WO2017122712A1 - Composition de résine durcissable, objet durci, matériau d'encapsulation et dispositif semi-conducteur - Google Patents
Composition de résine durcissable, objet durci, matériau d'encapsulation et dispositif semi-conducteur Download PDFInfo
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- WO2017122712A1 WO2017122712A1 PCT/JP2017/000746 JP2017000746W WO2017122712A1 WO 2017122712 A1 WO2017122712 A1 WO 2017122712A1 JP 2017000746 W JP2017000746 W JP 2017000746W WO 2017122712 A1 WO2017122712 A1 WO 2017122712A1
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- resin composition
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- 239000011342 resin composition Substances 0.000 title claims abstract description 235
- 239000004065 semiconductor Substances 0.000 title claims description 38
- 239000000463 material Substances 0.000 title description 18
- 238000005538 encapsulation Methods 0.000 title 1
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 109
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 238000006459 hydrosilylation reaction Methods 0.000 claims abstract description 30
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- -1 Isocyanurate compound Chemical class 0.000 claims description 142
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 39
- 239000003566 sealing material Substances 0.000 claims description 23
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 230000003287 optical effect Effects 0.000 claims description 21
- 239000003963 antioxidant agent Substances 0.000 claims description 18
- 229910004283 SiO 4 Inorganic materials 0.000 claims description 16
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical group COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000000704 physical effect Effects 0.000 abstract description 23
- 238000012360 testing method Methods 0.000 abstract description 23
- 230000035939 shock Effects 0.000 abstract description 11
- 238000004458 analytical method Methods 0.000 abstract description 2
- 238000005133 29Si NMR spectroscopy Methods 0.000 abstract 1
- 229910020485 SiO4/2 Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 79
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 59
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 39
- 229910052710 silicon Inorganic materials 0.000 description 38
- 229910052761 rare earth metal Inorganic materials 0.000 description 34
- 150000002910 rare earth metals Chemical group 0.000 description 33
- 230000032683 aging Effects 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 28
- 150000002430 hydrocarbons Chemical group 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 25
- 150000007942 carboxylates Chemical class 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 21
- 239000000203 mixture Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 18
- 230000004888 barrier function Effects 0.000 description 17
- 238000002156 mixing Methods 0.000 description 17
- 229910052697 platinum Inorganic materials 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 125000005372 silanol group Chemical group 0.000 description 14
- 239000007789 gas Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 238000010526 radical polymerization reaction Methods 0.000 description 13
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 229920002050 silicone resin Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229910052684 Cerium Inorganic materials 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 239000010703 silicon Substances 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229910052746 lanthanum Inorganic materials 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 8
- 229910052779 Neodymium Inorganic materials 0.000 description 8
- 229910052777 Praseodymium Inorganic materials 0.000 description 8
- 238000006482 condensation reaction Methods 0.000 description 8
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 8
- 229910052727 yttrium Inorganic materials 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229920002223 polystyrene Polymers 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002683 reaction inhibitor Substances 0.000 description 7
- 229910052703 rhodium Inorganic materials 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- 229910052717 sulfur Inorganic materials 0.000 description 7
- 229920002554 vinyl polymer Polymers 0.000 description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 6
- 150000004678 hydrides Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000010948 rhodium Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007797 corrosion Effects 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 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 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000000565 sealant Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- QBKTXRLYEHZACW-UHFFFAOYSA-K 2-ethylhexanoate;neodymium(3+) Chemical compound [Nd+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O QBKTXRLYEHZACW-UHFFFAOYSA-K 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 229910004298 SiO 2 Inorganic materials 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 4
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 4
- GGVUYAXGAOIFIC-UHFFFAOYSA-K cerium(3+);2-ethylhexanoate Chemical compound [Ce+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O GGVUYAXGAOIFIC-UHFFFAOYSA-K 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 150000008282 halocarbons Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
