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 PDF

Info

Publication number
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
Authority
CN
China
Prior art keywords
sio
ingredient
ketone composition
addition curable
silicon
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.)
Pending
Application number
CN201910185065.0A
Other languages
Chinese (zh)
Inventor
木村真司
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shin Etsu Chemical Co Ltd
Original Assignee
Shin Etsu Chemical Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Shin Etsu Chemical Co Ltd filed Critical Shin Etsu Chemical Co Ltd
Publication of CN110294936A publication Critical patent/CN110294936A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/38Polysiloxanes modified by chemical after-treatment
    • C08G77/382Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/398Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions 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
    • C08L83/04Polysiloxanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00Compositions 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
    • C08L83/14Compositions 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00Adhesives 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
    • C09J183/04Polysiloxanes
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00Semiconductor 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
    • H01L33/48Semiconductor 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
    • H01L33/52Encapsulations
    • H01L33/56Materials, e.g. epoxy or silicone resin
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/12Polysiloxanes containing silicon bound to hydrogen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/20Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04Polysiloxanes
    • C08G77/22Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00Properties
    • C08L2201/08Stabilised against heat, light or radiation or oxydation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00Applications
    • C08L2203/20Applications use in electrical or conductive gadgets
    • C08L2203/206Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00Polymer mixtures characterised by other features
    • C08L2205/02Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00Polymer mixtures characterised by other features
    • C08L2205/02Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00Polymer mixtures characterised by other features
    • C08L2205/03Polymer mixtures characterised by other features containing three or more polymers in a blend

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Power Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Led Device Packages (AREA)

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

Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device
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.
CN201910185065.0A 2018-03-23 2019-03-12 Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device Pending CN110294936A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
CN110294936A true CN110294936A (en) 2019-10-01

Family

ID=68026394

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910185065.0A Pending CN110294936A (en) 2018-03-23 2019-03-12 Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device

Country Status (4)

Country Link
JP (1) JP6923475B2 (en)
KR (1) KR102683130B1 (en)
CN (1) CN110294936A (en)
TW (1) TWI754797B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1079765A (en) * 1992-06-08 1993-12-22 通用电气公司 Temperature pressure sensitive adhesives
JP2000001619A (en) * 1998-06-15 2000-01-07 Dainippon Printing Co Ltd Resin composition having deodorizing function and interior member for construction
JP2002265787A (en) * 2001-03-06 2002-09-18 Shin Etsu Chem Co Ltd Addition-curable silicone resin composition
JP2008291148A (en) * 2007-05-25 2008-12-04 Shin Etsu Chem Co Ltd Silicone gel composition excellent in heat resistance
CN101747632A (en) * 2009-12-15 2010-06-23 陈俊光 Organic silicon rubber encapsulating material for high-power LED
CN103827218A (en) * 2011-12-08 2014-05-28 迈图高新材料日本合同公司 Hydrosilylation-curable silicone rubber composition
CN104212185A (en) * 2014-09-10 2014-12-17 杭州赢科新材料科技有限公司 Stable and non-oil-leaking type transparent silica gel for electronic component
CN105612219A (en) * 2013-09-03 2016-05-25 道康宁东丽株式会社 Silicone gel composition and use thereof
JP2017088776A (en) * 2015-11-13 2017-05-25 信越化学工業株式会社 Addition curable silicone resin composition, method of producing the composition, and optical semiconductor device

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60163966A (en) 1984-02-06 1985-08-26 Shin Etsu Chem Co Ltd Heat-resistant organopolysiloxane composition
JP3344286B2 (en) 1997-06-12 2002-11-11 信越化学工業株式会社 Addition-curable silicone resin composition
JP2004186168A (en) 2002-11-29 2004-07-02 Shin Etsu Chem Co Ltd Silicone resin composition for light emitting diode element
JP2012111836A (en) * 2010-11-24 2012-06-14 Sekisui Chem Co Ltd Sealing agent for optical semiconductor device, and optical semiconductor device using the same
JP2012197328A (en) * 2011-03-18 2012-10-18 Sekisui Chem Co Ltd Method of producing organopolysiloxane, composition for photosemiconductor device, and photosemiconductor device
FR2983622B1 (en) 2011-12-02 2014-01-24 Morpho WRITING DATA IN A NON-VOLATILE MEMORY OF A CHIP CARD
KR102338110B1 (en) * 2013-12-16 2021-12-09 모멘티브 파포만스 마테리아루즈 쟈판 고도가이샤 Addition-curable silicone composition

