CN106459102A - 有机硅氧烷、固化性有机硅组合物及半导体装置 - Google Patents
有机硅氧烷、固化性有机硅组合物及半导体装置 Download PDFInfo
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- CN106459102A CN106459102A CN201580034092.8A CN201580034092A CN106459102A CN 106459102 A CN106459102 A CN 106459102A CN 201580034092 A CN201580034092 A CN 201580034092A CN 106459102 A CN106459102 A CN 106459102A
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- composition
- organosiloxane
- curable silicone
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- 239000000203 mixture Substances 0.000 title claims abstract description 134
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 100
- 125000005375 organosiloxane group Chemical group 0.000 title claims abstract description 48
- 239000004065 semiconductor Substances 0.000 title claims abstract description 28
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 48
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 23
- -1 polysiloxanes Polymers 0.000 claims description 71
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 239000000126 substance Substances 0.000 claims description 25
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- 150000004678 hydrides Chemical class 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 9
- 238000007711 solidification Methods 0.000 claims description 8
- 230000008023 solidification Effects 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 230000001737 promoting effect Effects 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 3
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 239000007809 chemical reaction catalyst Substances 0.000 abstract 1
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 abstract 1
- 239000002585 base Substances 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 229920002554 vinyl polymer Polymers 0.000 description 18
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 17
- 229910020388 SiO1/2 Inorganic materials 0.000 description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 229910052684 Cerium Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 229910000077 silane Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- 229910020485 SiO4/2 Inorganic materials 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 150000003961 organosilicon compounds Chemical class 0.000 description 7
- KFJDQPJLANOOOB-UHFFFAOYSA-N 2h-benzotriazole-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=NNN=C12 KFJDQPJLANOOOB-UHFFFAOYSA-N 0.000 description 6
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229910020447 SiO2/2 Inorganic materials 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 125000005372 silanol group Chemical group 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 229910052693 Europium Inorganic materials 0.000 description 5
- 239000004954 Polyphthalamide Substances 0.000 description 5
- 239000002253 acid Substances 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
- 229920006375 polyphtalamide Polymers 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011787 zinc oxide Substances 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 150000003851 azoles Chemical class 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
