JP2012111875A - 硬化性樹脂組成物及び硬化物 - Google Patents
硬化性樹脂組成物及び硬化物 Download PDFInfo
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- JP2012111875A JP2012111875A JP2010262919A JP2010262919A JP2012111875A JP 2012111875 A JP2012111875 A JP 2012111875A JP 2010262919 A JP2010262919 A JP 2010262919A JP 2010262919 A JP2010262919 A JP 2010262919A JP 2012111875 A JP2012111875 A JP 2012111875A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 59
- -1 polysiloxane Polymers 0.000 claims abstract description 139
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 45
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 27
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims description 16
- 230000003287 optical effect Effects 0.000 claims description 14
- 239000004065 semiconductor Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- 238000007789 sealing Methods 0.000 claims description 4
- 238000004383 yellowing Methods 0.000 abstract description 31
- 230000000704 physical effect Effects 0.000 abstract description 18
- 239000000047 product Substances 0.000 description 32
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 26
- 229910000077 silane Inorganic materials 0.000 description 26
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 25
- 150000004756 silanes Chemical class 0.000 description 23
- 229910052697 platinum Inorganic materials 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 15
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
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- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 229910002808 Si–O–Si Inorganic materials 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000005108 alkenylthio group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 4
- 125000005110 aryl thio group Chemical group 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 229910052703 rhodium Inorganic materials 0.000 description 4
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 4
- 229920002050 silicone resin Polymers 0.000 description 4
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
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- 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- ZBKZYHAMFAHZHX-UHFFFAOYSA-N but-3-enylsilane Chemical class [SiH3]CCC=C ZBKZYHAMFAHZHX-UHFFFAOYSA-N 0.000 description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 3
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- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- 229910052763 palladium Inorganic materials 0.000 description 3
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 2
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
