JP6105966B2 - 硬化性シリコーン組成物、その硬化物、および光半導体装置 - Google Patents
硬化性シリコーン組成物、その硬化物、および光半導体装置 Download PDFInfo
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- JP6105966B2 JP6105966B2 JP2013027857A JP2013027857A JP6105966B2 JP 6105966 B2 JP6105966 B2 JP 6105966B2 JP 2013027857 A JP2013027857 A JP 2013027857A JP 2013027857 A JP2013027857 A JP 2013027857A JP 6105966 B2 JP6105966 B2 JP 6105966B2
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- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical group [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- DDJSWKLBKSLAAZ-UHFFFAOYSA-N cyclotetrasiloxane Chemical compound O1[SiH2]O[SiH2]O[SiH2]O[SiH2]1 DDJSWKLBKSLAAZ-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- KPWVUBSQUODFPP-UHFFFAOYSA-N ethenyl-(ethenyl-methyl-phenylsilyl)oxy-methyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C=C)O[Si](C)(C=C)C1=CC=CC=C1 KPWVUBSQUODFPP-UHFFFAOYSA-N 0.000 description 1
- 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
- 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 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- ZMMBQCILDZFYKX-UHFFFAOYSA-N methyl 2h-benzotriazole-5-carboxylate Chemical compound C1=C(C(=O)OC)C=CC2=NNN=C21 ZMMBQCILDZFYKX-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- OKQVTLCUHATGDD-UHFFFAOYSA-N n-(benzotriazol-1-ylmethyl)-2-ethyl-n-(2-ethylhexyl)hexan-1-amine Chemical compound C1=CC=C2N(CN(CC(CC)CCCC)CC(CC)CCCC)N=NC2=C1 OKQVTLCUHATGDD-UHFFFAOYSA-N 0.000 description 1
- 150000001367 organochlorosilanes Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical group [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 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
- 150000003852 triazoles Chemical class 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
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- H01L33/00—Semiconductor devices with at least one potential-jump barrier or surface barrier 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 with at least one potential-jump barrier or surface barrier 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
- H01L33/50—Wavelength conversion elements
- H01L33/501—Wavelength conversion elements characterised by the materials, e.g. binder
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
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- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
