CN110294936A - Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device - Google Patents
Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device Download PDFInfo
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- CN110294936A CN110294936A CN201910185065.0A CN201910185065A CN110294936A CN 110294936 A CN110294936 A CN 110294936A CN 201910185065 A CN201910185065 A CN 201910185065A CN 110294936 A CN110294936 A CN 110294936A
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- ketone composition
- addition curable
- silicon
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- 229910052710 silicon Inorganic materials 0.000 claims abstract description 12
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
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- 229930195733 hydrocarbon Natural products 0.000 claims description 13
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- 239000000463 material Substances 0.000 abstract description 47
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- QYLFHLNFIHBCPR-UHFFFAOYSA-N 1-ethynylcyclohexan-1-ol Chemical compound C#CC1(O)CCCCC1 QYLFHLNFIHBCPR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000001293 FEMA 3089 Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910020485 SiO4/2 Inorganic materials 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
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- 150000001336 alkenes Chemical class 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 2
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KWEKXPWNFQBJAY-UHFFFAOYSA-N (dimethyl-$l^{3}-silanyl)oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)C KWEKXPWNFQBJAY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 241000270708 Testudinidae Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
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- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 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 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000012790 confirmation Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 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 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VWWMOACCGFHMEV-UHFFFAOYSA-N dicarbide(2-) Chemical compound [C-]#[C-] VWWMOACCGFHMEV-UHFFFAOYSA-N 0.000 description 1
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- 125000006038 hexenyl 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
- 239000000017 hydrogel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- NYMPGSQKHIOWIO-UHFFFAOYSA-N hydroxy(diphenyl)silicon Chemical compound C=1C=CC=CC=1[Si](O)C1=CC=CC=C1 NYMPGSQKHIOWIO-UHFFFAOYSA-N 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical compound C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical class [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RWRDJVNMSZYMDV-UHFFFAOYSA-L radium chloride Chemical class [Cl-].[Cl-].[Ra+2] RWRDJVNMSZYMDV-UHFFFAOYSA-L 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- RSNQKPMXXVDJFG-UHFFFAOYSA-N tetrasiloxane Chemical compound [SiH3]O[SiH2]O[SiH2]O[SiH3] RSNQKPMXXVDJFG-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/398—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- 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
- C08L83/14—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 in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
The present invention provides a kind of addition curable silicon-ketone composition for generating solidfied material, and solidfied material firmness change under the high temperature conditions and weight reduce small, and permeability does not occur being exposed near ultraviolet~purple light under hot and humid environment.The addition curable silicon-ketone composition contains following compositions, and solidified by heating: the organopolysiloxane of the straight-chain represented by (A) following average composition formulas (1), in each molecule at least two alkenyl, (R1 3SiO1/2)a(R1 2R2SiO1/2)b(R1 2SiO)c(R1R2SiO)d…(1)；(B) hydrogen atom at least two and silicon atom bonding in each molecule and the organic hydrogen polysiloxanes without addition reactivity carbon-carbon double bond；(C) containing the hydrosilylation catalysts of platinum group metal；And (D) has the poly- organic metal siloxanes of Si-O-Ce key and Si-O-Ti key.
Description
Technical field
It is used as the light of sealing material partly the present invention relates to addition curable silicon-ketone composition, its solidfied material and by the solidfied material
Conductor device.
Background technique
As the sealing material of LED element, usually using epoxy resin, however propose in Patent Documents 1 to 3 using silicon
Ketone resin replaces epoxy resin as sealing material.Compared with epoxy resin, the heat resistance of silicone resin, weatherability, resistance to discoloration
Property is excellent, thus obtained centered on blue led, White LED using.
However, with the increase in recent years to the turn on angle of LED, the temperature near LED element rises, even if using silicon
When ketone resin, sealing material deterioration is still led to the problem of, generate cracking or the decline of the light transmittance caused by changing colour.
Further, increased using the case where short wavelength's LED element of height output, also caused because under hot and humid environment
So that it is powered and cause silicone resin deterioration, generate the silicone of liquid the emersion of silicone resin surface the phenomenon that (permeability) etc. and ask
Topic.
From such background, in recent years, the sealing material of LED element is required in a high temperauture environment reliably and with long-term
The light resistance of property (that is, heat resistance) or the short-wavelength light under hot and humid environment.
As the common silicone material for improving heat resistance, so far report have based on organic poly- silicon oxygen
In alkane, blend with 150 DEG C or more of temperature to the carboxylate and titanium compound of organopolysiloxane, cerium or zirconia compound into
Reaction product obtained from row heat treatment is as heat resistance organopolysiloxane composition (patent document 4) made of additive
Or it is blended with the Silica hydrogel composition (patent document 5) of same additives.However, the composition recorded in these patent documents is simultaneously
It is non-to generate the addition curable silicon-ketone composition with the solidfied material of rubber hardness, therefore it is not used to LED member as described above
Sealing material of part etc. is on the way.
