOTKQTCWQWMG-UHFFFAOYSA-N 0.000 description 1
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- GPWLZOISJZHVHX-UHFFFAOYSA-N trichloro(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(Cl)Cl GPWLZOISJZHVHX-UHFFFAOYSA-N 0.000 description 1
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- 239000005052 trichlorosilane Substances 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- BWPNIANVWARHPR-UHFFFAOYSA-N tridecyl dihydrogen phosphite Chemical compound CCCCCCCCCCCCCOP(O)O BWPNIANVWARHPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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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
-
- 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
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
-
- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/12—Mountings, e.g. non-detachable insulating substrates
- H01L23/14—Mountings, e.g. non-detachable insulating substrates characterised by the material or its electrical properties
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/14618—Containers
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
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- B32B2457/00—Electrical equipment
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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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
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Abstract
本發明之目的為提供一種使用聚矽氧高分子化合物的接著劑組成物,由於在製造中無需曝光、烘烤、顯影步驟,故製造成本為低價且生產性為高,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性為良好,耐熱性、耐光性等的硬化膜之可靠性為高,進而可抑制在三次元安裝製造為所需的背面研磨後的接著基板之翹曲。
本發明的聚矽氧接著劑組成物,其係包含:(A)含有非芳香族飽和烴基及烯基之有機聚矽氧烷;(B)一分子內含有2個以上SiH基之有機氫聚矽氧烷:相對於(A)成分中之烯基之(B)成分中之SiH基之莫耳比以成為0.5~10之量;(C)鉑系觸媒:有效量。
Description
本發明為關於具有接著性、耐熱性、藥品耐性、絕緣性及高透過率性,適用於保護玻璃與半導體元件,尤其CCD或CMOS等的固體攝像元件矽基板與保護玻璃之貼合用途的聚矽氧接著劑組成物及固體攝像裝置。
以往,CCD、CMOS影像感測器用封裝構造,為了保護感測器部分防止水分、塵埃等的異物,係採取藉由光硬化型感光性樹脂組成物來與保護玻璃接著之方法,而該光硬化型感光性樹脂組成物,係藉由點膠等的印刷法所塗布的液狀或薄膜狀者。
藉由此微影法的接著劑之成形,係首先在矽基板或玻璃基板上,塗布感光性接著劑組成物或層合感光性接著劑薄膜,以形成感光性接著劑層。其次,將該感光性接著劑層曝光、烘烤、顯影後,使保護玻璃基板(矽基板)密接,藉由加熱、加壓來接合接著劑層與保護玻璃。然後,藉由熱硬化、切割,而得到中空構造型封裝。作為如此的感光性樹脂組成物,已知有:具有丙烯酸樹脂、光
聚合性化合物及光聚合起始劑的感光性樹脂組成物(專利文獻1:日本特開2002-351070號公報);具有感光性的變性環氧樹脂、光聚合起始劑、稀釋溶劑及熱硬化性化合物的感光性樹脂組成物(專利文獻2:日本特開2003-177528號公報)等。
又,作為僅熱硬化性的接著劑,亦有揭示含有聚醯亞胺樹脂、硬化性化合物及矽烷偶合劑的接著性乾薄膜(專利文獻3:日本特開2003-253220號公報)。
然而,於專利文獻1及專利文獻2記載的感光性樹脂組成物中,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性係不充分,而且由於在製造中需要曝光、烘烤、顯影的3步驟,具有高價且生產性低之缺點。又,於專利文獻3記載的熱硬化性之接著劑中,接著性或耐熱性、耐光性等的特性亦不充分。
更,最近使用貫通電極(TSV)的三次元安裝技術係正在成為CMOS影像感測器製造之主流,於此三次元安裝中,必須在與保護玻璃接著之下,對熱硬化後的矽基板進行背面研磨,將矽基板予以薄膜化至100μm以下為止。此時,可不使薄型晶圓破裂地來進行研磨為重要者以外,接著基板之大撓曲係成為新的問題,特別是在8吋以上的大口徑晶圓係變顯著。
為了抑制接著基板之翹曲,亦揭示有含有環氧基之熱硬化性聚矽氧高分子化合物(專利文獻4:日本特開2012-188650號公報)。使用此聚矽氧組成物的接著基
板之翹曲量雖然為低,但在高溫長時間(例如50小時以上)之耐熱性試驗中分光特性會大幅下降,而成為問題。相同地亦揭示聚矽氧高分子化合物(專利文獻5:日本特開2012-229333號公報、專利文獻6:日本特開2013-82801號公報),雖然可展現出良好的接合性、耐熱性、背面研磨性,但由於是熱塑性而無法充分滿足作為永久膜所需的特性。
[專利文獻1]日本特開2002-351070號公報
[專利文獻2]日本特開2003-177528號公報
[專利文獻3]日本特開2003-253220號公報
[專利文獻4]日本特開2012-188650號公報
[專利文獻5]日本特開2012-229333號公報
