JP2014084418A - 硬化性シリコーン組成物、その硬化物、および光半導体装置 - Google Patents
硬化性シリコーン組成物、その硬化物、および光半導体装置 Download PDFInfo
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- JP2014084418A JP2014084418A JP2012235184A JP2012235184A JP2014084418A JP 2014084418 A JP2014084418 A JP 2014084418A JP 2012235184 A JP2012235184 A JP 2012235184A JP 2012235184 A JP2012235184 A JP 2012235184A JP 2014084418 A JP2014084418 A JP 2014084418A
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- JP
- Japan
- Prior art keywords
- group
- organopolysiloxane
- curable silicone
- formula
- silicone composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 100
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 230000003287 optical effect Effects 0.000 title claims abstract description 34
- 239000004065 semiconductor Substances 0.000 title claims abstract description 34
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 25
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 22
- 230000009257 reactivity Effects 0.000 abstract description 5
- -1 methylphenylvinylsiloxane unit Chemical group 0.000 description 86
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- 230000035699 permeability Effects 0.000 description 16
- 239000010703 silicon Substances 0.000 description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 229910000077 silane Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 9
- 229910052697 platinum Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- 125000005843 halogen group Chemical group 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- VMAWODUEPLAHOE-UHFFFAOYSA-N 2,4,6,8-tetrakis(ethenyl)-2,4,6,8-tetramethyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound C=C[Si]1(C)O[Si](C)(C=C)O[Si](C)(C=C)O[Si](C)(C=C)O1 VMAWODUEPLAHOE-UHFFFAOYSA-N 0.000 description 6
- 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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 150000003961 organosilicon compounds Chemical class 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052693 Europium Inorganic materials 0.000 description 4
- 229910004283 SiO 4 Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class 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
- 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
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 3
- RCNRJBWHLARWRP-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane;platinum Chemical compound [Pt].C=C[Si](C)(C)O[Si](C)(C)C=C RCNRJBWHLARWRP-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000003566 sealing material Substances 0.000 description 3
- 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 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000005046 Chlorosilane Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 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 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- BYLOHCRAPOSXLY-UHFFFAOYSA-N dichloro(diethyl)silane Chemical compound CC[Si](Cl)(Cl)CC BYLOHCRAPOSXLY-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 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 2
- KPWVUBSQUODFPP-UHFFFAOYSA-N ethenyl-(ethenyl-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C=C)O[Si](C)(C=C)C1=CC=CC=C1 KPWVUBSQUODFPP-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000002223 garnet Substances 0.000 description 2
- 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 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 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 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 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 2
- 125000005375 organosiloxane group Chemical group 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