- UCBVELLBUAKUNE-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)NC(=O)N(CC=C)C1=O UCBVELLBUAKUNE-UHFFFAOYSA-N 0.000 description 2
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- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 2
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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- RPSYTLHUQVECJJ-UHFFFAOYSA-N 2-chloroethyl(phenyl)silane Chemical compound ClCC[SiH2]C1=CC=CC=C1 RPSYTLHUQVECJJ-UHFFFAOYSA-N 0.000 description 2
- 125000006024 2-pentenyl group Chemical group 0.000 description 2
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- ILBWBNOBGCYGSU-UHFFFAOYSA-N [[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C ILBWBNOBGCYGSU-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
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- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 2
- PKXQRNZSCSZWQK-UHFFFAOYSA-N ethoxy-ethyl-phenylsilane Chemical compound CCO[SiH](CC)C1=CC=CC=C1 PKXQRNZSCSZWQK-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- 125000005394 methallyl group Chemical group 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
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- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 1
- FEIZMBLMTCAJSQ-UHFFFAOYSA-N ethoxy-dimethyl-prop-2-enylsilane Chemical compound CCO[Si](C)(C)CC=C FEIZMBLMTCAJSQ-UHFFFAOYSA-N 0.000 description 1
- PVPZVPJEQJLKLJ-UHFFFAOYSA-N ethoxy-ethyl-methylsilane Chemical compound CCO[SiH](C)CC PVPZVPJEQJLKLJ-UHFFFAOYSA-N 0.000 description 1
- CFGLBBNDCFSONI-UHFFFAOYSA-N ethoxymethyl(phenyl)silane Chemical compound C(C)OC[SiH2]C1=CC=CC=C1 CFGLBBNDCFSONI-UHFFFAOYSA-N 0.000 description 1
- PRJZPAJSRRGSNS-UHFFFAOYSA-N ethyl-methoxy-methylsilane Chemical compound CC[SiH](C)OC PRJZPAJSRRGSNS-UHFFFAOYSA-N 0.000 description 1
- XFRASVKMWKOGAU-UHFFFAOYSA-N ethyl-methoxy-phenylsilane Chemical compound CC[SiH](OC)c1ccccc1 XFRASVKMWKOGAU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 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 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VJOOEHFQQLYDJI-UHFFFAOYSA-N methoxy(dimethyl)silane Chemical compound CO[SiH](C)C VJOOEHFQQLYDJI-UHFFFAOYSA-N 0.000 description 1
- RSRCJPGCPWEIHN-UHFFFAOYSA-N methoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[SiH](OC)C1=CC=CC=C1 RSRCJPGCPWEIHN-UHFFFAOYSA-N 0.000 description 1
- GXZZVJSQHUMLNV-UHFFFAOYSA-N methoxy-methyl-phenylsilane Chemical compound CO[SiH](C)C1=CC=CC=C1 GXZZVJSQHUMLNV-UHFFFAOYSA-N 0.000 description 1
- ZKFHZTZYWXIDJJ-UHFFFAOYSA-N methyl(silyloxysilyloxysilyloxy)silane Chemical compound C[SiH2]O[SiH2]O[SiH2]O[SiH3] ZKFHZTZYWXIDJJ-UHFFFAOYSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- DJFBJKSMACBYBD-UHFFFAOYSA-N phosphane;hydrate Chemical group O.P DJFBJKSMACBYBD-UHFFFAOYSA-N 0.000 description 1