- 125000006038 hexenyl group Chemical group 0.000 description 4
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 4
- 239000002530 phenolic antioxidant Substances 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 3
- PPNFILUQDVDXDA-UHFFFAOYSA-K 2-ethylhexanoate;lanthanum(3+) Chemical compound [La+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O PPNFILUQDVDXDA-UHFFFAOYSA-K 0.000 description 3
- LJLKMNSTMFZSEO-UHFFFAOYSA-K 2-ethylhexanoate;praseodymium(3+) Chemical compound [Pr+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O LJLKMNSTMFZSEO-UHFFFAOYSA-K 0.000 description 3
- AGOMHFKGCMKLDA-UHFFFAOYSA-K 2-ethylhexanoate;yttrium(3+) Chemical compound [Y+3].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O AGOMHFKGCMKLDA-UHFFFAOYSA-K 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000008393 encapsulating agent Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 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 2
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- PFEFOYRSMXVNEL-UHFFFAOYSA-N 2,4,6-tritert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PFEFOYRSMXVNEL-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- 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
- 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 2
- MQSZOZMNAJHVML-UHFFFAOYSA-N 3-phenylbut-1-yn-1-ol Chemical compound OC#CC(C)C1=CC=CC=C1 MQSZOZMNAJHVML-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- UIEXFJVOIMVETD-UHFFFAOYSA-N P([O-])([O-])[O-].[Pt+3] Chemical compound P([O-])([O-])[O-].[Pt+3] UIEXFJVOIMVETD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229910018557 Si O Inorganic materials 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- YTEISYFNYGDBRV-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)C YTEISYFNYGDBRV-UHFFFAOYSA-N 0.000 description 2
- ILBWBNOBGCYGSU-UHFFFAOYSA-N [[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C ILBWBNOBGCYGSU-UHFFFAOYSA-N 0.000 description 2
- KWBVOMGZISVLGA-UHFFFAOYSA-N [[[(dimethyl-$l^{3}-silanyl)oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)C KWBVOMGZISVLGA-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000005376 alkyl siloxane group Chemical group 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 2
- OJUXMGHHPMOVCP-UHFFFAOYSA-N bis[[[ethenyl(dimethyl)silyl]oxy-dimethylsilyl]oxy]-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C=C OJUXMGHHPMOVCP-UHFFFAOYSA-N 0.000 description 2
- MFWYAJVOUCTAQI-UHFFFAOYSA-N bis[[ethenyl(dimethyl)silyl]oxy]-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C=C MFWYAJVOUCTAQI-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UOUILILVWRHZSH-UHFFFAOYSA-N dimethyl-tris[(dimethyl-$l^{3}-silanyl)oxy]silyloxysilicon Chemical compound C[Si](C)O[Si](O[Si](C)C)(O[Si](C)C)O[Si](C)C UOUILILVWRHZSH-UHFFFAOYSA-N 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MMCLUVJVJHWRRY-UHFFFAOYSA-N ethenyl-[[[ethenyl(dimethyl)silyl]oxy-dimethylsilyl]oxy-dimethylsilyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C=C MMCLUVJVJHWRRY-UHFFFAOYSA-N 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
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
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- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UERZMVLKPKHGER-UHFFFAOYSA-N prop-1-ene-1-thiol trimethoxysilane Chemical compound CO[SiH](OC)OC.SC=CC UERZMVLKPKHGER-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000005486 sulfidation Methods 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- 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
Definitions
- the curable resin composition may further contain a silane coupling agent (H).
- the component (E) is at least one hydrosilylation reaction catalyst selected from the group consisting of platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts.
- the curable silicone resin composition as described in any one.
- the component (E) is a platinum catalyst (preferably platinum fine powder, platinum black, platinum-supported silica fine powder, platinum-supported activated carbon, chloroplatinic acid, chloroplatinic acid and alcohol, aldehyde, or ketone complex.
- alkenyl group that the component (A) has in the molecule a substituted or unsubstituted alkenyl group such as a vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group (for example, a C 2-20 alkenyl group (particularly a C 2 ⁇ 10 alkenyl group) and the like.
- substituent include a halogen atom, a hydroxyl group, and a carboxyl group.
- alkenyl group a vinyl group is preferable.
- (A) component may have 1 type of alkenyl groups, and may have 2 or more types of alkenyl groups.
- the alkenyl group that component (A) has is preferably a group bonded to a silicon atom.
- component (C) examples include 1,1,3,3-tetramethyl-1,3-divinylsiloxane, 1,1,3,3,5,5-hexamethyl-1,5-divinyltrisiloxane, 1,1,3,3,5,5,7,7-octamethyl-1,7-divinyltetrasiloxane, 1,1,3,3,5,5,7,7,9,9-decamethyl-1, 1 to 1000 (Si—O) units such as 9-divinylpentasiloxane, 1,1,3,3,5,5,7,7,9,9-decamethyl-1,9-divinylpentasiloxane ( Examples thereof include linear polydimethylsiloxane having both ends vinyl type, preferably dimethyl silicone, and linear polydialkylsiloxanes such as dimethylsilicone (preferably linear polydiC 1-10 alkylsiloxane).
- Examples of the branched polyorganosiloxane include compounds represented by the above average unit formula, wherein b1 is a positive number.
- b2 / b1 is a number from 0 to 10
- b3 / b1 is a number from 0 to 0.5
- b4 / (b1 + b2 + b3 + b4) is a number from 0 to 0.3
- b5 / (b1 + b2 + b3 + b4) is from 0 to 0.4.
