JP2013035894A - シリコーン樹脂組成物、封止材料および発光ダイオード装置 - Google Patents
シリコーン樹脂組成物、封止材料および発光ダイオード装置 Download PDFInfo
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- JP2013035894A JP2013035894A JP2011170805A JP2011170805A JP2013035894A JP 2013035894 A JP2013035894 A JP 2013035894A JP 2011170805 A JP2011170805 A JP 2011170805A JP 2011170805 A JP2011170805 A JP 2011170805A JP 2013035894 A JP2013035894 A JP 2013035894A
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- JP
- Japan
- Prior art keywords
- group
- alkenyl group
- hydrosilyl
- resin composition
- silicone resin
- 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.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 79
- 229920002050 silicone resin Polymers 0.000 title claims abstract description 75
- 239000000463 material Substances 0.000 title abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 228
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 60
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 57
- 239000010703 silicon Substances 0.000 claims abstract description 36
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 19
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 18
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- 229920001296 polysiloxane Polymers 0.000 claims description 136
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 95
- -1 polysiloxane Polymers 0.000 claims description 85
- 238000007789 sealing Methods 0.000 claims description 80
- 125000000524 functional group Chemical group 0.000 claims description 72
- 239000002994 raw material Substances 0.000 claims description 72
- 239000003054 catalyst Substances 0.000 claims description 62
- 150000003377 silicon compounds Chemical class 0.000 claims description 61
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 52
- 230000005494 condensation Effects 0.000 claims description 44
- 238000009833 condensation Methods 0.000 claims description 42
- 125000003700 epoxy group Chemical group 0.000 claims description 41
- 239000003566 sealing material Substances 0.000 claims description 24
- 239000003112 inhibitor Substances 0.000 claims description 19
- 150000002430 hydrocarbons Chemical group 0.000 description 59
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 49
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 39
- 239000000203 mixture Substances 0.000 description 38
- 125000005372 silanol group Chemical group 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 31
- 238000000034 method Methods 0.000 description 25
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 24
- 238000002156 mixing Methods 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 238000006482 condensation reaction Methods 0.000 description 20
- 229920001577 copolymer Polymers 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 230000009257 reactivity Effects 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 13
- 229910052697 platinum Inorganic materials 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 239000004205 dimethyl polysiloxane Substances 0.000 description 12
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 12
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 239000002210 silicon-based material Substances 0.000 description 10
