WO2012063822A1 - Composition de résine de silicone thermodurcissable, ainsi que structure contenant une résine de silicone et corps d'encapsulation d'un élément semiconducteur obtenus au moyen de cette composition - Google Patents
Composition de résine de silicone thermodurcissable, ainsi que structure contenant une résine de silicone et corps d'encapsulation d'un élément semiconducteur obtenus au moyen de cette composition Download PDFInfo
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- WO2012063822A1 WO2012063822A1 PCT/JP2011/075727 JP2011075727W WO2012063822A1 WO 2012063822 A1 WO2012063822 A1 WO 2012063822A1 JP 2011075727 W JP2011075727 W JP 2011075727W WO 2012063822 A1 WO2012063822 A1 WO 2012063822A1
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- WIPO (PCT)
- Prior art keywords
- group
- compound
- silicone resin
- zirconium
- mass
- Prior art date
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- 229920002050 silicone resin Polymers 0.000 title claims abstract description 73
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 51
- 239000011342 resin composition Substances 0.000 title claims abstract description 31
- 230000003287 optical effect Effects 0.000 title claims description 65
- 239000004065 semiconductor Substances 0.000 title claims description 63
- 239000008393 encapsulating agent Substances 0.000 title description 4
- -1 silane compound Chemical class 0.000 claims abstract description 116
- 229910000077 silane Inorganic materials 0.000 claims abstract description 65
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 55
- 150000003606 tin compounds Chemical class 0.000 claims abstract description 45
- 150000003752 zinc compounds Chemical class 0.000 claims abstract description 43
- 125000005372 silanol group Chemical group 0.000 claims abstract description 30
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 239000011701 zinc Substances 0.000 claims description 23
- 150000002363 hafnium compounds Chemical class 0.000 claims description 22
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 21
- 229910052709 silver Inorganic materials 0.000 claims description 21
- 239000004332 silver Substances 0.000 claims description 21
- 239000003566 sealing material Substances 0.000 claims description 19
- 150000003755 zirconium compounds Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 238000007789 sealing Methods 0.000 claims description 13
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 82
- 229910052726 zirconium Inorganic materials 0.000 description 80
- 239000000203 mixture Substances 0.000 description 61
- 150000001875 compounds Chemical class 0.000 description 48
- 150000002430 hydrocarbons Chemical group 0.000 description 40
- 229910052735 hafnium Inorganic materials 0.000 description 35
- 150000007942 carboxylates Chemical class 0.000 description 24
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical group [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 24
- 238000001723 curing Methods 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 16
- 229910052725 zinc Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 125000002723 alicyclic group Chemical group 0.000 description 13
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 13
- 125000000962 organic group Chemical group 0.000 description 13
- 238000005486 sulfidation Methods 0.000 description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 11
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229940125904 compound 1 Drugs 0.000 description 7
- 229940125782 compound 2 Drugs 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- MBMLMWLHJBBADN-UHFFFAOYSA-N Ferrous sulfide Chemical compound [Fe]=S MBMLMWLHJBBADN-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 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 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- 235000014692 zinc oxide Nutrition 0.000 description 4
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000005609 naphthenate group Chemical group 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000013500 performance material Substances 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
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- QWOVEJBDMKHZQK-UHFFFAOYSA-N 1,3,5-tris(3-trimethoxysilylpropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound CO[Si](OC)(OC)CCCN1C(=O)N(CCC[Si](OC)(OC)OC)C(=O)N(CCC[Si](OC)(OC)OC)C1=O QWOVEJBDMKHZQK-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PARCMDAOZHNXLU-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O.CCCCC(CC)C(O)=O PARCMDAOZHNXLU-UHFFFAOYSA-N 0.000 description 2
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 description 2
- VADFQXONMAETJP-UHFFFAOYSA-N 7,7-dimethyloctanoic acid zinc Chemical compound [Zn].CC(C)(C)CCCCCC(O)=O.CC(C)(C)CCCCCC(O)=O VADFQXONMAETJP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- JTRZHCXUXZWCJI-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C(=O)OOCCCC.C1(=CC=CC2=CC=CC=C12)C(=O)OOCCCC.[Zr] Chemical compound C1(=CC=CC2=CC=CC=C12)C(=O)OOCCCC.C1(=CC=CC2=CC=CC=C12)C(=O)OOCCCC.[Zr] JTRZHCXUXZWCJI-UHFFFAOYSA-N 0.000 description 2
- 229930192627 Naphthoquinone Natural products 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- KTBGHSAYBDIBHX-UHFFFAOYSA-N butyl 2-methylpropaneperoxoate;zirconium Chemical compound [Zr].CCCCOOC(=O)C(C)C.CCCCOOC(=O)C(C)C KTBGHSAYBDIBHX-UHFFFAOYSA-N 0.000 description 2
- HQGSPVKMKYMQFD-UHFFFAOYSA-N butyl 7,7-dimethyloctaneperoxoate zirconium Chemical compound [Zr].CCCCOOC(=O)CCCCCC(C)(C)C.CCCCOOC(=O)CCCCCC(C)(C)C HQGSPVKMKYMQFD-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
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- 125000002704 decyl group Chemical group [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])* 0.000 description 2
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- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
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- 125000001400 nonyl 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])[H] 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- MTBVDKSFTCGOTN-UHFFFAOYSA-N octane pentane-2,4-dione tin(4+) Chemical compound [Sn+4].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O.CCCCCCC[CH2-].CCCCCCC[CH2-] MTBVDKSFTCGOTN-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 2
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- ASBGGHMVAMBCOR-UHFFFAOYSA-N ethanolate;zirconium(4+) Chemical compound [Zr+4].CC[O-].CC[O-].CC[O-].CC[O-] ASBGGHMVAMBCOR-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
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- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
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- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- 125000005447 octyloxy group Chemical group [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])O* 0.000 description 1
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- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 description 1
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- 125000003944 tolyl group Chemical group 0.000 description 1
- IZRJPHXTEXTLHY-UHFFFAOYSA-N triethoxy(2-triethoxysilylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CC[Si](OCC)(OCC)OCC IZRJPHXTEXTLHY-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JBYXACURRYATNJ-UHFFFAOYSA-N trimethoxy(1-trimethoxysilylhexyl)silane Chemical compound CCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC JBYXACURRYATNJ-UHFFFAOYSA-N 0.000 description 1
- XLUIBHBNUCWHGE-UHFFFAOYSA-N trimethoxy(1-trimethoxysilyloctyl)silane Chemical compound CCCCCCCC([Si](OC)(OC)OC)[Si](OC)(OC)OC XLUIBHBNUCWHGE-UHFFFAOYSA-N 0.000 description 1
- JFFBPULXPLWPAA-UHFFFAOYSA-N trimethoxy(10-trimethoxysilyldecyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCCCCC[Si](OC)(OC)OC JFFBPULXPLWPAA-UHFFFAOYSA-N 0.000 description 1
- GFKCWAROGHMSTC-UHFFFAOYSA-N trimethoxy(6-trimethoxysilylhexyl)silane Chemical compound CO[Si](OC)(OC)CCCCCC[Si](OC)(OC)OC GFKCWAROGHMSTC-UHFFFAOYSA-N 0.000 description 1
- BMQGQVPUOLXPKP-UHFFFAOYSA-N trimethoxy(7-trimethoxysilylheptyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC[Si](OC)(OC)OC BMQGQVPUOLXPKP-UHFFFAOYSA-N 0.000 description 1
- MBIWXZXQMMLFAB-UHFFFAOYSA-N trimethoxy(9-trimethoxysilylnonyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCCCC[Si](OC)(OC)OC MBIWXZXQMMLFAB-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Images
Classifications
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- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
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- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
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- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
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- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
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- H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
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- H01—ELECTRIC ELEMENTS
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- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
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- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
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- H01L33/56—Materials, e.g. epoxy or silicone resin
Definitions
- the present invention relates to a thermosetting silicone resin composition, and a silicone resin-containing structure and an optical semiconductor element encapsulant obtained using the same.
- Tin compounds are widely used as moisture-curing catalysts, but silicone resin compositions containing tin compounds are inferior in stability at room temperature, such as gelation at room temperature, and inferior in thermosetting properties. It was.
- an object of the present invention is to provide a thermosetting silicone resin composition containing a tin compound that is excellent in stability at room temperature and thermosetting.
- the present inventors have found that a silicone resin composition containing a predetermined amount of a zinc compound and a tin compound in combination with a predetermined organopolysiloxane is stable at room temperature and heat. It was found that the curability was excellent, and the present invention was completed. That is, the present invention provides the following (1) to (7).
- thermosetting silicone resin composition wherein the zinc compound (D) is a zinc compound represented by the following formula (d1) or the following formula (d2).
- Zn (O—CO—R 1 ) 2 (d1) Zn (R 2 COCHCOR 3 ) 2 (d2)
- R 1 represents an alkyl group having 1 to 18 carbon atoms or an aryl group.
- R 2 and R 3 are the same or different and each represents a monovalent hydrocarbon group or alkoxy group having 1 to 18 carbon atoms.
