WO2015186324A1 - オルガノシロキサン、硬化性シリコーン組成物、および半導体装置 - Google Patents
オルガノシロキサン、硬化性シリコーン組成物、および半導体装置 Download PDFInfo
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- WO2015186324A1 WO2015186324A1 PCT/JP2015/002718 JP2015002718W WO2015186324A1 WO 2015186324 A1 WO2015186324 A1 WO 2015186324A1 JP 2015002718 W JP2015002718 W JP 2015002718W WO 2015186324 A1 WO2015186324 A1 WO 2015186324A1
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- WO
- WIPO (PCT)
- Prior art keywords
- group
- curable silicone
- organosiloxane
- silicone composition
- component
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 78
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 40
- 239000004065 semiconductor Substances 0.000 title claims abstract description 25
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 239000002318 adhesion promoter Substances 0.000 claims abstract description 20
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 18
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 239000002683 reaction inhibitor Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 12
- 229910052710 silicon Inorganic materials 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 4
- 239000007809 chemical reaction catalyst Substances 0.000 abstract description 2
- -1 glycidoxy group Chemical group 0.000 description 64
- 239000000047 product Substances 0.000 description 23
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 12
- 229910052684 Cerium Inorganic materials 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 150000003961 organosilicon compounds Chemical class 0.000 description 8
- 125000005372 silanol group Chemical group 0.000 description 8
- 229910004298 SiO 2 Inorganic materials 0.000 description 7
- 229910004283 SiO 4 Inorganic materials 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 229910052693 Europium Inorganic materials 0.000 description 5
- 239000004954 Polyphthalamide Substances 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 229920006375 polyphtalamide Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000035515 penetration Effects 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000005023 xylyl group Chemical group 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 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 3
- 125000003493 decenyl group Chemical group [H]C([*])=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 3
- 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 3
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 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 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 3
- 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 3
- 125000004344 phenylpropyl group Chemical group 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
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- VYGUBTIWNBFFMQ-UHFFFAOYSA-N [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O Chemical group [N+](#[C-])N1C(=O)NC=2NC(=O)NC2C1=O VYGUBTIWNBFFMQ-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 2
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 239000002223 garnet Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
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- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 2
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- HMVBQEAJQVQOTI-SOFGYWHQSA-N (e)-3,5-dimethylhex-3-en-1-yne Chemical compound CC(C)\C=C(/C)C#C HMVBQEAJQVQOTI-SOFGYWHQSA-N 0.000 description 1
- GRGVQLWQXHFRHO-AATRIKPKSA-N (e)-3-methylpent-3-en-1-yne Chemical compound C\C=C(/C)C#C GRGVQLWQXHFRHO-AATRIKPKSA-N 0.000 description 1
- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical compound O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 description 1
- FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 description 1
- ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- AJARSKDYXXACJR-UHFFFAOYSA-N 1-[(dibutylamino)methyl]benzotriazole-4-carboxylic acid Chemical compound C1=CC=C2N(CN(CCCC)CCCC)N=NC2=C1C(O)=O AJARSKDYXXACJR-UHFFFAOYSA-N 0.000 description 1
- LQPDFQFGNCXQSL-UHFFFAOYSA-N 1-[(dioctylamino)methyl]benzotriazole-4-carboxylic acid Chemical compound C1=CC=C2N(CN(CCCCCCCC)CCCCCCCC)N=NC2=C1C(O)=O LQPDFQFGNCXQSL-UHFFFAOYSA-N 0.000 description 1
- KGEPBYXGRXRFGU-UHFFFAOYSA-N 1-[[bis(2-ethylhexyl)amino]methyl]benzotriazole-4-carboxylic acid Chemical compound C1=CC=C2N(CN(CC(CC)CCCC)CC(CC)CCCC)N=NC2=C1C(O)=O KGEPBYXGRXRFGU-UHFFFAOYSA-N 0.000 description 1
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Definitions
- the present invention relates to a novel organosiloxane, a curable silicone composition containing the same as an adhesion promoter, and a semiconductor device produced using the same.
- Hydrosilylation reaction curable silicone compositions generally have poor adhesion to substrates such as metals and organic resins, especially thermoplastic resins, so for example organopolysiloxanes having alkenyl groups bonded to silicon atoms, silicon atoms Organohydrogenpolysiloxane having a bonded hydrogen atom, one or more functional groups selected from an epoxy group, a glycidoxy group, and an alkoxysilyl group, and one type selected from a crosslinkable vinyl group and a hydrosilyl group (Si-H group) Curable silicone composition comprising an adhesion promoter comprising an isocyanuric acid derivative each having the above groups and a catalyst for hydrosilylation reaction (see Patent Document 1), an organopoly having at least two alkenyl groups in one molecule Siloxane, at least two silicon-bonded hydrogen atoms in one molecule
- a curable silicone composition comprising an organohydrogenpolysiloxane having an isocyanuric ring having an
- An object of the present invention is to provide a novel organosiloxane, a curable silicone composition containing the same as an adhesion promoter and forming a cured product with excellent adhesion to various substrates, and a trust comprising the composition It is an object of the present invention to provide a semiconductor device which is excellent in performance.
- the organosiloxanes of the present invention have the general formula: (Wherein R 1 is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms having no aliphatic unsaturated bond, R 2 is an alkenyl group having 2 to 12 carbon atoms, R 3 is the same or different alkyl group having 1 to 3 carbon atoms, and X is a general formula: (Wherein, R 1 is the same as the above, R 4 is the same or different alkylene group, p is an integer of 0 to 50, and q is 0 or 1). And m is an integer of 0 to 50, and n is an integer of 1 to 50.
- the curable silicone composition of the present invention contains the above organosiloxane as an adhesion promoter, and is preferably cured by a hydrosilylation reaction, and more preferably, (A) 100 parts by mass of organopolysiloxane having at least two alkenyl groups in one molecule, (B) An organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule ⁇ 0.1 to 0.1 mol in total of the alkenyl groups contained in the (A) component and the (C) component Amount providing 10.0 moles of silicon-bonded hydrogen atoms ⁇ , (C) 0.01 to 50 parts by mass of an adhesion promoter comprising the above organosiloxane, and (D) a catalyst for hydrosilylation reaction (an amount sufficient to accelerate the curing of the present composition) It consists of at least.