- content of the rare earth metal atom in the curable resin composition of this invention is not specifically limited,
- (A) component, (B) component, (C) component, (D) component total content (100 % By weight) is preferably 5 ppm or more and less than 5000 ppm, more preferably 7 ppm or more and less than 1000 ppm, and even more preferably 10 ppm or more and less than 300 ppm.
- the heat resistance and the corrosion resistance against a corrosive gas are further improved.
- the content of the carboxylate (I) of the rare earth metal atom is not particularly limited, but is preferably 0.008 to 1.000% by weight with respect to the total amount (100% by weight) of the curable resin composition, for example.
- the amount is preferably 0.010 to 0.500% by weight, more preferably 0.015 to 0.400% by weight.
- the content of the rare earth metal atom is in the above range, and the content of the carboxylate (I) of the carboxylate of the rare earth metal atom is in the above range, thereby providing heat resistance and corrosion resistance to corrosive gas. Even better.
- the curable resin composition of the present invention may contain a hydrosilylation reaction inhibitor in order to adjust the speed of the curing reaction (hydrosilylation reaction).
- hydrosilylation reaction inhibitor examples include alkyne alcohols such as 3-methyl-1-butyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, and phenylbutynol; 3-methyl-3 -Enyne compounds such as pentene-1-yne and 3,5-dimethyl-3-hexen-1-yne; and thiazole, benzothiazole, benzotriazole and the like.
- the said hydrosilylation reaction inhibitor can be used individually by 1 type or in combination of 2 or more types.
- the content of the hydrosilylation reaction inhibitor varies depending on the crosslinking conditions of the curable resin composition, but practically, the content in the curable resin composition is preferably in the range of 0.00001 to 5% by weight. .
- the curable resin composition of the present invention includes, as other optional components, precipitated silica, wet silica, fumed silica, calcined silica, titanium oxide, alumina, glass, quartz, aluminosilicate, iron oxide, zinc oxide, calcium carbonate, Inorganic fillers such as carbon black, silicon carbide, silicon nitride, and boron nitride; inorganic fillers obtained by treating these fillers with organosilicon compounds such as organohalosilanes, organoalkoxysilanes, and organosilazanes; silicone resins, epoxy resins, Organic resin fine powders such as fluororesins; fillers such as conductive metal powders such as silver and copper, stabilizers (ultraviolet absorbers, light-resistant stabilizers, heat stabilizers, etc.), flame retardants (phosphorous flame retardants, Halogen flame retardants, inorganic flame retardants, etc.), flame retardant aids, reinforcing materials (other fill
- the curable resin composition of the present invention is not particularly limited, but the compound contained in the curable resin composition with respect to the total number of alkenyl groups bonded to silicon atoms present in the compound contained in the curable resin composition
- the ratio (also molar ratio) of the total number of hydrosilyl groups present in is 0.2 to 4 mol (more preferably 0.5 to 3 mol, still more preferably 0.8 to 2 mol) (Composition composition) is preferable.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Power Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Led Device Packages (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Abstract
La présente invention vise à proposer une composition de résine durcissable capable de donner un objet durci dont les propriétés physiques, dans un test de résistance à la chaleur à une température élevée de 200 °C ou plus, changent peu et qui, dans un test de choc thermique, etc. présente une grande fiabilité. La composition de résine durcissable comprend les composants suivants. (A) Un organopolysiloxane qui possède un ou plusieurs groupes alcényle dans la molécule et possède des motifs Q représentés par la formule SiO4/2 et qui satisfait à l'exigence suivante. Dans une analyse par RMN du 29Si, pour satisfaire à la relation suivante, dans laquelle a est l'intégrale de -120 à -115 