- the organopolysiloxane (A) is composed of R 3 SiO 1/2 units (wherein each R independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) and SiO 4/2 units as repeating units, the ratio of R 3 SiO 1/2 units to 1 mol of SiO 4/2 units is 0.5 to 1.2 mol, and furthermore, to 1 mol of SiO 4/2 units, At least one of R 2 SiO 2/2 units and RSiO 3/2 units (wherein each R independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms)
- the above-mentioned including a silicone resin, which may have a unit of 1.0 mol or less and a total of each unit of 1.0 mol or less, and has a silanol group of less than 6.0% by mass) 1) or thermosetting type according to (2) Silicone resin composition.
- thermosetting silicone resin composition according to any one of (1) to (3), further comprising a zirconium compound (E) and / or a hafnium compound (F).
- thermosetting silicone resin composition according to any one of (1) to (4), further comprising a bis (alkoxy) alkane and / or an isocyanurate derivative.
- a silicone resin comprising: a member containing silver; and a silicone resin layer obtained by curing the thermosetting silicone resin composition according to any one of (1) to (5), which covers the member. Containing structure.
- thermosetting silicone resin composition containing a tin compound and having excellent stability at room temperature and thermosetting.
- thermosetting silicone resin composition of the present invention includes an organopolysiloxane (A) having a silanol group, a silane compound (B) having an alkoxysilyl group, A tin compound (C) and a zinc compound (D) are contained, and the content of the tin compound (C) is 100 parts by mass in total of the organopolysiloxane (A) and the silane compound (B).
- thermosetting silicone resin composition having a mass ratio (C / D) of the tin compound (C) to the zinc compound (D) of less than 1.
- the organopolysiloxane (A) contained in the composition of the present invention is an organopolysiloxane having one or more, preferably two or more silanol groups in one molecule.
- the hydrocarbon group of the organopolysiloxane (A) is not particularly limited, and examples thereof include aromatic groups such as phenyl groups; alkyl groups; alkenyl groups;
- the main chain of the organopolysiloxane (A) may be linear, branched, or network. Some of them may have an alkoxysilyl group having 1 to 6 carbon atoms.
- organopolysiloxane (A) examples include organopolydialkylsiloxanes in which two or more silanol groups are bonded to the terminal.
- Such an organopolysiloxane (A) is preferably an organopolydimethylsiloxane in which two silanol groups are bonded to both ends, and a straight chain in which two silanol groups are bonded to both ends. More preferred is a linear organopolydimethylsiloxane (linear organopolydimethylsiloxane- ⁇ , ⁇ -diol), and specific examples thereof include those represented by the following formula (a1).
- R 4 s are the same or different and each represents an alkyl group or aryl group having 1 to 18 carbon atoms, and n represents an integer of 1 or more.
- Examples of the alkyl group having 1 to 18 carbon atoms represented by R 4 include linear or branched groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, and a tert-butyl group.
- n can be a numerical value corresponding to the weight average molecular weight of the organopolysiloxane (A), and is preferably an integer of 10 to 15,000.
- examples of the organopolysiloxane (A) include silicone resins having a network of main chains.
- examples of such a silicone resin include, for example, R 3 SiO 1/2 units (wherein each R independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms) and SiO 4 / Examples include silicone resin A1 having 2 units as a repeating unit.
- R in R 3 SiO 1/2 unit is, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, iso-butyl group, tert-butyl group, pentyl.
- alkyl group such as hexyl group
- cycloalkyl group such as cyclopentyl group, cyclohexyl group
- alkenyl group such as vinyl group, allyl group, isopropenyl group, butenyl group, pentenyl group, hexenyl group
- aryl group such as phenyl group
- Halogenated alkyl groups such as chloromethyl group, 3-chloropropyl group, 1-chloro-2-methylpropyl group, 3,3,3-trifluoropropyl group
- a phenyl group is preferable, and a methyl group is more preferable.
- the ratio of R 3 SiO 1/2 units to 1 mol of SiO 4/2 units is 0.5 to 1.2 mol, preferably 0.65 to 1.15 mol.
- the cured product of the composition of the present invention has appropriate strength and excellent transparency.
- the silicone resin A1 has an R 2 SiO 2/2 unit and an RSiO 3/2 unit (wherein R is independently an unsubstituted or substituted carbon number of 1 to 6 with respect to 1 mol of SiO 4/2 units. At least one of each unit may be 1.0 mol or less and the total of each unit may be 1.0 mol or less, more preferably The R 2 SiO 2/2 unit and the RSiO 3/2 unit are 0.2 to 0.8 mol, and the total of the units is 1.0 mol or less. Thus, if it is a mixture ratio, the composition of this invention is excellent in transparency. Specific examples of such a blending ratio include a combination of 0.2 mol of R 2 SiO 2/2 units and 0.7 mol of RSiO 3/2 units with respect to 1 mol of SiO 4/2 units.
- the silicone resin A1 has a silanol group of less than 6.0% by mass.
- the content of silanol groups is preferably 0.1% by weight or more, and more preferably 0.2 to 3.0% by weight. When the content of the silanol group is within this range, the hardness of the cured product of the composition of the present invention is appropriate, the adhesiveness is good, and the strength is also appropriate.
- the silicone resin A1 may have an alkoxysilyl group. Examples of the resin having a silanol group and an alkoxy group include MK resin (manufactured by Asahi Kasei Wacker Silicone).
- the method for producing the silicone resin A1 is not particularly limited, and can be produced by a conventionally known method.
- the alkoxy group-containing silane compound corresponding to each unit can be substantially hydrolyzed and condensed in an organic solvent. Can be obtained as containing no volatile components.
- R 3 SiOMe and Si (OMe) 4 are co-hydrolyzed and condensed in an organic solvent together with R 2 Si (OMe) 2 and / or RSi (OMe) 3 as desired.
- each R independently represents an unsubstituted or substituted monovalent hydrocarbon group having 1 to 6 carbon atoms, and Me represents a methyl group).
- organic solvent those capable of dissolving organopolysiloxane produced by cohydrolysis / condensation reaction are preferable, and specific examples thereof include toluene, xylene, methylene chloride, naphtha mineral spirit and the like.
- Such a silicone resin A1 may be a commercially available product, such as “SR1000” manufactured by Momentive Performance Materials Japan GK.
- the molecular weight of the organopolysiloxane (A) is preferably 1,000 to 1,000,000, and more preferably 6,000 to 100,000.
- the molecular weight of the organopolysiloxane (A) is a weight average molecular weight in terms of polystyrene by gel permeation chromatography (GPC) using chloroform as a solvent.
- GPC gel permeation chromatography
- Organopolysiloxane (A) may be used individually by 1 type, and may use 2 or more types together.
- the composition of the present invention contains a silane compound (B) from the viewpoint of thermosetting.
- the silane compound (B) contained in the composition of the present invention has one or more, preferably two or more alkoxysilyl groups in one molecule.
- the alkoxysilyl group means an alkoxy group bonded directly to a silicon atom.
- silane compound (B) component for example, a compound having one silicon atom in one molecule and having two or more alkoxy groups bonded to the silicon atom (hereinafter also referred to as “silane compound B1”); Organopolysiloxane having two or more silicon atoms in one molecule, the skeleton being a polysiloxane skeleton, and having two or more alkoxy groups bonded to the silicon atom (hereinafter also referred to as “silane compound B2”); Etc.
- the silane compound (B) may have one or more organic groups in one molecule, and may include, for example, at least one heteroatom selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.
- Specific examples include an alkyl group (preferably having 1 to 6 carbon atoms), a (meth) acrylate group, an alkenyl group, an aryl group, and combinations thereof.
- Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group.
- Examples of the alkenyl group include vinyl group, allyl group, propenyl group, isopropenyl group, 2-methyl-1-propenyl group, 2-methylallyl group and the like.
- Examples of the aryl group include a phenyl group and a naphthyl group. Of these, a methyl group, a (meth) acrylate group, and a (meth) acryloxy
- Silane compound B1 As silane compound B1, what is represented by a following formula (b1) is mentioned, for example. Si (OR 5 ) n R 6 4-n (b1) In the formula (b1), n represents 2, 3 or 4, R 5 represents an alkyl group, and R 6 represents an organic group. The organic group represented by R 6 has the same meaning as described as the organic group that the silane compound (B) can have.
- silane compound B1 examples include dialkoxysilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane, diethyldimethoxysilane, diethyldiethoxysilane, diphenyldimethoxysilane, and diphenyldiethoxysilane; methyltrimethoxysilane, methyltriethoxysilane, Trialkoxysilanes such as ethyltrimethoxysilane, ethyltriethoxysilane, phenyltrimethoxysilane, and phenyltriethoxysilane; tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, and tetraisopropyloxysilane; ⁇ - (meth) acryloxy (Meth) acryloxyalkyltrialkoxysilanes such as propyltrimethoxysilane and
- (meth) acryloxytrialkoxysilane means acryloxytrialkoxysilane or methacryloxytrialkoxysilane. The same applies to (meth) acrylate groups and (meth) acryloxyalkyl groups.
- silane compound B2 examples include compounds represented by the following formula (b2-1).
- R 7 is an organic group
- R 8 is hydrogen and / or an alkyl group
- m is 0 ⁇ m ⁇ 2
- n is 0 ⁇ n ⁇ 2
- m + n is 0 ⁇ m + n ⁇ 3.