- the semiconductor device of the present invention is characterized in that the semiconductor element is sealed with a cured product of the above curable silicone composition, and preferably, the semiconductor element is a light emitting element.
- the organosiloxane of the present invention is a novel compound and is characterized in that it can impart excellent adhesion to a curable silicone composition.
- the curable silicone composition of the present invention is characterized in that it forms a cured product which is excellent in adhesion to various substrates in contact during curing.
- the semiconductor device of the present invention is characterized in that it has excellent reliability because the semiconductor element is coated with the cured product of the above composition.
- organosiloxane of the present invention has the general formula: Is represented by
- R 1 is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms which has no aliphatic unsaturated bond. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group, decyl Alkyl groups such as undecyl group and dodecyl group; aryl groups such as phenyl group, tolyl group, xylyl group and naphthyl group; aralkyl groups such as benzyl group, phenethyl group and phenylpropyl group; hydrogen atoms of these groups Examples thereof are groups in which part or all of them are substituted with a halogen atom such as
- R 2 is an alkenyl group having 2 to 12 carbon atoms.
- a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, a decenyl group, an undecenyl group and a dodecenyl group are exemplified, preferably a vinyl group.
- R 3 is the same or different alkyl group having 1 to 3 carbon atoms. Specifically, a methyl group, an ethyl group and a propyl group are exemplified, preferably a methyl group.
- X is a general formula: Is a group represented by
- R 1 is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms without an aliphatic unsaturated bond, and the same groups as above are exemplified.
- R 4 is the same or different alkylene group having 2 to 12 carbon atoms. Specifically, ethylene, propylene group, butylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, decylene group, undecylene group, dodecylene group are exemplified, preferably ethylene group and propylene group .
- p is an integer of 0 to 50, preferably an integer of 0 to 30, and more preferably an integer of 0 to 10. Also, in the formula, q is 0 or 1.
- m is an integer of 0 to 50, preferably an integer of 0 to 30, and more preferably an integer of 0 to 15.
- n is an integer of 1 to 50, preferably an integer of 1 to 30, and more preferably an integer of 1 to 15.
- M + n is an integer of 2 to 100, preferably an integer of 2 to 50, and more preferably an integer of 2 to 30.
- organosiloxanes are not limited, and, for example, And an organosiloxane represented by the general formula: The method of making the compound represented by (.) React under an acid or a base catalyst is mentioned.
- R 1 in the formula is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms without an aliphatic unsaturated bond, and the same groups as above are exemplified.
- R 2 is an alkenyl group having 2 to 12 carbon atoms, and the same groups as described above are exemplified.
- m and n are integers as described above.
- organosiloxanes examples include the following.
- m ' is an integer of 1 to 50
- n is an integer of 1 to 50.
- R 1 is the same or different and is a monovalent hydrocarbon group having 1 to 12 carbon atoms having no aliphatic unsaturated bond, and the same groups as above are exemplified.
- R 3 is the same or different alkyl group having 1 to 3 carbon atoms, and the same groups as above are exemplified.
- R 4 is the same or different alkylene group having 2 to 12 carbon atoms, and the same groups as above are exemplified.
- p is an integer as described above, and q is 0 or 1.
- Examples of such a compound include the following.
- the above preparation method it is necessary to react an amount of at least 1 mol to 2 mol of the above-mentioned compound with 1 mol of the above-mentioned organosiloxane.
- the amount of the above compound is at least the lower limit of the above range, the resulting organosiloxane can impart sufficient adhesiveness to the curable silicone composition, while at the same time the upper limit of the above range is obtained.
- the organosiloxane reacts with silicon-bonded hydrogen atoms in the hydrosilylation reaction-curable silicone composition to improve the transmittance of the resulting cured product.
- Examples of the acid used in the above preparation method include hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polybasic carboxylic acid, trifluoromethanesulfonic acid and ion exchange resin.
- Inorganic alkalis such as potassium hydroxide, sodium hydroxide, calcium hydroxide, and magnesium hydroxide; Triethylamine, diethylamine, monoethanolamine, diethanolamine, triethanolamine, triethanolamine, aqueous ammonia, tetramer
- organic base compounds such as methyl ammonium hydroxide, alkoxysilane having an amino group, aminopropyl trimethoxysilane, sodium silanolate, potassium silanolate and the like.
- organic solvent can be used in the above preparation method.
- examples of the organic solvent which can be used include ethers, ketones, acetates, aromatic or aliphatic hydrocarbons, ⁇ -butyrolactone, and a mixture of two or more of them.
- Preferred organic solvents include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ⁇ -butyrolactone, toluene and xylene. It is illustrated.
- this reaction is promoted by heating, and when using an organic solvent, it is preferable to carry out the reaction at the reflux temperature.
- the curable silicone composition of the present invention is characterized by containing the above-mentioned organosiloxane as an adhesion promoter.
- the curing mechanism of such a curable silicone composition is not limited, and hydrosilylation reaction, condensation reaction, radical reaction may be exemplified, and preferably hydrosilylation reaction.
- this hydrosilylation reaction curable silicone composition (A) 100 parts by mass of organopolysiloxane having at least two alkenyl groups in one molecule, (B) An organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule ⁇ 0.1 to 0.1 mol in total of the alkenyl groups contained in the (A) component and the (C) component Amount providing 10 moles of silicon-bonded hydrogen atoms ⁇ , It is preferable that the adhesive promoter (C) comprises (C) 0.01 to 50 parts by mass of the above-mentioned organosiloxane, and (D) a catalyst for hydrosilylation reaction.
- Component (A) is an organopolysiloxane having at least two alkenyl groups in one molecule, which is the main component of the present composition.
- the alkenyl group in component (A) has a carbon number of 2 to 4 such as vinyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl and the like 12 alkenyl groups are exemplified, preferably a vinyl group.