ppm et b est l'intégrale de -105 à -95 ppm b/(a +b) > 0,98. (B) Un polyorganosilsesquioxane de type échelle ayant un ou plusieurs groupes alcényle dans la molécule. (C) Un polyorganosiloxane linéaire comportant des groupes alcényle au niveau des deux extrémités. (D) Un hydrogénopolyorganosiloxane ayant au moins deux groupes hydrosilyle dans la molécule. (E) Un catalyseur d'hydrosilylation contenant un métal du groupe du platine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017561150A JPWO2017122712A1 (ja) | 2016-01-15 | 2017-01-12 | 硬化性樹脂組成物、硬化物、封止材、及び半導体装置 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016006661 | 2016-01-15 | ||
| JP2016-006661 | 2016-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2017122712A1 true WO2017122712A1 (fr) | 2017-07-20 |
Family
ID=59311816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2017/000746 WO2017122712A1 (fr) | 2016-01-15 | 2017-01-12 | Composition de résine durcissable, objet durci, matériau d'encapsulation et dispositif semi-conducteur |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPWO2017122712A1 (fr) |
| TW (1) | TW201736514A (fr) |
| WO (1) | WO2017122712A1 (fr) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020070324A (ja) * | 2018-10-30 | 2020-05-07 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物、その硬化物、及び光半導体装置 |
| JP2020513466A (ja) * | 2016-12-20 | 2020-05-14 | ダウ シリコーンズ コーポレーション | 硬化性シリコーン組成物 |
| KR20200075278A (ko) * | 2018-12-18 | 2020-06-26 | 주식회사 엠알케이 | 고점착, 광확산 기능과 다양한 양면 이형 점착력을 가진 기능성 실리콘 점착제 및 이를 이용한 필름 |
| JP2021169642A (ja) * | 2020-04-14 | 2021-10-28 | 信越化学工業株式会社 | シリル化イソシアヌレート化合物及び金属腐食防止剤 |
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| WO2014109349A1 (fr) * | 2013-01-09 | 2014-07-17 | 株式会社ダイセル | Composition de résine durcissable, et produit durci associé |
| WO2014125964A1 (fr) * | 2013-02-14 | 2014-08-21 | 株式会社ダイセル | Composition de résine durcissable, produit durci, dispositif semi-conducteur à élément d'étanchéité |
| WO2015186722A1 (fr) * | 2014-06-06 | 2015-12-10 | 株式会社ダイセル | Composition de résine durcissable, produit durci, matériau d'étanchéité et dispositif semi-conducteur |
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2017
- 2017-01-12 JP JP2017561150A patent/JPWO2017122712A1/ja active Pending
- 2017-01-12 WO PCT/JP2017/000746 patent/WO2017122712A1/fr active Application Filing
- 2017-01-13 TW TW106101111A patent/TW201736514A/zh unknown
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| JP2010100758A (ja) * | 2008-10-24 | 2010-05-06 | Adeka Corp | ケイ素含有硬化性組成物 |
| JP2012140622A (ja) * | 2010-12-31 | 2012-07-26 | Cheil Industries Inc | 封止材用透光性樹脂、該透光性樹脂を含む封止材および電子素子 |
| JP2013216827A (ja) * | 2012-04-11 | 2013-10-24 | Kaneka Corp | ポリシロキサン系組成物 |
| WO2014109349A1 (fr) * | 2013-01-09 | 2014-07-17 | 株式会社ダイセル | Composition de résine durcissable, et produit durci associé |
| WO2014125964A1 (fr) * | 2013-02-14 | 2014-08-21 | 株式会社ダイセル | Composition de résine durcissable, produit durci, dispositif semi-conducteur à élément d'étanchéité |
| WO2015186722A1 (fr) * | 2014-06-06 | 2015-12-10 | 株式会社ダイセル | Composition de résine durcissable, produit durci, matériau d'étanchéité et dispositif semi-conducteur |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020513466A (ja) * | 2016-12-20 | 2020-05-14 | ダウ シリコーンズ コーポレーション | 硬化性シリコーン組成物 |
| US20200157345A1 (en) * | 2016-12-20 | 2020-05-21 | Dow Silicones Corporation | Curable silicone composition |
| JP2020070324A (ja) * | 2018-10-30 | 2020-05-07 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物、その硬化物、及び光半導体装置 |
| JP7021049B2 (ja) | 2018-10-30 | 2022-02-16 | 信越化学工業株式会社 | 付加硬化型シリコーン樹脂組成物、その硬化物、及び光半導体装置 |
| KR20200075278A (ko) * | 2018-12-18 | 2020-06-26 | 주식회사 엠알케이 | 고점착, 광확산 기능과 다양한 양면 이형 점착력을 가진 기능성 실리콘 점착제 및 이를 이용한 필름 |
| KR102186929B1 (ko) * | 2018-12-18 | 2020-12-04 | 주식회사 엠알케이 | 고점착, 광확산 기능과 다양한 양면 이형 점착력을 가진 기능성 실리콘 점착제 및 이를 이용한 필름 |
| JP2021169642A (ja) * | 2020-04-14 | 2021-10-28 | 信越化学工業株式会社 | シリル化イソシアヌレート化合物及び金属腐食防止剤 |
| JP7301018B2 (ja) | 2020-04-14 | 2023-06-30 | 信越化学工業株式会社 | シリル化イソシアヌレート化合物の混合物及び金属腐食防止剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2017122712A1 (ja) | 2018-11-01 |
| TW201736514A (zh) | 2017-10-16 |
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