- the organic group represented by R 7 has the same meaning as that described as the organic group that the silane compound (B) can have
- the alkyl group represented by R 8 can have the silane compound (B). It is synonymous with what was described as an alkyl group as an organic group.
- Examples of the silane compound B2 include silicone alkoxy oligomers such as methyl methoxy oligomer.
- the silicone alkoxy oligomer is a silicone resin having a main chain of polyorganosiloxane and a molecular terminal blocked with an alkoxysilyl group.
- the methylmethoxy oligomer corresponds to a compound represented by the formula (b2-1), and specific examples thereof include those represented by the following formula (b2-2).
- R 9 represents a methyl group
- a represents an integer of 1 to 100
- b represents an integer of 0 to 100.
- a commercially available product can be used, and examples thereof include x-40-9246 (weight average molecular weight: 6000, manufactured by Shin-Etsu Chemical Co., Ltd.).
- silane compound B3 a compound having at least one alkoxysilyl group at one end and having three or more alkoxy groups (derived from an alkoxysilyl group) in one molecule (hereinafter referred to as “silane compound B3”). Also called).
- Silane compound B3 can be obtained, for example, as a reaction product obtained by dealcoholization condensation of 1 mol or more of a silane compound having an alkoxylyl group with respect to 1 mol of polysiloxane having a silanol group at both ends.
- Examples of the silane compound having an alkoxy group used for producing the silane compound B3 include the compound represented by the formula (b1) and the compound represented by the formula (b2-1) described above. It is done.
- Examples of the silane compound B3 include those represented by the following formula (b3).
- n can be a numerical value corresponding to the molecular weight of the silane compound B3.
- the compound represented by the formula (b3) can be produced, for example, by modifying a polysiloxane having silanol groups at both ends with tetramethoxysilane (corresponding to the compound represented by the formula (b1)). it can.
- silane compound (B) those represented by the formula (b1) and those represented by the formula ((b2-1)) are preferable.
- Tetraalkoxysilane such as tetraethoxysilane; ⁇ - (meth) acryloxy
- (meth) acryloxyalkyltrialkoxysilanes such as propyltrimethoxysilane; methylmethoxy oligomers.
- the silane compound (B) is preferably a (meth) acryl-functional (meth) acryloxyalkyltrialkoxysilane.
- the molecular weight of the silane compound (B) is preferably 100 to 1,000,000, and more preferably 1000 to 100,000.
- the molecular weight shall be the weight average molecular weight of polystyrene conversion by the gel permeation chromatography (GPC) which uses chloroform as a solvent.
- a silane compound (B) may be used individually by 1 main, and may use 2 or more types together.
- the amount of the silane compound (B) is preferably 0.5 to 2000 parts by mass and more preferably 10 to 2000 parts by mass with respect to 100 parts by mass of the organopolysiloxane (A).
- the composition of the present invention contains a tin compound (C).
- the “tin compound” refers to a compound containing tin (Sn).
- the content of the tin compound (C) is 0.001 to 1 part by mass with respect to 100 parts by mass in total of the organopolysiloxane (A) and the silane compound (B), and the composition of the present invention at room temperature.
- the amount is preferably 0.001 to 0.5 parts by mass, more preferably 0.01 to 0.1 parts by mass, because thickening is suppressed and the stability at room temperature is excellent.
- the tin compound (C) is not particularly limited as long as it is a “tin compound”, and examples thereof include a divalent tin compound, a tetravalent tin compound, and the like. Preferably it is a compound.
- divalent tin compound examples include divalent tin carboxylates such as bis (2-ethylhexanoic acid) tin, di (n-octylic acid) tin, tin dinaphthenate, and tin distearate.
- divalent tin carboxylates such as bis (2-ethylhexanoic acid) tin, di (n-octylic acid) tin, tin dinaphthenate, and tin distearate.
- Examples of the tetravalent tin compound include those represented by the formula (c1); bis type and polymer type represented by the formula (c1); and the like.
- R 10 represents an alkyl group
- R 11 represents a hydrocarbon group
- a represents an integer of 1 to 3.
- Examples of the alkyl group represented by R 10 include those having 1 or more carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and an octyl group.
- the hydrocarbon group represented by R 11 is not particularly limited, and may be linear or branched, may have an unsaturated bond, oxygen atom, nitrogen atom, sulfur atom, etc. And, for example, an aliphatic hydrocarbon group such as a methyl group or an ethyl group; an alicyclic hydrocarbon group; an aromatic hydrocarbon group; a combination thereof;
- Examples of the screw type represented by the formula (c1) include those represented by the following formula (c2).
- R 10, R 11 has the same meaning as R 10, R 11 in the formula (c1), a is 1 or 2.
- tetravalent tin compounds include dimethyltin diacetate, dimethyltin bis (acetylacetonate), dibutyltin dilaurate, dibutyltin maleate, dibutyltin phthalate, dibutyltin dioctanoate, dibutyltin bis (2-ethylhexanoate) ), Dibutyltin bis (methyl maleate), dibutyltin bis (ethyl maleate), dibutyltin bis (butyl maleate), dibutyltin bis (octyl maleate), dibutyltin bis (tridecyl maleate), dibutyltin bis (benzyl maleate) , Dibutyltin diacetate, dioctyltin bis (ethyl maleate), dioctyltin bis (octyl maleate), dibutyltin dimethoxide, dibutyltin bis (
- dioctyltin-based ones are preferable.
- dioctyltin bis (acetylacetonate), a reaction product of dioctyltin salt and normal ethyl silicate, etc. are industrially available. is there.
- a tin compound (C) may be used individually by 1 type, and may use 2 or more types together. It does not specifically limit about the manufacturing method of a tin compound (C), For example, it can manufacture by a conventionally well-known method.
- the composition of the present invention contains the zinc compound (D) in combination with the tin compound (C) to delay the moisture curability by the tin compound (C).
- the content of the zinc compound (D) is larger than the content of the tin compound (C). That is, in the present invention, the value of the mass ratio (C / D) of the tin compound (C) to the zinc compound (D) is less than 1. Thereby, the composition of this invention is suppressed in the viscosity at room temperature, and is excellent in stability at room temperature.
- the value of the mass ratio (C / D) of the tin compound (C) to the zinc compound (D) is less than 1 and 0.01 or more because the composition of the present invention is more stable at room temperature. Is preferably 0.1 or less and more preferably 0.01 or more.
- the content of the zinc compound (D) is 0.01 to 5 parts by mass with respect to 100 parts by mass in total of the organopolysiloxane (A) and the silane compound (B).
- the composition of this invention is excellent also in thermosetting.
- the content of the zinc compound (D) is 0.01 to 5 parts by mass with respect to 100 parts by mass in total of the organopolysiloxane (A) and the silane compound (B). It is preferably 0.1 to 1 part by mass.
- the composition of this invention is excellent also in sulfidation resistance by containing a zinc compound (D).
- the zinc compound (D) is a corrosive gas in the air (for example, a gas having an unshared electron pair such as hydrogen sulfide and amines).
- a gas having an unshared electron pair such as hydrogen sulfide and amines.
- corrosion for example, discoloration
- the zinc compound (D) contained in the composition of the present invention is not particularly limited as long as it is a compound containing zinc.
- zinc salt such as zinc phosphate; zinc complex; zinc alcoholate; zinc white, zinc stannate Zinc oxides; and the like.
- a zinc salt and / or a zinc complex is preferable from the viewpoint of superior sulfidation resistance and transparency.
- the zinc salt is not particularly limited as long as it is a salt formed from zinc and an acid (including an inorganic acid and an organic acid).
- the zinc complex is not particularly limited as long as it is a chelate compound formed from zinc and a ligand.
- a zinc compound (D) does not contain a benzimidazole salt substantially from a heat resistant coloring viewpoint.
- the zinc compound (D) include compounds represented by the following formula (d1) or (d2); a zinc complex of a salicylic acid compound; a zinc complex of a diamine compound;
- R 1 represents an alkyl group having 1 to 18 carbon atoms or an aryl group.
- CO is a carbonyl group (C ⁇ O).
- Examples of the alkyl group having 1 to 18 carbon atoms represented by R 1 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a 1-ethylpentyl group, and a neononyl group. And a neodecyl group.
- Examples of the aryl group having 1 to 18 carbon atoms represented by R 1 include a phenyl group and a naphthyl group.
- examples of the zinc salt include those represented by the following formula (d1 ′).
- R 1 has the same meaning as R 1 in the formula (d1).
- Examples of the zinc compound (D) represented by the formula (d1) include zinc acetate, zinc 2-ethylhexanoate, zinc octoate, zinc neodecanate, zinc acetyl acetate, zinc (meth) acrylate, and zinc salicylate. It is done.
- Formula (d2) is as follows. Zn (R 2 COCHCOR 3 ) 2 (d2)
- R 2 and R 3 are the same or different and each represents a monovalent hydrocarbon group or alkoxy group having 1 to 18 carbon atoms.
- (R 2 COCHCOR 3 ) is any one of the following formulas, and is bonded to zinc by “C—O—”.