- An alkyl group having 1 to 12 carbon atoms such as hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl; carbons such as phenyl, tolyl, xylyl and naphthyl 6 to 20 aryl groups; aralkyl groups having 7 to 20 carbon atoms such as benzyl, phenethyl and phenylpropyl; and part or all of the hydrogen atoms of these groups may be fluorine atoms, chlorine atoms, Examples are groups substituted with a hal
- the molecular structure of the component (A) is not particularly limited, and examples thereof include linear, partially branched linear, branched, cyclic, and three-dimensional network structures.
- the component (A) may be one organopolysiloxane having these molecular structures, or a mixture of two or more organopolysiloxanes having these molecular structures.
- the property at 25 ° C. of the component (A) is not limited, and is, for example, liquid or solid.
- its viscosity at 25 ° C. is preferably in the range of 1 to 1,000,000 mPa ⁇ s, in particular in the range of 10 to 1,000,000 mPa ⁇ s Is preferred.
- the viscosity can be determined, for example, by measurement using a B-type viscometer according to JIS K 7117-1.
- dimethylpolysiloxane terminated with dimethylvinylsiloxy at both ends of molecular chain
- dimethylvinylsiloxy copolymer terminated with dimethylvinylsiloxy at both ends of branched chain
- dimethylvinylsiloxy group terminated at both ends of molecular chain Blocked dimethylsiloxane / methylphenylsiloxane copolymer
- Me, Vi and Ph respectively represent a methyl group, a vinyl group and a phenyl group, and x and x 'each represent an integer of 1 to 5,000.
- Component (B) is a crosslinking agent of the present composition, and is an organopolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule.
- Examples of the molecular structure of the component (B) include linear, partially branched linear, branched, cyclic and dendritic, and preferably linear and partially branched linear , Dendritic.
- the bonding position of the silicon-bonded hydrogen atom in the component (B) is not limited, and includes, for example, the end of the molecular chain and / or the side chain.
- the silicon-bonded group other than the silicon-bonded hydrogen atom in the component (B) alkyl groups such as methyl, ethyl and propyl; aryl groups such as phenyl, tolyl and xylyl; benzyl And aralkyl groups such as phenethyl and the like; halogenated alkyl groups such as 3-chloropropyl and 3,3,3-trifluoropropyl and the like, with preference given to methyl and phenyl.
- the viscosity of the component (B) is not limited, the viscosity at 25 ° C. is preferably in the range of 1 to 10,000 mPa ⁇ s, and particularly preferably in the range of 1 to 1,000 mPa ⁇ s. preferable.
- (B) component 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, tris (dimethylhydrogensiloxy) methylsilane, tris (dimethylhydro) Phenylsiloxy) phenylsilane, 1-glycidoxypropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1,5-glycidoxypropyl-1,3,5,7-tetramethylcyclotetrasiloxane, 1-Glycidoxypropyl-5-trimethoxysilylethyl-1,3,5,7-tetramethylcyclotetrasiloxane, blocked methylsiloxy hydroxyl group terminated methylsiloxy group, blocked molecular chain terminated trimethylsiloxy group Dimethyl siloxane / methyl hydrogen siloxane copolymer, molecular chain both ends dimethyl chain Dorogensiloxy group-capped dimethylpoly
- Me, Vi and Ph respectively represent a methyl group, a vinyl group and a phenyl group
- y and y 'each represent an integer of 1 to 100
- c, d, e and f each represent a positive number.
- the sum of c, d, e and f is 1.
- the content of the component (B) is such that the amount of silicon-bonded hydrogen atoms in this component is 0.1 to 10 moles with respect to 1 mole in total of the alkenyl groups contained in the components (A) and (C). And preferably in an amount of 0.5 to 5 moles. This is because the mechanical properties of the resulting cured product are good when the content of the component (B) is below the upper limit of the above range, while the curing of the resulting composition is above the lower limit of the above range It is because the nature is good.
- the component (C) is an adhesion promoter for imparting adhesiveness to the present composition.
- the component (C) is as described above.
- the content of the component (C) is in the range of 0.01 to 50 parts by mass, preferably in the range of 0.1 to 20 parts by mass with respect to 100 parts by mass of the component (A). This is because when the content of the component (C) is at least the lower limit of the above range, sufficient adhesiveness can be imparted to the composition to be obtained, while the composition obtained at the lower limit of the above range It is because it becomes difficult to inhibit the curability of a thing, and it can control coloring etc. of a hardening thing obtained.
- the component (D) is a hydrosilylation reaction catalyst for promoting the curing of the composition, and examples thereof include platinum catalysts, rhodium catalysts, and palladium catalysts.
- the component (D) is preferably a platinum-based catalyst because it can significantly accelerate the curing of the present composition.
- the platinum-based catalyst include fine platinum powder, chloroplatinic acid, alcohol solution of chloroplatinic acid, platinum-alkenyl siloxane complex, platinum-olefin complex, platinum-carbonyl complex, and preferably platinum-alkenyl siloxane complex. is there.
- the content of the component (D) is an amount effective to accelerate the curing of the present composition. Specifically, since the content of the component (D) can sufficiently accelerate the curing reaction of the present composition, the amount of the catalyst metal in the component (D) is 0.01 in mass unit with respect to the present composition. The amount is preferably in the range of -500 ppm, more preferably in the range of 0.01 to 100 ppm, and particularly preferably in the range of 0.01 to 50 ppm. Is preferred.
- the content of the component (E) is not limited, but is in the range of 0.0001 to 5 parts by mass with respect to 100 parts by mass in total of the components (A) to (D). Is preferred.
- the composition may contain an adhesion promoter other than the component (C) in order to improve the adhesion of the cured product to a substrate in contact with curing.
- the adhesion promoter is preferably an organosilicon compound having at least one alkoxy group bonded to a silicon atom in one molecule. Examples of this alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group and a methoxyethoxy group, and a methoxy group is particularly preferable.