- PKELYQZIUROQSI-UHFFFAOYSA-N phosphane;platinum Chemical class P.[Pt] PKELYQZIUROQSI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920006294 polydialkylsiloxane Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
【解決手段】本発明の硬化性樹脂組成物は、互いに反応してヒドロシリル化により炭素−ケイ素結合を形成可能なラダー型シルセスキオキサン(A)及び分子量100〜9000の直鎖ポリシロキサン(B)と、ヒドロシリル化触媒(C)とを含むことを特徴とする。本発明の硬化性樹脂組成物は、さらに、前記ラダー型シルセスキオキサン(A)及び/又は直鎖ポリシロキサン(B)と反応してヒドロシリル化により炭素−ケイ素結合を形成可能なイソシアヌル酸化合物(D)を含んでいてもよい。
【選択図】なし
Description
本発明の他の目的は、硬化後に、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性が得られる光半導体用封止剤を提供することにある。
また、本発明の他の目的は、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性を有する硬化物を提供することにある。
また、本発明の他の目的は、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性を有するLEDを提供することにある。
本発明のさらに他の目的は、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の諸物性に優れた光半導体装置を提供することにある。
本発明の硬化性樹脂組成物は、さらに、上記ラダー型シルセスキオキサン(A)及び/又は直鎖ポリシロキサン(B)と反応してヒドロシリル化により炭素−ケイ素結合を形成可能なイソシアヌル酸化合物(D)を含んでいてもよい。
本発明の硬化性樹脂組成物は、互いに反応してヒドロシリル化により炭素−ケイ素結合を形成可能なラダー型シルセスキオキサン(A)及び分子量100〜9000の直鎖ポリシロキサン(B)と、ヒドロシリル化触媒(C)とを含んでいる。互いに反応してヒドロシリル化により炭素−ケイ素結合を形成可能なラダー型シルセスキオキサン(A)及び分子量100〜9000の直鎖ポリシロキサン(B)としては、分子内に脂肪族炭素−炭素二重結合を有するラダー型シルセスキオキサン(以下、ビニル型ラダーシルセスキオキサンと称する)と分子内にSi−H結合を有する直鎖ポリシロキサン(以下、Si−H型直鎖ポリシロキサンと称する)との組み合わせ、又は、分子内にSi−H結合を有するラダー型シルセスキオキサン(以下、Si−H型ラダーシルセスキオキサンと称する)と分子内に脂肪族炭素−炭素二重結合を有する直鎖ポリシロキサン(以下、ビニル型直鎖ポリシロキサンと称する)との組み合わせが挙げられる。
一般に、ラダー型シルセスキオキサンは、架橋された三次元構造を有するポリシロキサンである。ポリシロキサンは、シロキサン結合(Si−O−Si)で構成された主鎖を有する化合物であり、その基本構成単位は、下記式(M)、(D)、(T)、(Q)(以下、それぞれM単位、D単位、T単位、Q単位という)に分類される。
で表される加水分解性シラン化合物の1種又は2種以上を、又は前記式(1)で表される加水分解性シラン化合物の1種又は2種以上と下記式(3)若しくは(3′)
で表されるシラン化合物の1種又は2種以上とを、加水分解・縮合反応(ゾルゲル反応)に付すことにより得ることができる。
ビニル型ラダーシルセスキオキサンとしては、前記ラダー型シルセスキオキサンのうち、末端又は側鎖に脂肪族炭素−炭素二重結合を有する基を持つ化合物であれば特に限定されず、例えば、前記式(L)で表されるラダー型シルセスキオキサンにおいて、末端のRの少なくとも1つ及び/又は側鎖のRの少なくとも1つが脂肪族炭素−炭素二重結合を有する基である化合物が挙げられる。
で表されるシラン化合物(S1)の1種又は2種以上とを反応させることにより製造できる。
Si−H型ラダーシルセスキオキサンとしては、前記ラダー型シルセスキオキサンのうち、末端又は側鎖にSi−H結合を有するものであれば特に限定されず、例えば、前記式(L)で表されるラダー型シルセスキオキサンにおいて、末端のRの少なくとも1つ及び/又は側鎖のRの少なくとも1つが水素原子又はSi−H結合を有する基である化合物が挙げられる。Si−H結合を有する基としては、例えば、前記式(1)で表される基において、3つのRのうち少なくとも1つが水素原子である基などが挙げられる。
で表される1種又は2種以上のシラン化合物(S2)とを反応させることにより製造できる。
本発明の硬化性樹脂組成物に含まれる分子量100〜9000の直鎖ポリシロキサン(B)は、シロキサン結合(Si−O−Si)で構成された主鎖を有する分子量100〜9000の直鎖状シロキサン化合物であって、分子内に脂肪族炭素−炭素二重結合を有する直鎖ポリシロキサン(ビニル型直鎖ポリシロキサン)と、分子内にSi−H結合を有する直鎖ポリシロキサン(Si−H型直鎖ポリシロキサン)が挙げられる。
本発明の硬化性樹脂組成物に含まれるヒドロシリル化触媒(C)としては、白金系触媒、ロジウム系触媒、パラジウム系触媒等の周知のヒドロシリル化反応用触媒が例示される。具体的には、白金微粉末、白金黒、白金担持シリカ微粉末、白金担持活性炭、塩化白金酸、塩化白金酸とアルコール、アルデヒド、ケトン等との錯体、白金のオレフィン錯体、白金−カルボニルビニルメチル錯体などの白金のカルボニル錯体、白金−ジビニルテトラメチルジシロキサン錯体や白金−シクロビニルメチルシロキサン錯体などの白金ビニルメチルシロキサン錯体、白金−ホスフィン錯体、白金−ホスファイト錯体等の白金系触媒、ならびに上記白金系触媒において白金原子の代わりにパラジウム原子又はロジウム原子を含有するパラジウム系触媒又はロジウム系触媒が挙げられる。これらは1種で用いてもよく、2種以上を併用してもよい。なかでも、白金ビニルメチルシロキサン錯体が、反応速度が良好であることから好ましい。