- examples of the zinc complex include those represented by the following formula (d2 ′).
- R 2, R 3 has the same meaning as R 2, R 3 in the formula (d2), R 2, R 3, which are in the same (R 2 COCHCOR 3) is interchanged May be.
- Examples of the monovalent hydrocarbon group having 1 to 18 carbon atoms represented by R 2 and R 3 in formula (d2) include, for example, an alkyl group or aryl group having 1 to 18 carbon atoms (R 1 in formula (d1) And the same meaning as an alkyl group or aryl group having 1 to 18 carbon atoms.
- Examples of the alkoxy group represented by R 2 and R 3 in the formula (d2) include a methoxy group, an ethoxy group, and a propoxy group.
- Examples of the zinc compound (D) represented by the formula (d2) include bis (acetylacetonato) zinc complex, 2,2,6,6,6 tetramethyl-3,5-heptanedionate zinc complex, and the like. Can be mentioned.
- the zinc compound (D) is preferably a compound represented by the formula (d1) or the formula (d2), or a combination thereof, because it is more excellent in thermosetting and more resistant to sulfide.
- the zinc compound (D) may be used alone or in combination of two or more.
- an acid is used in an amount of 1. per mol of at least one selected from the group consisting of zinc oxide, zinc carbonate, zinc hydroxide, zinc chloride, zinc sulfate and zinc nitrate. What is obtained by making it react 5 mol or more and less than 3 mol can be used.
- the acid used in this case is not particularly limited.
- inorganic acids such as phosphoric acid
- organic acids such as stearic acid, palmitic acid, lauric acid, 2-ethylhexanoic acid, (meth) acrylic acid, and neodecanoic acid; These esters; etc. are mentioned.
- the composition of the present invention may further contain a zirconium compound (E) and / or a hafnium compound (F). These are condensation catalysts and at the same time improve the long-term reliability of the composition of the present invention at high temperatures.
- the zirconium compound (E) and / or the hafnium compound (F) acts as a Lewis acid during the initial curing or after the initial curing of the composition of the present invention, and the organopolysiloxane (A) and the silane compound (B). It is thought that the crosslinking reaction with is promoted.
- the zirconium compound (E) and / or the hafnium compound (F) is activated by heating, and a silanol group (for example, a reaction between silanol groups or a reaction between a silanol group and an alkoxysilyl group) Can be condensed.
- a silanol group for example, a reaction between silanol groups or a reaction between a silanol group and an alkoxysilyl group
- the composition of the present invention is cured uniformly uniformly by heating.
- the content of the zirconium compound (E) and / or the hafnium compound (F) is such that the long-term reliability of the composition of the present invention at a high temperature is superior, so that the organopolysiloxane (A) and the silane compound (B)
- the total amount is preferably 0.001 to 1 part by mass, more preferably 0.01 to 0.5 part by mass, and 0.001 to 0.05 part by mass. Further preferred. Below, a zirconium compound (E) and a hafnium compound (F) are demonstrated separately.
- the zirconium compound (E) is not particularly limited as long as it has a zirconium atom and an organic group.
- the organic group possessed by zirconium is, for example, an organic carboxylate (—O—CO—R); an alkoxy group, a phenoxy group or the like in which a hydrocarbon group is bonded to an oxy group (—O—R).
- examples of the zirconium compound (E) include a compound represented by the following formula (e1) (compound E1), a compound represented by the following formula (e1 ′) (compound E1 ′), and the following formula:
- the compound (compound E2) etc. which are represented by (e2) are mentioned, These can be used conveniently.
- R 12 represents a hydrocarbon group having 1 to 18 carbon atoms.
- R ′ represents a monovalent hydrocarbon group having 1 to 18 carbon atoms
- R ′′ represents a monovalent hydrocarbon group or acyl group having 1 to 18 carbon atoms
- n is , Represents an integer of 0 to 2.
- R 13 is the same or different and represents a hydrocarbon group having 1 to 16 carbon atoms
- R 14 is the same or different and represents a hydrocarbon group having 1 to 18 carbon atoms
- m is 1 to 3 carbon atoms. Indicates an integer.
- Compound E1 is a zirconium metal salt containing zirconyl [(Zr ⁇ O) 2+ ] as a constituent element.
- the composition of this invention is more excellent in thermosetting by containing the compound E1.
- the acid used for producing the zirconium metal salt of compound E1 is not particularly limited, and examples thereof include carboxylic acid. Specific examples of carboxylic acid include acetic acid, propionic acid, octylic acid (2-ethyl ester).
- Hexanoic acid nonanoic acid, stearic acid, lauric acid and the like; alicyclic carboxylic acids such as naphthenic acid and cyclohexanecarboxylic acid; aromatic carboxylic acids such as benzoic acid; and the like.
- aliphatic carboxylate include zirconyl dioctylate and zirconyl dineodecanoate.
- alicyclic carboxylate include zirconyl naphthenate and zirconyl cyclohexane.
- the aromatic carboxylate include zirconyl benzoate. Among these, it is preferable that it is either one or both of zirconyl dioctylate and zirconyl naphthenate because it is more excellent in thermosetting.
- compound E1 ′ is a zirconyl complex containing zirconyl [(Zr ⁇ O) 2+ ] as a constituent element, and the composition of the present invention is more excellent in thermosetting property by containing compound E1 ′.
- the monovalent hydrocarbon group having 1 to 18 carbon atoms represented by R ′ and R ′′ in the above formula (e1 ′) include, for example, an alkyl group or aryl group having 1 to 18 carbon atoms (the above formula (d1) And the same meaning as the alkyl group or aryl group having 1 to 18 carbon atoms represented by R 1 therein.
- zirconyl complex represented by the above formula (e1 ′) examples include acetylacetonitrile-2-ethylhexanoyl-zirconyl, in which R represents a methyl group, R ′ represents an acyl group, and n represents 1.
- the compound E2 has 1 to 3 acyl groups (R 13 —CO—) as represented by the above formula (e2).
- the acyl group is included in the formula (e2) as a carboxylic acid ester.
- the plurality of R 13 may be the same or different.
- the plurality of R 13 may be the same or different.
- the hydrocarbon group represented by R 13 in the formula (e2) preferably has 3 to 16 carbon atoms, and more preferably 4 to 16 carbon atoms.
- the hydrocarbon group represented by R 13 may be linear or branched, may have an unsaturated bond, and may have a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.).
- Examples of the hydrocarbon group represented by R 13 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and combinations thereof.
- Examples of the alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group; naphthene ring (cycloparaffin ring derived from naphthenic acid); adamantyl A condensed ring hydrocarbon group such as a group or a norbornyl group;
- Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and azulene.
- Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, and an undecyl group.
- an alicyclic hydrocarbon group and an aromatic hydrocarbon group are preferable, and a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a naphthene ring (naphthate group as R 13 COO—), a phenyl group are more preferable, and a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, and a naphthene ring are more preferable.
- R 13 COO— having an alicyclic hydrocarbon group examples include a cyclopropylcarbonyloxy group, a cyclobutylcarbonyloxy group, a cyclopentylcarbonyloxy group, a cyclohexylcarbonyloxy group (cyclohexyl carbonate group), and a cycloheptylcarbonyloxy group.
- R 13 COO— having an aromatic hydrocarbon group include a phenylcarbonyloxy group, a naphthylcarbonyloxy group, an azulylcarboxy group, and the like.
- R 13 COO— having an aliphatic hydrocarbon group examples include acetate, propionate, butyrate, isobutyrate, octylate, 2-ethylhexanoate, nonanoate and laurate.
- R 13 COO- having an alicyclic hydrocarbon group R 13 COO- having an aromatic hydrocarbon group, 2-ethyl hexanoate are preferred, cyclopropylcarbonyl group, cyclopentylcarbonyl group, cyclohexylcarbonyl
- An oxy group, an adamantylcarbonyloxy group, a naphthate group, and a phenylcarbonyloxy group are more preferable, and a cyclopropylcarbonyloxy group, a cyclopentylcarbonyloxy group, a cyclohexylcarbonyloxy group, an adamantylcarbonyloxy group, and a naphthate group are more preferable.
- the number of carbon atoms of the hydrocarbon group represented by R 14 in formula (e2) is preferably 3 to 8.
- the hydrocarbon group represented by R 14 may be linear or branched, may have an unsaturated bond, and may have a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.).
- Examples of the hydrocarbon group represented by R 14 include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and combinations thereof.
- R 14 O— (alkoxy group) having an aliphatic hydrocarbon group examples include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, and an octyloxy group.
- R 14 O— (alkoxy group) having an aliphatic hydrocarbon group is preferably a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, or an isopropoxy group.