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000003944 tolyl group Chemical group 0.000 description 4
- 125000005023 xylyl group Chemical group 0.000 description 4
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 125000001246 bromo group Chemical group Br* 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 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
- 125000005388 dimethylhydrogensiloxy group Chemical group 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 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
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 230000003287 optical effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000004344 phenylpropyl group Chemical group 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 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
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000000703 Cerium Chemical class 0.000 description 2
- 241000555268 Dendroides Species 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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910020487 SiO3/2 Inorganic materials 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000005370 alkoxysilyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000004087 circulation Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 150000007973 cyanuric acids Chemical class 0.000 description 2
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 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
- 150000002118 epoxides Chemical class 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- 239000002223 garnet Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound 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
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 150000004767 nitrides Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 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
- 238000010992 reflux Methods 0.000 description 2
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 2
- 159000000000 sodium salts 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
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- 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
- YFSYFAJGRGDWQT-KTKRTIGZSA-N (z)-1-(benzotriazol-1-yl)octadec-9-en-1-one Chemical compound C1=CC=C2N(C(=O)CCCCCCC\C=C/CCCCCCCC)N=NC2=C1 YFSYFAJGRGDWQT-KTKRTIGZSA-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 class 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
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
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- 235000011149 sulphuric acid Nutrition 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- GQUJEMVIKWQAEH-UHFFFAOYSA-N titanium(III) oxide Chemical compound O=[Ti]O[Ti]=O GQUJEMVIKWQAEH-UHFFFAOYSA-N 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- 239000011667 zinc carbonate Substances 0.000 description 1
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- 235000004416 zinc carbonate Nutrition 0.000 description 1