- 238000007259 addition reaction Methods 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 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 9
- 238000003756 stirring Methods 0.000 description 9
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 229910020175 SiOH Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052770 Uranium Inorganic materials 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- JNDMLEXHDPKVFC-UHFFFAOYSA-N aluminum;oxygen(2-);yttrium(3+) Chemical compound [O-2].[O-2].[O-2].[Al+3].[Y+3] JNDMLEXHDPKVFC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920006267 polyester film Polymers 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 229910052720 vanadium Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910019901 yttrium aluminum garnet Inorganic materials 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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 group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 229910010293 ceramic material Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000013329 compounding Methods 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
- 230000007423 decrease Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229920006136 organohydrogenpolysiloxane Polymers 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- OQZAQBGJENJMHT-UHFFFAOYSA-N 1,3-dibromo-5-methoxybenzene Chemical compound COC1=CC(Br)=CC(Br)=C1 OQZAQBGJENJMHT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- JRGQKLFZSNYTDX-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)CCCOCC1CO1 JRGQKLFZSNYTDX-UHFFFAOYSA-N 0.000 description 1
- DAJFVZRDKCROQC-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)propyl-tripropoxysilane Chemical compound CCCO[Si](OCCC)(OCCC)CCCOCC1CO1 DAJFVZRDKCROQC-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 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
- 125000006042 4-hexenyl group Chemical group 0.000 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920006310 Asahi-Kasei Polymers 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229920004482 WACKER® Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- VBXBSTJDBPXOAD-UHFFFAOYSA-N acetyl acetate;platinum Chemical compound [Pt].CC(=O)OC(C)=O VBXBSTJDBPXOAD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- FNNYJATZZFNKNT-UHFFFAOYSA-N but-3-enyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCC=C FNNYJATZZFNKNT-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004956 cyclohexylene group Chemical group 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004979 cyclopentylene group Chemical group 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NNBRCHPBPDRPIT-UHFFFAOYSA-N ethenyl(tripropoxy)silane Chemical compound CCCO[Si](OCCC)(OCCC)C=C NNBRCHPBPDRPIT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005417 glycidoxyalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical class C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- OUCALNIJQUBGSL-UHFFFAOYSA-M methanol;tetramethylazanium;hydroxide Chemical compound [OH-].OC.C[N+](C)(C)C OUCALNIJQUBGSL-UHFFFAOYSA-M 0.000 description 1
- ACXIAEKDVUJRSK-UHFFFAOYSA-N methyl(silyloxy)silane Chemical compound C[SiH2]O[SiH3] ACXIAEKDVUJRSK-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