- Examples of the compound E2 having an alicyclic hydrocarbon group include zirconium alkoxycyclopropanecarboxylates such as zirconium trialkoxymonocyclopropanecarboxylate, zirconium dialkoxydicyclopropanecarboxylate, and zirconium monoalkoxytricyclopropanecarboxylate; Zirconium alkoxycyclopentane carboxylates such as zirconium trialkoxy monocyclopentane carboxylate, zirconium dialkoxy dicyclopentane carboxylate, zirconium monoalkoxy tricyclopentane carboxylate; zirconium tributoxy monocyclohexane carboxylate, zirconium dibutoxy dicyclohexane carboxylate , Zirconium mono Zirconium alkoxycyclohexanecarboxylates such as toxitricyclohexanecarboxylate, zirconium triisopropoxymonocyclohe
- Examples of the compound E2 having an aromatic hydrocarbon group include zirconium tributoxy monobenzene carboxylate, zirconium dibutoxy dibenzene carboxylate, zirconium monobutoxy tribenzene carboxylate, zirconium triisopropoxy monobenzene carboxylate, zirconium diiso Zirconium alkoxybenzene carboxylates such as propoxydibenzenecarboxylate and zirconium monoisopropoxytribenzenecarboxylate are listed.
- Examples of the compound E2 having an aliphatic hydrocarbon group include zirconium tributoxy monoisobutyrate, zirconium dibutoxy diisobutyrate, zirconium monobutoxy triisobutyrate, zirconium triisopropoxy monoisobutyrate, zirconium diisopropoxy.
- Zirconium alkoxybutyrate such as diisobutyrate, zirconium monoisopropoxytriisobutyrate; zirconium tributoxy mono-2-ethylhexanoate, zirconium dibutoxydi-2-ethylhexanoate, zirconium monobutoxytri-2-ethylhexanoate, zirconium Triisopropoxymono-2-ethylhexanoate, zirconium diisopropoxydi-2-ethylhexanoate, zirconium monoisopropoxytri-2 Zirconium alkoxy 2-ethylhexanoates such as tilhexanoate; zirconium tributoxy mononeodecanate, zirconium dibutoxy dineodecanate, zirconium monobutoxy trineodecanate, zirconium triisopropoxy mononeodecanate, zirconium diiso And zirconium
- the compound E2 having an alicyclic hydrocarbon group and the compound E2 having an aromatic hydrocarbon group are preferable, and zirconium trialkoxy mononaphthate, zirconium trialkoxy monoisobutyrate, zirconium trialkoxy mono 2-ethylhexano , Zirconium trialkoxy monocyclopropane carboxylate, zirconium trialkoxy cyclobutane carboxylate, zirconium trialkoxy monocyclopentane carboxylate, zirconium trialkoxy monocyclohexane carboxylate, zirconium trialkoxy monoadamantane carboxylate, zirconium trialkoxy mononaphthate More preferably, zirconium tributoxy mononaphthate, zirconium tributoxy monoi Butyrate, zirconium tributoxy mono-2-ethylhexanoate, zirconium tributoxy monocyclopropane carboxylate, zir
- the compound E2 is preferably an alkoxy group-containing zirconium metal salt having 1 to 3 acyl groups (ester bonds).
- alkoxy group-containing zirconium metal salt having 1 to 3 acyl groups include zirconium tributoxy mononaphthate, zirconium tributoxy monoisobutyrate, zirconium tributoxy mono 2-ethylhexanoate, zirconium tributoxy mononeo.
- Decanate zirconium dibutoxy dinaphthate, zirconium dibutoxy diisobutyrate, zirconium dibutoxy di-2-ethylhexanoate, zirconium dibutoxy dineodecanate, zirconium monobutoxy trinaphthate, zirconium monobutoxy triisobutyrate, Zirconium monobutoxytri-2-ethylhexanoate, zirconium monobutoxytrineodecanate, among others, zirconium tributoxymononaphthate, zirconium Um tributoxy monoisobutyrate, and it is preferably zirconium tributoxy least one selected from the group consisting of mono-2-ethylhexanoate.
- Zr (OR 14 ) 4 examples include zirconium tetramethoxide, zirconium tetraethoxide, zirconium tetranormal propoxide, zirconium tetraisopropoxide, zirconium tetranormal butoxide and the like.
- Examples of the carboxylic acid that can be used to produce the compound E2 include aliphatic carboxylic acids such as acetic acid, propionic acid, isobutanoic acid, octylic acid, 2-ethylhexanoic acid, nonanoic acid, and lauric acid; naphthenic acid, cyclopropane And alicyclic carboxylic acids such as carboxylic acid, cyclopentanecarboxylic acid, cyclohexylcarboxylic acid (cyclohexanecarboxylic acid), adamantanecarboxylic acid and norbornanecarboxylic acid; aromatic carboxylic acids such as benzoic acid; and the like.
- aliphatic carboxylic acids such as acetic acid, propionic acid, isobutanoic acid, octylic acid, 2-ethylhexanoic acid, nonanoic acid, and lauric acid
- naphthenic acid cyclopropan
- hafnium compound (F) Next, the hafnium compound (F) will be described.
- the hafnium compound (F) is not particularly limited as long as it is a compound having a hafnium atom and an organic group.
- the hafnium compound (F) is represented by the following formula (f1) because the long-term reliability at high temperatures of the composition of the present invention is more excellent.
- f2 a compound represented by the following formula (f2).
- n represents an integer of 1 to 4
- R 15 represents a hydrocarbon group
- R 16 represents an alkyl group having 1 to 18 carbon atoms.
- m represents an integer of 1 to 4
- R 16 represents an alkyl group having 1 to 18 carbon atoms
- R 17 and R 18 are the same or different and represent a hydrocarbon group having 1 to 18 carbon atoms or An alkoxy group is shown.
- the hydrocarbon group represented by R 15 in the formula (f1) may be linear or branched, may have an unsaturated bond, and has a hetero atom (for example, an oxygen atom, a nitrogen atom, a sulfur atom, etc.). be able to.
- Examples of the hydrocarbon group represented by R 15 include aliphatic hydrocarbon groups having 1 to 18 carbon atoms (including alkyl groups; unsaturated aliphatic hydrocarbon groups such as allyl groups; etc.), and alicyclic hydrocarbon groups. , Aryl groups (aromatic hydrocarbon groups), combinations thereof and the like.
- Examples of the aliphatic hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, and an undecyl group.
- Examples of the alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group; naphthene ring (cycloparaffin ring derived from naphthenic acid); adamantyl A condensed ring hydrocarbon group such as a group or a norbornyl group;
- Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and azulene.
- an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a combination thereof is preferable, and a cyclopropyl group, a cyclobutyl group, a cyclopentyl group , A cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a naphthene ring, an adamantyl group, a norbornyl group, a phenyl group, a naphthyl group and an azulene, more preferably at least one selected from the group consisting of a cyclopropyl group and a cyclopentyl group , A cyclohexyl group, an adamantyl group, a naphthene ring (naphthate group as R 15 COO—) and a phenyl group are more preferable, and a
- the number of carbon atoms of the alkyl group represented by R 16 in the formula (f1) is 1 to 18, and it is preferably 3 to 8 for the reason that it is excellent in thermosetting and excellent in resistance to sulfidation.
- Examples of the alkyl group represented by R 16 include a methyl group, an ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group, a pentyl group, a hexyl group, an octyl group, and the like.
- An ethyl group, a propyl group (n-propyl group, isopropyl group), a butyl group, and a pentyl group are preferable.
- hafnium compound (F) represented by the formula (f1) having an alicyclic hydrocarbon group as the hydrocarbon group represented by R 15 include, for example, hafnium alkoxy (mono-tri) cyclopropanecarboxylate.
- Hafnium tetracyclopropane carboxylate hafnium alkoxy (mono-tri) cyclopentane carboxylate, hafnium tetracyclopentane carboxylate, hafnium alkoxy (mono-tri) cyclohexane carboxylate, hafnium tetracyclohexane carboxylate, hafnium alkoxy (mono-tri) )
- hafnium compound (F) represented by the formula (f1) having an aromatic hydrocarbon group as the hydrocarbon group represented by R 15 include, for example, hafnium alkoxy (mono-tri) benzene carboxylate, hafnium And tetrabenzenecarboxylate.
- hafnium compound (F) represented by the formula (f1) having an aliphatic hydrocarbon group as the hydrocarbon group represented by R 15 include, for example, hafnium alkoxy (mono-tri) butyrate, hafnium tetrabutyrate. Rate, hafnium alkoxy (mono-tri) 2-ethyl hexanoate, hafnium tetra 2-ethyl hexanoate, hafnium alkoxy (mono-tri) neodecanate, hafnium tetraneodecanate, and the like.
- (mono to tri) means any one of mono, di and tri.
- hafnium trialkoxy mononaphthate hafnium trialkoxy monoisobutyrate, hafnium trialkoxy mono-2-ethylhexanoate, hafnium trialkoxy monocyclopropane are used because they are superior in thermosetting and sulfidation resistance.
- R 16 in the formula (f2) has the same meaning as R 16 in the formula (f1).
- the hydrocarbon group having 1 to 18 carbon atoms represented by R 17 and R 18 in formula (f2) is the same as the hydrocarbon group represented by R 15 in formula (f1) having 1 to 18 carbon atoms. It is.
- Examples of the alkoxy group represented by R 17 and R 18 in the formula (f2) include an alkoxy group having 1 to 18 carbon atoms such as a methoxy group, an ethoxy group, and a propoxy group.
- R 17 and R 18 in the formula (f2) may have a halogen such as a chlorine atom, a bromine atom, or a fluorine atom. In the formula (f2), R 17 and R 18 may be interchanged.