On the other hand, the heat resistance for having a kind of terres rares salt mixture containing 2 ethyl hexanoic acid is reported in patent document 6
Silicone rubber compound, and the total light transmittance reported at the wavelength 600nm of sheet material with a thickness of 2mm is 90% or more.However,
In the heat resistance silicone rubber compound, there is a problem of the translucency difference of the short-wavelength light near wavelength 400nm.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 11-001619 bulletin
Patent document 2: Japanese Unexamined Patent Publication 2002-265787 bulletin
Patent document 3: Japanese Unexamined Patent Publication 2004-186168 bulletin
Patent document 4: Japanese Unexamined Patent Application 60-163966 bulletin
Patent document 5: Japanese Unexamined Patent Publication 2008-291148 bulletin
Patent document 6: International Publication No. WO2013/079885 handbook
Summary of the invention
The technical problem to be solved in the present invention
The present invention is to carry out to solve the above-mentioned problems, and its purpose is to provide a kind of addition for generating solidfied material is solid
Change type silicon-ketone composition, solidfied material firmness change under the high temperature conditions and weight reduce it is small, even if in hot and humid environment
Under be exposed near ultraviolet~purple light permeability also do not occur.
Solve the technological means of technical problem
In order to reach above-mentioned technical problem, the present invention provides a kind of addition curable silicon-ketone composition, which is characterized in that contains
There are following compositions, and solidified by heating:
(A) straight-chain represented by following average composition formulas (1), in each molecule at least two alkenyl has
Machine polysiloxanes,
(R1 3SiO1/2)a(R1 2R2SiO1/2)b(R1 2SiO)c(R1R2SiO)d···(1)
In formula, R1It is each independently substituted or non-substituted monovalent hydrocarbon, R2For alkenyl, a and b are 0 or positive number, c and d
For positive number, and to meet a+b > 0,0.01≤(b+d)/(a+b+c+d)≤0.03 number；
(B) there is the hydrogen atom of at least two and silicon atom bonding in each molecule and do not have addition reactivity carbon carbon
The organic hydrogen polysiloxanes of double bond；
(C) containing the hydrosilylation catalysts of platinum group metal；And
(D) the poly- organic metal siloxanes with Si-O-Ce key and Si-O-Ti key.
If such addition curable silicon-ketone composition, then the firmness change and weight generated under the high temperature conditions is reduced
It is small, the solidfied material of permeability does not occur being exposed near ultraviolet~purple light under hot and humid environment yet.
In addition, the present invention provides a kind of silicone cure object, and solidifying above-mentioned addition curable silicon-ketone composition
At.
If such silicone cure object, then the applicable material for acting on optical elements such as sealing LED etc..
Furthermore it is preferred that the total light transmission when sheet with a thickness of 2mm is made in the silicone cure object, at the 400nm at initial stage
Rate is 80% or more, is within 10% with 250 DEG C of weight reduction rates after keeping 500 hours.
If such silicone cure object, then transparent excellent, under hot environment weight is reduced small, therefore is particularly suitable for
As the material for sealing optical element etc..
In addition, the present invention provides a kind of optical semiconductor device, which is characterized in that by using above-mentioned silicone cure object to light
Element is learned to be sealed.
If such optical semiconductor device, then since the weight under using the above-mentioned transparency excellent and hot conditions is reduced
Small silicone cure object is sealed optical element, therefore optical semiconductor device under the high temperature conditions excellent in reliability.
It is preferred that the optical element is the LED element for issuing the light of 300~440nm of wavelength, in 85 DEG C, 85%Rh environment
Under, when Xiang Suoshu LED element passes to the electric current of 500 hours 200mA, permeability does not occur for silicone cure object surface.
Under hot and humid environment permeability does not occur for such optical semiconductor device, therefore reliability is especially excellent
It is different.
Invention effect
As described above, then it is the addition for generating following solidfied material if addition curable silicon-ketone composition of the invention
Curing type silicon-ketone composition: transparent and resistance to thermochromism is excellent, firmness change and weight reduction under hot environment is small, even if
It is exposed near ultraviolet~purple light under hot and humid environment, the permeability deteriorated with silicone resin does not occur yet, cracking patience is good
Solidfied material.Therefore, protection of the addition curable silicon-ketone composition of the invention as LED element, sealing material, the change of wavelength
More, the constituent material or other Optical devices of adjustment material or eyeglass with or material used for optical part be particularly useful
's.
Detailed description of the invention
Fig. 1 is the schematic cross-section for indicating an example of optical semiconductor device of the invention.
Description of symbols
1: optical element；2: lead electrode；3: chip grafting material；4: gold thread；5: light reflects resin；6: silicone cure
Object；7: optical semiconductor device.