- H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/4805—Shape
- H01L2224/4809—Loop shape
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- H01L2224/42—Wire connectors; Manufacturing methods related thereto
- H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
- H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
- H01L2224/481—Disposition
- H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
- H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
- H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
- H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
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- H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
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- H01L2224/732—Location after the connecting process
- H01L2224/73251—Location after the connecting process on different surfaces
- H01L2224/73265—Layer and wire connectors
Description
(A)一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン{但し、下記(B)成分を除く}、
(B)一般式:
で表されるオルガノポリシロキサン、
(C)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノポリシロキサン{(A)成分と(B)成分中のアルケニル基の合計1モルに対して、(C)成分中のケイ素原子結合水素原子が0.1〜5モルとなる量}、
(D)蛍光体、および
(E)有効量のヒドロシリル化反応用触媒
から少なくともなり、(A)成分〜(E)成分の合計量に対して、(A)成分の含有量が20〜80質量%であり、(B)成分の含有量が0.1〜20質量%であり、(D)成分の含有量が0.1〜70質量%であることを特徴とする。
(A)成分は、本組成物の主剤であり、一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサンである。(A)成分中のアルケニル基としては、ビニル基、アリル基、ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、ノネニル基、デセニル基、ウンデセニル基、ドデセニル基等の炭素数2〜12のアルケニル基が例示され、好ましくは、ビニル基である。また、(A)成分中のアルケニル基以外のケイ素原子に結合する基としては、炭素数1〜12のアルキル基、炭素数6〜20のアリール基、および炭素数7〜20のアラルキル基が例示される。アルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基が例示され、好ましくは、メチル基である。アリール基としては、フェニル基、トリル基、キシリル基、ナフチル基、アントラセニル基、フェナントリル基、ピレニル基、およびこれらのアリール基の水素原子をメチル基、エチル基等のアルキル基;メトキシ基、エトキシ基等のアルコキシ基;塩素原子、臭素原子等のハロゲン原子で置換した基が例示され、好ましくは、フェニル基、ナフチル基である。また、アラルキル基としては、ベンジル基、フェネチル基、ナフチルエチル基、ナフチルプロピル基、アントラセニルエチル基、フェナントリルエチル基、ピレニルエチル基、およびこれらのアラルキル基の水素原子をメチル基、エチル基等のアルキル基;メトキシ基、エトキシ基等のアルコキシ基;塩素原子、臭素原子等のハロゲン原子で置換した基が例示される。
(R1R4 2SiO1/2)a(R5 2SiO2/2)b(R2SiO3/2)c
で表され、一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサンが例示される。
Me2ViSiO(MePhSiO)m'SiMe2Vi
MePhViSiO(MePhSiO)m'SiMePhVi
Me2ViSiO(MePhSiO)m'(Ph2SiO)n'SiMe2Vi
MePhViSiO(MePhSiO)m'(Ph2SiO)n'SiMePhVi
Ph2ViSiO(MePhSiO)m'SiPh2Vi
Ph2ViSiO(MePhSiO)m'(Ph2SiO)n'SiPh2Vi
MePhViSiO(Me2SiO)p'SiMePhVi
Ph2ViSiO(Me2SiO)p'SiPh2Vi