[專利文獻6]日本特開2013-82801號公報
本發明為有鑑於上述情事之發明,目的為以提供一種使用聚矽氧高分子化合物的加成硬化型聚矽氧接著劑組成物,由於在製造中無需曝光、烘烤、顯影步驟,故製造成本為低價且生產性為高,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性為良
好,耐熱性、耐光性等的硬化膜之可靠性為高,進而可抑制在三次元安裝製造為所需的背面研磨後的接著基板之翹曲。
本發明人為了達成上述目的經深入重複檢討之結果發現,下述聚矽氧接著劑組成物在作為CCD、CMOS影像感測器製造用接著劑為優異,遂而完成本發明。
因此,本發明為提供下述聚矽氧接著劑組成物及固體攝像裝置。
[1].一種聚矽氧接著劑組成物,其特徵係含有(A)~(C)成分而成:(A)含有非芳香族飽和一價烴基及烯基之有機聚矽氧烷;(B)一分子內含有2個以上SiH基之有機氫聚矽氧烷:相對於(A)成分中之烯基之(B)成分中之SiH基之莫耳比以成為0.5~10之量;(C)鉑系觸媒:有效量,且該(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷為有機聚矽氧烷(A-1)或高分子量化的有機聚矽氧烷(A-2):(A-1)包含以下述(I)~(III)所示之單位之重量平均分子量2,000~60,000之有機聚矽氧烷;
(A-2)將以下述一般式(1)所示之1種以上之有機氫聚矽氧烷、與該有機聚矽氧烷(A-1),以相對於上述有機聚矽氧烷(A-1)之總烯基,使上述有機氫聚矽氧烷之總SiH基成為莫耳比計0.4~0.8倍之量進行氫化矽烷化反應而成之重量平均分子量20,000~400,000之高分子量化的有機聚矽氧烷,
(I)以R1SiO3/2表示之矽氧烷單位(T單位):50~99莫耳%、
(II)以R2R3SiO2/2表示之矽氧烷單位(D單位):0~49莫耳%、
(III)以R4 3SiO1/2表示之矽氧烷單位(M單位):1~15莫耳%(式中,R1~R3分別為一價有機基,且以R1~R3所示之全部有機基中2~10莫耳%為碳數2~7之烯基,以R1~R3所示之全部有機基中40莫耳%以上為相同或相異的碳數5~10之包含下述環狀構造之任一者之非芳香族飽和一價烴基,
且10~40莫耳%為相同或相異的碳數6~15之取代或非取代之一價非環狀飽和烴基,更,殘餘部分為前述烯基、碳數5~10之環狀飽和一價烴基、碳數6~15之非環狀飽和一
價烴基以外的以R1~R3所示之有機基,及R4為相同或相異的碳數1~7之取代或非取代之一價烴基),
(式中,R5~R7係表示可相同或相異的烯基除外的碳數1~12之一價烴基,n為0~200之整數)。
[2].如前述[1]之接著劑組成物,其中,進而含有(D)反應控制劑。
[3].如前述[1]或[2]之接著劑組成物,其中,進而含有(E)抗氧化劑。
[4].如前述[1]~[3]中任一項之接著劑組成物,其中,進而含有(F)有機溶劑。
[5].如前述[4]之接著劑組成物,其中,前述(F)有機溶劑為沸點120~240℃之烴溶劑。
[6].如前述[1]~[5]中任一項之接著劑組成物,其中,使層合於選自矽晶圓、固體攝像元件矽晶圓、塑膠基板、陶瓷基板及金屬製電路基板之任1種之基板、與保護玻璃基板之間。
[7].一種固體攝像裝置,其係包含於選自矽晶圓、固體攝像元件矽晶圓、塑膠基板、陶瓷基板及金屬製電路基板之任1種之基板上,依序層合前述[1]~[5]中任一項之接著劑組成物之硬化物層及保護玻璃基板而成的層合物。
藉由使用本發明的聚矽氧接著劑組成物,由於在製造中無需曝光、烘烤、顯影步驟,故製造成本為低價且生產性為高,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性為良好,耐熱性、耐光性等的硬化膜之可靠性亦高,進而可抑制在三次元安裝製造為所需的背面研磨後的接著基板之翹曲,適合使用於CCD、CMOS影像感測器之製造。
以下,對於本發明的聚矽氧接著劑組成物詳細說明,但本發明並不限定於該等。
<聚矽氧接著劑組成物>
本發明的聚矽氧接著劑組成物,其特徵係包含(A)~(C)成分:(A)含有非芳香族飽和一價烴基及烯基之有機聚矽氧烷:100質量份;(B)一分子內含有2個以上SiH基之有機氫聚矽氧烷:相對於(A)成分中之烯基之(B)成分中之SiH基之莫耳比以成為0.5~10之量;(C)鉑系觸媒:有效量。
本發明的(A)成分為含有非芳香族飽和一價烴基及烯基之有機聚矽氧烷,接著劑組成物中所包含的有機聚矽氧烷可使用單獨1種,亦可併用2種以上。作為較佳使用者,大至可區分舉例如下述(A-1)、(A-2)之二者。以下,依序說明。
‧有機聚矽氧烷(A-1)
有機聚矽氧烷(A-1)為重量平均分子量(Mw)[藉由GPC(凝膠滲透層析法)所得的聚苯乙烯換算值]2,000~60,000,包含以下述(I)~(III)所示之單位之含有非芳香族飽和一價烴基及烯基之有機聚矽氧烷。
(I)以R1SiO3/2表示之矽氧烷單位(T單位):50~99莫耳%
(II)以R2R3SiO2/2表示之矽氧烷單位(D單位):0~49莫耳%
(III)以R4 3SiO1/2表示之矽氧烷單位(M單位):1~15莫耳%
以上述(I)~(III)所示之單位中,R1~R4分別為一價有機基。於此,一價有機基為由下述(i)~(iv)所示之基而成。
(i)碳數5~10之包含環狀構造之非芳香族飽和一價烴基,係包含下述所示的一價及/或二價環戊基骨架、環己基骨架、雙環[2.2.1]骨架、雙環[3.1.1]骨架
之任一者之碳數5~10(特以5~7)之包含環狀構造之一價非芳香族飽和一價烴基,具體而言可舉例如環戊基、環己基、降莰基、降莰乙基、金剛烷基等。
(ii)舉例如碳數6~15之取代(特以鹵取代)或非取代之碳數6~15之一價非環狀飽和一價烴基,具體而言可舉例如n-己基、辛基、n-癸基、n-十二烷基等,又較佳為n-己基、n-十二烷基。
(iii)碳數2~7之烯基,具體而言可舉例如乙烯基、烯丙基、丁烯基、己烯基、環己烯基、降莰烯基等,又較佳為乙烯基。
(iv)碳數1~7之取代(特以鹵取代)或非取代之一價烴基,具體而言可舉例如甲基、乙基、丙基、丁基、戊基等的烷基;苯基、甲苯基等的芳基;苄基等的芳烷基;氯甲基、3-氯丙基、3,3,3-三氟丙基等的鹵化烷基等,較佳為甲基、丙基、苯基。
此情形時,尤其就展現出耐藥品性而言重要的是包含環狀構造之非芳香族飽和一價烴基(非芳香族環狀飽和一價烴基(i))之含量,前述R1~R3之中,非芳香族環狀飽和一價烴基之含量較佳為40莫耳%以上,特佳為50~80莫耳%。只要是40莫耳%以上,可成為耐熱性、耐光性優異者。
又,為了使聚矽氧烷之接合性提昇,非環狀飽和一價烴基(ii)之含量亦為重要。前述R1~R3之中,碳數6~15之取代或非取代之一價非環狀飽和一價烴基之含量較佳為10~40莫耳%。只要是10莫耳%以上,可期待接合性之提昇,只要是40莫耳%以下,硬化後之膜不會變得過軟而具適度硬度。