Specific embodiment
As described above, it is desirable that develop a kind of generation firmness change under the high temperature conditions and weight reduce it is small, even if in height
The addition curable silicon-ketone composition that the solidfied material of permeability does not occur yet near ultraviolet~purple light is exposed under warm high humidity environment.
Present inventor is conscientiously studied, as a result, it has been found that, if adding containing following (A)~(D) ingredient
It at curing type silicon-ketone composition, then can reach above-mentioned technical problem, be suitable as optical element sealing use etc., so as to complete
The present invention.
I.e. the present invention is a kind of addition curable silicon-ketone composition, containing following (A)~(D) ingredient, and by adding
Heat is solidified:
(A) straight-chain represented by following average composition formulas (1), in each molecule at least two alkenyl has
Machine polysiloxanes,
(R1 3SiO1/2)a(R1 2R2SiO1/2)b(R1 2SiO)c(R1R2SiO)d···(1)
In formula, R1It is each independently substituted or non-substituted monovalent hydrocarbon, R2For alkenyl, a and b are 0 or positive number, c and d
For positive number, and to meet a+b > 0,0.01≤(b+d)/(a+b+c+d)≤0.03 number；
(B) there is the hydrogen atom of at least two and silicon atom bonding in each molecule and do not have addition reactivity carbon carbon
The organic hydrogen polysiloxanes of double bond；
(C) containing the hydrosilylation catalysts of platinum group metal；And
(D) the poly- organic metal siloxanes with Si-O-Ce key and Si-O-Ti key.
The present invention is described in detail below, but the present invention is not so limited.
< addition curable silicon-ketone composition >
Addition curable silicon-ketone composition of the invention containing following (A)~(D) ingredient by forming.Of the invention adds
At curing type silicon-ketone composition can using known method by following (A)~(D) ingredient and it is as needed it is following other
Ingredient is mixed and is prepared.
Each ingredient is described in detail below.
[(A) ingredient]
(A) ingredient in addition curable silicon-ketone composition of the invention is to be reacted with (B) ingredient described hereinafter
And the ingredient of solidfied material is formed, while having the effect of bringing stress to mitigate solidfied material obtained from this composition of solidification.(A)
Ingredient is organic poly- silicon of the straight-chain represented by following average composition formulas (1), in each molecule at least two alkenyl
Oxygen alkane.
(R1 3SiO1/2)a(R1 2R2SiO1/2)b(R1 2SiO)c(R1R2SiO)d···(1)
In formula, R1It is each independently substituted or non-substituted monovalent hydrocarbon, R2For alkenyl, a and b are 0 or positive number, c and d
For positive number, and to meet a+b > 0,0.01≤(b+d)/(a+b+c+d)≤0.03 number.
In above-mentioned average composition formula (1), the range that (b+d)/(a+b+c+d) is 0.01~0.03, preferably 0.013~
0.024 range.(b+d) when/(a+b+c+d) is less than 0.01, the solidfied material of above-mentioned silicon-ketone composition is under hot and humid environment
When being exposed near ultraviolet~purple light light, permeability occurs if solidfied material becomes fragile more than 0.03 and generates tortoise under high temperature environment
It splits.
In above-mentioned average composition formula (1), R1Represented substituted or non-substituted monovalent hydrocarbon is not particularly limited, respectively
From independently be preferably carbon atom number be 1~10 monovalent hydrocarbon, particularly preferably carbon atom number be 1~8 monovalent hydrocarbon, example
Methyl, ethyl, propyl, isopropyl, butyl, isobutyl group, tert-butyl, amyl, neopentyl, hexyl, cyclohexyl, pungent can such as be enumerated
The alkyl such as base, nonyl, decyl；The aryl such as phenyl, tolyl, xylyl, naphthalene；The virtues such as benzyl, phenylethyl, phenyl propyl
Alkyl etc., particularly preferably methyl.
In above-mentioned average composition formula (1), R2Represented alkenyl is not particularly limited, but is each independently preferably carbon
The alkenyl that the alkenyl that atomicity is 1~10, particularly preferably carbon atom number are 1~6, can enumerate vinyl, allyl, butylene
Base, pentenyl, hexenyl etc., particularly preferably vinyl.
It as the concrete example of (A) ingredient, is not particularly limited, two end trimethylsiloxy group of strand sealing end can be enumerated
Dimethylsiloxane methyl vinyl siloxane copolymer, two end trimethylsiloxy group of strand block dimethyl silica
Alkane diphenyl siloxane methyl vinyl silicone copolymer, two terminal dimethyl group vinyl siloxy of strand sealing end two
Methylsiloxane methyl vinyl silicone copolymer etc..
(A) ingredient can be used alone one kind, also can be used simultaneously molecular weight, the type with the organic group of silicon atom bonding
It is two or more etc. different.