HR3R6SiO(R6 2SiO)sSiR3R6H
で表されるオルガノシロキサン、(C2)平均単位式:
(HR3R6SiO1/2)d(HR3 2SiO1/2)e(R6 2SiO2/2)f(R2SiO3/2)g
で表されるオルガノポリシロキサン、または前記(C1)成分と(C2)成分の混合物である。
HMe2SiO(Ph2SiO)s'SiMe2H
HMePhSiO(Ph2SiO)s'SiMePhH
HMeNaphSiO(Ph2SiO)s'SiMeNaphH
HMePhSiO(Ph2SiO)s''(MePh2SiO)s'''SiMePhH
HMePhSiO(Ph2SiO)s''(Me2SiO)s'''SiMePhH
(HMe2SiO1/2)d(PhSiO3/2)g
(HMePhSiO1/2)d(PhSiO3/2)g
(HMePhSiO1/2)d(NaphSiO3/2)g
(HMe2SiO1/2)d(NaphSiO3/2)g
(HMePhSiO1/2)d(HMe2SiO1/2)e'(PhSiO3/2)g
(HMe2SiO1/2)d(Ph2SiO4/2)f'(PhSiO3/2)g
(HMePhSiO1/2)d(Ph2SiO4/2)f'(PhSiO3/2)g
(HMe2SiO1/2)d(Ph2SiO4/2)f'(NaphSiO3/2)g
(HMePhSiO1/2)d(Ph2SiO4/2)f'(NaphSiO3/2)g
(HMePhSiO1/2)d(HMe2SiO1/2)e'(NaphSiO3/2)g
(HMePhSiO1/2)d(HMe2SiO1/2)e'(Ph2SiO4/2)f'(NaphSiO3/2)g
(HMePhSiO1/2)d(HMe2SiO1/2)e'(Ph2SiO4/2)f'(PhSiO3/2)g
本発明の硬化物は、上記の硬化性シリコーン組成物を硬化してなることを特徴とする。硬化物の形状は特に限定されず、例えば、シート状、フィルム状が挙げられる。硬化物は、これを単体で取り扱うこともできるが、光半導体素子等を被覆もしくは封止した状態で取り扱うことも可能である。
本発明の光半導体装置は、上記の硬化性シリコーン組成物の硬化物により光半導体素子を封止してなることを特徴とする。このような本発明の光半導体装置としては、発光ダイオード(LED)、フォトカプラー、CCDが例示される。また、光半導体素子としては、発光ダイオード(LED)チップ、固体撮像素子が例示される。
反応容器に、フェニルトリメトキシシラン 400g(2.02mol)および1,3−ジビニル−1,3−ジフェニルジメチルジシロキサン 93.5g(0.30mol)を投入し、予め混合した後、トリフルオロメタンスルホン酸 1.74g(11.6mmol)を投入し、撹拌下、水 110g(6.1mol)を投入し、2時間加熱還流を行った。その後、85℃になるまで加熱常圧留去を行った。次いで、トルエン 89gおよび水酸化カリウム 1.18g(21.1mmol)を投入し、反応温度が120℃になるまで加熱常圧留去を行い、この温度で6時間反応させた。その後、室温まで冷却し、酢酸 0.68g(11.4mmol)を投入し、中和した。生成した塩を濾別した後、得られた透明な溶液から低沸点物を加熱減圧除去して、平均単位式:
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
で表されるオルガノポリシロキサンレジン 347g(収率:98%)を調製した。
反応容器に、式:
HO(MePhSiO)6H
で表されるメチルフェニルポリシロキサン 100g(0.233mol)、トルエン 100g、およびトリエチルアミン 29.7g(0.294mol)を投入し、撹拌下、ビニルジフェニルクロロシラン 59.9g(0.245mol)を投入した。室温で1時間撹拌した後、50℃に加熱し、3時間攪拌した。その後、メタノール 0.38gを投入し、次いで、水を投入した。水洗後、有機層から低沸物を加熱減圧留去して、式:
Ph2ViSiO(MePhSiO)6SiPh2Vi
で表される、無色透明なオルガノポリシロキサン(粘度447.5mPa・s、屈折率1.567)を調製した。
攪拌機、還流冷却管、温度計付きの四口フラスコに、1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン 82.2g、水 143g、トリフルオロメタンスルホン酸 0.38g、およびトルエン 500gを投入し、攪拌下、フェニルトリメトキシシラン 524.7gを1時間かけて滴下した。滴下終了後、1時間加熱還流した。その後、冷却し、下層を分離し、トルエン溶液層を3回水洗した。水洗したトルエン溶液層にメチルグリシドキシプロピルジメトキシシラン 314gと水 130gと水酸化カリウム 0.50gとを投入し、1時間加熱還流した。続いて、メタノールを留去し、過剰の水を共沸脱水で除いた。4時間加熱還流した後、トルエン溶液を冷却し、酢酸 0.55gで中和した後、3回水洗した。水を除去した後、トルエンを減圧下に留去して、粘度8,500mPa・sの平均単位式:
(Me2ViSiO1/2)0.18(PhSiO3/2)0.53(EpMeSiO2/2)0.29
で表される接着付与剤を調製した。
反応容器に、式:
HO(Me2SiO)12H
で表されるジメチルポリシロキサン 40.0g(0.045mol)、トルエン 62.0g、およびトリエチルアミン 10.9g(0.107mol)を投入し、撹拌下、ビニルジフェニルクロロシラン 22.0g(0.090mol)を投入した。室温で1時間撹拌した後、50℃に加熱し、3時間攪拌した。その後、水を投入し、水洗後、有機層から低沸物を加熱減圧留去して、式:
Ph2ViSiO(Me2SiO)12SiPh2Vi
で表される、無色透明なオルガノポリシロキサン(粘度36mPa・s、屈折率1.466)を得た。
反応容器に、参考例4で調製したオルガノポリシロキサン 10g、環状ジメチルシロキサン 2.81g、水酸化カリウム 0.0013gを投入し、加熱し、150℃で5時間反応させた。反応後、適量の酢酸を投入し、中和した。減圧下、低沸点成分を除去した後、ろ過して、式:
Ph2ViSiO(Me2SiO)17SiPh2Vi
で表される、無色透明なオルガノポリシロキサン(粘度35mPa・s、屈折率1.461)を得た。
反応容器に、参考例4で調製したオルガノポリシロキサン 10g、環状ジメチルシロキサン 5.61g、水酸化カリウム 0.0016gを投入し、加熱し、150℃で5時間反応させた。反応後、適量の酢酸を投入し、中和した。減圧下、低沸点成分を除去した後、ろ過して、式:
Ph2ViSiO(Me2SiO)17SiPh2Vi
で表される、無色透明なオルガノポリシロキサン(粘度39mPa・s、屈折率1.461)を得た。
下記の成分を用いて、表1に示した硬化性シリコーン組成物を調製した。なお、表1中、(E)成分の含有量は、質量単位における、硬化性シリコーン組成物に対する白金金属の含有量(ppm)で示した。
(A−1)成分:平均単位式:
(Me2ViSiO1/2)0.2(PhSiO3/2)0.8
で表されるシリコーンレジン
(A−2)成分:参考例1で調製した、平均単位式:
(MePhViSiO1/2)0.23(PhSiO3/2)0.77
で表されるオルガノポリシロキサンレジン
(A−3)成分:平均単位式:
(Me2ViSiO1/2)4(SiO4/2)1
(A−4)成分:粘度3,000mPa・sの分子鎖両末端ジメチルビニルシロキシ基封鎖メチルフェニルポリシロキサン
(A−5)成分:参考例2で調製した、式:
Ph2ViSiO(MePhSiO)6SiPh2Vi
で表されるオルガノポリシロキサン
(A−6)成分:平均単位式:
(Me2ViSiO1/2)0.28(Me2SiO2/2)0.72
で表されるオルガノポリシロキサン
(B−1)成分:参考例4で調製したオルガノポリシロキサン
(B−2)成分:参考例5で調製したオルガノポリシロキサン
(B−3)成分:参考例6で調製したオルガノポリシロキサン
(C−1)成分:式:
HMe2SiOPh2SiOSiMe2H
で表されるオルガノトリシロキサン
(C−2)成分:平均単位式:
(Me2HSiO1/2)0.6(PhSiO3/2)0.84
で表されるシリコーンレジン
(D−1)成分:TAG系蛍光体(INTEMATIX製の製品名:NTAG4851)
(D−2)成分:YAG系蛍光体(INTEMATIX製の製品名:NYAG4454)
(D−3)成分:シリケート系蛍光体(INTEMATIX製の製品名:EY4453)
(E−1)成分:白金−1,3−ジビニル−1,1,3,3−テトラメチルジシロキサン錯体の1,3,5,7−テトラメチル−1,3,5,7−テトラビニルシクロテトラシロキサンの溶液(白金として0.1質量%含有する溶液)
(F−1)成分:参考例3で調製した接着付与剤
(F−2)成分:25℃における粘度が30mPa・sである分子鎖両末端シラノール基封鎖メチルビニルシロキサンオリゴマーと3−グリシドキシプロピルトリメトキシシランの縮合反応物からなる接着付与剤
(G−1)成分:1,3,5,7−テトラメチル−1,3,5,7−テトラビニルシクロテトラシロキサン
(H−1)成分:平均粒径13μmのアルミナ粒子(日本アエロジル社製の製品名AluC805)
表1に示した硬化性シリコーン組成物を調製し、該組成物に対して表1に示した部数の蛍光体をそれぞれ添加し、30秒攪拌した後、シンキー製真空遊星式攪拌機ARV−310を用いて、公転1600rpm、自転800rpm、真空度2Paの条件下で2分間攪拌した。この蛍光体含有硬化性シリコーン組成物0.5gをガラス板(50mm×50mm×2mm)上に塗布し、熱循環式オーブンに入れ、室温から150℃まで30分かけて昇温し、150℃で1時間保持した後、冷却、室温に戻して、蛍光体含有硬化物を作製した。
硬化物の平坦性は、硬化物の表面をオリンパス製レーザー顕微鏡LEXT OLS4000を用いて、観察し、硬化物の表面にしわが生じているものを”×”、硬化物の表面に凹凸が生じているものを”△”、硬化物の表面にしわほとんど観察されないものを”○”、硬化物の表面にしわが全く観察されないものを”◎”、として評価した。
硬化物内部の蛍光体の分散性は、ガラス上に塗布硬化したサンプルを目視により観察し、蛍光体が凝集し縞状になっているものを”×”、蛍光体が凝集し島状になっているものを”△”、蛍光体の凝集がほとんど観察されないものを”○”、蛍光体の凝集が全く観察されないものを”◎”、として評価した。