本発明の硬化性樹脂組成物は、上記ラダー型シルセスキオキサン(A)及び/又は直鎖ポリシロキサン(B)と反応してヒドロシリル化により炭素−ケイ素結合を形成可能なイソシアヌル酸化合物(D)を含んでいても良い。このようなイソシアヌル酸化合物(D)としては、分子内に脂肪族炭素−炭素二重結合を有するイソシアヌル酸化合物が挙げられ、具体的には、ジアリルイソシアヌル酸;トリアリルイソシアヌル酸;及び、ジアリルメチルイソシアヌル酸、ジアリルエチルイソシアヌル酸、ジアリルメチルイソシアヌル酸などのジアリルC1-10アルキルイソシアヌル酸等のアリル基含有イソシアヌル酸が挙げられる。イソシアヌル酸化合物(D)は1種で用いてもよく、2種以上を併用してもよい。なかでも、ジアリルイソシアヌル酸及びジアリルC1-10アルキルイソシアヌル酸が好ましい。
本発明の封止剤は、上記硬化性樹脂組成物を含んでいる。本発明の封止剤は、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れ、光半導体素子等の封止剤として好適に使用できる。
本発明の硬化性樹脂組成物は、上記ヒドロシリル化触媒(C)を使用したヒドロシリル化反応により硬化できる。ヒドロシリル化反応の条件は特に限定されず、上記触媒を使用して従来公知の条件で行なえばよいが、脱泡を効率よく行い、さらに表面の凹凸を低減するために40〜100℃[好ましくは、60〜100℃]でプリベークを1〜5時間行い、100〜180℃[好ましくは、120〜150℃]で3時間〜10時間程度硬化を行なうのが好ましい。得られた硬化物は、Tj=180℃通電試験を行っても、透明性が変わらずさらにクラックも入らず、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れている。また、水蒸気バリア性も、従来のジメチルシリコーン樹脂と比較して約1/3と優れている。
本発明のLEDは、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れた上記硬化物によって封止されているため、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れている。また、本発明の光半導体装置は、前記の、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れたLEDを含むため、高温耐熱性、柔軟性、透明性、耐熱黄変性、耐光黄変性等の物性に優れている。
300ml四つ口フラスコに、ラダー型末端エトキシ基フェニルメチルシルセスキオキサン(重量平均分子量はMw2200、1分子当たりのエトキシ基の含有重量は1.5wt%、フェニル/メチル(モル比)=1/1)10gと、10重量%水酸化テトラメチルアンモニウム3.0g、メチルイソブチルケトン200g、ジメチルエトキシビニルシラン5.5gを仕込んだ。45℃で1時間加熱し、反応終了とした。酢酸エチル100gを加えた後に、500gの水で、5回水洗浄を行った。洗浄後の上層をエバポレータで濃縮した後に真空ポンプで30分減圧に引いた。得量7.8gで、液体のラダー型ビニルフェニルメチルシルセスキオキサン(ビニル型ラダーシルセスキオキサンに相当する化合物)が得られた。重量平均分子量はMw1700、1分子当たりのビニル基の含有量(平均)は4.6wt%であった。
[ラダー型ビニルフェニルメチルシルセスキオキサンの1H−NMRスペクトル]
1H−NMR(CDCl3)δ: 0.1( br), 5.4-6.2( br), 6.8-7.8( br)
合成例1で得られたラダー型ビニルフェニルメチルシルセスキオキサン6.00gとジアリルメチルイソシアヌル酸0.30g(四国化成製)と1,1,3,3,5,5−ヘキサメチルトリシロキサン1.41g(Gelest製)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を3μL仕込み、再度攪拌し、硬化性樹脂組成物1を得た。
得られた硬化性樹脂組成物1をガラスプレートに塗布し、オーブン中、60℃で1時間、150℃で5時間加熱すると無色透明な硬化物1が得られた。硬化物1の物性を表1に、光線透過率を図1に示した。
合成例1で得られたラダー型ビニルフェニルメチルシルセスキオキサン0.60gとジアリルメチルイソシアヌル酸0.030g(四国化成製)と1,1,3,3,5,5,7,7−オクタメチルテトラシロキサン0.14g(fluorochem製)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を0.6μL仕込み、再度攪拌し、硬化性樹脂組成物2を得た。
得られた硬化性樹脂組成物2をガラスプレートに塗布し、オーブン中、60℃で1時間、150℃で5時間加熱すると無色透明な硬化物2が得られた。
合成例1で得られたラダー型ビニルフェニルメチルシルセスキオキサン(6.00g)と1,1,3,3,5,5,7,7−オクタメチルテトラシロキサン(1.53g、fluorochem)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を6μL仕込み、再度攪拌し、硬化性樹脂組成物3を得た。
得られた硬化性樹脂組成物3をガラスプレートに塗布し、オーブン中、60℃で1時間、150℃で5時間加熱すると無色透明な硬化物3が得られた。
合成例1で得られたラダー型ビニルフェニルメチルシルセスキオキサン(0.60g)と1,1,3,3−テトラメチルジシロキサン0.10g(東京化成製)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を0.6μL仕込み、再度攪拌し、硬化性樹脂組成物4を得た。
得られた硬化性樹脂組成物4をガラスプレートに塗布し、オーブン中、60℃で1時間、120℃で3時間加熱すると無色透明な硬化物4が得られた。