(A) viscosity of the ingredient at 25 DEG C is not particularly limited, but due to the workability of composition or the light of solidfied material
It learns or mechanical characteristic is more excellent, therefore preferably preferably 50~100,000mPas, more preferably 1,000~50,000mPa
S, particularly preferably 1, the range of 000~10,000mPas.When meeting the viscosity, the degree of polymerization is usually 50~1,000,
Preferably 200~800, more preferably 200~600.
(A) molecular weight of ingredient is not particularly limited, but based on GPC (the gel infiltration for having used THF (tetrahydrofuran) solvent
Saturating chromatography) measurement standard polystyren conversion weight average molecular weight (Mw) be preferably 1,000~100,000, more preferably
5,000~70,000, particularly preferably 10,000~50,000.
In addition, (A) ingredient has at least two alkenyl in each molecule, preferably there are 3~30 alkenyls.(if A) ingredient
Alkenyl with such number can then further increase effect of the invention.
[(B) ingredient]
(B) ingredient in addition curable silicon-ketone composition of the invention is to have at least two and silicon in each molecule
The hydrogen atom (that is, SiH yl) of atomistic binding and the organic hydrogen polysiloxanes for not having addition reactivity carbon-carbon double bond, and it is upper
It states (A) ingredient and carries out hydrosilylation reactions, and play a role as crosslinking agent.
(B) molecular structure of the organic hydrogen polysiloxanes of ingredient is not particularly limited, such as can enumerate straight-chain, ring
Shape, branched, tridimensional network (resin-like) etc., preferably straight-chain or ring-type.
(B) organic hydrogen polysiloxanes of ingredient preferably averagely have 3~300 SiH bases in 1 molecule, further preferably
With 4~150 SiH bases.
In (B) ingredient of 100g, the content with the hydrogen atom of silicon atom bonding in (B) ingredient is preferably
0.001~5 mole, particularly preferably 0.01~2 mole.
(B) position of the SiH base in the organic hydrogen polysiloxanes molecule of ingredient can be in the end of strand, can also be
Non-end, or can be in end and non-end.
Silicon atom key in the organic hydrogen polysiloxanes molecule of (B) ingredient, in addition to the silicon atom bonding hydrogen atom
It closes organic group to be not particularly limited, such as preferably non-substituted or replacing, that carbon atom number is 1~10 monovalent hydrocarbon, more
Preferably non-substituted or replacing, that carbon atom number is 1~6 monovalent hydrocarbon can enumerate and (A) as its concrete example
R is used as in ingredient1And the identical monovalent hydrocarbon of group exemplified.
The concrete example of organic hydrogen polysiloxanes as (B) ingredient can enumerate 1,1,3,3- tetramethyl disiloxane, 1,
3,5,7- tetramethyl-ring tetrasiloxane, methyl hydrogen cyclopolysiloxane, dimethylsiloxane methylhydrogensiloxacopolymer cyclocopolymer,
Three (dimethyl hydrogen siloxy) methyl-monosilanes, three (dimethyl hydrogen siloxy) phenyl silanes, two end trimethyl silicane oxygen of strand
It is total that base blocks methylhydrogenpolysi,oxane, two end trimethylsiloxy group of strand sealing end dimethylsiloxane methylhydrogensiloxacopolymer
Polymers, two end trimethylsiloxy group of strand sealing end dimethylsiloxane methylhydrogensiloxacopolymer methyl phenyl siloxane are total
Polymers, two terminal dimethyl group hydrogen siloxy of strand block dimethyl polysiloxane, two terminal dimethyl group hydrogen siloxy of strand
Block dimethylsiloxane methylhydrogensiloxacopolymer copolymer, two terminal dimethyl group hydrogen siloxy of strand blocks dimethyl silica
Alkane methyl phenyl siloxane copolymer, two terminal dimethyl group hydrogen siloxy of strand block methyl phenyl silicone, by formula:
(CH3)2HSiO1/2Represented siloxane unit and formula: (CH3)3SiO1/2Represented siloxane unit and formula: SiO4/2Institute's table
Copolymer that the siloxane unit that shows is formed, by formula: (CH3)2HSiO1/2Represented siloxane unit and formula: SiO4/2It is represented
Siloxane unit formed copolymer, by mixture of two or more formation in these organopolysiloxanes etc..
(B) viscosity of the ingredient at 25 DEG C is not particularly limited, but due to the workability of composition or the light of solidfied material
It learns or mechanical characteristic is more excellent, therefore preferably satisfy 0.1~5,000mPas, more preferably meet 0.5~1,000mPas, spy
The range of 2~500mPas is not preferably satisfied, is the range of liquid preferably under room temperature (25 DEG C).When meeting the viscosity,
Silicon atom number (or degree of polymerization) in 1 molecule of organic hydrogen polysiloxanes is usually 2~1,000, preferably 3~300, more excellent
It is selected as 4~150.