- a substituted or unsubstituted monovalent hydrocarbon group such as an alkyl group, an alkenyl group, an aryl group, an aralkyl group or a halogenated alkyl group; 3 -Glycidoxyalkyl groups such as -glycidoxypropyl group and 4-glycidoxybutyl group; epoxy such as 2- (3,4-epoxycyclohexyl) ethyl group and 3- (3,4-epoxycyclohexyl) propyl group Examples thereof include a cyclohexylalkyl group; an epoxy alkyl group such as a 3,4-epoxybutyl group and a 7,8-epoxyoctyl group; an acrylic group-containing monovalent organic group such as a 3-methacryloxypropyl group; and a hydrogen atom.
- the organosilicon compound preferably has a silicon-bonded alkenyl group or a silicon-bonded hydrogen atom.
- organosilicon compounds include organosilane compounds, organosiloxane oligomers, and alkyl silicates.
- organosilane compounds include organosilane compounds, organosiloxane oligomers, and alkyl silicates.
- alkyl silicates examples of the molecular structure of this organosiloxane oligomer or alkyl silicate include linear, partially branched linear, branched, cyclic, and network-like, and in particular, linear, branched or network-like. Is preferred.
- silane compounds such as 3-glycidoxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, etc.
- siloxane compound having at least one silicon-bonded alkenyl group or silicon-bonded hydrogen atom and at least one silicon-bonded alkoxy group a silane compound or silicon compound having at least one silicon-bonded alkoxy group in one molecule
- examples thereof include a mixture of a siloxane compound having at least one atom-bonded hydroxy group and at least one silicon-bonded alkenyl group, methylpolysilicate, ethylpolysilicate, and epoxy group-containing ethylpolysilicate.
- the present composition contains a phosphor for converting the wavelength of light emitted from the light emitting element formed by sealing or covering the cured product of the present composition to obtain light of a desired wavelength. It is also good.
- phosphors oxide-based phosphors, oxynitride-based phosphors, nitride-based phosphors, sulfide-based phosphors, oxysulfide-based phosphors, which are widely used for light-emitting diodes (LEDs) Examples are yellow, red, green and blue light emitting phosphors composed of body and the like.
- oxide-based phosphors As oxide-based phosphors, yttrium, aluminum, garnet-based YAG-based green to yellow light-emitting phosphors including cerium ions, terbium, aluminum, garnet-based TAG-based yellow light-emitting phosphors including cerium ions, Examples are silicate based green to yellow light emitting phosphors including cerium and europium ions. Examples of oxynitride phosphors include silicon including europium ions, aluminum, oxygen, and nitrogen-based sialon red to green light emitting phosphors.
- nitride-based phosphors examples include calcium, strontium, aluminum, silicon, and cathode-based red light-emitting phosphors based on nitrogen, including europium ions.
- a sulfide type fluorescent substance ZnS type green color development fluorescent substance containing a copper ion and an aluminum ion is illustrated.
- the oxysulfide phosphor include europium ion Y 2 O 2 S based red phosphors may be exemplified. These phosphors may be used alone or in combination of two or more.
- the content of the phosphor is in the range of 0.1 to 70% by mass, preferably 1 to 20% by mass, with respect to the total amount of the components (A) to (D). It is in the range.
- inorganic fillers such as silica, glass, alumina and zinc oxide as other optional components; fine particles of organic resin such as polymethacrylate resin; It may contain dyes, pigments, flame retardants, solvents and the like.
- the present composition further contains Al, Ag, Cu, Fe, Sb, Si, Sn, in order to sufficiently suppress discoloration of silver plating of silver electrodes and substrates in optical semiconductor devices due to sulfur-containing gas in the air.
- rare earth elements include yttrium, cerium and europium.
- an oxide of the surface of the zinc oxide fine powder Al 2 O 3 , AgO, Ag 2 O, Ag 2 O 3 , CuO, Cu 2 O, FeO, Fe 2 O 3 , Fe 3 O 4 , Sb 2 O 3 , SiO 2 , SnO 2 , Ti 2 O 3 , TiO 2 , Ti 3 O 5 , ZrO 2 , Y 2 O 3 , CeO 2 , Eu 2 O 3 , and a mixture of two or more of these oxides.
- Ru is
- the organosilicon compound has no alkenyl group and exemplified by organosilane, organosilazane, polymethylsiloxane, organohydrogenpolysiloxane and organosiloxane oligomer Specifically, organochlorosilanes such as trimethylchlorosilane, dimethylchlorosilane and methyltrichlorosilane; methyltrimethoxysilane, methyltriethoxysilane, phenyltrimethoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, ⁇ - Organotrialkoxysilanes such as methacryloxypropyltrimethoxysilane; Diorganodisilanes such as dimethyldimethoxysilane, dimethyldiethoxysilane and diphenyldimethoxysilane Luc
- the present composition may further contain a triazole compound as an optional component because it can further suppress the color change of the silver plating of the silver electrode or the substrate due to the sulfur-containing gas in the air.
- a triazole compound as an optional component because it can further suppress the color change of the silver plating of the silver electrode or the substrate due to the sulfur-containing gas in the air.
- a triazole compound as an optional component because it can further suppress the color change of the silver plating of the silver electrode or the substrate due to the sulfur-containing gas in the air.
- a triazole compound as an optional component because it can further suppress the color change of the silver plating of the silver electrode or the substrate due to the sulfur-containing gas in the air.
- 1H-1,2,3-triazole, 2H-1,2,3-triazole, 1H-1,2,4-triazole, 4H-1,2,4- Triazole benzotriazole, tolyltriazole, carboxybenzotriazole, methyl 1H-benzotriazole-5-
- the composition may further contain a cerium-containing organopolysiloxane as another optional component in order to suppress heat-induced cracking of the resulting cured product.
- a cerium-containing organopolysiloxane can be prepared, for example, by the reaction of cerium chloride or a cerium salt of a carboxylic acid with an alkali metal salt of a silanol group-containing organopolysiloxane.
- cerium salts of carboxylic acids include cerium 2-ethylhexanoate, cerium naphthenate, cerium oleate, cerium laurate and cerium stearate.
- alkali metal salt of the above silanol group-containing organopolysiloxane a potassium salt of a diorganopolysiloxane in which both molecular chain terminals are blocked by silanol groups, and a diorganopolysiloxane in which both molecular chain terminals are blocked by silanol groups
- Sodium salt of one of the molecular chains, the potassium salt of a diorganopolysiloxane blocked at one molecular chain end with a silanol group, and one molecular chain end at a triorganosiloxy group, and the molecular chain end with a silanol group examples are sodium salts of diorganopolysiloxanes in which one molecular chain end is blocked with a triorganosiloxy group.