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011253 protective coating Substances 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000002683 reaction inhibitor Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000005372 silanol group Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 2
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 125000003944 tolyl group Chemical group 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
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 2
- 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 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 1
- IDXCKOANSQIPGX-UHFFFAOYSA-N (acetyloxy-ethenyl-methylsilyl) acetate Chemical compound CC(=O)O[Si](C)(C=C)OC(C)=O IDXCKOANSQIPGX-UHFFFAOYSA-N 0.000 description 1
- AWFOOUAPWFZKQK-UHFFFAOYSA-N (acetyloxy-methyl-phenylsilyl) acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)C1=CC=CC=C1 AWFOOUAPWFZKQK-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
- 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
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 1
- RMZNKGBPQWTSFN-UHFFFAOYSA-N 2,2-diphenylethoxy(methyl)silane Chemical compound C[SiH2]OCC(C1=CC=CC=C1)C1=CC=CC=C1 RMZNKGBPQWTSFN-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 1
- KSLSOBUAIFEGLT-UHFFFAOYSA-N 2-phenylbut-3-yn-2-ol Chemical compound C#CC(O)(C)C1=CC=CC=C1 KSLSOBUAIFEGLT-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PRGQSGOSJPDWNL-UHFFFAOYSA-N C1(=CC=CC2=CC3=CC=CC=C3C=C12)[SiH2][SiH2][SiH3] Chemical compound C1(=CC=CC2=CC3=CC=CC=C3C=C12)[SiH2][SiH2][SiH3] PRGQSGOSJPDWNL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- BFJMRDORZHTMEZ-UHFFFAOYSA-N [acetyloxy(2-phenylethenyl)silyl] acetate Chemical compound C1(=CC=CC=C1)C=C[SiH](OC(C)=O)OC(C)=O BFJMRDORZHTMEZ-UHFFFAOYSA-N 0.000 description 1
- RQVFGTYFBUVGOP-UHFFFAOYSA-N [acetyloxy(dimethyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(C)OC(C)=O RQVFGTYFBUVGOP-UHFFFAOYSA-N 0.000 description 1
- ZGKIFMFVVLNYAN-UHFFFAOYSA-N [diacetyloxy(anthracen-1-yl)silyl] acetate Chemical compound C1=CC=C2C=C3C([Si](OC(C)=O)(OC(C)=O)OC(=O)C)=CC=CC3=CC2=C1 ZGKIFMFVVLNYAN-UHFFFAOYSA-N 0.000 description 1
- TVJPBVNWVPUZBM-UHFFFAOYSA-N [diacetyloxy(methyl)silyl] acetate Chemical compound CC(=O)O[Si](C)(OC(C)=O)OC(C)=O TVJPBVNWVPUZBM-UHFFFAOYSA-N 0.000 description 1
- VLFKGWCMFMCFRM-UHFFFAOYSA-N [diacetyloxy(phenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C1=CC=CC=C1 VLFKGWCMFMCFRM-UHFFFAOYSA-N 0.000 description 1
- UCLSUQHCFCXETM-UHFFFAOYSA-N [diacetyloxy(pyren-1-yl)silyl] acetate Chemical compound C1=C2C([Si](OC(C)=O)(OC(C)=O)OC(=O)C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 UCLSUQHCFCXETM-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- BTHCBXJLLCHNMS-UHFFFAOYSA-N acetyloxysilicon Chemical compound CC(=O)O[Si] BTHCBXJLLCHNMS-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
- H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
- H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
- H01L2224/321—Disposition
- H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/32245—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/4805—Shape
- H01L2224/4809—Loop shape
- H01L2224/48091—Arched
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/481—Disposition
- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
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Abstract
【解決手段】 (A)平均単位式で表され、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、任意の(B)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水素原子を有さない直鎖状オルガノポリシロキサン、(C)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ポリシロキサンであって、本成分中、式:H(CH3)2SiO(C6H5)2SiOSi(CH3)2Hで表されるオルガノトリシロキサンを少なくとも80質量%有するオルガノポリシロキサン、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硬化性シリコーン組成物。