(B) molecular weight of ingredient is not particularly limited, but based on the standard polyphenyl second for having used the GPC of THF solvent to measure
The Mw of alkene conversion is preferably 100~10,000, more preferably 200~5,000, particularly preferably 500~3,000.
(B) blended amount of ingredient is not particularly limited, but preferably in following hydrosilylation catalysts ((C) ingredient)
In the presence of, to make addition curable silicon-ketone composition solidify for full amount, more preferably make the SiH in (B) ingredient opposite
The amount that the molar ratio of alkenyl in above-mentioned (A) ingredient is 0.4~4.0, further preferably make above-mentioned molar ratio 0.6~
3.0 amount.
[(C) ingredient]
(C) ingredient is the hydrosilylation catalysts (platinum group metal type hydrogenation silylation catalyst) containing platinum group metal,
Being somebody's turn to do (C) ingredient is as promotion and the catalysts for reacting (hydrosilylation reactions) of above-mentioned (A) ingredient and (B) ingredient
And the ingredient to play a role.
As (C) ingredient, as long as promoting the silane of the SiH base in the alkenyl and above-mentioned (B) ingredient in above-mentioned (A) ingredient
Any catalyst may be used in alkanisation addition reaction.(C) ingredient can be used alone one kind, also can be used simultaneously two or more.Make
For such catalyst, such as the platinums group metal such as platinum, palladium, rhodium or the modified chloroplatinic acid of chloroplatinic acid, alcohol, chloroplatinic acid and alkene can be enumerated
The platinum families such as hydro carbons, the complex of vinylsiloxane or acetylide, tetrakis triphenylphosphine palladium, three (triphenylphosphine) radium chlorides
Metallic compound, particularly preferably platinum compounds.(C) ingredient can be used alone one kind, also can be used simultaneously two or more.
(C) blended amount of ingredient is not particularly limited, and can be the effective quantity as hydrosilylation catalysts, with platinum family
The mass conversion meter of metal, relative to the gross mass of above-mentioned (A) ingredient and (B) ingredient preferably in the range of 0.1~1000ppm
It is interior, more preferably in the range of 1~500ppm.
[(D) ingredient]
(D) ingredient in addition curable silicon-ketone composition of the invention is poly- with Si-O-Ce key and Si-O-Ti key
Organic metal siloxanes, for the additive of the heat resistance for improving addition curable silicon-ketone composition of the invention.
It is preferred that (D) ingredient be Ce content be 50~5,000ppm, Ti content is 50~5,000ppm, the viscosity at 25 DEG C
For the poly- organic metal siloxanes of 10~10,000mPas.
As (D) ingredient, such as preferably with 150 DEG C or more of temperature to by following (i), (ii) and (iii) ingredient shape
At mixture be heat-treated obtained from reaction product.
(i) viscosity at 25 DEG C is the organopolysiloxane of 10~10,000mPas: 100 mass parts；
(ii) the terres rares carboxylate containing cerium carboxylate represented by the following general formula (D-1): in terms of cerium conversion, relative to
(i) ingredient of 100 mass parts is the amount of 0.05~5 mass parts,
(R3COO)yCe···(D-1)
In formula, R3For monovalent hydrocarbon of the same race or not of the same race, y is 3 or 4；And
(iii) it at least one of titanium compound or its hydrolytic condensate represented by the following general formula (D-2): is converted with titanium
Meter, (i) ingredient relative to 100 mass parts are the amount of 0.05~5 mass parts,
(R4O)4Ti···(D-2)
In formula, R4For monovalent hydrocarbon of the same race or not of the same race.
It, can as long as viscosity at 25 DEG C is 10~10,000mPas as the organopolysiloxane of (i) ingredient
Use known ingredient.
As the terres rares carboxylate of (ii) ingredient, 2 ethyl hexanoic acid, aphthenic acids, oleic acid, lauric acid, tristearin can be exemplified
The cerium salt of acid etc..
As the titanium compound of (iii) ingredient, the tetraalkoxy titaniums such as four tetrabutyl titanates or its hydrolytic condensation can be exemplified
Object etc..
(D) blended amount of ingredient is not particularly limited, but from assigning heat resistance to obtained solidfied material, inhibit discoloration or hard
The angle of degree decline is set out, relative to total 100 mass parts of above-mentioned (A)~(C) ingredient, preferably 0.01~5 mass parts, more
Preferably 0.01~3 mass parts, further preferably 0.5~3 mass parts.
[other compositions]
It, can be as needed in addition curable of the invention other than above-mentioned (A)~(D) ingredient as neccessary composition
Other compositions illustrated by below being blended in silicon-ketone composition.