以前述R1~R3所示之全部有機基中,較佳為2~10莫耳%為碳數2~7之烯基(iii),特佳為4~8莫耳%。只要是2莫耳%以上,可期待於硬化時得到充分的交聯密度,只要是10莫耳%以下,硬化後之膜不會變得過硬而具適度硬度。
尚,當R1~R3之合計量未達100莫耳%時,剩餘之基為上述(iv)之基,又,R4亦為上述(iv)之基,但作為R4亦可包含(i)~(iii)之基無妨。
作為本發明的(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷,如同上述,適合的有機聚矽氧烷(A-1)為包含T單位50~99莫耳%、D單位0~49莫耳%、M單位1~15莫耳%。
作為(A-1)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷,以在不超過40℃之溫度下具有固體形狀者就操作上而言係較佳。
藉由包含T單位50~99莫耳%,較佳為55~90莫耳%,更佳為60~85莫耳%,(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷在40℃以下容易成為固體,
適合於基板間之接合。
藉由包含D單位49莫耳%以下,較佳為45莫耳%以下,更佳為40莫耳%以下,(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷在40℃以下容易成為固體,且使用於接著劑組成物時,可充分地接合基板彼此。
又,(A-1)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷中,就後述之熱安定性之觀點而言,以不殘留反應性之末端基(亦即,矽烷醇基等)為較佳。因此,較佳於末端導入M單位之構造,作為M單位之含量,較佳為包含1莫耳%以上。又較佳為1~15莫耳%,更佳為3~10莫耳%。
藉由包含M單位1~15莫耳%,可使(A-1)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷成為反應性末端基為充分減少之構造。只要是1莫耳%以上,可使成為矽烷醇基等的反應性末端基為充分減少之構造。又,只要是15莫耳%以下,則未有所謂因為末端基變得過多而使分子量相對變小之虞,故合適。
當存在著未以M單位封閉的分子末端基(亦即,矽烷醇基等)時,該等反應性末端基之含量以儘可能少者為較佳。只要在分子內具有少量的矽烷醇基之末端殘基,則可抑制加熱時因縮合反應而生成之水、及可能成為釋氣(outgas)之原因,由於耐熱性提昇故較佳。又,矽烷醇基之OH基之總量,以全樹脂固形物中的5質量%以下
為較佳,又較佳為3質量%以下。藉由導入M單位,可使如此般的反應性末端基減少至所希望之量。
上述構造之有機聚矽氧烷,可藉由邊控制作為原料之水解性矽烷之水解、及縮合反應邊進行而製造。
可作為原料使用的水解性矽烷方面,可舉例如甲基三氯矽烷、苯基三氯矽烷、n-丙基三氯矽烷、異丙基三氯矽烷、n-丁基三氯矽烷、異丁基三氯矽烷、n-戊基三氯矽烷、異戊基三氯矽烷、n-己基三氯矽烷、環己基三氯矽烷、n-辛基三氯矽烷、n-癸基三氯矽烷、n-十二烷基三氯矽烷、雙環[2.2.1]庚基三氯矽烷(下述(C1))、雙環[2.2.1]壬基三氯矽烷(下述(C2))、二甲基二氯矽烷、n-丙基甲基二氯矽烷、異丙基甲基二氯矽烷、n-丁基甲基二氯矽烷、異丁基甲基二氯矽烷、n-己基甲基二氯矽烷、n-辛基甲基二氯矽烷、n-癸基甲基二氯矽烷、n-十二烷基甲基二氯矽烷、環己基甲基二氯矽烷、二苯基二氯矽烷、雙環[2.2.1]庚基甲基二氯矽烷(下述(C3))、雙環[2.2.1]壬基甲基二氯矽烷(下述(C4))、及該等之水解性基為甲氧基、乙氧基者。
尤其具有複數個環狀構造之下述(C1)~(C4)存在橋(endo)體、掛(exo)體之立體異構物,但不管任一種均可使用。
(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷之分子量分布極為重要。亦即,以GPC(凝膠滲透層析法),以聚苯乙烯標準物質製作之校正線獲得之重量平均分子量之值為2,000以上。含有非芳香族飽和一價烴基之有機聚矽氧烷之重量平均分子量只要是2,000以上,可得到硬化後具充分膜強度者,只要是60,000以下,含有非芳香族飽和一價烴基之有機聚矽氧烷之分子量之再現性為良好,可安定地進行合成。作為含有非芳香族飽和一價烴基之有機聚矽氧烷之重量平均分子量之範圍,又較佳為3,000~50,000左右,更佳為5,000~30,000左右。
作為可進行如此般的分析、解析之GPC裝置,可使用Tosoh(股)製之HLC-8120GPC、HLC-8220GPC、HLC-8230GPC(以下亦同)。
有機聚矽氧烷(A-2)為將前述有機聚矽氧烷(A-1)作為原料並使其高分子量化者。
亦即,在鉑系觸媒之存在下,將前述(A-1)、與以下述一般式(1)所示之1種以上之有機氫聚矽氧烷,以相對於前述含有烯基之有機聚矽氧烷(A-1)之總烯基,使前述式(1)之有機氫聚矽氧烷之總SiH基成為0.4~0.8倍之量進行氫化矽烷化反應(hydrosilylation reaction)而成者,且重量平均分子量為20,000~400,000之有機聚矽氧烷。
相對於(A-1)成分之總烯基,式(1)成分之總SiH量較佳為0.4~0.8倍。只要是0.4倍以上,分子量之增加為充分,樹脂強度會提昇。又,只要是0.8倍以下,可藉由接著劑組成物之交聯反應而硬化。
作為前述R5~R7之烯基除外的碳數1~12之一價烴基,具體而言可示例如甲基、丙基、己基、環己基、癸基、十二烷基等的烷基、苯基等的芳基。特佳為甲基、環己基、苯基。
以上述一般式(1)所示之有機氫聚矽氧烷之聚合度n,較佳為0~200之整數,又較佳為20~150,特佳為40~120之整數。n只要是200以下,於合成時,與含有烯基之有機聚矽氧烷(A-1)之烯基之氫化矽烷化反應未有不易進行之虞,可充分地進行反應,又,硬化後的有機聚矽氧烷與矽基板之密接性亦變得良好。
又,只要是上述之範圍內,亦可使用相異的有機氫聚矽氧烷來進行加成反應。
含有烯基之有機聚矽氧烷(A-1)、與有機氫聚矽氧烷(1)之反應,例如,將含有烯基之有機聚矽氧烷(A-1)溶解於有機溶劑中,於添加氫化矽烷化觸媒之鉑系金屬觸媒後,邊加熱至50~150℃邊滴下有機氫聚矽氧烷(1),藉此可得到高分子量化的有機聚矽氧烷。
鉑系觸媒為用於促進與SiH基之氫化矽烷化加成反應之觸媒,作為此加成反應觸媒,可舉例如鉑黑、氯化鉑、氯化鉑酸、氯化鉑酸與一元醇之反應物、氯化鉑酸與烯烴類之錯合物、鉑雙乙醯乙酸酯等鉑系觸媒、鈀系觸媒、銠系觸媒等鉑族金屬觸媒。尚,此加成反應觸媒之調配量為成為觸媒之量,但通常以鉑族金屬計相對於(A-1)成分之質量較佳調配1~800ppm,特佳調配2~300ppm左右。
該等氫化矽烷化加成反應後的有機聚矽氧烷之分子
量,對於接著劑組成物之特性,尤其是加熱時之熱變形、於接著界面之空孔發生等會造成影響。