【選択図】 図1
Description
(A)平均単位式:
(R1R2R3SiO1/2)a(R4 2SiO2/2)b(R2SiO3/2)c
(式中、R1は炭素数1〜12のアルキル基であり、R2は同じかまたは異なる、炭素数6〜20のアリール基もしくは炭素数7〜20のアラルキル基であり、R3は炭素数2〜12のアルケニル基であり、R4は同じかまたは異なる、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、もしくはフェニル基であり、a、b、およびcは、それぞれ、0.01≦a≦0.5、0≦b≦0.7、0.1≦c<0.9、かつa+b+c=1を満たす数である。)
で表され、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、
(B)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水素原子を有さない直鎖状オルガノポリシロキサン(本組成物に対して、0〜70質量%)、
(C)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ポリシロキサンであって、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサンを本成分中、少なくとも80質量%有するオルガノポリシロキサン{(A)成分中と(B)成分中のアルケニル基の合計1モルに対して、本成分中のケイ素原子結合水素原子が0.1〜5モルとなる量}、および
(D)有効量のヒドロシリル化反応用触媒
から少なくともなることを特徴とする。
(A)成分のオルガノポリシロキサンは、本組成物の主剤であり、平均単位式:
(R1R2R3SiO1/2)a(R4 2SiO2/2)b(R2SiO3/2)c
で表され、一分子中に少なくとも2個のアルケニル基を有する。
R2SiX3
で表されるシラン化合物、および一般式(II−1):
R1R2R3SiOSiR1R2R3
で表されるジシロキサンおよび/または一般式(II−2):
R1R2R3SiX
で表されるシラン化合物を、酸もしくはアルカリの存在下、加水分解・縮合反応させる方法が挙げられる。
R2SiX3
で表されるシラン化合物は、オルガノポリシロキサンに、式:R2SiO3/2で表されるシロキサン単位を導入するための原料である。式中、R2は炭素数6〜20のアリール基または炭素数7〜20のアラルキル基であり、前記と同様の基が例示され、好ましくは、フェニル基またはナフチル基である。また、式中、Xはアルコキシ基、アシロキシ基、ハロゲン原子、または水酸基である。Xのアルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基が例示される。また、Xのアシロキシ基としては、アセトキシ基が例示される。また、Xのハロゲン原子としては、塩素原子、臭素原子が例示される。
R1R2R3SiOSiR1R2R3
で表されるジシロキサンは、オルガノポリシロキサンに、式:R1R2R3SiO1/2で表されるシロキサン単位を導入するための原料である。式中、R1は炭素数1〜12のアルキル基であり、前記と同様の基が例示され、好ましくは、メチル基である。また、式中、R2は炭素数6〜20のアリール基または炭素数7〜20のアラルキル基であり、前記と同様の基が例示され、好ましくは、フェニル基またはナフチル基である。また、式中、R3は炭素数2〜12のアルケニル基であり、前記と同様の基が例示され、好ましくは、ビニル基である。
R1R2R3SiX
で表されるシラン化合物も、オルガノポリシロキサンに、式:R1R2R3SiO1/2で表されるシロキサン単位を導入するための原料である。式中、R1は炭素数1〜12のアルキル基であり、前記と同様の基が例示され、好ましくは、メチル基である。また、式中、R2は炭素数6〜20のアリール基または炭素数6〜20のアラルキル基であり、前記と同様の基が例示され、好ましくは、フェニル基またはナフチル基である。また、式中、R3は炭素数2〜12のアルケニル基であり、前記と同様の基が例示され、好ましくは、ビニル基である。また、式中、Xはアルコキシ基、アシロキシ基、ハロゲン原子、または水酸基であり、前記と同様の基が例示される。
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサンを本成分中、少なくとも80質量%有するオルガノポリシロキサンである。これは、上記のオルガノトリシロキサンを架橋剤として用いると、上記(A)成分に対して、良好な反応性を有し、本組成物を速やかに硬化することができるからである。また、上記のようなオルガノトリシロキサンは、本組成物の粘度を低下させ、本組成物の取扱作業性を向上することができる。
本発明の硬化物は、上記の硬化性シリコーン組成物を硬化してなることを特徴とする。硬化物の形状は特に限定されず、例えば、シート状、フィルム状が挙げられる。硬化物は、これを単体で取り扱うこともできるが、光半導体素子等を被覆もしくは封止した状態で取り扱うことも可能である。
本発明の光半導体装置は、上記の硬化性シリコーン組成物の硬化物により光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光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、光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。
硬化性シリコーン組成物の硬化速度を、示差走査熱量計(SIIナノテクノロジー社製のDSC7000)を用いて、加熱速度10℃/分で測定したときの発熱ピーク温度(℃)、およびキュラストメータ(ALPHA TECHNOLOGIES社製のRHEOMETER MDR2000)を用いて、測定温度150℃、ダイの振れ角1°で測定したときの、トルク値が1dNmに達するまでの時間(秒)により評価した。
硬化性シリコーン組成物をプレスを用いて150℃、2時間で硬化させ、厚み1mmの硬化フィルムを作製した。その硬化フィルムの水蒸気透過率をJIS Z0208のカップ法に準拠して、温度40℃、相対湿度90%の条件で測定した。
硬化性シリコーン組成物を用いて、150℃、2時間加熱して、図1で示される光半導体装置を作製した。この光半導体装置を、50℃、相対湿度75%、硫化水素ガス濃度20ppmの条件下で24時間暴露試験した。光半導体装置の暴露試験前後での発光効率の変化を測定し、光半導体装置の信頼性を評価した。
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。室温まで冷却し、酢酸 0.68g(11.4mmol)を投入し、中和反応を行った。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、無色透明なガム状粘稠液体 347g(収率:98%)を得た。
[(CH3)(C6H5)CH2=CHSiO1/2]0.23(C6H5SiO3/2)0.77
で表されるオルガノポリシロキサンであることがわかった。このオルガノポリシロキサンの質量平均分子量(Mw)は1617であり、分散度(Mw/Mn)は1.16であった。
合成例1で調製したオルガノポリシロキサン 77.9質量部、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサン 21.9質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が1となる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度8,300mPa・sの硬化性シリコーン組成物を調製した。
合成例1で調製したオルガノポリシロキサン 64.7質量部、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 15.2質量部、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサン 20.0質量部(上記オルガノポリシロキサン中と上記メチルフェニルポリシロキサン中のビニル基の合計1モルに対し、本成分中のケイ素原子結合水素原子が1となる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度4,300mPa・sの硬化性シリコーン組成物を調製した。