As other compositions, such as the light scattering agents such as crystallinity silica or supporting material can be enumerated；Fluorophor；Stone
Oil based solvent；The viscosity adjusters such as the non-reactive silicone oil without reactive functional groups；By except above-mentioned (A) ingredient and above-mentioned
(B) the adhesiveness enhancer that the compound other than ingredient is formed, the compound is in 1 molecule containing 1 or more by (methyl)
At least one or more in functional group's group that acrylic, epoxy group, alkoxysilyl, amide groups and acid anhydride form
It is a；Addition reactions inhibitor such as 2- acetenyl 2- lauryl alcohol, 1- ethynylcyclohexanol etc..These other compositions can be used alone one
Kind, it also can be used simultaneously two or more.
< silicone cure object >
It can make addition curable silicon-ketone composition of the invention using well known curing method under well known condition of cure
Solidified and silicone cure object is made.The condition of cure of addition curable silicon-ketone composition of the invention is not particularly limited,
But such as can by with 80~200 DEG C, preferably heated with 120~180 DEG C and make its solidification.Heating time is, for example, 0.5
Minute~5 hours or so, preferably 30~180 minutes or so, for precision prescribeies such as LED sealing use, more preferably
Extend curing time.
It is preferred that addition curable silicon-ketone composition of the invention will be made to solidify (for example, heating 2 hours with 150 DEG C) and obtain
Silicone cure object when the sheet with a thickness of 2mm is made, the total light transmittance at the 400nm at initial stage is 80% or more.
In addition, for making addition curable silicon-ketone composition of the invention solidify (for example, with 150 DEG C heat 2 hours) and
Obtained silicone cure object, preferably the firmness change rate with 250 DEG C after keeping 300 hours are within 30%, and weight reduction rates are
Within 10%.
If such silicone cure object, then since the transparency is excellent, the weight reduction under hot environment is small, especially
It is suitable as the material for sealing optical element etc..
< optical semiconductor device >
In addition, the present invention provides a kind of optical semiconductor device, by using above-mentioned addition curable silicon-ketone composition
Solidfied material (silicone cure object) optical element is sealed.
Fig. 1 is the schematic cross-section of an example of optical semiconductor device of the invention.Photosemiconductor dress shown in Fig. 1
It sets in 7, optical element 1 is fixed on a pair of lead wires electricity using chip grafting material (die bonding material) 3
In the framework of pole 2, light reflection resin 5 is formed in the peripheral part of optical element 1.Optical element 1 and lead electrode 2 pass through gold thread
4 connections, and with casting addition curable silicon-ketone composition of the invention and cured silicone cure object 6 is sealed.
As the optical element that the solidfied material using addition curable silicon-ketone composition of the invention is sealed to form, such as can
Enumerate LED, semiconductor laser, photodiode, phototransistor, solar cell, CCD etc..Such optical element can lead to
It crosses following manner to be sealed: being coated with the sealing formed by addition curable silicon-ketone composition of the invention on the optical element
Material makes the sealing material of coating solid under well known condition of cure using well known curing method, for example under the above conditions
Change.The optical semiconductor device of the invention as obtained from by this method sealing optical element uses the addition for generating solidfied material
Curing type silicon-ketone composition is sealed semiconductor element, therefore excellent in reliability, the solidfied material transparency it is excellent and
Firmness change and weight reduction under hot environment is small, does not send out being exposed near ultraviolet~purple light under hot and humid environment
Raw permeability.
Furthermore it is preferred that optical semiconductor device use of the invention the addition curable silicon-ketone composition is solidified (for example,
Be heating and curing 2 hours with 150 DEG C) made of solidfied material the LED of light for issuing 300~440nm of wavelength is sealed, 85
DEG C, under 85%Rh environment, when Xiang Suoshu LED passes to the electric current of 500 hours 200mA, permeability does not occur for silicone cure object surface.
Permeability does not occur under hot and humid environment for such optical semiconductor device, therefore reliability is especially excellent.
As described above, protection and sealing material of the addition curable silicon-ketone composition of the invention as LED element, wave
The long change and adjustment constituent material of material or eyeglass, other Optical devices with or material used for optical part be special
Useful.
Embodiment
Hereinafter, the present invention is specifically described using synthesis example, Examples and Comparative Examples, but the present invention is not limited by it
It is fixed.
In following examples, indicate that the symbol of the composition of silicone oil or silicone resin is as follows.
M:(CH3)3SiO1/2
MVi: (CH2=CH) (CH3)2SiO1/2
DH: (CH3)HSiO2/2
D:(CH3)2SiO2/2
DVi: (CH2=CH) (CH3)SiO2/2
[synthesis example 1]
(D) preparation of ingredient
It will be pre-mixed that (rare earth element content is 6 matter using cerium as the turpentine oil solution of the 2 ethyl hexanoic acid salt of principal component
Amount %) (titanium quality is in the 2 ethyl hexanoic acid salt to 10 mass parts (cerium amount is 0.55 part) with four tetrabutyl titanates, 2.1 mass parts
0.3 times of cerium quality) made of mixture the viscosity of 100 mass parts is added to when being sufficiently stirred is the two of 100mPas
End trimethylsiloxy group blocks in dimethyl polysiloxane, obtains the dispersion liquid of yellow-white.A small amount of nitrogen is passed to thereto,
It is heated simultaneously, flows out turpentine oil, then heated 1 hour with 300 DEG C, obtain dense transparent poly- organic metal russet
Siloxanes.