- hafnium compound (F) represented by the formula (f2) examples include, for example, hafnium alkoxide (mono to tri) 2,4-pentadionate, hafnium-2,4-pentadionate, and hafnium alkyl pentadionate.
- hafnium di-n-butoxide (bis-2,4-pentadionate), hafnium-2,4-pentadionate, hafnium tetramethylpentadionate, hafnium tri Preferably it is a fluoropentadionate.
- the composition of the present invention may further contain an additive as necessary within the range not impairing the object and effects of the present invention.
- the additives include fillers such as inorganic fillers, antioxidants, lubricants, ultraviolet absorbers, thermal light stabilizers, dispersants, antistatic agents, polymerization inhibitors, antifoaming agents, curing accelerators, solvents, Fluorescent substances (inorganic substances, organic substances), anti-aging agents, radical inhibitors, adhesion improvers, flame retardants, surfactants, storage stability improvers, ozone anti-aging agents, thickeners, plasticizers, radiation blockers, Examples include nucleating agents, coupling agents, conductivity imparting agents, phosphorus peroxide decomposing agents, pigments, metal deactivators, physical property modifiers, adhesion imparting agents, and adhesion assistants.
- Examples of the fluorescent substance include a YAG phosphor, a ZnS phosphor, a Y 2 O 2 S phosphor, a red light emitting phosphor, a blue light emitting phosphor, and a green light emitting phosphor.
- adhesion-imparting agent or adhesion assistant examples include known epoxy silane coupling agents such as epoxy silane and epoxy silane oligomer; bis (alkoxy) alkanes; isocyanurate derivatives; ) Alkane and / or isocyanurate derivatives are preferred.
- Examples of the bis (alkoxy) alkane include 1,2-bis (triethoxysilyl) ethane, 1,6-bis (trimethoxysilyl) hexane, 1,7-bis (trimethoxysilyl) heptane, 1,8- It is preferably at least one selected from the group consisting of bis (trimethoxysilyl) octane, 1,9-bis (trimethoxysilyl) nonane and 1,10-bis (trimethoxysilyl) decane.
- Bis (trimethoxysilyl) hexane is more preferred. It is preferable that the isocyanurate derivative is represented by the following formula.
- each R independently represents a monovalent hydrocarbon group having an organic group or an aliphatic unsaturated bond, and a substituent such as an epoxy group, a glycidoxy group, an alkoxysilyl group, or a (meth) acryloyl group. You may have.
- the organic group represented by R in the above formula is not particularly limited, and examples thereof include alkyl groups such as methyl, ethyl, propyl, and butyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups.
- Aralkyl groups such as benzyl group and phenethyl group; cycloalkyl groups such as cyclopentyl group and cyclohexyl group; alkyl halide groups;
- the monovalent hydrocarbon group having an aliphatic unsaturated bond represented by R in the above formula is not particularly limited, and examples thereof include a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, and a heptenyl group.
- Examples of the isocyanurate derivative represented by the above formula include tris- (3-trimethoxysilylpropyl) isocyanurate.
- attachment imparting agents or adhesion assistant when using bis (alkoxy) alkane, it is 0.1 with respect to a total of 100 mass parts of organopolysiloxane (A) and silane compound (B) mentioned above.
- the amount is preferably 5 parts by mass.
- an isocyanurate derivative when used, it is preferably 0.1 to 10 parts by mass with respect to 100 parts by mass in total of the above-described organopolysiloxane (A) and silane compound (B), and preferably 0.1 to 5 parts by mass. More preferred is part by mass.
- the composition of the present invention preferably contains substantially no water for the reason of excellent storage stability.
- substantially free of water means that the amount of water in the composition of the present invention is 0.1% by mass or less.
- the composition of this invention does not contain a solvent substantially from the reason that it is excellent in working environment property.
- substantially free of solvent means that the amount of the solvent in the composition of the present invention is 1% by mass or less.
- the production method of the composition of the present invention is not particularly limited, and for example, the above-described organopolysiloxane (A), silane compound (B), tin compound (C), zinc compound (D), and as desired.
- the method of manufacturing by mixing a zirconium compound (E) and / or a hafnium compound (F) and an additive as needed is mentioned.
- the composition of the present invention can be produced as a one-pack type or a two-pack type.
- the composition of this invention can be used as a sealing material (for example, for optical semiconductor elements), for example.
- a sealing material for example, for optical semiconductor elements
- an optical semiconductor element which can use the composition of this invention as a sealing material a light emitting diode (LED), an organic electroluminescent element (organic EL), a laser diode, an LED array etc. are mentioned, for example.
- the LED include a high power LED, a high luminance LED, and a general luminance LED.
- the composition of the present invention can be used for applications such as display materials, optical recording medium materials, optical equipment materials, optical component materials, optical fiber materials, optical / electronic functional organic materials, and semiconductor integrated circuit peripheral materials. .
- Examples of the adherend of the composition of the present invention include metals (eg, Group 11 metals), glass, rubber, semiconductors (eg, optical semiconductor elements), resins such as polyphthalamide, and the like.
- the Group 11 metal is preferably at least one selected from the group consisting of copper, silver and gold.
- the composition of the present invention is preferably used in the presence of a silver-containing member because it is more excellent in transparency and sulfidation resistance.
- the silicone resin layer obtained from the composition of the present invention can be adhered to an adherend.
- the usage method provided with the hardening process which hardens the composition of this invention in presence of the member containing silver, for example is mentioned.
- the said usage method is demonstrated as a usage method (henceforth "the usage method of this invention") of the composition of this invention.
- Examples of the member containing silver used in the method of use of the present invention include silver and silver plating, and specific examples include a reflector and the like.
- the curing step may be a step of curing the composition of the present invention by heating and / or light irradiation.
- the temperature for heating the composition of the present invention is preferably around 80 ° C. to 150 ° C., more preferably around 150 ° C.
- light used when light irradiating the composition of this invention an ultraviolet-ray, an electron beam etc. are mentioned, for example.
- the silicone resin-containing structure of the present invention includes a member containing silver and a silicone resin layer obtained by curing the composition of the present invention that covers the member.
- the said silicone resin layer may cover the said member directly, and may cover it through another layer (for example, a resin layer, a glass layer, an air layer).
- the silicone resin-containing structure of the present invention preferably has an optical semiconductor element. It does not specifically limit as an optical semiconductor element, For example, what was illustrated as an optical semiconductor element which can use the composition of this invention as a sealing material is mentioned.
- the silicone resin-containing structure of the present invention has an optical semiconductor element, for example, an aspect in which the silicone resin layer covers the member via the optical semiconductor element (that is, the optical semiconductor element is the silicone resin layer). And the above-mentioned member); an embodiment in which the above-mentioned silicone resin layer directly covers the optical semiconductor element and the above-mentioned member arranged in parallel;
- the optical semiconductor element may be arrange
- FIG. 1 is a cross-sectional view schematically showing an example of a laminate as the silicone resin-containing structure of the present invention.
- the laminated body 100 is provided with the member 120 containing silver.
- a silicone resin layer 102 is directly disposed on the member 120.
- FIG. 2 is a cross-sectional view schematically showing another example of a laminate as the silicone resin-containing structure of the present invention.
- the stacked body 200 includes a member 220 containing silver.
- the optical semiconductor element 203 is directly disposed on the member 220, and the silicone resin layer 202 is directly disposed on the optical semiconductor element 203.
- a transparent layer for example, a resin layer, a glass layer, an air layer, etc. (not shown) may be disposed between the silicone resin layer 202 and the optical semiconductor element 203.
- the sealed optical semiconductor element of the present invention includes a frame having a recess, an optical semiconductor element disposed at the bottom of the recess, a member including silver disposed on the inner surface of the recess, and filling the recess. And a sealing material obtained by curing the composition of the present invention, which seals the optical semiconductor element and the member. It does not specifically limit as a member containing silver, For example, what was illustrated as a member containing silver used for the usage method of this invention is mentioned. Moreover, it does not specifically limit as an optical semiconductor element, For example, what was illustrated as an optical semiconductor element which can use the composition of this invention as a sealing material is mentioned.
- the sealed optical semiconductor element of the present invention can have one or two or more of the above optical semiconductor elements per one.
- FIG. 3 is a cross-sectional view schematically showing an example of the sealed optical semiconductor element of the present invention.
- the optical semiconductor element sealing body 300 includes a frame 304 having a recess 302.
- the bottom surface of the recess 302 is open. Therefore, the frame body 304 is formed with end portions (end portion 312 and end portion 314) so as to surround the opening.
- a substrate 310 having an external electrode 309 is disposed below the frame body 304.
- the substrate 310 forms the bottom of the recess 302.
- An optical semiconductor element 303 is disposed at the bottom of the recess 302.
- the optical semiconductor element 303 is disposed in the concave portion 302 so that the upper surface is a light emitting layer (not shown).
- the lower surface of the optical semiconductor element 303 is fixed by the mount member 301.
- the mount member 301 is, for example, silver paste, resin, or the like.
- Each electrode (not shown) of the optical semiconductor element 303 and the external electrode 309 are wire bonded by a conductive wire 307.
- a reflector 320 is disposed as a member containing silver.