加成反應後的高分子量化的有機聚矽氧烷之重量平均分子量Mw,係使用GPC(凝膠滲透層析法)並以聚苯乙烯標準物質製作之校正線獲得之重量平均分子量之值,較佳為20,000~400,000。只要是上述之重量平均分子量,可成為耐熱性優異、且未產生空孔的有機聚矽氧烷。作為重量平均分子量之範圍,又較佳為25,000~300,000左右,更佳為30,000~150,000左右。
(B)成分為交聯劑,係一分子內含有至少2個以上(較佳為3個以上)SiH基之有機氫聚矽氧烷,可使用直鏈狀、支鏈狀或環狀者。
作為前述(B)成分,可示例如下述一般式(2)或(3),但不限定於該等。
前述(B)成分之有機氫聚矽氧烷,藉由旋轉黏度計所得25℃時之黏度較佳為1~5,000mPa‧s,又較佳為1~2,000mPa‧s,更佳為5~500mPa‧s。此有機氫聚矽氧烷可為2種以上的混合物。
前述(B)成分之使用量,相對於(A)成分中之烯基量之(B)成分中之SiH基之莫耳比(SiH基/烯基),以成為0.5~10(特以1~5)之範圍之方式來進行調配為佳。此SiH基與烯基之莫耳比只要是0.5以上,交聯密度不會變低,亦不會產生所謂組成物未硬化之問題。只要是10以下,交聯密度不會變得過高,亦可抑制於接合後的耐熱性試驗時起因於殘留SiH基之發泡,故較佳。
(C)成分為鉑系觸媒(即,鉑族金屬觸媒),可舉例如氯化鉑酸、氯化鉑酸之醇溶液、氯化鉑酸與醇之反應物、氯化鉑酸與烯烴化合物之反應物、氯化鉑酸與含有乙烯基之矽氧烷之反應物等。
前述(C)成分之添加量為有效量,通常而言,相對於前述(A)及(B)成分之合計,以鉑部分(質量換算)計
為1~5,000ppm,較佳為5~2,000ppm。只要是1ppm以上,聚矽氧接著劑組成物之硬化性不會降低,交聯密度亦不會變低。只要是5,000ppm以下,保存安定性會變得良好。
本發明的聚矽氧接著劑組成物中,除了上述(A)、(B)、(C)成分以外,亦可含有下述(D)、(E)、(F)成分、其他成分。
(D)成分為反應控制劑,其係於調合聚矽氧接著劑組成物乃至塗布至基材之際,用來不使處理液在加熱硬化前即引起增黏或凝膠化,因應所需而任意添加之成分。
作為具體例,可舉例如3-甲基-1-丁炔-3-醇、3-甲基-1-戊炔-3-醇、3,5-二甲基-1-己炔-3-醇、1-乙炔基環己醇、3-甲基-3-三甲基矽氧烷-1-丁炔、3-甲基-3-三甲基矽氧烷-1-戊炔、3,5-二甲基-3-三甲基矽氧烷-1-己炔、1-乙炔基-1-三甲基矽氧烷環己烷、雙(2,2-二甲基-3-丁氧基)二甲基矽烷、1,3,5,7-四甲基-1,3,5,7-四乙烯基環四矽氧烷、1,1,3,3-四甲基-1,3-二乙烯基二矽氧烷等,較佳為1-乙炔基環己醇、及3-甲基-1-丁炔-3-醇。
前述(D)成分之調配量,通常而言,相對於前述(A)及(B)成分之合計100質量份,只要是0~8.0質量份之範圍即可,較佳為0.01~8.0質量份,特佳為0.05~2.0質量份。只要是8.0質量份以下,聚矽氧接著劑組成物之
硬化性不會降低,只要是0.01質量份以上,可充分發揮反應控制之效果。
更,本發明的組成物中,為了使熱安定性提昇,亦可調配作為(E)成分之抗氧化劑。
(E)成分之抗氧化劑,較佳由受阻酚系化合物、受阻胺系化合物、有機磷化合物及有機硫化合物所成之群中所選出之至少1種的化合物。
受阻酚系化合物:
在本發明所使用的受阻酚系化合物未特別限定者,較佳可舉例如下述受阻酚系化合物。
1,3,5-三甲基-2,4,6-參(3,5-二-t-丁基-4-羥基苄基)苯(商品名:IRGANOX 1330)、2,6-二-t-丁基-4-甲基酚(商品名:Sumilizer BHT)、2,5-二-t-丁基-氫醌(商品名:Nocrac NS-7)、2,6-二-t-丁基-4-乙基酚(商品名:Nocrac M-17)、2,5-二-t-戊基氫醌(商品名:Nocrac DAH)、2,2’-亞甲基雙(4-甲基-6-t-丁基酚)(商品名:Nocrac NS-6)、3,5-二-t-丁基-4-羥基-苄基膦酸二乙酯(商品名:IRGANOX 1222)、4,4’-硫代雙(3-甲基-6-t-丁基酚)(商品名:Nocrac 300)、2,2’-亞甲基雙(4-乙基-6-t-丁基酚)(商品名:Nocrac NS-5)、4,4’-亞丁基雙(3-甲基-6-t-丁基酚)(ADEKA STAB AO-40)、2-t-丁基-6-(3-t-丁基-2-羥基-5-甲基苄基)-4-甲基苯基丙烯酸酯(商品名:Sumilizer GM)、2-[1-(2-羥基-3,5-二-t-戊基
苯基)乙基]-4,6-二-t-戊基苯基丙烯酸酯(商品名:Sumilizer GS)、2,2’-亞甲基雙[4-甲基-6-(α-甲基-環己基)酚]、4,4’-亞甲基雙(2,6-二-t-丁基酚)(商品名:SEENOX 226M)、4,6-雙(辛硫基甲基)-o-甲酚(商品名:IRGANOX 1520L)、2,2’-乙烯雙(4,6-二-t-丁基酚)、十八烷基-3-(3,5-二-t-丁基-4-羥基苯基)丙酸酯(商品名:IRGANOX 1076)、1,1,3-參-(2-甲基-4-羥基-5-t-丁基苯基)丁烷(商品名:ADEKA STAB AO-30)、肆[亞甲基-(3,5-二-t-丁基-4-羥基氫肉桂酸酯)]甲烷(商品名:ADEKA STAB AO-60)、三乙二醇雙[3-(3-t-丁基-5-甲基-4-羥基苯基)丙酸酯](商品名:IRGANOX 245)、2,4-雙-(n-辛硫基)-6-(4-羥基-3,5-二-t-丁基苯胺基)-1,3,5-三嗪(商品名:IRGANOX 565)、N,N’-六亞甲基雙(3,5-二-t-丁基-4-羥基-氫化肉桂醯胺)(商品名:IRGANOX 1098)、1,6-己二醇-雙[3-(3,5-二-t-丁基-4-羥基苯基)丙酸酯](商品名:IRGANOX 259)、2,2-硫代-二乙烯雙[3-(3,5-二-t-丁基-4-羥基苯基)丙酸酯](商品名:IRGANOX 1035)、3,9-雙[2-[3-(3-t-丁基-4-羥基-5-甲基苯基)丙醯氧基]1,1-二甲基乙基]2,4,8,10-四螺[5.5]十一烷(商品名:Sumilizer GA-80)、參-(3,5-二-t-丁基-4-羥基苄基)異氰酸酯(商品名:IRGANOX 3114)、雙(3,5-二-t-丁基-4-羥基苄基膦酸乙基)鈣/聚乙烯蠟混合物(50:50)(商品名:IRGANOX 1425WL)、異辛基-3-(3,5-二-t-丁基-4-羥基苯基)丙酸酯(商品名:IRGANOX 1135)、4,4’-硫代雙(6-t-丁基-3-甲基酚)(商品名:Sumilizer WX-R)、6-[3-(3-t-丁
基-4-羥基-5-甲基苯基)丙氧基]-2,4,8,10-四-t-丁基二苯并[d,f][1,3,2]二噁磷環庚烷(商品名:Sumilizer GP)等。
受阻胺系化合物:
在本發明所使用的受阻胺系化合物未特別限定者,較佳可舉例如下述受阻胺系化合物。