- the group to be bonded to the silicon atom in this organopolysiloxane is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, neopentyl group, An alkyl group having 1 to 12 carbon atoms such as hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, and dodecyl group; phenyl group, tolyl group, xylyl group, naphthyl group etc.
- aralkyl groups of 7 to 20 carbon atoms such as benzyl, phenethyl and phenylpropyl; and part or all of the hydrogen atoms of these groups as fluorine atoms And groups substituted by halogen atoms such as chlorine atom and bromine atom.
- the above reaction includes alcohols such as methanol, ethanol, isopropanol and butanol; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as hexane and heptane; organics such as mineral split, ligroin and petroleum ether It is carried out in a solvent at room temperature or by heating. Moreover, as for the reaction product obtained, it is preferable to distill off an organic solvent and a low boiling point component as needed, or to filter a deposit. Also, in order to promote this reaction, dialkylformamide, hexaalkylphosphoamide and the like may be added.
- the content of the cerium atom in the cerium-containing organopolysiloxane prepared in this manner is preferably in the range of 0.1 to 5% by mass.
- the content of the cerium-containing organopolysiloxane is not limited, but preferably, an amount such that the content of the cerium atom in the composition is in the range of 10 to 2,000 ppm by mass, preferably in the range of 20 to 2,000 ppm The amount is in the range of 20 to 1,000 ppm, or in the range of 20 to 500 ppm. This can improve the heat resistance of the cured product to be obtained when the content of the cerium-containing organopolysiloxane is at least the lower limit of the above range, and on the other hand, when it is at the upper limit of the above range, This is because the change in emission chromaticity when used can be reduced.
- composition proceeds curing at room temperature or heating, heating is preferred for rapid curing.
- the heating temperature is preferably in the range of 50 to 200 ° C.
- the semiconductor device of the present invention is characterized in that a semiconductor element is sealed with a cured product of the above-mentioned curable silicone composition.
- a semiconductor device of the present invention include a light emitting diode (LED), a photocoupler, and a CCD.
- LED light emitting diode
- tip and a solid-state image sensor are illustrated.
- FIG. 1 A cross-sectional view of a single surface mounted LED as an example of the semiconductor device of the present invention is shown in FIG.
- a light emitting element (LED chip) 1 is die-bonded on a lead frame 2, and the light emitting element (LED chip) 1 and a lead frame 3 are wire-bonded by bonding wires 4.
- a frame 5 is provided around the light emitting element (LED chip) 1, and the light emitting element (LED chip) 1 inside the frame 5 is made of the cured product 6 of the curable silicone composition of the present invention It is sealed.
- the light emitting element (LED chip) 1 is die-bonded to the lead frame 2, and the light emitting element (LED chip) 1 and the lead frame 3 are bonded by gold bonding wire.
- wire bonding with 4 and then filling the curable silicone composition of the present invention inside the frame material 5 provided around the light emitting element (LED chip) 1 curing is carried out by heating at 50 to 200 ° C. The method of making it be illustrated.
- Me, Vi, Ph and Ep each represent a methyl group, a vinyl group, a phenyl group and a 3-glycidoxypropyl group.
- Example 1 In the reaction vessel, the average formula: 190 g of an organosiloxane represented by the formula: 598 g of the compound represented by and 0.23 g of potassium silanolate were added, and the mixture was heated at 120 to 130 ° C. for 6 hours to obtain a pale yellow liquid.
- This liquid has an average formula of: (Where X is the formula: Is a group represented by ) It turned out that it is an organosiloxane represented.
- Example 2 In the reaction vessel, the formula: 26 g of an organosiloxane represented by the formula: 30 g of the compound represented by and 1.7 g of calcium hydroxide were added, and the mixture was heated at 100 ° C. for 6 hours to obtain a pale yellow liquid.
- This liquid has an average formula of: (Where X is the formula: Is a group represented by ) It turned out that it is an organosiloxane represented.
- Example 3 In the reaction vessel, the formula: 10 g of an organosiloxane represented by the formula: 9.8 g of the compound represented by and 1.1 g of calcium hydroxide were added, and the mixture was heated at 120 to 130 ° C. for 6 hours to obtain a pale yellow liquid.
- This liquid has an average formula of: (Where X is the formula: Is a group represented by ) It turned out that it is an organosiloxane represented.
- Examples 4 to 8, Comparative Examples 1 to 3 The curable silicone composition shown in Table 1 was prepared using the following ingredients.
- content of (D) component was shown with content (ppm) of platinum metal with respect to the curable silicone composition in a mass unit.
- SiH / Vi indicates the number of moles of silicon-bonded hydrogen atoms in the component (B) to 1 mole in total of the alkenyl groups contained in the components (A) and (C).
- A-1) Component: Average unit formula: (Me 2 ViSiO 1/2 ) 0.2 (PhSiO 3/2 ) 0.8 Organopolysiloxane (A-2) component represented by: average unit formula prepared in Reference Example 1 (MePhViSiO 1/2 ) 0.23 (PhSiO 3/2 ) 0.77 Organopolysiloxane (A-3) component: Molecular chain both terminal dimethylvinylsiloxy group-blocked methylphenylpolysiloxane having a viscosity of 3,000 mPa ⁇ s
- Component (B-1) Formula: HMe 2 SiOPh 2 SiOSiMe 2 H Organotrisiloxane represented by
- component (C) The following components were used as component (C).
- C-1) Component Adhesion promoter consisting of an organosiloxane prepared in Example 1
- C-2) Component Adhesion promoter consisting of an organosiloxane prepared in Example 2
- C-3) Component Component: Example 3
- the adhesion promoter (C-4) component consisting of an organosiloxane prepared in the following procedure: Condensation of 3-glycidoxypropyltrimethoxysilane with methyl-vinylsiloxane oligomer blocked with both chain terminal silanol groups having a viscosity of 30 mPa ⁇ s at 25 ° C.