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- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ZMYXZXUHYAGGKG-UHFFFAOYSA-N propoxysilane Chemical compound CCCO[SiH3] ZMYXZXUHYAGGKG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 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
- LFBULLRGNLZJAF-UHFFFAOYSA-N trimethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CO[Si](OC)(OC)COCC1CO1 LFBULLRGNLZJAF-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Abstract
【解決手段】飽和炭化水素基および芳香族炭化水素基から選択される1価の炭化水素基が結合されるケイ素原子、および、アルケニル基が結合されるケイ素原子を含むケイ素含有成分を有し、ケイ素含有成分1g当たりのアルケニル基のmol数が、200〜2000μmol/gであるシリコーン樹脂組成物を調製する。シリコーン樹脂組成物からなる封止材料を、半硬化状態のシート形状に形成した封止層7を発光ダイオード装置2に設ける。
【選択図】図3
Description
一般式(1):
(X1)3Si−R1 (1)
(一般式(1)中、R1は、アルケニル基を示し、X1は、ハロゲン原子、アルコキシ基、フェノキシ基またはアセトキシ基を示す。但し、X1は、同一または互いに相異なっていてもよい。)
上記一般式(1)において、R1で示されるアルケニル基は、例えば、直鎖状または分岐状のエチレン系不飽和炭化水素基であって、例えば、1価の置換または非置換のアルケニル基であり、具体的には、R1の末端に二重結合を有する末端アルケニル基、および、R1の途中に二重結合を有するアルケニル基などのアルケニル基が挙げられる。アルケニル基の炭素数は、例えば、2〜10、好ましくは、2〜5である。
一般式(2):
上記一般式(2)中、R2で示される1価の炭化水素基において、飽和炭化水素基としては、例えば、炭素数1〜6の直鎖状または分岐状のアルキル基(メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、ペンチル基、ヘキシル基など)、例えば、炭素数3〜6のシクロアルキル基(シクロペンチル基、シクロヘキシル基など)などが挙げられる。
A、B、C、C’およびDは水素側鎖含有オルガノポリシロキサンを構成する。
E、F、G、G’およびHは、水素両末端含有オルガノポリシロキサンを構成する。
一般式(5):
(X2)3Si−R5 (5)
(一般式(5)中、R5は、エポキシ構造含有基を示し、X2は、ハロゲン原子、アルコキシ基、フェノキシ基、またはアセトキシ基を示す。但し、X2は、同一または互いに相異なっていてもよい。)
一般式(5)において、R5で示されるエポキシ構造含有基としては、例えば、エポキシ基、例えば、グリシジルエーテル基、例えば、エポキシシクロヘキシル基などのエポキシシクロアルキル基などが挙げられる。
一般式(6):
上記一般式(6)中、R6で示される2価の炭化水素基において、飽和炭化水素基としては、例えば、炭素数1〜6のアルキレン基(メチレン基、エチレン基、プロピレン基、ブチレン基など)、例えば、炭素数3〜8のシクロアルキレン基(シクロペンチレン基、シクロヘキシレン基など)などが挙げられる。
一般式(8):
一般式(9):
上記一般式(7)〜(9)において、R7で示される飽和炭化水素基および芳香族炭化水素基としては、第1の原料成分におけるシラノール基両末端ポリシロキサンの上記一般式(2)のR2で例示した飽和炭化水素基および芳香族炭化水素基と同様のものが挙げられる。1価の炭化水素基として、好ましくは、メチル基、フェニル基、さらに好ましくは、メチル基が挙げられる。
また、得られたピーク強度の積分値Bを、1価の炭化水素基が有する水素原子数Zで割ることにより、1価の炭化水素基1分子当たりのピーク強度の積分値B/Zを得る。次いで、B/Zに、下記式(11)に示す1価の炭化水素基とシロキサン部分とを有する主鎖部分の分子量を掛けることにより、主鎖部分の質量部B’が求められる。
上記した主鎖部分の質量部B’が、ケイ素含有成分の平均分子量であると近似されるので、B’/A’(g/mol)が、アルケニル基1molに対するケイ素含有成分のg数となり、その逆数、すなわち、A’/B’(mol/g)が、ケイ素含有成分1g当たりのアルケニル基のmol数、すなわち、アルケニル基当量(アルケニル基含有量)として算出される。
シラノール基両末端ポリジメチルシロキサン(シラノール基両末端ポリシロキサン、数平均分子量1500、シラノール基当量1.33mmol/g)100gと、ビニルトリメトキシシラン(アルケニル基・シラノール縮合反応性官能基併有ケイ素化合物、ビニル基当量6.75mmol/g)5.93g(40.0mmol)と、(3−グリシドキシプロピル)トリメトキシシラン(エポキシ基・シラノール縮合反応性官能基併有ケイ素化合物、エポキシ基当量4.2mmol/g)1.05g(4.4mmol)とを配合して、それらを撹拌混合して混合物を調製した。
ビニル末端メチルヒドロシロキサン−ジメチルシロキサン共重合体(アルケニル基・ヒドロシリル基併有オルガノポリシロキサン、上記一般式(8)に相当、ビニル基当量0.84mmol/g)30gと、水酸化テトラメチルアンモニウム(ヒドロシリル化抑制剤)の10質量%メタノール溶液14.3μL(水酸化テトラメチルアンモニウム量:0.013mmol)とを配合し、その後、ジメチルポリシロキサン−co−メチルハイドロジェンポリシロキサン(アルケニル基不含/ヒドロシリル基含有オルガノポリシロキサン、一般式(3)中、R3がすべてメチル基、a=10、b=10、b’=0;数平均分子量2000、粘度20mPa・s(25℃)、ヒドロシリル基当量7.14mmol/g)10.6gを配合し、混合物を調製した。混合物のヒドロシリル基当量は1.87mmol/gであった。
ビニル末端メチルヒドロシロキサン−ジメチルシロキサン共重合体(アルケニル基・ヒドロシリル基併有オルガノポリシロキサン、上記一般式(8)に相当、ビニル基当量0.3mmol/g)30gと、水酸化テトラメチルアンモニウム(ヒドロシリル化抑制剤)の10質量%メタノール溶液14.3μL(水酸化テトラメチルアンモニウム量:0.013mmol)とを配合し、その後、アルケニル基不含/ヒドロシリル基含有オルガノポリシロキサン(一般式(3)中、R3がすべてメチル基、a=10、b=10、b’=0;数平均分子量2000、粘度20mPa・s(25℃)、ヒドロシリル基当量7.14mmol/g)3.8gを配合し、混合物を調製した。混合物のヒドロシリル基当量は0.80mmol/gであった。
シラノール基両末端ジメチルポリシロキサン(シラノール基両末端ポリシロキサン、数平均分子量11500;シラノール基当量0.17mmol/g)100gと、ビニルトリメトキシシラン(アルケニル基・シラノール縮合反応性官能基併有ケイ素化合物、ビニル基当量6.75mmol/g)0.773g(5.22mmol)と、(3−グリシドキシプロピル)トリメトキシシラン(エポキシ基・シラノール縮合反応性官能基併有ケイ素化合物、エポキシ基当量4.23mmol/g)0.137g(0.58mmol)とを配合して、それらを撹拌混合して混合物を調製した。