- the concave portion 302 is filled with a sealing material 308, and the sealing material 308 seals the optical semiconductor element 303 and the reflector 320.
- the sealing material 308 is obtained by curing the composition of the present invention.
- the sealing material 308 may be filled up to the hatched portion 306 in the recess 302. Further, the portion indicated by 308 in the recess 302 may be another transparent layer, and the sealing material 308 may be disposed only in the hatched portion 306.
- Such a sealing material 308 can contain a fluorescent material or the like.
- the end part (end part 312 and end part 314) of the frame body 304 may be integrally coupled to form the bottom part of the recess 302.
- the reflector 320 is disposed not only on the inner surface of the recess 302 but also on the bottom of the recess 302.
- the optical semiconductor element 303 is disposed on the reflector 320 disposed at the bottom of the recess 302.
- the encapsulating material 308 obtained by curing the composition of the present invention is used in such an optical semiconductor element encapsulant 300, corrosion (for example, discoloration) of the reflector 320, which is a member containing silver, is used. ) Can be suppressed. Further, since the sealing material 308 filled in the recess 302 has low hardness and small curing shrinkage, it can be prevented from being peeled off from the recess 302 due to the curing shrinkage or the conductive wire 307 being disconnected.
- FIG. 4 is a cross-sectional view schematically showing another example of the sealed optical semiconductor element of the present invention.
- a sealed optical semiconductor element 400 shown in FIG. 4 is obtained by arranging a lens 401 on the sealed optical semiconductor element 300 shown in FIG.
- the lens 401 a lens formed using the composition of the present invention can be used.
- FIG. 5 is a cross-sectional view schematically showing still another example of the sealed optical semiconductor element of the present invention.
- a substrate 510 and inner leads 505 are arranged inside a resin 506 having a lamp function.
- the substrate 510 has a frame having a recess, an optical semiconductor element 503 is disposed at the bottom of the recess, and a reflector 520 is disposed on the inner surface of the recess, and the composition of the present invention is cured in the recess.
- a sealing material 502 obtained in this manner is disposed.
- the reflector 520 may be disposed at the bottom of this recess.
- the optical semiconductor element 503 is fixed on the substrate 510 with a mount member 501.
- Each electrode (not shown) of the optical semiconductor element 503 is wire-bonded by a conductive wire 507.
- the resin 506 may be formed using the composition of the present invention.
- FIG. 6 is a schematic view showing an example of an LED display using the composition of the present invention and / or the sealed optical semiconductor element of the present invention.
- An LED display 600 shown in FIG. 6 includes a housing 604 in which a light shielding member 605 is disposed.
- a plurality of optical semiconductor element sealing bodies 601 are arranged in a matrix in the housing 604.
- the optical semiconductor element sealing body 601 is sealed with a sealing material 606.
- the sealing material 606 a sealing material obtained by curing the composition of the present invention can be used.
- the optical semiconductor element sealing body 601 the optical semiconductor element sealing body of this invention can be used.
- silicone resin-containing structure of the present invention and the sealed optical semiconductor element of the present invention examples include automobile lamps (for example, headlamps, tail lamps, directional lamps, etc.), household lighting equipment, and industrial use. Illuminating fixtures, stage lighting fixtures, displays, signals, projectors, and the like.
- thermosetting silicone resin composition ⁇ Manufacture of thermosetting silicone resin composition>
- the components shown in Table 1 below were used in the amounts shown in the same table (unit: parts by mass), and these were uniformly mixed with a vacuum stirrer to produce a thermosetting silicone resin composition.
- the amount of component (C) indicates the amount relative to the total amount (100 parts by mass) when the total amount of component (A) and component (B) is 100 parts by mass. Yes.
- thermosetting silicone resin composition produced by mixing the components shown in Table 1 below was placed under conditions of 55% RH and 23 ° C. and allowed to elapse for 24 hours.
- the composition that did not gel within 24 hours was further cured under the condition of 150 ° C., and JIS-A hardness after 8 hours and JIS-A hardness after 168 hours (“saturation”). Hardness ”), and an increase in hardness (points) after 168 hours with respect to 8 hours elapsed was determined.
- the gel does not gel and the hardness rise exceeds 65% of the saturation hardness, it is evaluated as “ ⁇ ” as being excellent in stability and thermosetting at room temperature.
- thermosetting silicone resin composition If it is 50 to 65%, it is evaluated as “ ⁇ ” as being somewhat inferior in thermosetting, and when the increase in hardness is less than 50% with respect to the saturation hardness, or a thermosetting silicone resin composition When the JIS-A hardness could not be measured, it was evaluated as “x” as being inferior in thermosetting property or stability at room temperature.
- ⁇ Transparency> A cured product (thickness: 2 mm) obtained by curing the obtained thermosetting silicone resin composition at 150 ° C. for 12 hours, in accordance with JIS K0115: 2004, an ultraviolet / visible absorption spectrum measuring device ( Shimadzu Corporation) was used to measure the transmittance (%) at a wavelength of 400 nm. If the transmittance (%) is 80% or more, it can be evaluated as having excellent transparency.
- thermosetting silicone resin composition was applied on silver plating so as to have a thickness of about 1 mm and cured under conditions of 150 ° C. and 3 hours to obtain a cured sample for evaluation of sulfidation resistance.
- Organopolysiloxane 1 Polydimethylsiloxane- ⁇ , ⁇ -diol represented by the following formula (ss10, Shin-Etsu Chemical Co., Ltd., weight average molecular weight: 49000, reactive functional group: silanol group, average number of functional groups: 2)
- Organopolysiloxane 2 Silanol dimethyl silicone oil at both ends (PRX-413, manufactured by Toray Dow Corning, weight average molecular weight: 4000, reactive functional group: silanol group, average number of functional groups: 2)
- Organopolysiloxane 3 Silicone resin (SR1000, manufactured by Momentive Performance Materials Japan GK, weight average molecular weight: 4000, reactive functional group: silanol group)
- Organopolysiloxane 4 Hydrolysis condensate of methylphenyldichlorosilane having a silanol group and a phenyl group (weight average molecular weight: 870, reactive functional group: silanol group)
- Silane compound 1 Trimethoxysilylsiloxane at both ends produced as follows (weight average molecular weight: 55000, reactive functional group: methoxysilyl group, average functional group number: 6) A 500 mL three-necked flask is equipped with a stirrer and a reflux condenser, and 100 parts by mass of polysiloxane having silanol groups at both ends (ss10, manufactured by Shin-Etsu Chemical Co., Ltd.), 10 parts by mass of tetramethoxysilane, and 0 parts of acetic acid. .1 part by mass was added, and the mixture was reacted at 100 ° C. for 6 hours in a nitrogen atmosphere. The disappearance of silanol groups of ss10 was confirmed by 1 H-NMR analysis, and the resulting reaction product was designated as silane compound 1.
- the main structure of the silane compound 1 is represented by the following formula.
- Silane compound 2 terminal polymethoxysilylsiloxane produced as follows (weight average molecular weight: 60000, reactive functional group: methoxysilyl group, average number of functional groups: 14)
- a 500 mL three-necked flask is equipped with a stirrer and a reflux condenser, 100 parts by mass of a polysiloxane having silanol groups at both ends (ss10, manufactured by Shin-Etsu Chemical Co., Ltd.), a partial hydrolyzate of methyltrimethoxysilane (KC) -89, manufactured by Shin-Etsu Chemical Co., Ltd.) and 10 parts by mass of acetic acid and 0.1 part by mass of acetic acid were added and reacted at 140 ° C. for 15 hours in a nitrogen atmosphere, and disappearance of silanol groups possessed by ss10 by 1 H-NMR analysis
- the reaction product thus obtained was designated as Silane Compound 2.
- Silane compound 3 Silicone alkoxy oligomer (x-40-9246, manufactured by Shin-Etsu Chemical Co., Ltd., weight average molecular weight: 6000, reactive functional group: alkoxysilyl group, average functional group number: 0 ⁇ n ⁇ 2)
- Silane compound 4 methyl alkoxy resin type silicone oligomer containing 14% by mass of methoxy group (XR31-B2733, manufactured by Momentive Performance Materials Japan GK, weight average molecular weight: 20000, reactive functional group: Alkoxysilyl group)
- Silane compound 5 Silicone alkoxy oligomer having an alkoxysilyl group and a phenyl group and no silanol group (KR480, manufactured by Shin-Etsu Chemical Co., Ltd., reactive functional group: alkoxysilyl group)
- Tin compound 1 Dibutyltin diacetate (U-200, manufactured by Nitto Kasei Co., Ltd.)
- Tin compound 2 Reaction product of dioctyltin salt and normal ethyl silicate (Si (OC 2 H 5 ) 4 ) (s-1, manufactured by Nitto Kasei Co., Ltd.)
- Tin compound 3 bis (2-ethylhexanoic acid) tin (Neostan U-28, manufactured by Nitto Kasei Co., Ltd.)
- Zinc compound 1 bis (2-ethylhexanoic acid) zinc (Octope Zn, manufactured by Hope Pharmaceutical Co., Ltd.)