p,p’-二辛基二苯胺(商品名:IRGANOX 5057)、苯基-α-萘胺(Nocrac PA)、聚(2,2,4-三甲基-1,2-二氫喹啉)(商品名:Nocrac 224,224-S)、6-乙氧基-2,2,4-三甲基-1,2-二氫喹啉(商品名:Nocrac AW)、N,N’-二苯基-p-苯二胺(商品名:Nocrac DP)、N,N’-二-β-萘基-p-苯二胺(商品名:Nocrac White)、N-苯基-N’-異丙基-p-苯二胺(商品名:Nocrac 810NA)、N,N’-二烯丙基-p-苯二胺(商品名:Nonflex TP)、4,4’(α,α-二甲基苄基)二苯胺(商品名:Nocrac CD)、p,p-甲苯磺醯胺基二苯胺(商品名:Nocrac TD)、N-苯基-N’-(3-甲基丙烯醯氧基-2-羥基丙基)-p-苯二胺(商品名:Nocrac G1)、N-(1-甲基庚基)-N’-苯基-p-苯二胺(商品名:Ozonon 35)、N,N’-二-sec-丁基-p-苯二胺(商品名:Sumilizer BPA)、N-苯基-N’-1,3-二甲基丁基-p-苯二胺(商品名:Antigene 6C)、烷基化二苯胺(商品名:Sumilizer 9A)、琥珀酸二甲基-1-(2-羥基乙基)-4-羥基-2,2,6,6-四甲基哌啶聚縮合物(商品名:Tinuvin 622LD)、聚[[6-(1,1,3,3-四甲基丁基)胺基-1,3,5-三嗪-2,4-二基][(2,2,6,6-四甲基-4-哌啶基)亞胺基]六亞甲基[(2,2,6,6-四甲基-4-哌啶基)亞胺基]](商品名:CHIMASSORB 944)、
N,N’-雙(3-胺基丙基)乙烯二胺-2,4-雙[N-丁基-N-(1,2,2,6,6-五甲基-4-哌啶基)胺基]-6-氯-1,3,5-三嗪縮合物(商品名:CHIMASSORB 119FL)、雙(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯(商品名:TINUVIN 123)、雙(2,2,6,6-四甲基-4-哌啶基)癸二酸酯(商品名:TINUVIN 770)、2-(3,5-二-t-丁基-4-羥基苄基)-2-n-丁基丙二酸雙(1,2,2,6,6-五甲基-4-哌啶基)(商品名:TINUVIN 144)、雙(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯(商品名:TINUVIN 765)、肆(1,2,2,6,6-五甲基-4-哌啶基)1,2,3,4-丁烷四羧酸酯(商品名:LA-57)、肆(2,2,6,6-四甲基-4-哌啶基)1,2,3,4-丁烷四羧酸酯(商品名:LA-52)、1,2,3,4-丁烷四羧酸與1,2,2,6,6-五甲基-4-哌啶醇及1-十三醇之混合酯化物(商品名:LA-62)、1,2,3,4-丁烷四羧酸與2,2,6,6-四甲基-4-哌啶醇及1-十三醇之混合酯化物(商品名:LA-67)、1,2,3,4-丁烷四羧酸與1,2,2,6,6-五甲基-4-哌啶醇及3,9-雙(2-羥基-1,1-二甲基乙基)-2,4,8,10-四螺[5.5]十一烷基之混合酯化物(商品名:LA-63P)、1,2,3,4-丁烷四羧酸與2,2,6,6-四甲基-4-哌啶醇及3,9-雙(2-羥基-1,1-二甲基乙基)-2,4,8,10-四螺[5.5]十一烷基之混合酯化物(商品名:LA-68LD)、(2,2,6,6-四亞甲基-4-哌啶基)-2-丙烯羧酸酯(商品名:ADEKA STAB LA-82)、(1,2,2,6,6-五甲基-4-哌啶基)-2-丙烯羧酸酯(商品名:ADEKA STAB LA-87)等。
有機磷化合物:
在本發明所使用的有機磷化合物未特別限定者,較佳
可舉例如下述有機磷化合物。
雙(2,4-二-t-丁基苯基)[1,1-聯苯基]-4,4’-二基雙亞磷酸酯、9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物(商品名:SANKO-HCA)、亞磷酸三乙酯(商品名:JP302)、三-n-丁基亞磷酸酯(商品名:304)、三苯基亞磷酸酯(商品名:ADEKA STAB TPP)、二苯基單辛基亞磷酸酯(商品名:ADEKA STAB C)、三(p-甲苯基)亞磷酸酯(商品名:Chelex-PC)、二苯基單癸基亞磷酸酯(商品名:ADEKA STAB 135A)、二苯基單(十三烷基)亞磷酸酯(商品名:JPM313)、參(2-乙基己基)亞磷酸酯(商品名:JP308)、苯基二癸基亞磷酸酯(ADEKA STAB 517)、三癸基亞磷酸酯(商品名:ADEKA STAB 3010)、四苯基二丙二醇二亞磷酸酯(商品名:JPP100)、雙(2,4-二-t-丁基苯基)新戊四醇二亞磷酸酯(商品名:ADEKA STAB PEP-24G)、參(十三烷基)亞磷酸酯(商品名:JP333E)、雙(壬基苯基)新戊四醇二亞磷酸酯(商品名:ADEKA STAB PEP-4C)、雙(2,6-二-t-丁基-4-甲基苯基)新戊四醇二亞磷酸酯(商品名:ADEKA STAB PEP-36)、雙[2,4-二(1-苯基異丙基)苯基]新戊四醇二亞磷酸酯(商品名:ADEKA STAB PEP-45)、三硫代亞磷酸三月桂酯(商品名:JPS312)、參(2,4-二-t-丁基苯基)亞磷酸酯(IRGAFOS 168)、參(壬基苯基)亞磷酸酯(商品名:ADEKA STAB 1178)、雙十八烷基新戊四醇二亞磷酸酯(商品名:ADEKA STAB PEP-8)、參(單,二壬基苯基)亞磷酸酯(商品名:ADEKA STAB 329K)、亞磷酸三油酯(商品
名:Chelex-OL)、參十八烷基亞磷酸酯(商品名:JP318E)、4,4’-亞丁基雙(3-甲基-6-t-丁基苯基雙十三烷基)亞磷酸酯(商品名:JPH1200)、四(C12-C15混合烷基)-4,4’-異丙烯二苯基二亞磷酸酯(商品名:ADEKA STAB 1500)、四(十三烷基)-4,4’-亞丁基雙(3-甲基-6-t-丁基酚)二亞磷酸酯(商品名:ADEKA STAB 260)、六(十三烷基)-1,1,3-參(2-甲基-5-t-丁基-4-羥基苯基)丁烷-三亞磷酸酯(商品名:ADEKA STAB 522A)、氫化雙苯酚A亞磷酸酯聚合物(HBP)、肆(2,4-二-t-丁基苯基氧基)4,4’-聯苯-二-膦(商品名:P-EPQ)、肆(2,4-二-t-丁基-5-甲基苯基氧基)4,4’-聯苯-二-膦(商品名:GSY-101P)、2-[[2,4,8,10-肆(1,1-二甲基乙基)二苯并[d,f][1,3,2]二噁磷環庚烷-6-基]氧基]-N,N-雙[2-[[2,4,8,10-肆(1,1-二甲基乙基)二苯并[d,f][1,3,2]二噁磷環庚烷-6-基]氧基]-乙基]乙胺(商品名:IRGAFOS 12)、2,2’-亞甲基雙(4,6-二-t-丁基苯基)辛基亞磷酸酯(商品名:ADEKA STAB HP-10)等。
有機硫化合物:
在本發明所使用的有機硫化合物未特別限定者,較佳可舉例如下述有機硫化合物。
二月桂基-3,3’-硫代二丙酸酯(商品名:Sumilizer TPL-R)、二(十四烷基)-3,3’-硫代二丙酸酯(商品名:Sumilizer TPM)、雙十八烷基-3,3’-硫代二丙酸酯(商品名:Sumilizer TPS)、新戊四醇肆(3-月桂基硫代丙酸酯)(商品名:Sumilizer TP-D)、雙十三烷基-3,3’-硫代二丙