合成例1で調製したオルガノポリシロキサン 76.3質量部、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサン 20.0質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が0.9モルとなる量)、平均式:
H(CH3)2SiO(C6H5)2.5SiOSi(CH3)2H
で表されるオルガノポリシロキサン 3.5質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が0.1モルとなる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度11,500mPa・sの硬化性シリコーン組成物を調製した。
合成例1で調製したオルガノポリシロキサン 77.8質量部、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノポリシロキサン 18.7質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が0.72モルとなる量)、平均単位式:
(C6H5SiO3/2)0.4[(CH3)2HSiO1/2)0.6
で表されるオルガノトリシロキサン 3.3質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が0.28モルとなる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度10,600mPa・sの硬化性シリコーン組成物を調製した。
合成例1で調製したオルガノポリシロキサン 65.2質量部、平均式:
H(CH3)2SiO(C6H5)2.5SiOSi(CH3)2H
で表されるオルガノポリシロキサン 34.8質量部(上記オルガノポリシロキサン中のビニル基1モルに対し、本成分中のケイ素原子結合水素原子が1モルとなる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度28,500mPa・sの硬化性シリコーン組成物を調製した。
合成例1で調製したオルガノポリシロキサン 53.6質量部、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 15.2質量部、平均式:
H(CH3)2SiO(C6H5)2.5SiOSi(CH3)2H
で表されるオルガノポリシロキサン 31.2質量部(上記オルガノポリシロキサン中と上記メチルフェニルポリシロキサン中のビニル基の合計1モルに対し、本成分中のケイ素原子結合水素原子が1となる量)、および白金−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溶液(白金を0.1質量%含有) 0.2質量部を混合して、粘度12,300mPa・sの硬化性シリコーン組成物を調製した。
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサンを用いると、硬化性シリコーン組成物の粘度が低下し、また、その硬化速度が速くなることがわかった。
実施例1で調製した硬化性シリコーン組成物を用いて光半導体装置を作製した。この光半導体装置の信頼性を評価したところ、暴露試験前後での光半導体装置の発光効率の変化は観察されなかった。
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 (4)
- (A)平均単位式:
(R1R2R3SiO1/2)a(R4 2SiO2/2)b(R2SiO3/2)c
(式中、R1は炭素数1〜12のアルキル基であり、R2は同じかまたは異なる、炭素数6〜20のアリール基もしくは炭素数7〜20のアラルキル基であり、R3は炭素数2〜12のアルケニル基であり、R4は同じかまたは異なる、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、もしくはフェニル基であり、a、b、およびcは、それぞれ、0.01≦a≦0.5、0≦b≦0.7、0.1≦c<0.9、かつa+b+c=1を満たす数である。)
で表され、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、
(B)一分子中に少なくとも2個のアルケニル基を有し、ケイ素原子結合水素原子を有さない直鎖状オルガノポリシロキサン(本組成物に対して、0〜70質量%)、
(C)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ポリシロキサンであって、式:
H(CH3)2SiO(C6H5)2SiOSi(CH3)2H
で表されるオルガノトリシロキサンを本成分中、少なくとも80質量%有するオルガノポリシロキサン{(A)成分中と(B)成分中のアルケニル基の合計1モルに対して、本成分中のケイ素原子結合水素原子が0.1〜5モルとなる量}、および
(D)有効量のヒドロシリル化反応用触媒
から少なくともなる硬化性シリコーン組成物。 - (A)成分中、R2がフェニル基またはナフチル基である、請求項1記載の硬化性シリコーン組成物。
- 請求項1または2記載の硬化性シリコーン組成物を硬化してなる硬化物。
- 請求項1または2記載の硬化性シリコーン組成物の硬化物で光半導体素子が封止された光半導体装置。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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JP2012235184A JP6157085B2 (ja) | 2012-10-24 | 2012-10-24 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
KR1020157013087A KR101875382B1 (ko) | 2012-10-24 | 2013-10-23 | 경화성 실리콘 조성물, 이의 경화물, 및 광반도체 장치 |
US14/438,102 US9683084B2 (en) | 2012-10-24 | 2013-10-23 | Curable silicone composition, cured product thereof, and optical semiconductor device |
CN201380055100.8A CN104755569B (zh) | 2012-10-24 | 2013-10-23 | 可固化有机硅组合物、其固化产物及光学半导体器件 |
EP13792109.4A EP2912129B1 (en) | 2012-10-24 | 2013-10-23 | Curable silicone composition, cured product thereof, and optical semiconductor device |
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JP6081774B2 (ja) | 2012-10-30 | 2017-02-15 | 東レ・ダウコーニング株式会社 | 硬化性シリコーン組成物、その硬化物、および光半導体装置 |
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JP2022178085A (ja) * | 2021-05-19 | 2022-12-02 | デュポン・東レ・スペシャルティ・マテリアル株式会社 | 硬化性シリコーン組成物、封止剤、及び光半導体装置 |
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KR20150080521A (ko) | 2015-07-09 |
WO2014065433A1 (en) | 2014-05-01 |
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CN104755569B (zh) | 2017-12-22 |
EP2912129A1 (en) | 2015-09-02 |
KR101875382B1 (ko) | 2018-07-06 |
JP6157085B2 (ja) | 2017-07-05 |
US20150284514A1 (en) | 2015-10-08 |
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