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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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/10—Polycondensates containing more than one epoxy group per molecule of polyamines with epihalohydrins or precursors thereof
-
- 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
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及由通式表示的有机硅氧烷;至少包含(A)一分子中具有至少2个烯基的有机聚硅氧烷、(B)一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷、(C)包含所述有机硅氧烷的粘合促进剂、及(D)氢化硅烷化反应用催化剂的固化性有机硅组合物;以及一种通过所述组合物的固化物对半导体元件密封而成的半导体装置。本发明提供:新型的有机硅氧烷;固化性有机硅组合物,其含有该有机硅氧烷作为粘合促进剂、对于各种基材形成粘合性优异的固化物;以及使用该组合物而成的可靠性优异的半导体装置。
Description
技术领域
本发明涉及新型的有机硅氧烷、含有该有机硅氧烷作为粘合促进剂的固化性有机硅组合物、以及使用该组合物而成的半导体装置。
背景技术
一般而言,氢化硅烷化反应固化性有机硅组合物对于金属或有机树脂、特别是热塑性树脂等基材的粘合性不足,因此例如提出有:固化性有机硅组合物,其包含:具有结合于硅原子的烯基的有机聚硅氧烷、具有与硅原子结合的氢原子的有机氢化聚硅氧烷、包含异氰脲酸衍生物的粘合促进剂、以及氢化硅烷化反应用催化剂,其中,所述异氰脲酸衍生物分别具有选自如下的一种以上的基团:选自环氧基、环氧丙氧基、烷氧基甲硅烷基中的一种以上的官能团、交联性的乙烯基和氢化硅烷基(Si-H基团)(参照专利文献1);固化性有机硅组合物,其包含:一分子中具有至少2个烯基的有机聚硅氧烷、一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷、一分子中具有烯丙基、环氧基及有机甲硅烷氧基的含异氰脲环的有机硅氧烷、以及氢化硅烷化反应用催化剂(参照专利文献2);以及固化性有机硅组合物,其包含:具有结合于硅原子的烯基的有机聚硅氧烷、具有结合于硅原子的氢原子的有机氢化聚硅氧烷、粘合促进剂、以及氢化硅烷化反应用催化剂,其中,所述粘合促进剂含有:分别具有烷氧基甲硅烷基和/或环氧基和2价含甲硅烷氧基单元的基团的异氰脲酸衍生物、具有烷氧基和/或环氧基且不含异氰脲环的硅烷或硅氧烷化合物(参照专利文献3)。
但是,即使是这些固化有机硅组合物,在固化过程中对于接触的基材也存在粘合力不充分的问题。
现有技术文献
专利文献
专利文献1:日本特开2010-065161号公报
专利文献2:日本特开2011-057755号公报
专利文献3:日本特开2011-208120号公报
发明内容
发明所要解决的问题
本发明的目的在于提供新型的有机硅氧烷、含有该有机硅氧烷作为粘合促进剂、对于各种基材形成粘合性优异的固化物的固化性有机硅组合物、以及使用该组合物而成的可靠性优异的半导体装置。
解决问题的技术方案
本发明的有机硅氧烷由以下通式表示:
[化学式1]
(式中,R1为相同或不同的、不具有脂肪族不饱和键的碳原子数1~12的一价烃基,R2为碳原子数2~12的烯基,R3为相同或不同的碳原子数1~3的烷基,X为通式:
[化学式2]
(式中,R1与上述相同,R4为相同或不同的亚烷基,p为0~50的整数、q为0或1)表示的基团,m为0~50的整数,n为1~50的整数。}。
本发明的固化性有机硅组合物含有上述有机硅氧烷作为粘合促进剂,优选通过氢化硅烷化反应固化,进一步优选至少包含以下组分:
(A)一分子中具有至少2个烯基的有机聚硅氧烷100质量份;
(B)一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷{其量为相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,使提供与硅原子结合的氢原子的量为0.1~10.0摩尔};
(C)包含上述有机硅氧烷的粘合促进剂0.01~50质量份;及
(D)氢化硅烷化反应用催化剂(其量为充分促进本组合物固化的量)。
本发明的半导体装置的特征在于,通过上述固化性有机硅组合物的固化物对半导体元件进行密封,优选该半导体元件为发光元件。
发明效果
本发明的有机硅氧烷为新型的化合物,其特征在于可以对固化性有机硅组合物赋予优异的粘合性。此外,本发明的固化性有机硅组合物的特征在于,在固化过程中对于接触的各种基材形成粘合性优异的固化物。由于本发明的半导体装置通过上述组合物的固化物对半导体元件进行包覆,因此其特征还在于可靠性优异。
附图说明
图1是作为本发明的半导体装置一例的LED的剖面图。
具体实施方式
首先,对本发明的有机硅氧烷详细地进行说明。
本发明的有机硅氧烷由通式:
[化学式3]
表示。
式中,R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基。具体而言,可示例:甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、新戊基、己基、环己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基等烷基;苯基、甲苯基、二甲苯基、萘基等芳基;苄基、苯乙基、苯丙基等芳烷基;将这些基团的氢原子中的一部分或全部被氟原子、氯原子、溴原子等卤素原子取代的基团,优选为甲基、苯基。
式中,R2为碳原子数2~12的烯基。具体而言,可示例:乙烯基、烯丙基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基,优选为乙烯基。
式中,R3为相同或不同的碳原子数1~3的烷基。具体而言,可示例甲基、乙基、丙基,优选为甲基。
式中,X为通式:
[化学式4]
表示的基团。
式中,R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基,可示例与上述同样的基团。
式中,R4为相同或不同的碳原子数2~12的亚烷基。具体而言,可示例:亚乙基、亚丙基、亚丁基、亚戊基、亚己基、亚庚基、亚辛基、亚壬基、亚癸基、亚十一烷基、亚十二烷基,优选为亚乙基、亚丙基。
式中,p为0~50的整数,优选为0~30的整数,进一步优选为0~10的整数。此外,式中,q为0或1。
式中,m为0~50的整数,优选为0~30的整数,进一步优选为0~15的整数。此外,式中,n为1~50的整数,优选为1~30的整数,进一步优选为1~15的整数。此外,m+n为2~100的整数,优选为2~50的整数,进一步优选为2~30的整数。这是因为:当m为上限以上时,对固化性有机硅组合物的溶解性减少;当n为下限以上时,粘合促进剂容易进入固化性有机硅组合物,另一方面,当n为上限以下时,不易发生固化阻碍。另外是因为:当m+n为下限以上时,容易溶解于固化性有机硅组合物,另一方面,当m+n为上限以下时,操作性提高。