酸酯(商品名:Sumilizer TL)、2-巰基苯并咪唑(商品名:Sumilizer MB)、雙十三烷基-3,3’-硫代二丙酸酯(商品名:ADEKA STAB AO-503A)、1,3,5-參-β-十八烷基硫代丙醯氧基乙基異氰酸酯、3,3’-硫代雙丙酸雙十二烷基酯(商品名:IRGANOX PS 800FL)、3,3’-硫代雙丙酸雙十八烷基酯(商品名:IRGANOX PS 802FL)等。
上述抗氧化劑之中,當考量與(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷、(B)成分、及後述的有機溶劑之相溶性時,特佳可舉例如ADEKA STAB AO-60、IRGANOX 1076、IRGANOX 1135、IRGANOX 1520L(以上為商品名)等。
相對於(A)成分100質量份而言,作為(E)成分之添加量為0.1~5質量份,較佳為0.2~3質量份。較此少時,無法得到充分的效果,添加較此多時,有無法得到相溶性之可能性。
尚,(E)成分不限定於1種,可合併複數種使用。
又,本發明中,除了(A)、(B)、(C)、(D)及(E)成分以外,可含有(F)有機溶劑。
作為本發明的接著劑組成物中所包含的(A)有機聚矽氧烷,使用前述的含有非芳香族飽和一價烴基之有機聚矽氧烷(A-1)、及高分子量化的有機聚矽氧烷(A-2),此情形時,(F)成分以能溶解(A)、(B)、(C)、(D)及(E)成分,並藉由旋轉塗布等習知的塗膜形成方法來形成膜厚1~200μm之薄膜為宜。此時,又較佳的膜厚為5~180μm,
更佳為30~150μm,以可形成如此般範圍的膜厚的(F)有機溶劑為較佳。
如此般地,作為溶解(A)、(B)、(C)、(D)及(E)成分的(F)有機溶劑,可使用酮、酯、醇等以外者。又,醚系溶劑雖亦可溶解本發明的接著劑組成物,但考量作業性或安全性,例如溶劑之臭氣等時,較佳為非芳香族烴。
作為如此般的(F)有機溶劑,可舉例如碳數4~15之非芳香族烴化合物,具體例方面,例如戊烷、己烷、環戊烷、環己烷、甲基環己烷、辛烷、異辛烷、異壬烷、癸烷、十一烷、異十二烷、檸檬烯、蒎烯等。
該等之中,作為賦予可旋轉塗布、且安全性亦高的接著劑組成物的(F)有機溶劑,較佳為沸點120~240℃之烴溶劑。即,就此觀點而言,較佳為異壬烷、癸烷、異癸烷、十二烷、異十二烷。沸點只要是120℃以上,揮發速度為慢且旋轉塗布時之塗布性亦良好,故較佳。又,沸點只要是240℃以下,藉由塗布烴溶劑後的加熱乾燥而容易揮發,不易殘留於膜內。因此,接著劑組成物即使在基板接合後的加熱製程中被曝露於高溫之際,亦可抑制於接合面的氣泡之形成,故較佳。
相對於(A)及(B)成分100質量份而言,作為(F)成分之添加量為10~1,000質量份,較佳為20~200質量份。較此少時,接著劑組成物之黏度會變得過高,而無法塗布至晶圓,添加較此多時,塗布後無法得到充分的膜
厚。
尚,(F)成分不限定於1種,可合併複數種使用。
上述成分以外,在不損及本發明效果之範圍內,可進而於本發明的接著劑組成物中添加使用於一般的接著劑組成物的成分。
例如,為了提昇塗布性,本發明的接著劑組成物中亦可添加習知的界面活性劑。未特別限定者,具體而言舉例如聚氧乙烯月桂醚、聚氧乙烯十八烷基醚、聚氧乙烯十六烷基醚、聚氧乙烯油基醚等的聚氧乙烯烷基醚類、聚氧乙烯辛基酚醚、聚氧乙烯壬基酚醚等的聚氧乙烯烷基芳基醚類、聚氧乙烯聚氧丙烯嵌段共聚物類、去水山梨醇單月桂酸酯、去水山梨醇單十六酸酯、去水山梨醇單硬脂酸酯等的去水山梨醇脂肪酸酯類、聚氧乙烯去水山梨醇單月桂酸酯、聚氧乙烯去水山梨醇單十六酸酯、聚氧乙烯去水山梨醇單硬脂酸酯、聚氧乙烯去水山梨醇三油酸酯、聚氧乙烯去水山梨醇三硬脂酸酯等的聚氧乙烯去水山梨醇脂肪酸酯之非離子系界面活性劑、Eftop EF301、EF303、EF352(Tokem Products)、Megafac F171、F172、F173(DIC Co.)、Fluorad FC430、FC431(住友3M)、AashiGuard AG710、Surflon S-381、S-382、SC101、SC102、SC103、SC104、SC105、SC106、Surfynol E1004、KH-10、KH-20、KH-30、KH-40(旭硝子)等的氟系
界面活性劑、有機矽氧烷聚合物KP341、X-70-092、X-70-093(信越化學工業)、丙烯酸系或甲基丙烯酸系Polyflow No.75,No.95(Kyoeisha Chemical Co.,Ltd)。該等可使用單獨,或組合2種以上使用。
又,基本而言本發明的接著劑組成物不與矽晶圓等的基板或玻璃基板等的基材反應,但為了更提高接著劑組成物之接著性,亦可添加習知的接著助劑,例如矽烷偶合劑。
藉由使用如此般的聚矽氧接著劑組成物,由於在製造中無需曝光、烘烤、顯影步驟,故製造成本為低價且生產性為高,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性為良好,耐熱性、耐光性等的硬化膜之可靠性亦高,進而可抑制在三次元安裝製造為所需的背面研磨後的接著基板之翹曲。
接著,對於使用上述接著劑組成物的本發明的CCD、CMOS影像感測器製造時的矽晶圓與玻璃基板之接合方法進行說明。
首先,將上述接著劑組成物塗布至基板上。作為上述基板,可列舉例如固體攝像元件矽晶圓等。
作為塗布法,可採用習知的微影法技術來進行。例如,可藉由浸漬法、旋轉塗布法、輥塗布法等的手法來進行塗布。
於此,為了減少與保護玻璃基板之接合時之釋氣,因應所需地,亦可藉由預備加熱(預烘烤)來使溶劑等予以預
先揮發。預備加熱,可例如以40~100℃來進行。
可將如此般操作所得到的附有接著劑組成物之矽基板(固體攝像元件矽晶圓),以使用接合裝置來與保護玻璃基板進行暫時接合。作為暫時接合之條件,接合溫度較佳為50~200℃,又較佳為70~150℃,接合前保持時間較佳為0~10分,又較佳為1~5分,接合時減壓較佳為100mbar以下,又較佳為10mbar以下之條件。更,接合壓力可以0.1~50kN,又較佳為0.5~20kN來進行暫時接合。更,因應所需地亦可將暫時接合基板加熱來使組成物硬化。作為熱硬化溫度,較佳為100~220℃,又較佳為120~200℃,硬化時間較佳為1~60分,又較佳可以3~30分來進行。
因此,於選自矽晶圓、固體攝像元件矽晶圓、塑膠基板、陶瓷基板及金屬製電路基板之任1種之基板上,形成本發明相關的接著劑組成物層,並包含於其上方配置保護玻璃基板而成的層合物,可得到使用於CCD或CMOS的固體攝像裝置。尚,在此裝置之製造時,可將接著劑組成物層形成至上述矽晶圓等的基板上,再將保護玻璃基板層合至其上方,或亦可將接著劑組成物層形成至保護玻璃基板上,再將矽晶圓等的基板層合至其上方之方式來進行。
以下為表示合成例及比較合成例、實施例及
比較例來具體地說明本發明,但本發明並不限定於下述之例。尚,下述例中,Me為表示甲基,黏度為藉由旋轉黏度計所測定在25℃時之值,重量平均分子量為藉由GPC所得到的聚苯乙烯換算值。