[Examples 1 to 5, the Comparative Examples 1 to 5]
Following compositions are blended with blended amount shown in table 1 (unit: mass parts), obtain addition curable silicon-ketone composition.
(A-1) average composition formula MVi 2D445DVi 4.5Represented by (vinyl: 0.19 mM/g), viscosity 5.0Pas
Organopolysiloxane
(A-2) average composition formula M2D550DVi 5.5Represented by (vinyl: 0.13 mM/g), viscosity 10.0Pas
Organopolysiloxane
(A-3) average composition formula MVi 2D440DVi 9Represented by (vinyl: 0.33 mM/g), viscosity 5.0Pas
Organopolysiloxane
(A-4) average composition formula MVi 2D450Represented by (vinyl: 0.06 mM/g), viscosity be that 5.0Pas has
Machine polysiloxanes
(A-5) average composition formula MVi 2D405DVi 45Represented by (vinyl: 1.38 mMs/g), viscosity 5.0Pas
Organopolysiloxane
(A-6) average composition formula MVi 2D550DVi 1Represented by (vinyl: 0.07 mM/g), viscosity 10.0Pas
Organopolysiloxane
(A-7) average composition formula MVi 2D445DVi 2.5Represented by (vinyl: 0.13 mM/g), viscosity 4.8Pas
Organopolysiloxane
(A-8) average composition formula MVi 2D440DVi 11.5Represented by (vinyl: 0.40 mM/g), viscosity 5.3Pa
The organopolysiloxane of s
(A-9) average composition formula MVi 2D435DVi 16Represented by (vinyl: 0.53 mM/g), viscosity 5.5Pas
Organopolysiloxane
(B) average composition formula M2DH 4D24Represented by (SiH base: 1.81 mMs/g), viscosity be 25mPas it is organic
Polysiloxanes
(C) platinum-divinyl tetramethyl disiloxane complex compound toluene solution (platinum content is 1 mass %)
(D) poly- organic metal siloxanes obtained in above-mentioned synthesis example 1
Other compositions:
(E) compound (adhesiveness enhancer) represented by following formula (2):
[chemical formula 2]
(F) 1- ethynylcyclohexanol (addition reaction controlling agent)
[table 1]
For addition curable silicon-ketone composition obtained in above-described embodiment 1~5 and the Comparative Examples 1 to 5, pass through following examinations
It tests and is evaluated.Show the result in table 2.
[light transmittance]
Addition curable silicon-ketone composition obtained in each embodiment and each comparative example heat within 2 hours with 150 DEG C
To be solidified, the solidfied material of 2mm thickness is made.Using spectrophotometer, the wavelength of the 400nm of the solidfied material measured
Light transmittance (optical path length 2mm).
[hardness (initial stage) of solidfied material]
Addition curable silicone resin component obtained in each embodiment and each comparative example is carried out 2 hours with 150 DEG C
Heating.Use Durometer A type hardness tester meter, the hardness of the solidfied material measured at 25 DEG C.
[hardness after heat-resistance test]
After solidfied material used in above-mentioned Determination of Hardness is taken care of in the environment of 250 DEG C, 500 hours, use
Durometer A type hardness tester meter measures the hardness of solidfied material at 25 DEG C.
[weight rate (w residual rate) of heat-resistance test]
Measure the initial stage weight of solidfied material used in above-mentioned determination of light transmittance and in the environment of 250 DEG C, 300 hours into
Weight after row keeping.The ratio of weight after finding out heat-resistance test when initial stage weight is set as 100 is as w residual
Rate.
[high temperature energizing test]
Use the optical semiconductor device shown in FIG. 17 equipped with the LED chip that glow peak is 405nm as optical element.
Optical element 1 is fixed in the framework with a pair of lead wires electrode 2 using chip grafting material 3.Optics is connected by gold thread 4
After element 1 and lead electrode 2, it is cast in addition curable silicon-ketone composition obtained in each embodiment and each comparative example, and in
150 DEG C solidify 2 hours, and optical semiconductor device 7 is made.Manufactured optical semiconductor device is set to be powered with 350mA under 120 DEG C of environment
It shines.After 500 hours, micro- sem observation is carried out to the appearance of sealing resin, confirmation has the generation of no cracking.It, will not in table 2
Cracking, situation without exception are generated labeled as zero, will be labeled as the case where producing cracking ×.