制备这种有机硅氧烷的方法并没有限定,例如可举出使通式:
[化学式5]
表示的有机硅氧烷与通式:
[化学式6]
表示的化合物在酸或碱催化剂下反应的方法。
在上述的有机硅氧烷中,式中的R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基,可示例与上述同样的基团。此外,式中,R2为碳原子数2~12的烯基,可示例与上述同样的基团。此外,式中,m和n为与上述同样的整数。
作为这种有机硅氧烷,可示例如下的化合物。予以说明,式中,m’为1~50的整数,n为1~50的整数。
[化学式7]
[化学式8]
[化学式9]
另外,在上述的化合物中,式中,R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基,可示例与上述同样的基团。此外,式中,R3为相同或不同的碳原子数1~3的烷基,可示例与上述同样的基团。此外,式中,R4为相同或不同的碳原子数2~12的亚烷基,可示例与上述同样的基团。此外,式中,p为与上述同样的整数,q为0或1。
作为这种化合物,可示例如下的化合物。
[化学式10]
在上述的制备方法中,需要相对于上述的有机硅氧烷每1摩尔,使上述的化合物的量为至少1摩尔~2摩尔进行反应。这是因为:当上述的化合物的量为上述范围的下限以上时,得到的有机硅氧烷可以对固化性有机硅组合物赋予充分的粘合性,另一方面,当上述的化合物的量为上述范围的上限以下时,得到的有机硅氧烷与氢化硅烷化反应固化性有机硅组合物中的与硅原子结合的氢原子反应,可以提高得到的固化物的透过率。
作为上述的制备方法中使用的酸,可示例:盐酸、醋酸、甲酸、硝酸、草酸、硫酸、磷酸、聚磷酸、多元羧酸、三氟甲磺酸、离子交换树脂。此外,作为上述的制备方法中使用的碱,可示例:氢氧化钾、氢氧化钠、氢氧化钙、氢氧化镁等无机碱;三乙基胺、二乙基胺、单乙醇胺、二乙醇胺、三乙醇胺、氨水、四甲基氢氧化铵、具有氨基的烷氧基硅烷、氨丙基三甲氧基硅烷、硅醇钠、硅醇钾等有机碱化合物。
在上述的制备方法中,可以使用有机溶剂。作为可以使用的有机溶剂,可示例:醚类、酮类、乙酸酯类、芳香族或脂肪烃、γ-丁内酯、以及它们两种以上的混合物。作为优选的有机溶剂,可示例:丙二醇单甲醚、丙二醇单甲醚乙酸酯、丙二醇单乙醚、丙二醇单丙醚、丙二醇单丁醚、丙二醇单叔丁醚、γ-丁内酯、甲苯、二甲苯。
在上述的制备方法中,通过加热促进该反应,在使用有机溶剂的情况下,优选在其回流温度下进行反应。
接着,对本发明的固化性有机硅组合物进行说明。
本发明的固化性有机硅组合物的特征在于,含有上述有机硅氧烷作为粘合促进剂。这种固化性有机硅组合物的固化机理并没有限定,可示例氢化硅烷化反应、缩合反应、自由基反应,优选为氢化硅烷化反应。作为该氢化硅烷化反应固化性有机硅组合物,优选至少包含以下组分:
(A)一分子中具有至少2个烯基的有机聚硅氧烷100质量份;
(B)一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷{其量为相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,使提供与硅原子结合的氢原子的量为0.1~10摩尔};
(C)包含上述有机硅氧烷的粘合促进剂0.01~50质量份;及
(D)氢化硅烷化反应用催化剂。
(A)成分为作为本组合物的主剂,其为一分子中具有至少2个烯基的有机聚硅氧烷。作为(A)成分中的烯基,可示例:乙烯基、烯丙基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基等碳原子数为2~12个烯基,优选为乙烯基。此外,作为(A)成分中除了烯基以外的结合于硅原子的基团,可示例:甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、新戊基、己基、环己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基等碳原子数为1~12个烷基;苯基、甲苯基、二甲苯基、萘基等碳原子数为6~20个芳基;苄基、苯乙基、苯丙基等碳原子数为7~20个芳烷基;将这些基团的氢原子中的一部分或全部被氟原子、氯原子、溴原子等卤素原子取代的基团。予以说明,在(A)成分中的硅原子中,可以在不损害本发明的目的范围内具有少量的羟基或甲氧基、乙氧基等烷氧基。
(A)成分的分子结构并没有特别限定,可示例直链状、具有一部分支链的直链状、支链状、环状及三维网状结构。(A)成分可以为具有这些分子结构的一种有机聚硅氧烷、或具有这些分子结构的两种以上的有机聚硅氧烷混合物。
(A)成分在25℃时的性状并没有限定,例如为液态状或固体状。在(A)成分为液态状的情况下,其在25℃时的粘度优选为1~1,000,000mPa·s的范围内,特别优选为10~1,000,000mPa·s的范围内。予以说明,该粘度例如可以通过根据JIS K 7117-1使用B型粘度计的测定而求出。
作为这种(A)成分,除了分子链两末端由二甲基乙烯基甲硅烷氧基封端的二甲基聚硅氧烷、分子链两末端由二甲基乙烯基甲硅烷氧基封端的二甲基硅氧烷-甲基乙烯基硅氧烷共聚物、分子链两末端由二甲基乙烯基甲硅烷氧基封端的二甲基硅氧烷-甲基苯基硅氧烷共聚物、分子链两末端由二甲基乙烯基甲硅烷氧基封端的甲基苯基聚硅氧烷、分子链两末端由三甲基甲硅烷氧基封端的二甲基硅氧烷-甲基乙烯基硅氧烷共聚物、分子链两末端由三甲基甲硅烷氧基封端的二甲基硅氧烷-甲基乙烯基硅氧烷-甲基苯基硅氧烷共聚物、包含(CH3)3SiO1/2单元和(CH3)2(CH2=CH)SiO1/2单元和SiO4/2单元的共聚物、包含(CH3)2(CH2=CH)SiO1/2单元和SiO4/2单元的共聚物之外,可示例如下的有机聚硅氧烷。予以说明,式中,Me、Vi、Ph分别表示甲基、乙烯基、苯基,x、x’分别为1~5,000的整数。
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
(B)成分为本组合物的交联剂,为一分子中具有至少2个与硅原子结合的氢原子的有机聚硅氧烷。作为(B)成分的分子结构,例如可举出直链状、具有一部分支链的直链状、支链状、环状、树枝状,优选为直链状、具有一部分支链的直链状、树枝状。(B)成分中与硅原子结合的氢原子的结合位置并没有限定,例如可举出分子链的末端和/或侧链。此外,作为(B)成分中除了与硅原子结合的氢原子以外的结合于硅原子的基团,可示例:甲基、乙基、丙基等烷基;苯基、甲苯基、二甲苯基等芳基;苄基、苯乙基等芳烷基;3-氯丙基、3,3,3-三氟丙基等卤化烷基,优选为甲基、苯基。此外,(B)成分的粘度并没有限定,在25℃时的粘度优选为1~10,000mPa·s的范围内,特别优选为1~1,000mPa·s的范围内。