- Adhesion promoter consisting of reactants
- Component (D-1) 1,3,5,7-Tetramethyl-1,3,5,7-tetravinyl of a platinum-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex Cyclotetrasiloxane solution (solution containing 0.1% by mass as platinum)
- the adhesion of the cured product of the curable silicone composition was measured as follows.
- a 2 mm-thick fluorocarbon resin spacer with a 5 mm diameter hole was placed on a bonding test panel (aluminum plate, PPA resin plate, silver plate), and a curable silicone composition was placed in the hole of the spacer. And then allowed to stand in a hot air circulating oven at 150 ° C. for 1 hour to produce a cylindrical cured product of 5 mm in diameter ⁇ 2 mm in height. The cured product was peeled at a speed of 50 mm / min using a die shear strength measuring device, and the load (MPa) at that time was measured.
- MPa load
- a surface-mounted light emitting diode (LED) was produced using the curable silicone composition as follows.
- the lead frames 2 and 3 extend from the side wall toward the center of the inner bottom of the cylindrical polyphthalamide (PPA) resin frame member 5 (inside diameter 2.0 mm, depth 1.0 mm) whose bottom is closed.
- the LED chip 1 is placed on the central portion of the lead frame 2, and the LED chip 1 and the lead frame 3 are removed from each other in the unsealed light emitting diode electrically connected by the bonding wire 4.
- the foamed curable silicone composition was injected by a dispenser. Thereafter, the curable silicone composition was cured by heating at 100 ° C. for 30 minutes and then at 150 ° C. for 1 hour in a heating oven to produce the light emitting diode shown in FIG.
- the 16 light emitting diodes fabricated by the above method are subjected to 1000 cycles of heat cycle test with one cycle of temperature cycle of -40 ° C for 30 minutes and then at 125 ° C for 30 minutes, and then electricity is applied to light the LED Was evaluated and evaluated as follows.
- the following components were used as the component (A) in addition to the component (A-2).
- the viscosity is a value at 25 ° C., and was measured using a B-type viscometer according to JIS K 7117-1. Further, the content of the vinyl group was measured by analysis such as FT-IR, NMR, GPC and the like.
- B-3) Component: Average unit formula: (PhSiO 3/2 ) 0.4 (HMe 2 SiO 1/2 ) 0.6
- the above-mentioned components (C-1) and (C-4) were used.
- Component (E) 1-ethynylcyclohexane-1-ol
- the hardness of the curable silicone composition was measured as follows.
- a surface-mounted light emitting diode (LED) was produced using the curable silicone composition as follows.
- the lead frames 2 and 3 extend from the side wall toward the center of the inner bottom of the cylindrical polyphthalamide (PPA) resin frame member 5 (inside diameter 2.0 mm, depth 1.0 mm) whose bottom is closed.
- the LED chip 1 is placed on the central portion of the lead frame 2, and the LED chip 1 and the lead frame 3 are removed from each other in the unsealed light emitting diode electrically connected by the bonding wire 4.
- the foamed curable silicone composition was injected by a dispenser. Thereafter, the curable silicone composition was cured by heating at 100 ° C. for 30 minutes and then at 150 ° C. for 1 hour in a heating oven to produce a surface mount type light emitting diode shown in FIG.
- the curable silicone composition of the present invention is excellent in fluidity and can be cured to uniformly disperse the phosphor and form a cured product having a high refractive index, so that an optical semiconductor such as a light emitting diode (LED) etc. It is suitable as a sealing agent or covering agent of the light emitting element in an apparatus.