於裝置有攪拌裝置、冷卻裝置、溫度計的1L燒瓶中,裝入水234g(13莫耳)、甲苯35g,並以油浴加熱至80℃。於滴液漏斗中裝入環己基三氯矽烷108.8g(0.5莫耳)、n-己基三氯矽烷65.9g(0.3莫耳)、二甲基二氯矽烷6.5g(0.05莫耳)、甲基乙烯基二氯矽烷7.1g(0.05莫耳)、三甲基氯矽烷10.9g(0.1莫耳),將燒瓶內邊攪拌邊進行1小時之滴下,滴下結束後,進而以80℃、1小時來進行攪拌熟成。冷卻至室溫之同時使其靜置,除去已分離的水相,接著混合10質量%硫酸鈉水溶液並攪拌10分鐘後,再靜置30分鐘,以水洗淨操作來除去已分離的水相並重複進行至甲苯相成為中性為止,之後停止反應。予以裝置酯接液管(ester adapter),加熱迴流包含有機聚矽氧烷之甲苯相,將水自甲苯相中除去,於內溫到達110℃後進一步持續1小時,然後冷卻至室溫。過濾所得到的有機聚矽氧烷溶液並除去不溶物,接著,藉由減壓蒸餾來除去甲苯,而得到固體的有機聚矽氧烷(A-I)115.2g。
所得到的有機聚矽氧烷(A-I)為包含T單位80
莫耳%、D單位10莫耳%與M單位10莫耳%,末端為每100g的有機聚矽氧烷(A-I)含有矽烷醇基0.09莫耳、乙烯基0.043莫耳。外觀為無色透明固體,重量平均分子量為7,500。全部有機基中之環己基含量為38莫耳%,n-己基含量為23莫耳%,乙烯基之含量為3.8莫耳%。又,以R1~R3所示之全部有機基中之50莫耳%為環己基,30莫耳%為n-己基,15莫耳%為甲基,5莫耳%為乙烯基。
與合成例1以相同之手法,於2L燒瓶中裝入水468g(26莫耳)、甲苯70g,並以油浴加熱至80℃。除了於滴液漏斗中裝入降莰三氯矽烷275.6g(1.2莫耳)、n-己基三氯矽烷65.8g(0.3莫耳)、二甲基二氯矽烷25.8g(0.2莫耳)、甲基乙烯基二氯矽烷14.2g(0.1莫耳)、三甲基氯矽烷21.8g(0.2莫耳)以外,與合成例1相同地調製,而得到固體的有機聚矽氧烷228.8g。
所得到的有機聚矽氧烷為包含T單位75莫耳%、D單位15莫耳%與M單位10莫耳%,每100g含有矽烷醇基0.07莫耳、乙烯基0.039莫耳。外觀為無色透明固體,重量平均分子量為9,300。全部有機基中之降莰基含量為44莫耳%,n-己基含量為11莫耳%,乙烯基之含量為3.7莫耳%。又,以R1~R3所示之全部有機基中之57莫耳%為降莰基,14莫耳%為n-己基,24莫耳%為甲基,5莫耳%為乙烯基。
作為含有烯基之有機聚矽氧烷,將以合成例2-1所得到的固態的有機聚矽氧烷100g溶解於甲苯100g中,並調製成固形物濃度50質量%之溶液。相對於樹脂以鉑原子成為20ppm之方式,將鉑系觸媒添加至此溶液中,於加溫至60℃之狀態下,作為含有氫化矽烷基之化合物,滴下以下述式(4)所示之化合物(SiH當量2,287g/mol)44.6g(此量以H/Vi比(相對於總烯基之SiH基之比率)為相當於0.5)時,觀測到反應所引起的發熱。以100℃進行2小時反應,結束反應。之後,藉由減壓餾除來濃縮,並將甲苯餾除,將反應生成物進行固形化,而得到有機聚矽氧烷(A-II)。又,將此樹脂藉由GPC來測定重量平均分子量Mw時為41,000,每100g含有乙烯基0.019莫耳。
與合成例1相同地,於1L燒瓶中裝入水234g(13莫耳)、甲苯35g,並以油浴加熱至80℃。除了於滴液漏斗中裝入降莰三氯矽烷160.7g(0.7莫耳)、n-十二烷基三氯
矽烷45.6g(0.15莫耳)、甲基乙烯基二氯矽烷7.1g(0.05莫耳)、三甲基氯矽烷10.9g(0.1莫耳)以外,與合成例1相同地調製,而得到固體的有機聚矽氧烷143.8g。
所得到的有機聚矽氧烷為包含T單位85莫耳%、D單位5莫耳%與M單位10莫耳%,每100g含有矽烷醇基0.1莫耳、乙烯基0.034莫耳。外觀為無色透明固體,重量平均分子量為6,100。全部有機基中之降莰基含量為56莫耳%,n-十二烷基含量為12莫耳%,乙烯基之含量為4.0莫耳%。又,以R1~R3所示之全部有機基中之74莫耳%為降莰基,16莫耳%為n-十二烷基,5莫耳%為甲基,5莫耳%為乙烯基。
除了作為含有烯基之有機聚矽氧烷,使用以合成例3-1所得到的固態的有機聚矽氧烷100g,作為含有氫化矽烷基之化合物,使用以下述式(5)所示之化合物(SiH當量1,547g/mol)31.6g(此量以H/Vi比為相當於0.6)以外,與合成例2-2進行相同之反應,而得到重量平均分子量46,400的有機聚矽氧烷(A-III)。此樹脂每100g含有乙烯基0.02莫耳。
與合成例1相同地,於1L燒瓶中裝入水234g(13莫耳)、甲苯35g,並以油浴加熱至80℃。除了於滴液漏斗中裝入苯基三氯矽烷137.5g(0.65莫耳)、二苯基二氯矽烷50.6g(0.2莫耳)、甲基乙烯基二氯矽烷7.1g(0.05莫耳)、三甲基氯矽烷10.8g(0.1莫耳)以外,與合成例1相同地調製,而得到固態的有機聚矽氧烷(A-IV)137g。
所得到的有機聚矽氧烷(A-IV)為包含T單位65莫耳%、D單位25莫耳%與M單位10莫耳%,末端為每100g的有機聚矽氧烷含有矽烷醇基0.01莫耳、乙烯基0.034莫耳。外觀為無色透明固體,重量平均分子量為11,700。又,以R1~R3所示之全部有機基中之92莫耳%為苯基(芳香族不飽和烴基),4莫耳%為甲基,4莫耳%為乙烯基。
與合成例1相同地,於1L燒瓶中裝入水234g(13莫耳)、甲苯35g,並以油浴加熱至80℃。除了於滴液漏斗中裝入降莰三氯矽烷91.8g(0.4莫耳)、n-己基三氯矽烷24.7g(0.15莫耳)、二甲基二氯矽烷45.2g(0.35莫耳)、甲基乙烯基二氯矽烷7.1g(0.05莫耳)、三甲基氯矽烷5.4g(0.05莫耳)以外,與合成例1相同地調製,而得到固體的有機聚矽氧烷(A-V)143.8g。
所得到的有機聚矽氧烷為包含T單位55莫耳%、D單位40莫耳%與M單位5莫耳%,每100g含有矽烷醇基0.12莫耳、乙烯基0.044莫耳。外觀為無色透明固體,重量平均分子量為10,500。全部有機基中之降莰基含量為27莫耳%,n-己基含量為10莫耳%,乙烯基為3.3莫耳%。又,以R1~R3所示之全部有機基中之30莫耳%為降莰基,11莫耳%為n-己基,55莫耳%為甲基,4莫耳%為乙烯基。
將作為(A)成分的以上述所合成的有機聚矽氧烷A-I、A-II、A-III、與比較有機聚矽氧烷A-IV、A-V作為基質,如表1所記載之組成分別調配(B)成分、(C)成分、(D)成分、(E)成分、(F)成分,之後使其攪拌、混合、溶解。特以,作為(B)成分為使用下述所表示的(B-I)、(B-II)。
又,作為(C)成分使用鉑觸媒CAT-PL-50T(信越化學工業(股)製),作為(D)成分使用乙炔基環己醇,作為(E)成分使用苯酚系抗氧化劑ADEKA STAB AO-60,作為(F)成分使用異壬烷。將該等組成物以鐵氟龍(註冊商標)製0.2μm過濾器進行精密過濾,得到實施例1~3的本發明的接著劑組成物、及比較例1、2的接著劑組成物。