作为这种(B)成分,除了1,1,3,3-四甲基二硅氧烷、1,3,5,7-四甲基环四硅氧烷、三(二甲基氢甲硅烷氧基)甲基硅烷、三(二甲基氢甲硅烷氧基)苯基硅烷、1-环氧丙氧基丙基-1,3,5,7-四甲基环四硅氧烷、1,5-环氧丙氧基丙基-1,3,5,7-四甲基环四硅氧烷、1-环氧丙氧基丙基-5-三甲氧基甲硅烷基乙基-1,3,5,7-四甲基环四硅氧烷、分子链两末端由三甲基甲硅烷氧基封端的甲基氢聚硅氧烷、分子链两末端由三甲基甲硅烷氧基封端的二甲基硅氧烷-甲基氢硅氧烷共聚物、分子链两末端由二甲基氢甲硅烷氧基封端的二甲基聚硅氧烷、分子链两末端由二甲基氢甲硅烷氧基封端的二甲基硅氧烷-甲基氢硅氧烷共聚物、分子链两末端由三甲基甲硅烷氧基封端的甲基氢硅氧烷-二苯基硅氧烷共聚物、分子链两末端由三甲基甲硅烷氧基封端的甲基氢硅氧烷-二苯基硅氧烷-二甲基硅氧烷共聚物、三甲氧基硅烷的水解缩合物、包含(CH3)2HSiO1/2单元和SiO4/2单元的共聚物、以及包含(CH3)2HSiO1/2单元和SiO4/2单元和(C6H5)SiO3/2单元的共聚物之外,可示例如下的有机氢化聚硅氧烷。予以说明,式中,Me、Vi、Ph分别表示甲基、乙烯基、苯基,y、y’分别为1~100的整数,c、d、e、f分别为正数,其中,c、d、e、f的合计为1。
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
(B)成分的含量为相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,使本成分中与硅原子结合的氢原子的量为0.1~10摩尔,优选的量为0.5~5摩尔。这是因为:当(B)成分的含量为上述范围的上限以下时,得到的固化物的机械特性良好,另一方面,当(B)成分的含量为上述范围的下限以上时,得到的组合物的固化性良好。
(C)成分为用于对本组合物赋予粘合性的粘合促进剂。关于(C)成分,如上所述。(C)成分的含量相对于(A)成分100质量份为0.01~50质量份的范围内,优选为0.1~20质量份的范围内。这是因为:当(C)成分的含量为上述范围的下限以上时,可以对得到的组合物赋予充分的粘合性,另一方面,当(C)成分的含量为上述范围的下限以下时,不易阻碍得到的组合物的固化性,另外可以抑制得到的固化物的着色等。
(D)成分为用于促进本组合物的固化的氢化硅烷化反应用催化剂,可示例铂系催化剂、铑系催化剂、钯系催化剂。特别是由于可以显著地促进本组合物的固化,因此(D)成分优选为铂系催化剂。作为该铂系催化剂,可示例铂微粉末、氯铂酸、氯铂酸的乙醇溶液、铂-烯基硅氧烷络合物、铂-烯烃络合物、铂-羰基络合物,优选为铂-烯基硅氧烷络合物。
(D)成分的含量为用于促进本组合物的固化的有效量。具体而言,从可以充分地促进本组合物的固化反应方面考虑,(D)成分的含量相对于本组合物,使(D)成分中的催化剂金属以质量单位计优选的量为0.01~500ppm的范围内,进一步优选的量为0.01~100ppm的范围内,特别优选的量为0.01~50ppm的范围内。
另外,在本组合物中,作为其它任意的成分,可以含有2-甲基-3-丁炔-2-醇、3,5-二甲基-1-己炔-3-醇、2-苯基-3-丁炔-2-醇等炔醇;3-甲基-3-戊烯-1-炔、3,5-二甲基-3-己烯-1-炔等烯炔化合物;1,3,5,7-四甲基-1,3,5,7-四乙烯基环四硅氧烷、1,3,5,7-四甲基-1,3,5,7-四己烯基环四硅氧烷、苯并三唑等(E)氢化硅烷化反应抑制剂。在本组合物中,该(E)成分的含量并没有限定,相对于上述(A)成分~(D)成分的合计100质量份,优选为0.0001~5质量份的范围内。
在本组合物中,为了提高相对于在固化过程中接触的基材的固化物的粘合性,还可以含有除了(C)成分以外的粘合促进剂。作为该粘合促进剂,优选一分子中具有至少1个结合于硅原子的烷氧基的有机硅化合物。作为该烷氧基,可示例甲氧基、乙氧基、丙氧基、丁氧基、甲氧基乙氧基,特别优选甲氧基。此外,作为除了结合于该有机硅化合物硅原子的烷氧基以外的基团,可示例:烷基、烯基、芳基、芳烷基、卤化烷基等取代或未取代的一价烃基;3-环氧丙氧基丙基、4-环氧丙氧基丁基等环氧丙氧基烷基;2-(3,4-环氧环己基)乙基、3-(3,4-环氧环己基)丙基等环氧环己基烷基;3,4-环氧丁基、7,8-环氧辛基等环氧烷基;3-甲基丙烯酰氧基丙基等含丙烯酸基的一价有机基团;氢原子。该有机硅化合物优选具有与硅原子结合的烯基或与硅原子结合的氢原子。作为这种有机硅化合物,可示例:有机硅烷化合物、有机硅氧烷低聚物、烷基硅酸盐。作为该有机硅氧烷低聚物或烷基硅酸盐的分子结构,可示例直链状、具有一部分支链的直链状、支链状、环状、网状,特别优选为直链状、支链状、网状。作为这种有机硅化合物,可示例:3-环氧丙氧基丙基三甲氧基硅烷、2-(3,4-环氧环己基)乙基三甲氧基硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷等硅烷化合物;一分子中分别具有至少各1个与硅原子结合的烯基或与硅原子结合的氢原子及与硅原子结合的烷氧基的硅氧烷化合物;由下列化合物构成的混合物:具有至少1个与硅原子结合的烷氧基的硅烷化合物或硅氧烷化合物、一分子中分别具有至少各1个与硅原子结合的羟基及与硅原子结合的烯基的硅氧烷化合物;甲基聚硅酸盐;乙基聚硅酸盐;含环氧基的乙基聚硅酸盐。
在本组合物中,还可以配入荧光体,其用于对从用本组成的固化物密封或包覆而成的发光元件发出的光的波长进行转换而得到所期望波长的光。作为这种荧光体,可示例被广泛利用于发光二极管(LED)的包含氧化物系荧光体、氧氮化物系荧光体、氮化物系荧光体、硫化物系荧光体、氧硫化物系荧光体等的黄色、红色、绿色、蓝色发光荧光体。作为氧化物系荧光体,可示例:包含铈离子的钇、铝、石榴石系的YAG系绿色~黄色发光荧光体、包含铈离子的铽、铝、石榴石系的TAG系黄色发光荧光体、以及包含铈或铕离子的硅酸盐系绿色~黄色发光荧光体。作为氧氮化物系荧光体,可示例包含铕离子的硅、铝、氧、氮系的赛隆(SiAlON)系红色~绿色发光荧光体。作为氮化物系荧光体,可示例包含铕离子的钙、锶、铝、硅、氮系的CASN(CaAlSiN3)系红色发光荧光体。作为硫化物系荧光体,可示例包含铜离子或铝离子的ZnS系绿色发色荧光体。作为氧硫化物系荧光体,可示例包含铕离子的Y2O2S系红色发光荧光体。这些荧光体可以使用一种或两种以上的混合物。在本组合物中,荧光体的含量相对于(A)成分~(D)成分的合计量为0.1~70质量%的范围内,优选为1~20质量%的范围内。
另外,在本组合物中,只要不损害本发明的目的,则作为其它任意的成分,可以含有二氧化硅、玻璃、氧化铝、氧化锌等无机质填充剂;聚甲基丙烯酸酯树脂等有机树脂微粉末;耐热剂、染料、颜料、阻燃剂、溶剂等。
在本组合物中,为了充分地抑制空气中的含硫气体导致光半导体装置中的银电极或基板镀银变色,还可以含有选自由表面包覆有选自由Al、Ag、Cu、Fe、Sb、Si、Sn、Ti、Zr及稀土元素构成的组中的至少一种元素的氧化物的氧化锌微粉末、以不具有烯基的有机硅化合物进行表面处理的氧化锌微粉末、以及碳酸锌的水合物微粉末构成的组中的平均粒径为0.1nm~5μm的至少一种微粉末。
在表面包覆有氧化物的氧化锌微粉末中,作为稀土元素,可示例钇、铈、铕。作为氧化锌微粉末表面的氧化物,可示例:Al2O3、AgO、Ag2O、Ag2O3、CuO、Cu2O、FeO、Fe2O3、Fe3O4、Sb2O3、SiO2、SnO2、Ti2O3、TiO2、Ti3O5、ZrO2、Y2O3、CeO2、Eu2O3、以及这些氧化物的两种以上的混合物。