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1079765A (en) * 1992-06-08 1993-12-22 通用电气公司 Temperature pressure sensitive adhesives
JP2000001619A (en) * 1998-06-15 2000-01-07 Dainippon Printing Co Ltd Resin composition having deodorizing function and interior member for construction
JP2002265787A (en) * 2001-03-06 2002-09-18 Shin Etsu Chem Co Ltd Addition-curable silicone resin composition
JP2008291148A (en) * 2007-05-25 2008-12-04 Shin Etsu Chem Co Ltd Silicone gel composition excellent in heat resistance
CN101747632A (en) * 2009-12-15 2010-06-23 陈俊光 Organic silicon rubber encapsulating material for high-power LED
CN103827218A (en) * 2011-12-08 2014-05-28 迈图高新材料日本合同公司 Hydrosilylation-curable silicone rubber composition
CN105612219A (en) * 2013-09-03 2016-05-25 道康宁东丽株式会社 Silicone gel composition and use thereof
CN104212185A (en) * 2014-09-10 2014-12-17 杭州赢科新材料科技有限公司 Stable and non-oil-leaking type transparent silica gel for electronic component
JP2017088776A (en) * 2015-11-13 2017-05-25 信越化学工業株式会社 Addition curable silicone resin composition, method of producing the composition, and optical semiconductor device

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN115885015B (en) * 2020-07-13 2024-04-05 陶氏东丽株式会社 Silicone gel composition, cured product thereof, and use thereof
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

Also Published As

Publication number Publication date
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

Similar Documents

Publication Publication Date Title
CN110294936A (en) Addition curable silicon-ketone composition, silicone cure object and optical semiconductor device
TWI679244B (en) Addition-curable silicone resin composition, method for producing the same, and optical semiconductor device
JP4519869B2 (en) Semiconductor device
KR101565762B1 (en) Curable organopolysiloxane composition and cured product thereof
KR101267306B1 (en) Curable organopolysiloxane resin composition and optical part molded therefrom
RU2401846C2 (en) Functional polyorganosiloxanes and curable composition based on said polyorganosiloxanes
CN103571208B (en) Curability silicone resin component
JP5279197B2 (en) Curable organosilicon composition and cured product thereof
CN108795053B (en) Addition-curable silicone composition, method for producing same, silicone cured product, and optical element
KR20130088791A (en) Curable organopolysiloxane composition, sealing materials for optical device and optical device
TWI849039B (en) Addition curing silicone resin composition and optical element
KR20120067945A (en) Curable organopolysiloxane composition, optical element sealing material and optical element
CN108795049A (en) Addition curable silicon-ketone composition, the manufacturing method of the composition and optical semiconductor device
CN101981088B (en) Organopolysiloxane, method of manufacturing thereof, curable silicone composition, and cured product thereof
KR20170129248A (en) Organopolysiloxane, its preparation method, and curable silicone composition
JP7388865B2 (en) Addition-curing silicone composition, cured product thereof, and semiconductor device
JP2510577B2 (en) Curable silicone gel composition
TWI834881B (en) Addition-hardening polysilicone resin composition, method of manufacturing the composition, and optical semiconductor device
TW202104378A (en) Silicone resin composition for die-bonding cured product light-emitting diode element and method for producing said composition
JP2019156968A (en) Addition curable silicone composition, optical element encapsulation material, and optical element
TWI854043B (en) Curable composition, cured product thereof, and semiconductor device
JP6905486B2 (en) Additive-curable silicone compositions, silicone cured products, and semiconductor devices
JP2023122154A (en) Addition curable type silicone resin composition, silicone cured product and optical device
TW202436518A (en) Curable hotmelt silicone composition,encapsulant, hotmelt adhesives, and optical semiconductor device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20191001