表1に示した実施例8および比較例1の硬化性蛍光体含有シリコーン組成物8gをムサシ製10mLのシリンジに充填し、I−Chiun Industry製5730LEDにディスペンサーを用いて、5.4μLづつ18個のLEDに塗布した後、5.4μLを200回分アルミ皿に捨て打ちし、その後、5.4μLづつ18個のLEDに塗布、5.4μLを200回分アルミ皿に捨て打ちし、その後、5.4μLづつ18個のLEDに塗布、5.4μLを200回分アルミ皿に捨て打ちし、その後、5.4μLづつ18個のLEDに塗布し、合計72個のLEDに塗布した。得られたLEDを熱循環式オーブンに投入し、室温から150℃まで30分かけて昇温し、150℃で1時間保持した後、冷却、室温に戻して、蛍光体含有のシリコーン硬化物で封止されたLEDを得た。インスツルメンツシステムズ社製積分球ISP250、分光器CAS−140CTを用いて、該LED一つ一つを、60mA通電して測定し、72個のLED測定の結果得られるCIE座標のy軸のばらつき幅を検証した。実施例8のy軸のばらつき幅は0.012であった。一方、比較例1の硬化性シリコーン組成物のy軸のばらつき幅は0.02であり、実施例8の組成は、40%色ばらつきが改善することが確認された。
2 リードフレーム
3 リードフレーム
4 ボンディングワイヤ
5 枠材
6 硬化性シリコーン組成物の硬化物
Claims (8)
- (A)一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン{但し、下記(B)成分を除く}、
(B)一般式:
で表されるオルガノポリシロキサン、
(C)一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノポリシロキサン{(A)成分と(B)成分中のアルケニル基の合計1モルに対して、(C)成分中のケイ素原子結合水素原子が0.1〜5モルとなる量}、
(D)蛍光体、および
(E)有効量のヒドロシリル化反応用触媒
から少なくともなり、(A)成分〜(E)成分の合計量に対して、(A)成分の含有量が20〜80質量%であり、(B)成分の含有量が0.1〜20質量%であり、(D)成分の含有量が0.1〜70質量%である硬化性シリコーン組成物。 - (A)成分が、(A1)平均単位式:
(R1R4 2SiO1/2)a(R5 2SiO2/2)b(R2SiO3/2)c
(式中、R1は炭素数2〜12のアルケニル基であり、R2はフェニル基またはナフチル基であり、R4は同じかまたは異なる、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、炭素数6〜20のアリール基、もしくは炭素数7〜20のアラルキル基であり、R5は同じかまたは異なる、炭素数1〜12のアルキル基、炭素数2〜12のアルケニル基、もしくはフェニル基であり、a、b、およびcは、それぞれ、0.01≦a≦0.5、0≦b≦0.7、0.1≦c<0.9、かつa+b+c=1を満たす数である。)
で表され、一分子中に少なくとも2個のアルケニル基を有するオルガノポリシロキサン、または、前記(A1)成分と(A2)一般式:
で表されるオルガノポリシロキサンの混合物{(A)成分〜(E)成分の合計量に対して、(A2)成分の含有量は多くとも50質量%である。}である、請求項1に記載の硬化性シリコーン組成物。 - (C)成分が、(C1)一般式:
HR3R6SiO(R6 2SiO)sSiR3R6H
(式中、R3は同じかまたは異なる炭素数1〜12のアルキル基であり、R6は同じかまたは異なる、炭素数1〜12のアルキル基、炭素数6〜20のアリール基、もしくは炭素数7〜20のアラルキル基であり、sは0〜100の整数である。)
で表されるオルガノポリシロキサン、(C2)平均単位式:
(HR3R6SiO1/2)d(HR3 2SiO1/2)e(R6 2SiO2/2)f(R2SiO3/2)g
(式中、R2はフェニル基またはナフチル基であり、R3およびR6は前記と同様の基であり、d、e、f、およびgは、それぞれ、0.01≦d≦0.7、0≦e≦0.5、0≦f≦0.7、0.1≦g<0.9、かつd+e+f+g=1を満たす数である。)
で表される、一分子中に少なくとも2個のケイ素原子結合水素原子を有するオルガノポリシロキサン、または前記(C1)成分と(C2)成分の混合物である、請求項1または2記載の硬化性シリコーン組成物。 - (C1)成分中の少なくとも1個のR6がフェニル基またはナフチル基である、請求項3記載の硬化性シリコーン組成物。
- (C1)成分と(C2)成分の混合物において、(C1)成分と(C2)成分の質量比が0.5:9.5〜9.5:0.5である、請求項3記載の硬化性シリコーン組成物。
- 更に、(F)接着付与剤{(A)成分〜(E)成分の合計100質量部に対して0.01〜10質量部}を含む、請求項1乃至5のいずれか1項に記載の硬化性シリコーン組成物。
- 請求項1乃至6のいずれか1項に記載の硬化性シリコーン組成物を硬化してなる硬化物。
- 請求項1乃至6のいずれか1項に記載の硬化性シリコーン組成物の硬化物により発光素子が封止もしくは被覆された光半導体装置。
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US20150368554A1 (en) | 2015-12-24 |
CN105073897B (zh) | 2018-05-01 |
WO2014126265A1 (en) | 2014-08-21 |
KR101655756B1 (ko) | 2016-09-08 |
EP2956508A1 (en) | 2015-12-23 |
US9453158B2 (en) | 2016-09-27 |
TWI609926B (zh) | 2018-01-01 |
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