- LED light emitting diode
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Abstract
Description
で表される基であり、mは0~50の整数、nは1~50の整数である。}
で表される。
(A)一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン 100質量部、
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノハイドロジェンポリシロキサン{(A)成分と(C)成分に含まれるアルケニル基の合計1モルに対して、0.1~10.0モルのケイ素原子結合水素原子を提供する量}、
(C)上記のオルガノシロキサンからなる接着促進剤 0.01~50質量部、および
(D)ヒドロシリル化反応用触媒(本組成物の硬化を促進するに十分な量)
から少なくともなるものである。
本発明の硬化性シリコーン組成物は、上記のオルガノシロキサンを接着促進剤として含有することを特徴とする。このような硬化性シリコーン組成物の硬化機構は限定されず、ヒドロシリル化反応、縮合反応、ラジカル反応が例示され、好ましくは、ヒドロシリル化反応である。このヒドロシリル化反応硬化性シリコーン組成物としては、
(A)一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン 100質量部、
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノハイドロジェンポリシロキサン{(A)成分と(C)成分に含まれるアルケニル基の合計1モルに対して、0.1~10モルのケイ素原子結合水素原子を提供する量}、
(C)上記のオルガノシロキサンからなる接着促進剤 0.01~50質量部、および
(D)ヒドロシリル化反応用触媒
から少なくともなるものが好ましい。
ViMe2SiO(Me2SiO)xSiMe2Vi
ViPhMeSiO(Me2SiO)xSiMePhVi
ViPh2SiO(Me2SiO)xSiPh2Vi
ViMe2SiO(Me2SiO)x(Ph2SiO)x'SiMe2Vi
ViPhMeSiO(Me2SiO)x(Ph2SiO)x'SiPhMeVi
ViPh2SiO(Me2SiO)x(Ph2SiO)x'SiPh2Vi
ViMe2SiO(MePhSiO)zSiMe2Vi
MePhViSiO(MePhSiO)xSiMePhVi
Ph2ViSiO(MePhSiO)xSiPh2Vi
ViMe2SiO(Ph2SiO)x(PhMeSiO)x'SiMe2Vi
ViPhMeSiO(Ph2SiO)x(PhMeSiO)x'SiPhMeVi
ViPh2SiO(Ph2SiO)x(PhMeSiO)x'SiPh2Vi
HMe2SiO(Ph2SiO)ySiMe2H
HMePhSiO(Ph2SiO)ySiMePhH
HMeNaphSiO(Ph2SiO)ySiMeNaphH
HMePhSiO(Ph2SiO)y(MePhSiO)y'SiMePhH
HMePhSiO(Ph2SiO)y(Me2SiO)y'SiMePhH
(HMe2SiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(PhSiO3/2)d
(HMePhSiO1/2)c(NaphSiO3/2)d
(HMe2SiO1/2)c(NaphSiO3/2)d
(HMePhSiO1/2)c(HMe2SiO1/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(PhSiO3/2)e
(HMe2SiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(Ph2SiO2/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(NaphSiO3/2)e
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(NaphSiO3/2)f
(HMePhSiO1/2)c(HMe2SiO1/2)d(Ph2SiO2/2)e(PhSiO3/2)f
本発明の半導体装置は、上記の硬化性シリコーン組成物の硬化物により半導体素子を封止してなることを特徴とする。このような本発明の半導体装置としては、発光ダイオード(LED)、フォトカプラー、CCDが例示される。また、半導体素子としては、発光ダイオード(LED)チップ、固体撮像素子が例示される。
反応容器に、フェニルトリメトキシシラン 400g(2.02mol)および1,3-ジビニル-1,3-ジフェニルジメチルジシロキサン 93.5g(0.30mol)を投入し、予め混合した後、トリフルオロメタンスルホン酸 1.74g(11.6mmol)を投入し、撹拌下、水 110g(6.1mol)を投入し、2時間加熱還流を行った。その後、85℃になるまで加熱常圧留去を行った。次いで、トルエン 89gおよび水酸化カリウム 1.18g(21.1mmol)を投入し、反応温度が120℃になるまで加熱常圧留去を行い、この温度で6時間反応させた。その後、室温まで冷却し、酢酸 0.68g(11.4mmol)を投入し、中和した。生成した塩を濾別した後、得られた透明な溶液から低沸点物を加熱減圧除去して、平均単位式:
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
で表されるオルガノポリシロキサンレジン 347g(収率:98%)を調製した。
反応容器に、平均式:
で表されるオルガノシロキサンであることがわかった。
反応容器に、式:
で表されるオルガノシロキサンであることがわかった。
反応容器に、式:
で表されるオルガノシロキサンであることがわかった。
下記の成分を用いて、表1に示した硬化性シリコーン組成物を調製した。なお、表1中、(D)成分の含有量は、質量単位における、硬化性シリコーン組成物に対する白金金属の含有量(ppm)で示した。また、表1中、SiH/Viは、(A)成分および(C)成分に含まれるアルケニル基の合計1モルに対する、(B)成分中のケイ素原子結合水素原子のモル数を示した。
(A-1)成分: 平均単位式:
(Me2ViSiO1/2)0.2(PhSiO3/2)0.8
で表されるオルガノポリシロキサン
(A-2)成分: 参考例1で調製した、平均単位式
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
で表されるオルガノポリシロキサン
(A-3)成分: 粘度3,000mPa・sの分子鎖両末端ジメチルビニルシロキシ基封鎖メチルフェニルポリシロキサン
(B-1)成分: 式:
HMe2SiOPh2SiOSiMe2H
で表されるオルガノトリシロキサン
(C-1)成分: 実施例1で調製したオルガノシロキサンからなる接着促進剤
(C-2)成分: 実施例2で調製したオルガノシロキサンからなる接着促進剤
(C-3)成分: 実施例3で調製したオルガノシロキサンからなる接着促進剤
(C-4)成分: 25℃における粘度が30mPa・sである分子鎖両末端シラノール基封鎖メチルビニルシロキサンオリゴマーと3-グリシドキシプロピルトリメトキシシランの縮合反応物からなる接着促進剤
(D-1)成分: 白金-1,3-ジビニル-1,1,3,3-テトラメチルジシロキサン錯体の1,3,5,7-テトラメチル-1,3,5,7-テトラビニルシクロテトラシロキサンの溶液(白金として0.1質量%含有する溶液)
直径5mmの穴を開けた、厚さ2mmのフッ素樹脂製のスペーサーを接着用テストパネル(アルミニウム板、PPA樹脂板、銀板)上に設置し、上記スペーサーの穴の中に硬化性シリコーン組成物を流し込んだ後、150℃の熱風循環式オーブン中で1時間放置することで、直径5mm×高さ2mmの円柱状の硬化物を作製した。この硬化物を、ダイシェア強度測定装置を用い50mm/分の速度で剥離し、そのときの荷重(MPa)を測定した。