合成例1で得られたラダー型フェニルメチルシルセスキオキサンビニル誘導体A(0.60g)とSi−H末端ポリシロキサン0.28g(Gelest製、分子量400〜500)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を0.6μL仕込み、再度攪拌し、硬化性樹脂組成物5を得た。
得られた硬化性樹脂組成物5をガラスプレートに塗布し、オーブン中、60℃で1時間、120℃で3時間加熱すると無色透明な硬化物5が得られた。
ラダー型末端トリメチルシリル基フェニルメチルビニルシルセスキオキサン(0.60g)と1,1,3,3−テトラメチルジシロキサン0.14g(東京化成製)とを6mlのスクリュー管に秤量し、2時間室温で攪拌したところ、相溶性が良好で、透明で均一な溶液が得られた。得られた混合液に白金ビニルメチルシロキサン錯体(和光純薬製;白金1.6wt%)を0.6μL仕込み、再度攪拌し、硬化性樹脂組成物6を得た。
得られた硬化性樹脂組成物6をガラスプレートに塗布し、オーブン中、60℃で1時間、120℃で3時間加熱すると無色透明な硬化物6が得られた。
実施例7
パッケージには3×2Al2O3パッケージ(京セラ製)、LED素子にはOBL−CH2424(ジェネライツ製)、ダイボンド材にはKJR−3000M2(信越シリコーン製)、金線にはSR−30(田中貴金属製)を使用してLEDパッケージを組み立てた。
実施例1〜6で得られた硬化性樹脂組成物1〜6をそのパッケージの中で硬化(60℃で1時間、150℃で5時間)させ、ユニバーサル基板のリード線上に半田で固定し、通電試験用試料(樹脂1〜6)を作製した。
硬化性樹脂組成物をエポキシ樹脂(CELVENUS W0910、ダイセル化学工業株式会社製)に変えた以外は実施例7と同様にして、通電試験用試料(エポキシ樹脂)を作製した。
Claims (6)
- 互いに反応してヒドロシリル化により炭素−ケイ素結合を形成可能なラダー型シルセスキオキサン(A)及び分子量100〜9000の直鎖ポリシロキサン(B)と、ヒドロシリル化触媒(C)とを含むことを特徴とする硬化性樹脂組成物。
- さらに、前記ラダー型シルセスキオキサン(A)及び/又は直鎖ポリシロキサン(B)と反応してヒドロシリル化により炭素−ケイ素結合を形成可能なイソシアヌル酸化合物(D)を含む、請求項1記載の硬化性樹脂組成物。
- 請求項1又は2記載の硬化性樹脂組成物を含む光半導体用封止剤。
- 請求項1又は2記載の硬化性樹脂組成物を硬化して得られる硬化物。
- 請求項4記載の硬化物を含むLED。
- 請求項5記載のLEDを含む光半導体装置。
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JP2012233117A (ja) * | 2011-05-06 | 2012-11-29 | Kaneka Corp | 硬化性組成物 |
JP2013056981A (ja) * | 2011-09-07 | 2013-03-28 | Daicel Corp | ラダー型シルセスキオキサン及びその製造方法、並びに、硬化性樹脂組成物及びその硬化物 |
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US9646904B2 (en) | 2013-01-09 | 2017-05-09 | Daicel Corporation | Curable resin composition, and cured product of same |
KR20150065822A (ko) * | 2013-01-09 | 2015-06-15 | 주식회사 다이셀 | 경화성 수지 조성물 및 그의 경화물 |
JP6027222B2 (ja) * | 2013-02-14 | 2016-11-16 | 株式会社ダイセル | 硬化性樹脂組成物、硬化物、封止材、及び半導体装置 |
US9481791B2 (en) | 2013-02-14 | 2016-11-01 | Daicel Corporation | Curable resin composition and cured product thereof, encapsulant, and semiconductor device |
JPWO2014125964A1 (ja) * | 2013-02-14 | 2017-02-02 | 株式会社ダイセル | 硬化性樹脂組成物、硬化物、封止材、及び半導体装置 |
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US9644098B2 (en) | 2013-02-14 | 2017-05-09 | Daicel Corporation | Curable resin composition and cured product thereof, encapsulant, and semiconductor device |
JP2015110694A (ja) * | 2013-12-06 | 2015-06-18 | サンユレック株式会社 | シリコーン樹脂組成物 |
JP2016216599A (ja) * | 2015-05-20 | 2016-12-22 | 株式会社ダイセル | 硬化性シリコーン樹脂組成物及びその硬化物 |
JP2021536519A (ja) * | 2018-08-31 | 2021-12-27 | ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG | 硬化性オルガノポリシロキサン組成物、封止材及び半導体デバイス |
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CN103154145B (zh) | 2015-09-16 |
KR20140006811A (ko) | 2014-01-16 |
WO2012070525A1 (ja) | 2012-05-31 |
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