在以有机硅化合物进行表面处理的氧化锌微粉末中,该有机硅化合物不具有烯基,可示例:有机硅烷、有机硅氮烷、聚甲基硅氧烷、有机氢化聚硅氧烷及有机硅氧烷低聚物,具体而言,可示例:三甲基氯硅烷、二甲基氯硅烷、甲基三氯硅烷等有机氯硅烷;甲基三甲氧基硅烷、甲基三乙氧基硅烷、苯基三甲氧基硅烷、乙基三甲氧基硅烷、正丙基三甲氧基硅烷、γ-甲基丙烯酰氧基丙基三甲氧基硅烷等有机三烷氧基硅烷;二甲基二甲氧基硅烷、二甲基二乙氧基硅烷、二苯基二甲氧基硅烷等二有机二烷氧基硅烷;三甲基甲氧基硅烷、三甲基乙氧基硅烷等三有机烷氧基硅烷;这些有机烷氧基硅烷的部分缩合物;六甲基二硅氮烷等有机硅氮烷;聚甲基硅氧烷、有机氢化聚硅氧烷、具有硅烷醇基或烷氧基的有机硅氧烷低聚物、包含R8SiO3/2单元(式中,R8为甲基、乙基、丙基等烷基;苯基等芳基中所示例的除烯基之外的一价烃基)或SiO4/2单元的具有硅烷醇基或烷氧基的树脂状有机聚硅氧烷。
另外,在本组合物中,从可以抑制空气中的含硫气体导致的银电极或基板镀银的变色方面考虑,作为任意的成分,还可以含有三唑系化合物。具体而言,可示例:1H-1,2,3-三唑、2H-1,2,3-三唑、1H-1,2,4-三唑、4H-1,2,4-三唑、2-(2'-羟基-5'-甲基苯基)苯并三唑、1H-1,2,3-三唑、2H-1,2,3-三唑、1H-1,2,4-三唑、4H-1,2,4-三唑、苯并三唑、甲苯基三唑、羧基苯并三唑、1H-苯并三唑-5-羧酸甲酯、3-氨基-1,2,4-三唑、4-氨基-1,2,4-三唑、5-氨基-1,2,4-三唑、3-巯基-1,2,4-三唑、氯苯并三唑、硝基苯并三唑、氨基苯并三唑、环己烷[1,2-d]三唑、4,5,6,7-四羟基甲苯基三唑、1-羟基苯并三唑、乙基苯并三唑、萘并三唑、1-N,N-双(2-乙基己基)-[(1,2,4-三唑-1-基)甲基]胺、1-[N,N-双(2-乙基己基)氨基甲基]苯并三唑、1-[N,N-双(2-乙基己基)氨基甲基]甲苯基三唑、1-[N,N-双(2-乙基己基)氨基甲基]羧基苯并三唑、1-[N,N-双(2-羟基乙基)-氨基甲基]苯并三唑、1-[N,N-双(2-羟基乙基)-氨基甲基]甲苯基三唑、1-[N,N-双(2-羟基乙基)-氨基甲基]羧基苯并三唑、1-[N,N-双(2-羟基丙基)氨基甲基]羧基苯并三唑、1-[N,N-双(1-丁基)氨基甲基]羧基苯并三唑、1-[N,N-双(1-辛基)氨基甲基]羧基苯并三唑、1-(2',3'-二-羟基丙基)苯并三唑、1-(2',3'-二-羧基乙基)苯并三唑、2-(2'-羟基-3',5'-二-叔丁基苯基)苯并三唑、2-(2'-羟基-3',5'-戊基苯基)苯并三唑、2-(2'-羟基-4'-辛氧基苯基)苯并三唑、2-(2'-羟基-5'-叔丁基苯基)苯并三唑、1-羟基苯并三唑-6-羧酸、1-油酰苯并三唑、1,2,4-三唑-3-醇、5-氨基-3-巯基-1,2,4-三唑、5-氨基-1,2,4-三唑-3-羧酸、1,2,4-三唑-3-羧酰胺、4-氨基尿唑及1,2,4-三唑-5-酮。该三唑系化合物的含量并没有特别限定,在本组合物中以质量单位计的量为0.01ppm~3%的范围内,优选的量为0.1ppm~1%的范围内。
在本组合物中,为了抑制得到的固化物的热老化导致的裂缝,作为其它任意的成分,还可以含有含铈有机聚硅氧烷。含铈有机聚硅氧烷例如可以通过氯化铈或羧酸的铈盐与含硅烷醇基有机聚硅氧烷的碱金属盐的反应而制备。
作为上述羧酸的铈盐,可示例:2-乙基己酸铈、环烷酸铈、油酸铈、月桂酸铈及硬脂酸铈。
另外,作为上述含硅烷醇基有机聚硅氧烷的碱金属盐,可示例:分子链两末端由硅烷醇基封端的二有机聚硅氧烷的钾盐、分子链两末端由硅烷醇基封端的二有机聚硅氧烷的钠盐、分子链单末端由硅烷醇基封端且一个分子链单末端由三有机甲硅烷氧基封端的二有机聚硅氧烷的钾盐、及分子链单末端由硅烷醇基封端且一个分子链单末端由三有机甲硅烷氧基封端的二有机聚硅氧烷的钠盐。予以说明,作为该有机聚硅氧烷中结合于硅原子的基团,可示例:甲基、乙基、丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、新戊基、己基、环己基、庚基、辛基、壬基、癸基、十一烷基及十二烷基等碳原子数为1~12个的烷基;苯基、甲苯基、二甲苯基及萘基等碳原子数为6~20个的芳基;苄基、苯乙基及苯丙基等碳原子数为7~20个的芳烷基;以及将这些基团的氢原子的一部分或全部被氟原子、氯原子、溴原子等卤素原子取代的基团。
上述的反应通过在甲醇、乙醇、异丙醇及丁醇等醇;甲苯及二甲苯等芳香烃;己烷及庚烷等脂肪烃;矿物油精、轻石油及石油醚等有机溶剂中、在室温下或加热而进行。此外,得到的反应产物优选根据需要蒸馏除去有机溶剂或低沸点成分、或过滤沉析物。此外,为了促进该反应,可以添加二烷基甲酰胺、六烷基磷酰胺等。这样所制备的含铈有机聚硅氧烷中的铈原子的含量优选为0.1~5质量%的范围内。
含铈有机聚硅氧烷的含量并没有限定,相对于本组合物,使铈原子以质量单位计优选的量为10~2,000ppm的范围内、为20~2,000ppm的范围内、为20~1,000ppm的范围内、或者为20~500ppm的范围内。这是因为:当含铈有机聚硅氧烷的含量为上述范围的下限以上时,可以提高得到的固化物的耐热性,另一方面,当含铈有机聚硅氧烷的含量为上述范围的上限以下时,可以减少用于光半导体器件时的发光色度变化。
本组合物在室温下或通过加热而进行固化,但为了迅速地使其固化,优选进行加热。作为该加热温度,优选为50~200℃的范围内。
接着,对本发明的半导体装置详细地进行说明。
本发明的半导体装置的特征在于,通过上述固化性有机硅组合物的固化物对半导体元件密封而成。作为这种本发明的半导体装置,可示例发光二极管(LED)、光电耦合器、CCD。此外,作为半导体元件,可示例发光二极管(LED)芯片、固态图像传感器。
作为本发明的半导体装置一例的单体表面贴装型LED的剖面图示于图1。图1所示的LED其发光元件(LED芯片)1芯片焊接在引线框架2上,该发光元件(LED芯片)1与引线框架3通过键合线4进行引线键合。在该发光元件(LED芯片)1的周围设有框架5,该框架5内侧的发光元件(LED芯片)1由本发明固化性有机硅组合物的固化物6密封。
作为制造如图1所示的表面贴装型LED的方法,可示例如下方法:将发光元件(LED芯片)1芯片焊接在引线框架2上,将该发光元件(LED芯片)1与引线框架3经金制的键合线4进行引线键合,接着,在设置于发光元件(LED芯片)1周围的框架5内侧填充本发明的固化性有机硅组合物之后,在50~200℃下进行加热,由此使其固化。
实施例
通过实施例详细地说明本发明的有机硅氧烷、固化性有机硅组合物及半导体装置。予以说明,式中,Me、Vi、Ph、Ep分别表示甲基、乙烯基、苯基、3-环氧丙氧基丙基。
[参考例1]
在反应容器中投入苯基三甲氧基硅烷400g(2.02mol)和1,3-二乙烯基-1,3-二苯基二甲基二硅氧烷93.5g(0.30mol),预混合后,投入三氟甲磺酸1.74g(11.6mmol),在搅拌下投入水110g(6.1mol),加热回流2小时。其后,进行加热常压蒸馏使温度达到85℃。接着,投入甲苯89g和氢氧化钾1.18g(21.1mmol),进行加热常压蒸馏使反应温度达到120℃,在该温度下反应6小时。其后,冷却至室温,投入醋酸0.68g(11.4mmol)并进行中和。滤除生成的盐之后,从得到的透明溶液中加热减压除去低沸点物质,制备成平均单元式:
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
表示的有机聚硅氧烷树脂347g(收率:98%)。
[实施例1]
在反应容器中加入平均式:
[化学式11]
表示的有机硅氧烷190g、式:
[化学式12]
表示的化合物598g和硅醇钾0.23g,在120~130℃下加热6小时,得到浅黄色液体。NMR分析的结果可知:该液体为平均式:
[化学式13]
(式中,X为式:
[化学式14]
表示的基团)
表示的有机硅氧烷。
[实施例2]
在反应容器中加入式:
[化学式15]
表示的有机硅氧烷26g、式:
[化学式16]
表示的化合物30g和氢氧化钙1.7g,在100℃下加热6小时,得到浅黄色液体。NMR分析的结果可知:该液体为平均式:
[化学式17]
(式中,X为式:
[化学式18]
表示的基团)
表示的有机硅氧烷。
[实施例3]
在反应容器中加入式:
[化学式19]
表示的有机硅氧烷10g、式:
[化学式20]
表示的化合物9.8g、氢氧化钙1.1g,在120~130℃下加热6小时,得到浅黄色液体。NMR分析的结果可知:该液体为平均式:
[化学式21]
(式中,X为式:
[化学式22]
表示的基团)
表示的有机硅氧烷。
[实施例4~8、比较例1~3]
使用下述成分制备如表1所示的固化性有机硅组合物。予以说明,表1中,(D)成分的含量以质量单位中的相对于固化性有机硅组合物的铂金属的含量(ppm)来表示。此外,表1中,SiH/Vi表示相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,(B)成分中与硅原子结合的氢原子的摩尔数。
作为(A)成分,使用以下成分:
(A-1)成分:平均单元式:
(Me2ViSiO1/2)0.2(PhSiO3/2)0.8
表示的有机聚硅氧烷
(A-2)成分:参考例1中制备的平均单元式
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
表示的有机聚硅氧烷
(A-3)成分:粘度为3,000mPa·s的分子链两末端由二甲基乙烯基甲硅烷氧基封端的甲基苯基聚硅氧烷
作为(B)成分,使用以下成分:
(B-1)成分:式:
HMe2SiOPh2SiOSiMe2H
表示的有机三硅氧烷
作为(C)成分,使用以下成分:
(C-1)成分:包含实施例1中制备的有机硅氧烷的粘合促进剂
(C-2)成分:包含实施例2中制备的有机硅氧烷的粘合促进剂
(C-3)成分:包含实施例3中制备的有机硅氧烷的粘合促进剂
(C-4)成分:包含在25℃时的粘度为30mPa·s的分子链两末端由硅烷醇基封端的甲基乙烯基硅氧烷低聚物与3-环氧丙氧基丙基三甲氧基硅烷的缩合反应物的粘合促进剂
作为(D)成分,使用以下成分:
(D-1)成分:铂-1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷络合物的1,3,5,7-四甲基-1,3,5,7-四乙烯基环四硅氧烷的溶液(含有铂为0.1质量%的溶液)
固化性有机硅组合物固化物的粘合力按照如下进行测定。
[粘合力]
将开有直径为5mm的孔、厚度为2mm的氟树脂制垫片设置在粘合用测试板(铝板、PPA树脂板、银板)上,向上述垫片的孔中注入固化性有机硅组合物之后,在150℃的热风循环式烘箱中放置1小时,由此制作成直径5mm×高度2mm的圆柱状固化物。使用剪切强度测定装置以50mm/分钟的速度对该固化物进行剥离,测定此时的负荷(MPa)。
使用固化性有机硅组合物按照如下制作表面贴装型的发光二极管(LED)。
[发光二极管的制作]
堵住底部的圆筒状聚邻苯二甲酰胺(PPA)树脂制框架5(内径2.0mm、深度1.0mm)中,引线框架2、3从侧壁向框架5内底部的中心部延伸,在引线框架2的中央部上载置有LED芯片1,在LED芯片1与引线框架3通过键合线4进行电连接的未密封的发光二极管内,利用点胶机注入经脱泡的固化性有机硅组合物。其后,加热烘箱中在100℃下加热30分钟,接着在150℃下加热1小时,使固化性有机硅组合物固化,由此制作成如图1所示的发光二极管。
[墨水试验]
将用上述方法制作的16个发光二极管浸渍在市售的红色墨水中,50℃下放置24小时。放置后,用显微镜观察红色墨水向发光二极管的渗入情况,按照如下进行评价:
◎:确认有墨水渗入的发光二极管为2个以下。
△:确认有墨水渗入的发光二极管为3个~8个。
×:确认有墨水渗入的发光二极管为9个以上。
[断线]
将用上述方法制作的16个发光二极管在-40℃下30分钟、接着在125℃下30分钟的温度循环设为1次循环,进行1000次循环的温度循环试验,随后通电检测LED的点亮情况,按照如下进行评价:
◎:点亮的发光二极管为14个以上。
○:点亮的发光二极管为8个~13个。
△:点亮的发光二极管为7个以下。
[表1]
[实施例8~9、比较例4~5]
使用以下成分制备如表2所示的固化性有机硅组合物。予以说明,表2中,(D)成分的含量以质量单位中的相对于固化性有机硅组合物的铂金属的含量(ppm)来表示。此外,表2中,SiH/Vi表示相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,(B)成分中与硅原子结合的氢原子的摩尔数。
作为(A)成分,除了上述(A-2)成分以外,可使用以下成分。此外,粘度为25℃时的值,根据JIS K 7117-1使用B型粘度计进行测定。此外,乙烯基的含量通过FT-IR、NMR、GPC等分析进行测定。
(A-4)成分:粘度为300mPa·s、平均式:
Me2ViSiO(Me2SiO)150SiMe2Vi
表示的分子链两末端由二甲基乙烯基甲硅烷氧基封端的二甲基聚硅氧烷(乙烯基的含量=0.48质量%)
(A-5)成分:粘度为10,000mPa·s、平均式:
Me2ViSiO(Me2SiO)500SiMe2Vi
表示的分子链两末端由二甲基乙烯基甲硅烷氧基封端的二甲基聚硅氧烷(乙烯基的含量=0.15质量%)
(A-6)成分:25℃时为白色固体状、为甲苯可溶性的平均单元式:
(Me2ViSiO1/2)0.15(Me3SiO1/2)0.47(SiO4/2)0.38(HO1/2)0.0001
表示的一分子中具有2个以上乙烯基的有机聚硅氧烷树脂(乙烯基的含量=5.4质量%)
(A-7)成分:25℃时为白色固体状、为甲苯可溶性的平均单元式:
(Me2ViSiO1/2)0.15(Me3SiO1/2)0.38(SiO4/2)0.47(HO1/2)0.01
表示的一分子中具有2个以上乙烯基的有机聚硅氧烷(乙烯基的含量=4.2质量%)
(A-8)成分:25℃时为白色固体状、为甲苯可溶性的平均单元式:
(PhSiO3/2)0.75(Me2ViSiO1/2)0.25
表示的一分子中具有2个以上乙烯基的有机聚硅氧烷(乙烯基的含量=5.6质量%)
作为(B)成分,除了上述(B-1)成分以外,可使用以下成分:
(B-2)成分:平均式:
Me3SiO(MeHSiO)55SiMe3
表示的粘度为20mPa·s的分子链两末端由三甲基甲硅烷氧基封端的聚甲基氢硅氧烷(与硅原子结合的氢原子含量=1.6质量%)
(B-3)成分:平均单元式:
(PhSiO3/2)0.4(HMe2SiO1/2)0.6
表示的粘度为25mPa·s的一分子中具有2个以上与硅原子结合的氢原子的支链状有机聚硅氧烷(与硅原子结合的氢原子的含量=0.65质量%)
作为(C)成分,使用上述的(C-1)成分和(C-4)成分。
作为(D)成分,使用以下成分:
(D-2)成分:铂的1,3-二乙烯基四甲基二硅氧烷络合物的1,3-二乙烯基四甲基二硅氧烷溶液(铂金属的含量=约5000ppm)
作为(E)成分,使用以下成分:
(E-1)成分:1-乙炔基环己烷-1-醇
固化性有机硅组合物的硬度按照如下进行测定。
[固化物的硬度]
在150℃下以5MPa的压力对固化性有机硅组合物加压成形1小时,由此制作成片状固化物。按照JIS K 6253中规定由A型硬度计测定该片状固化物的硬度。其结果示于表2。
使用固化性有机硅组合物按照如下制作表面贴装型的发光二极管(LED)。
[发光二极管的制作]
堵住底部的圆筒状聚邻苯二甲酰胺(PPA)树脂制框架5(内径2.0mm、深度1.0mm)中,引线框架2、3从侧壁向框架5内底部的中心部延伸,在引线框架2的中央部上载置有LED芯片1,在LED芯片1与引线框架3通过键合线4进行电连接的未密封的发光二极管内,利用点胶机注入经脱泡的固化性有机硅组合物。其后,加热烘箱中在100℃下加热30分钟,接着在150℃下加热1小时,使固化性有机硅组合物固化,由此制作成如图1所示的表面贴装型的发光二极管。
[固化物的初期剥离率]
对于用上述方法制作的20个发光二极管,用光学显微镜观察引线框架2、3、以及键合线4与固化物6之间的剥离状态,可看到剥离的发光二极管的个数比例示于表2。
[吸湿回流焊后的剥离率]
将用上述方法制作的20个发光二极管放入85℃、85%的恒温恒湿室168小时之后,在280℃的烘箱内放置30秒,然后返回到室温(25℃),用光学显微镜观察引线框架2、3、以及键合线4与固化物6之间的剥离状态,可看到剥离的发光二极管的个数比例示于表2。
[表2]
由表2的结果表明:实施例8~9的固化性有机硅组合物的固化物与比较例4~5的固化性有机硅组合物相比,具有高的耐剥离性。
工业上的可利用性
本发明的固化性有机硅组合物其流动性优异,经固化能够形成荧光体均匀地分散且高折射率的固化物,因此适于用作发光二极管(LED)等光半导体装置中的发光元件的密封剂或包覆剂。
符号说明
1 发光元件
2 引线框架
3 引线框架
4 键合线
5 框架
6 固化性有机硅组合物的固化物
权利要求书(按照条约第19条的修改)
1.一种有机硅氧烷,其由以下通式表示:
[化学式23]
(式中,R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基,R2为碳原子数2~12的烯基,R3为相同或不同的碳原子数1~3的烷基,X为以下通式表示的基团,
(式中,R1与上述相同,R4为相同或不同的亚烷基,p为0~50的整数,q为0或1),
m为0~50的整数,n为1~50的整数。}
2.根据权利要求1所述的有机硅氧烷,其中,R4为亚乙基或亚丙基。
3.一种粘合促进剂,其包含权利要求1或2所述的有机硅氧烷。
4.一种固化性有机硅组合物,其含有权利要求1或2所述的有机硅氧烷作为粘合促进剂。
5.根据权利要求4所述的固化性有机硅组合物,其通过氢化硅烷化反应固化。
6.根据权利要求5所述的固化性有机硅组合物,其中,通过氢化硅烷化反应固化的固化性有机硅组合物至少包含以下组分:
(A)一分子中具有至少2个烯基的有机聚硅氧烷100质量份;
(B)一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷{其量为相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,使提供与硅原子结合的氢原子的量为0.1~10摩尔};
(C)粘合促进剂0.1~10质量份,所述粘合促进剂包含权利要求1或2所述的有机硅氧烷;及
(D)氢化硅烷化反应用催化剂(其量为充分促进本组合物固化的量)。
7.根据权利要求6所述的固化性有机硅组合物,其还含有(E)氢化硅烷化反应抑制剂{相对于(A)成分~(D)成分的合计100质量份,所述(E)氢化硅烷化反应抑制剂的量为0.0001~5质量份}。
8.一种半导体装置,其特征在于,通过权利要求4~7中任一项所述的固化性有机硅组合物的固化物对半导体元件进行密封。
9.根据权利要求8所述的半导体装置,其中,半导体元件为发光元件。
Claims (9)
1.一种有机硅氧烷,其由以下通式表示:
[化学式23]
(式中,R1为相同或不同的不具有脂肪族不饱和键的碳原子数1~12的一价烃基,R2为碳原子数2~12的烯基,R3为相同或不同的碳原子数1~3的烷基,X为以下通式表示的基团,
(式中,R1与上述相同,R4为相同或不同的亚烷基,p为0~50的整数,q为0或1),
m为0~50的整数,n为1~50的整数。}
2.根据权利要求1所述的有机硅氧烷,其中,R4为亚乙基或亚丙基。
3.一种粘合促进剂,其包含权利要求1或2所述的有机硅氧烷。
4.一种固化性有机硅组合物,其含有权利要求1或2所述的有机硅氧烷作为粘合促进剂。
5.根据权利要求4所述的固化性有机硅组合物,其通过氢化硅烷化反应固化。
6.根据权利要求11所述的固化性有机硅组合物,其中,通过氢化硅烷化反应固化的固化性有机硅组合物至少包含以下组分:
(A)一分子中具有至少2个烯基的有机聚硅氧烷100质量份;
(B)一分子中具有至少2个与硅原子结合的氢原子的有机氢化聚硅氧烷{其量为相对于(A)成分和(C)成分中所含的烯基合计每1摩尔,使提供与硅原子结合的氢原子的量为0.1~10摩尔};
(C)粘合促进剂0.1~10质量份,所述粘合促进剂包含权利要求1或2所述的有机硅氧烷;及
(D)氢化硅烷化反应用催化剂(其量为充分促进本组合物固化的量)。
7.根据权利要求6所述的固化性有机硅组合物,其还含有(E)氢化硅烷化反应抑制剂{相对于(A)成分~(D)成分的合计100质量份,所述(E)氢化硅烷化反应抑制剂的量为0.0001~5质量份}。
8.一种半导体装置,其特征在于,通过权利要求4~7中任一项所述的固化性有机硅组合物的固化物对半导体元件进行密封。
9.根据权利要求8所述的半导体装置,其中,半导体元件为发光元件。
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EP3153517A4 (en) | 2017-12-20 |
CN106459102B (zh) | 2019-07-23 |
JPWO2015186324A1 (ja) | 2017-05-25 |
TW201609772A (zh) | 2016-03-16 |
JP6552488B2 (ja) | 2019-07-31 |
KR20170015357A (ko) | 2017-02-08 |
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