底部が塞がった円筒状のポリフタルアミド(PPA)樹脂製枠材5(内径2.0mm、深さ1.0mm)の内底部の中心部に向かって、リードフレーム2、3が側壁から延出しており、リードフレーム2の中央部上にLEDチップ1が載置されており、LEDチップ1とリードフレーム3はボンディングワイヤ4により電気的に接続している未封止の発光ダイオード内に、脱泡した硬化性シリコーン組成物をディスペンサーにより注入した。その後、加熱オーブン中、100℃で30分、続いて150℃で1時間加熱して、硬化性シリコーン組成物を硬化させることにより、図1に示す発光ダイオードを作製した。
上記の方法で作製した16個の発光ダイオードを、市販の赤インクに浸漬し、50℃で24時間放置した。放置後、顕微鏡で赤インクの発光ダイオード内への浸み込みを観察し、次のように評価した。
◎: インクの浸み込みが確認された発光ダイオードが2個以下である。
△: インクの浸み込みが確認された発光ダイオードが3個~8個である。
×: インクの浸み込みが確認された発光ダイオードが9個以上である。
上記の方法で作製した16個の発光ダイオードを、-40℃で30分間、次いで125℃で30分間の温度サイクルを1サイクルとするヒートサイクル試験を1000サイクル行い、その後、通電してLEDの点灯を調査し、次のように評価した。
◎: 点灯した発光ダイオードが14個以上である。
○: 点灯した発光ダイオードが8個~13個である。
△: 点灯した発光ダイオードが7個以下である。
次の成分を用いて、表2に示した硬化性シリコーン組成物を調製した。なお、表2中、(D)成分の含有量は、質量単位における、硬化性シリコーン組成物に対する白金金属の含有量(ppm)で示した。また、表2中、SiH/Viは、(A)成分および(C)成分に含まれるアルケニル基の合計1モルに対する、(B)成分中のケイ素原子結合水素原子のモル数を示した。
(A-4)成分: 粘度300mPa・sであり、平均式:
Me2ViSiO(Me2SiO)150SiMe2Vi
で表される分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルポリシロキサン(ビニル基の含有量=0.48質量%)
(A-5)成分: 粘度10,000mPa・sであり、平均式:
Me2ViSiO(Me2SiO)500SiMe2Vi
で表される分子鎖両末端ジメチルビニルシロキシ基封鎖ジメチルポリシロキサン(ビニル基の含有量=0.15質量%)
(A-6)成分: 25℃において白色固体状で、トルエン可溶性である、平均単位式:
(Me2ViSiO1/2)0.15(Me3SiO1/2)0.47(SiO4/2)0.38(HO1/2)0.0001
で表される一分子中に2個以上のビニル基を有するオルガノポリシロキサンレジン(ビニル基の含有量=5.4質量%)
(A-7)成分: 25℃において白色固体状で、トルエン可溶性である、平均単位式:
(Me2ViSiO1/2)0.15(Me3SiO1/2)0.38(SiO4/2)0.47(HO1/2)0.01
で表される一分子中に2個以上のビニル基を有するオルガノポリシロキサン(ビニル基の含有量=4.2質量%)
(A-8)成分: 25℃において白色固体状で、トルエン可溶性の平均単位式:
(PhSiO3/2)0.75(Me2ViSiO1/2)0.25
で表される一分子中に2個以上のビニル基を有するオルガノポリシロキサン(ビニル基の含有量=5.6質量%)
(B-2)成分: 平均式:
Me3SiO(MeHSiO)55SiMe3
で表される、粘度20mPa・sの分子鎖両末端トリメチルシロキシ基封鎖ポリメチルハイドロジェンシロキサン(ケイ素原子結合水素原子含有量=1.6質量%)
(B-3)成分: 平均単位式:
(PhSiO3/2)0.4(HMe2SiO1/2)0.6
で表される、粘度25mPa・sの一分子中に2個以上のケイ素原子結合水素原子を有する分岐鎖状オルガノポリシロキサン(ケイ素原子結合水素原子の含有量=0.65質量%)
(D-2)成分: 白金の1,3-ジビニルテトラメチルジシロキサン錯体の1,3-ジビニルテトラメチルジシロキサン溶液(白金金属の含有量=約5000ppm)
(E-1)成分: 1-エチニルシクロヘキサン-1-オール
硬化性シリコーン組成物を150℃で1時間、5MPaの圧力でプレス成形することによりシート状の硬化物を作製した。このシート状の硬化物の硬さをJIS K 6253に規定されるタイプAデュロメータにより測定した。その結果を表2に示した。
底部が塞がった円筒状のポリフタルアミド(PPA)樹脂製枠材5(内径2.0mm、深さ1.0mm)の内底部の中心部に向かって、リードフレーム2、3が側壁から延出しており、リードフレーム2の中央部上にLEDチップ1が載置されており、LEDチップ1とリードフレーム3はボンディングワイヤ4により電気的に接続している未封止の発光ダイオード内に、脱泡した硬化性シリコーン組成物をディスペンサーにより注入した。その後、加熱オーブン中、100℃で30分、続いて150℃で1時間加熱して、硬化性シリコーン組成物を硬化させることにより、図1に示す表面実装型の発光ダイオードを作製した。
上記の方法で作製した20個の発光ダイオードについて、リードフレーム2、3、およびボンディングワイヤ4と硬化物6間での剥離状態を光学顕微鏡で観察し、剥離が見られた発光ダイオードの個数の割合を表2に示した。
上記の方法で作製した20個の発光ダイオードを、85℃、85%の恒温恒湿室に168時間入れた後、280℃のオーブン内に30秒間置き、その後、室温(25℃)下に戻して、リードフレーム2、3、およびボンディングワイヤ4と硬化物6間での剥離状態を光学顕微鏡で観察し、剥離が見られた発光ダイオードの個数の割合を表2に示した。
2 リードフレーム
3 リードフレーム
4 ボンディングワイヤ
5 枠材
6 硬化性シリコーン組成物の硬化物
Claims (9)
- R4がエチレン基またはプロピレン基である、請求項1に記載のオルガノシロキサン。
- 請求項1または2に記載のオルガノシロキサンからなる接着促進剤。
- 請求項1または2に記載のオルガノシロキサンを接着促進剤として含有する硬化性シリコーン組成物。
- ヒドロシリル化反応で硬化する、請求項4に記載の硬化性シリコーン組成物。
- ヒドロシリル化反応で硬化する硬化性シリコーン組成物が、
(A)一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン 100質量部、
(B)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノハイドロジェンポリシロキサン{(A)成分と(C)成分に含まれるアルケニル基の合計1モルに対して、0.1~10モルとなる量のケイ素原子結合水素原子を提供する量}、
(C)請求項1または2に記載のオルガノシロキサンからなる接着促進剤 0.1~10質量部、および
(D)ヒドロシリル化反応用触媒(本組成物の硬化を促進するに十分な量)
から少なくともなる、請求項11記載の硬化性シリコーン組成物。 - さらに、(E)ヒドロシリル化反応抑制剤{(A)成分~(D)成分の合計100質量部に対して0.0001~5質量部}を含有する、請求項6に記載の硬化性シリコーン組成物。
- 半導体素子が、請求項4乃至7のいずれか1項に記載の硬化性シリコーン組成物の硬化物により封止されていることを特徴とする半導体装置。
- 半導体素子が発光素子である、請求項8に記載の半導体装置。
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JP2019085465A (ja) * | 2017-11-02 | 2019-06-06 | 信越化学工業株式会社 | 付加硬化型シリコーン組成物、硬化物、及び光学素子 |
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CN106459102A (zh) | 2017-02-22 |
JP6552488B2 (ja) | 2019-07-31 |
CN106459102B (zh) | 2019-07-23 |
US9944772B2 (en) | 2018-04-17 |
TWI675039B (zh) | 2019-10-21 |
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