使用表1之實施例1~3及比較例1、2所表示之組成物,於8吋矽晶圓上利用旋轉塗布機,以表1記載的膜厚來塗布各實施例及比較例的接著劑組成物。然後,為了除去溶劑,藉由加熱板以80℃、5分鐘來進行預烘烤。對於所得到的附有接著劑組成物之8吋矽晶圓,使用接合裝置,並以接合溫度100℃、接合前保持時間1分鐘、接合時減壓4×10-3mbar、接合壓力2kN,來進行暫時接合。更,將此暫時接合基板以150℃、5分鐘來使其熱硬化,而得到最終的接合基板。
接著,依據下述方法來實施各評估。
8吋的晶圓接合,係使用EVG公司的晶圓接合裝置
520IS來進行。接合後,以目測來確認冷卻至室溫後之界面之接著狀況,當在界面未產生氣泡等異常時,以「○」表示;當產生異常時,以「×」表示。
使用磨床(DAG810 DISCO製)來進行矽基板之背面研磨。最終將基板厚度磨至50μm,然後使用光學顯微鏡來檢查有無裂痕、剝離等異常。當未產生異常時,以「○」表示;當產生異常時,以「×」表示。
將已對矽晶圓進行背面研磨後的接合體,於空氣中下230℃、或260℃、3分鐘加熱板上加熱後,檢查有無外觀異常。當未產生外觀異常時,評估為良好,以「○」表示;當產生外觀異常(剝離)時,評估為不良,以「×」表示。
作為耐光性試驗,係進行以下所示的短期耐光性、長期耐光性試驗。關於短期耐光性,係將接著劑組成物旋轉塗布至膜厚500μm的玻璃基板,之後進行150℃、10分鐘的熱硬化,測定初期的透過率(波長400nm),接著,於空氣中下230℃、或260℃、3分鐘加熱板上加熱後,再次測定加溫後的透過率(波長400nm),求得減衰率(%)=加
溫後的透過率(波長400nm)/初期的透過率(波長400nm)×100。將減衰率90%以上評估為「○」;較90%低者評估為「×」。
關於長期耐光性,係將接著劑組成物旋轉塗布至膜厚500μm的玻璃基板,之後進行150℃、10分鐘的熱硬化,測定初期的透過率(波長400nm),接著,在模擬太陽光(將波長350nm以下截止)500萬勒克斯的照射後,再次測定透過率(波長400nm),求得減衰率(%)=照射後的透過率(波長400nm)/初期的透過率(波長400nm)×100。將減衰率90%以上評估為「○」;較90%低者評估為「×」。
將使用接著劑組成物的8吋矽晶圓基板與保護玻璃基板予以接合熱硬化後的基板,以利用背面研磨裝置,對於矽側實施初期研磨至725~100μm,測定背面研磨後的接合8吋晶圓之翹曲量。
將上述評估結果記載於表1中。
如上述表1之比較例1所示般,當使用未含有降莰基之苯基聚矽氧樹脂時,耐光性、翹曲性會惡化,比較例2之降莰基之含量為少時,翹曲性雖為良好,但耐熱性為降低。另一方面,實施例1~3皆為耐熱性、耐光性、翹曲性為優異。亦即顯示只要是本發明的接著劑組成物,則可滿足上述要求特性。
如上述般,只要是本發明的接著劑組成物,
由於在製造中無需曝光、烘烤、顯影步驟,故製造成本為低價且生產性為高,作為接著劑所要求的接著性、熱硬化後的氣密封閉性、低吸濕性等的特性為良好,耐熱性、耐光性等的硬化膜之可靠性為高,進而可抑制在三次元安裝製造為所需的背面研磨後的接著基板之翹曲。
尚,本發明並不限定於上述實施形態。上述實施形態為示例,具有與本發明的申請專利範圍中所記載的技術思想實質上相同的構成,並發揮同樣的作用效果,所有內容均包含在本發明的技術範圍內。
Claims (7)
- 一種聚矽氧接著劑組成物,其特徵係含有(A)~(C)成分而成:(A)含有非芳香族飽和一價烴基及烯基之有機聚矽氧烷;(B)一分子內含有2個以上SiH基之有機氫聚矽氧烷:相對於(A)成分中之烯基之(B)成分中之SiH基之莫耳比以成為0.5~10之量;(C)鉑系觸媒:有效量,且該(A)成分之含有非芳香族飽和一價烴基之有機聚矽氧烷為有機聚矽氧烷(A-1)或高分子量化的有機聚矽氧烷(A-2):(A-1)包含以下述(I)~(III)所示之單位之重量平均分子量2,000~60,000之有機聚矽氧烷;(A-2)將以下述一般式(1)所示之1種以上之有機氫聚矽氧烷、與該有機聚矽氧烷(A-1),以相對於上述有機聚矽氧烷(A-1)之總烯基,使上述有機氫聚矽氧烷之總SiH基成為莫耳比計0.4~0.8倍之量進行氫化矽烷化反應而成之重量平均分子量20,000~400,000之高分子量化的有機聚矽氧烷,(I)以R1SiO3/2表示之矽氧烷單位(T單位):50~99莫耳%、(II)以R2R3SiO2/2表示之矽氧烷單位(D單位):0~49莫耳%、(III)以R4 3SiO1/2表示之矽氧烷單位(M單位):1~15莫耳%(式中,R1~R3分別為一價有機基,且以R1~R3所示之全部有機基中2~10莫耳%為碳數2~7之烯基,以R1~R3所示之全部有機基中40莫耳%以上為相同或相異的碳數5~10之包含下述環狀構造之任一者之非芳香族飽和一價烴基,且10~40莫耳%為相同或相異的碳數6~15之取代或非取代之一價非環狀飽和烴基,更,殘餘部分為前述烯基、碳數5~10之環狀飽和一價烴基、碳數6~15之非環狀飽和一價烴基以外的以R1~R3所示之有機基,及R4為相同或相異的碳數1~7之取代或非取代之一價烴基),(式中,R5~R7係表示可相同或相異的烯基除外的碳數1~12之一價烴基,n為0~200之整數)。
- 如請求項1之接著劑組成物,其中,進而含有(D)反應控制劑。
- 如請求項1之接著劑組成物,其中,進而含有(E)抗氧化劑。
- 如請求項1之接著劑組成物,其中,進而含有(F)有機溶劑。
- 如請求項4之接著劑組成物,其中,前述(F)有機溶劑為沸點120~240℃之烴溶劑。
- 如請求項1~5中任一項之接著劑組成物,其中,使層合於選自矽晶圓、固體攝像元件矽晶圓、塑膠基板、陶瓷基板及金屬製電路基板之任1種之基板、與保護玻璃基板之間。
- 一種固體攝像裝置,其係包含於選自矽晶圓、固體攝像元件矽晶圓、塑膠基板、陶瓷基板及金屬製電路基板之任1種之基板上,依序層合請求項1~5中任一項之接著劑組成物之硬化物層及保護玻璃基板而成的層合物。
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CN105722939A (zh) | 2016-06-29 |
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TW201531544A (zh) | 2015-08-16 |
KR102045519B1 (ko) | 2019-11-18 |
US9796892B2 (en) | 2017-10-24 |
JP6119874B2 (ja) | 2017-04-26 |
US20160289519A1 (en) | 2016-10-06 |
WO2015072418A1 (ja) | 2015-05-21 |
EP3070137A4 (en) | 2017-06-28 |
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EP3070137B1 (en) | 2023-12-27 |
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