- Zinc compound 2 bis (neodecanoic acid) zinc produced as follows: 2 mol of neodecanoic acid is added to 1 mol of zinc oxide (manufactured by Kanto Chemical Co., Inc.) and stirred at room temperature, and a transparent uniform liquid (bis ( Neodecanoic
- Zirconium compound 1 Zirconyl naphthenate (Nippon Chemical Industry Co., Ltd.)
- Zirconium compound 2 zirconium tributoxy mononaphthate produced as follows: 11.4 g (0.026 mol) of zirconium tetrabutoxide having a concentration of 87.5% by mass (manufactured by Kanto Chemical Co., Ltd.) and naphthenic acid (manufactured by Tokyo Chemical Industry Co., Ltd., carboxy 6.6 g (0.026 mol) of the average number of carbon atoms of the hydrocarbon group bonded to the group: 15, neutralization value 220 mg, and so on.) was put into a three-necked flask and stirred at room temperature for about 2 hours under a nitrogen atmosphere The target compound was obtained.
- the neutralization value of naphthenic acid is the amount of KOH required to neutralize 1 g of naphthenic acid.
- the qualitative properties of the synthesized product were analyzed using a Fourier transform infrared spectrophotometer (FT-IR). As a result, absorption near 1700 cm ⁇ 1 attributed to COOH derived from carboxylic acid disappeared after the reaction, and a peak derived from COOZr near 1450 to 1560 cm ⁇ 1 was confirmed.
- the resultant composite is designated as zirconium compound 2.
- the average number of carbon atoms of R in the naphthate group (RCOO—) of the zirconium compound 2 is 15.
- Hafnium compound 1 Hafnium tributoxy mononaphthate produced as follows: 47 g (0.01 mol) of hafnium tetrabutoxide (manufactured by Gelest) having a concentration of 45% by mass and naphthenic acid (manufactured by Tokyo Chemical Industry, bound to a carboxy group) Average number of carbon atoms of hydrocarbon group to be: 15, neutralization value 220 mg, where the neutralization value of naphthenic acid is the amount of KOH necessary to neutralize 1 g of naphthenic acid.) 2.55 g (0 .01 mol) was added to a three-necked flask and stirred for about 2 hours at room temperature under a nitrogen atmosphere to obtain the target compound.
- the qualitative properties of the synthesized product were analyzed using a Fourier transform infrared spectrophotometer (FT-IR). As a result, absorption near 1700 cm ⁇ 1 attributed to COOH derived from carboxylic acid disappeared after the reaction, and a peak derived from COOH f near 1,450 to 1,560 cm ⁇ 1 was confirmed.
- the resultant composite is referred to as hafnium compound 1.
- the average number of carbon atoms of R in the naphthate group (RCOO—) of the hafnium compound 1 is 15.
- Titanium compound Titanium isopropoxybis (acetylacetonate) (trade name: TC-100, manufactured by Matsumoto Trading Co., Ltd.)
- Aluminum compound ethyl acetoacetate aluminum diisopropoxide (trade name: ALCH, manufactured by Kawaken Fine Chemicals)
- Epoxy compound Epoxy silane oligomer (trade name: x-41-1053, manufactured by Shin-Etsu Chemical Co., Ltd.)
- Bisalkoxyalkane Bistrimethoxysilylhexane (trade name: Z6830, manufactured by Toray Dow Corning)
- Isocyanurate derivative Tris- (3-trimethoxysilylpropyl) isocyanurate (trade name: x-12-965, manufactured by Shin-Etsu Chemical Co., Ltd.)
- each of Examples 1 to 12 is excellent in both stability at room temperature and thermosetting property, and also in transparency and sulfidation resistance. I understood. In more detail, even if only one of the tin compound and the zinc compound is contained, the stability at room temperature and the thermosetting property are not excellent (Comparative Examples 1 to 5, 9 to 13). As a result, it was found that the thermosetting property was excellent (Examples 1 to 12). Note that Comparative Examples 6 to 8 in which the value of the mass ratio (C / D) of the tin compound to the zinc compound was 1 or more gelled and were inferior in stability at room temperature.
- Comparative Example 9 in which a titanium compound was used in combination with a tin compound and Comparative Example 10 in which an aluminum compound was used in combination with a tin compound were gelled and had poor stability at room temperature.
- the composition of the present invention is excellent in stability at room temperature, the pot life can be set with a sufficient length, and is excellent in the balance between stability at room temperature and thermosetting.
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Abstract
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CN201180054196.7A CN103210041B (zh) | 2010-11-10 | 2011-11-08 | 热固化型有机硅树脂组合物、以及使用该组合物而得的含有有机硅树脂的结构体和光半导体元件密封体 |
KR1020137006541A KR101332171B1 (ko) | 2010-11-10 | 2011-11-08 | 열경화형 실리콘 수지 조성물, 및, 이것을 이용하여 얻어지는 실리콘 수지 함유 구조체 및 광반도체 소자 봉지체 |
JP2012505525A JP5045861B2 (ja) | 2010-11-10 | 2011-11-08 | 熱硬化型シリコーン樹脂組成物、ならびに、これを用いて得られるシリコーン樹脂含有構造体および光半導体素子封止体 |
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PCT/JP2011/075727 WO2012063822A1 (fr) | 2010-11-10 | 2011-11-08 | Composition de résine de silicone thermodurcissable, ainsi que structure contenant une résine de silicone et corps d'encapsulation d'un élément semiconducteur obtenus au moyen de cette composition |
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JP (1) | JP5045861B2 (fr) |
KR (1) | KR101332171B1 (fr) |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015016000A1 (fr) * | 2013-08-01 | 2015-02-05 | 株式会社ダイセル | Composition de résine durcissable et dispositif semi-conducteur produit à partir de celle-ci |
WO2015016001A1 (fr) * | 2013-08-02 | 2015-02-05 | 株式会社ダイセル | Composition de résine durcissable et dispositif à semi-conducteur l'utilisant |
WO2015019767A1 (fr) * | 2013-08-06 | 2015-02-12 | 株式会社ダイセル | Composition de résine durcissable et dispositif à semi-conducteur l'employant |
JP2018032692A (ja) * | 2016-08-23 | 2018-03-01 | パナソニックIpマネジメント株式会社 | 発光装置、及び、照明装置 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2014119907A1 (fr) * | 2013-01-31 | 2014-08-07 | Kolon Industries, Inc. | Résine de silicone et son procédé de préparation |
CN111072712A (zh) * | 2019-12-23 | 2020-04-28 | 东莞市贝特利新材料有限公司 | 一种有机硅增粘剂及其制备方法和高透明自粘性加成型有机硅橡胶组合物 |
CN113337245B (zh) * | 2021-07-26 | 2022-03-25 | 深圳市希顺有机硅科技有限公司 | 一种脱醇型光伏组件密封胶及其制备方法 |
CN115627120B (zh) * | 2022-10-26 | 2023-06-16 | 深圳市华思电子科技有限公司 | 一种单组份无溶剂加成型有机硅三防涂料 |
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- 2011-11-08 CN CN201180054196.7A patent/CN103210041B/zh not_active Expired - Fee Related
- 2011-11-08 WO PCT/JP2011/075727 patent/WO2012063822A1/fr active Application Filing
- 2011-11-08 JP JP2012505525A patent/JP5045861B2/ja not_active Expired - Fee Related
- 2011-11-08 KR KR1020137006541A patent/KR101332171B1/ko active IP Right Grant
- 2011-11-10 TW TW100141042A patent/TWI540183B/zh not_active IP Right Cessation
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2015016000A1 (fr) * | 2013-08-01 | 2015-02-05 | 株式会社ダイセル | Composition de résine durcissable et dispositif semi-conducteur produit à partir de celle-ci |
JP5736524B1 (ja) * | 2013-08-01 | 2015-06-17 | 株式会社ダイセル | 硬化性樹脂組成物及びそれを用いた半導体装置 |
WO2015016001A1 (fr) * | 2013-08-02 | 2015-02-05 | 株式会社ダイセル | Composition de résine durcissable et dispositif à semi-conducteur l'utilisant |
JP5736525B1 (ja) * | 2013-08-02 | 2015-06-17 | 株式会社ダイセル | 硬化性樹脂組成物及びそれを用いた半導体装置 |
WO2015019767A1 (fr) * | 2013-08-06 | 2015-02-12 | 株式会社ダイセル | Composition de résine durcissable et dispositif à semi-conducteur l'employant |
JP5830201B2 (ja) * | 2013-08-06 | 2015-12-09 | 株式会社ダイセル | 硬化性樹脂組成物及びそれを用いた半導体装置 |
JP2018032692A (ja) * | 2016-08-23 | 2018-03-01 | パナソニックIpマネジメント株式会社 | 発光装置、及び、照明装置 |
Also Published As
Publication number | Publication date |
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CN103210041B (zh) | 2014-06-11 |
TW201237105A (en) | 2012-09-16 |
JP5045861B2 (ja) | 2012-10-10 |
KR20130034666A (ko) | 2013-04-05 |
CN103210041A (zh) | 2013-07-17 |
KR101332171B1 (ko) | 2013-11-25 |
TWI540183B (zh) | 2016-07-01 |
JPWO2012063822A1 (ja) | 2014-05-12 |
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