[high temperature and humidity energizing test]
In the environment of 85 DEG C, 85%Rh, made with 200mA using made of method identical with above-mentioned high temperature energizing test
Optical semiconductor device electrified light emitting.After 500 hours, micro- sem observation is carried out to the appearance of sealing resin, is confirmed whether to seep
Oil.In table 2, by not there is a situation where permeability, it is without exception be labeled as zero, will the case where permeability have occurred labeled as ×.
[table 2]
As shown in Table 2 above, in Examples 1 to 5, the transparency is excellent, and the firmness change under hot conditions is small, and weight subtracts
When young (that is, w residual rate is big).In addition, also not seeped even if being exposed near ultraviolet~purple light under hot and humid environment
Oil or cracking, are good.On the other hand, the organic poly- containing alkenyl of the condition for being unsatisfactory for (A) ingredient of the invention is being used
In the comparative example 1~4 of siloxanes, cracking is produced in high temperature energizing test or is had occurred in high temperature and humidity energizing test
Permeability.In addition, without containing (D) ingredient of the invention comparative example 5 in, the physical property under hot conditions become significantly,
Cracking is produced in high temperature energizing test.
In addition, the present invention is not limited by above embodiment.Above embodiment is to illustrate, and is had and power of the invention
The substantially identical composition of the technical concept recorded in sharp claim and the technical solution for playing identical function and effect are all contained in this
In the technical scope of invention.
Claims (5)
1. a kind of addition curable silicon-ketone composition, which is characterized in that solidified containing following compositions, and by heating:
(A) straight-chain represented by following average composition formulas (1), in each molecule at least two alkenyl is organic poly-
Siloxanes,
(R1 3SiO1/2)a(R1 2R2SiO1/2)b(R1 2SiO)c(R1R2SiO)d···(1)
In formula, R1It is each independently substituted or non-substituted monovalent hydrocarbon, R2For alkenyl, a and b are 0 or positive number, and c and d are positive
Number, and to meet a+b > 0,0.01≤(b+d)/(a+b+c+d)≤0.03 number；
(B) there is the hydrogen atom of at least two and silicon atom bonding in each molecule and do not have addition reactivity carbon-carbon double bond
Organic hydrogen polysiloxanes；
(C) containing the hydrosilylation catalysts of platinum group metal；And
(D) the poly- organic metal siloxanes with Si-O-Ce key and Si-O-Ti key.
2. a kind of silicone cure object, which is characterized in that by solidifying addition curable silicon-ketone composition described in claim 1
It forms.
3. silicone cure object according to claim 2, which is characterized in that being made the silicone cure object with a thickness of 2mm
Sheet when, the total light transmittance at the 400nm at initial stage is 80% or more, is with 250 DEG C of weight reduction rates after keeping 500 hours
Within 10%.
4. a kind of optical semiconductor device, which is characterized in that by using silicone cure object described in claim 2 or 3 to optics
Element is sealed.
5. optical semiconductor device according to claim 4, which is characterized in that the optical element be issue wavelength 300~
The LED element of the light of 440nm, under 85 DEG C, 85%Rh environment, when Xiang Suoshu LED element passes to the electric current of 500 hours 200mA,
Permeability does not occur for silicone cure object surface.
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| JP2018057222A JP6923475B2 (en) | 2018-03-23 | 2018-03-23 | Additive-curable silicone compositions, silicone cured products, and opto-semiconductor devices |
| JP2018-057222 | 2018-03-23 |
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|---|---|---|---|---|
| CN112322048A (en) * | 2020-11-03 | 2021-02-05 | 杭州之江新材料有限公司 | Organic silicon gel composition and preparation method and application thereof |
| CN112625247A (en) * | 2019-10-08 | 2021-04-09 | 信越化学工业株式会社 | Curable composition, cured product thereof, and semiconductor device |
| CN115885015A (en) * | 2020-07-13 | 2023-03-31 | 陶氏东丽株式会社 | Silicone gel composition, cured product thereof, and use thereof |
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| WO2021161580A1 (en) | 2020-02-13 | 2021-08-19 | 富士高分子工業株式会社 | Heat resistant silicone resin composition and heat resistant silicone resin composite material |
| JP2021132138A (en) * | 2020-02-20 | 2021-09-09 | 日機装株式会社 | Semiconductor light-emitting device |
| CN111534130B (en) * | 2020-06-01 | 2021-07-30 | 深圳市新纶科技股份有限公司 | Heat-conducting powder modifier, heat-conducting silica gel and preparation method thereof |
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Also Published As
| Publication number | Publication date |
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| JP2019167473A (en) | 2019-10-03 |
| TW201940595A (en) | 2019-10-16 |
| KR102683130B1 (en) | 2024-07-10 |
| TWI754797B (en) | 2022-02-11 |
| KR20190111796A (en) | 2019-10-02 |
| JP6923475B2 (en) | 2021-08-18 |
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