シラノール基両末端ポリジメチルシロキサン(シラノール基両末端ポリシロキサン、数平均分子量3000;シラノール基当量0.66mmol/g)100gと、ビニルトリメトキシシラン(アルケニル基・シラノール縮合反応性官能基併有ケイ素化合物、ビニル基当量6.75mmol/g)2.96g(20.0mmol)と、(3−グリシドキシプロピル)トリメトキシシラン(エポキシ基・シラノール縮合反応性官能基併有ケイ素化合物、エポキシ基当量0.42mmol/g)0.53g(0.22mmol)とを配合して、それらを撹拌混合して混合物を調製した。
ビニル末端メチルヒドロシロキサン−ジメチルシロキサン共重合体(アルケニル基・ヒドロシリル基併有オルガノポリシロキサン、上記一般式(8)に相当、ビニル基当量0.079mmol/g)30gと、水酸化テトラメチルアンモニウム(ヒドロシリル化抑制剤)の10質量%メタノール溶液14.3μL(水酸化テトラメチルアンモニウム量:0.013mmol)とを配合し、その後、ジメチルポリシロキサン−co−メチルハイドロジェンポリシロキサン(アルケニル基不含/ヒドロシリル基含有オルガノポリシロキサン、一般式(3)中、R3がすべてメチル基、a=10、b=10、b’=0;数平均分子量2000、粘度20mPa・s(25℃)、ヒドロシリル基当量7.14mmol/g)1.00gを配合した。混合物のヒドロシリル基当量は0.23mmol/gであった。
ビニル末端メチルヒドロシロキサン−ジメチルシロキサン共重合体(アルケニル基・ヒドロシリル基併有オルガノポリシロキサン、上記一般式(8)に相当、ビニル基当量0.13mmol/g)30gと、水酸化テトラメチルアンモニウム(ヒドロシリル化抑制剤)の10質量%メタノール溶液14.3μL(水酸化テトラメチルアンモニウム量:0.013mmol)とを配合し、その後、ジメチルポリシロキサン−co−メチルハイドロジェンポリシロキサン(アルケニル基不含/ヒドロシリル基含有オルガノポリシロキサン、一般式(3)中、R3がすべてメチル基、a=10、b=10、b’=0;数平均分子量2000、粘度20mPa・s(25℃)、ヒドロシリル基当量7.14mmol/g)1.63gを配合した。混合物のヒドロシリル基当量は0.37mmol/gであった。
1.ビニル基当量(ケイ素含有成分1g当たりのビニル基のmol数)の測定
各実施例および各比較例で得られたシリコーン樹脂組成物を、それぞれ、重ベンゼンに溶解させてサンプルを調製し、そのサンプルを1H−NMRにより測定した。
2.発光ダイオード装置(封止層)の外観の評価
付加反応硬化型シリコーン樹脂組成物(LR7665、旭化成ワッカーシリコーン社製)のA液(アルケニル基含有ポリシロキサン)と、B液(アルケニル基不含/ヒドロシリル基含有オルガノポリシロキサン)とを混合した混合溶液(混合比率(A/B)=1/1)75gに、YAG:Ce15gを混合し、25℃で1時間攪拌することにより、蛍光体含有樹脂組成物を調製した(蛍光体濃度15質量%)。
7 封止層
11 発光ダイオード素子
Claims (7)
- 飽和炭化水素基および芳香族炭化水素基から選択される1価の炭化水素基が結合されるケイ素原子、および、アルケニル基が結合されるケイ素原子を含むケイ素含有成分を含有するシリコーン樹脂組成物であり、
前記ケイ素含有成分1g当たりのアルケニル基のmol数が、200〜2000μmol/gであることを特徴とする、シリコーン樹脂組成物。 - アルケニル基とシラノール縮合反応性官能基とを併有するアルケニル基・シラノール縮合反応性官能基併有ケイ素化合物、シラノール基両末端ポリシロキサン、および、アルケニル基を含まずヒドロシリル基を含むアルケニル基不含/ヒドロシリル基含有オルガノポリシロキサンを含有する前記ケイ素含有成分と、
エポキシ基とシラノール縮合反応性官能基とを併有するエポキシ基・シラノール縮合反応性官能基併有ケイ素化合物と、
縮合触媒と、
付加触媒と
を含有する原料成分から調製されることを特徴とする、請求項1に記載のシリコーン樹脂組成物。 - アルケニル基とヒドロシリル基とを併有するアルケニル基・ヒドロシリル基併有オルガノポリシロキサン、および、アルケニル基を含まずヒドロシリル基を含むアルケニル基不含/ヒドロシリル基含有オルガノポリシロキサンを含有する前記ケイ素含有成分と、
ヒドロシリル化触媒と、
ヒドロシリル化抑制剤と
を含有する原料成分から調製されることを特徴とする、請求項1に記載のシリコーン樹脂組成物。 - 請求項1〜3のいずれか一項に記載のシリコーン樹脂組成物からなることを特徴とする、封止材料。
- 半硬化状態であることを特徴とする、請求項4に記載の封止材料。
- シート形状に形成されていることを特徴とする、請求項4または5に記載の封止材料。
- 発光ダイオード素子と、
請求項4〜6のいずれか一項に記載の封止材料から形成され、前記発光ダイオード素子を封止する封止層と
を備えることを特徴とする、発光ダイオード装置。
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EP20120178445 EP2554600A3 (en) | 2011-08-04 | 2012-07-30 | Silicone resin composition, encapsulating material, and light emitting diode device |
KR20120084254A KR20130016087A (ko) | 2011-08-04 | 2012-08-01 | 실리콘 수지 조성물, 봉지 재료 및 발광 다이오드 장치 |
US13/564,932 US8883950B2 (en) | 2011-08-04 | 2012-08-02 | Silicone resin composition, encapsulating material, and light emitting diode device |
TW101128146A TW201308697A (zh) | 2011-08-04 | 2012-08-03 | 聚矽氧樹脂組合物、密封材料及發光二極體裝置 |
CN201210284753.0A CN102911503B (zh) | 2011-08-04 | 2012-08-06 | 有机硅树脂组合物、封装材料以及发光二极管装置 |
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KR20170068550A (ko) * | 2014-10-16 | 2017-06-19 | 스미토모 오사카 세멘토 가부시키가이샤 | 표면 수식 금속 산화물 입자 분산액 및 그 제조 방법, 표면 수식 금속 산화물 입자-실리콘 수지 복합 조성물, 표면 수식 금속 산화물 입자-실리콘 수지 복합체, 광학 부재, 및 발광 장치 |
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US8883950B2 (en) | 2014-11-11 |
KR20130016087A (ko) | 2013-02-14 |
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