[go: up one dir, main page]

WO2018088316A1 - Composition de silicone durcissable et dispositif semi-conducteur optique l'utilisant - Google Patents

Composition de silicone durcissable et dispositif semi-conducteur optique l'utilisant Download PDF

Info

Publication number
WO2018088316A1
WO2018088316A1 PCT/JP2017/039673 JP2017039673W WO2018088316A1 WO 2018088316 A1 WO2018088316 A1 WO 2018088316A1 JP 2017039673 W JP2017039673 W JP 2017039673W WO 2018088316 A1 WO2018088316 A1 WO 2018088316A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mass
carbon atoms
curable silicone
silicone composition
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.)
Ceased
Application number
PCT/JP2017/039673
Other languages
English (en)
Japanese (ja)
Inventor
香須美 竹内
真弓 水上
森田　好次
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.)
DuPont Toray Specialty Materials KK
Original Assignee
Dow Corning Toray 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 Dow Corning Toray Co Ltd filed Critical Dow Corning Toray Co Ltd
Priority to CN201780080034.8A priority Critical patent/CN110088207B/zh
Priority to KR1020197016211A priority patent/KR102498396B1/ko
Priority to JP2018550171A priority patent/JPWO2018088316A1/ja
Publication of WO2018088316A1 publication Critical patent/WO2018088316A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/296—Organo-silicon compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/852—Encapsulations
    • H10H20/854—Encapsulations characterised by their material, e.g. epoxy or silicone resins
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
    • H01L2224/31—Structure, shape, material or disposition of the layer connectors after the connecting process
    • H01L2224/32—Structure, shape, material or disposition of the layer connectors after the connecting process of an individual layer connector
    • H01L2224/321—Disposition
    • H01L2224/32151—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/32221—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/32245—Disposition the layer connector connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/4805—Shape
    • H01L2224/4809—Loop shape
    • H01L2224/48091—Arched
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/481—Disposition
    • H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
    • H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73251—Location after the connecting process on different surfaces
    • H01L2224/73265—Layer and wire connectors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation

Definitions

  • the present invention relates to a curable silicone composition, and more specifically, a curable silicone composition that can be suitably used as a sealing material or protective coating material for an optical semiconductor element in an optical semiconductor device such as a light emitting diode (LED), and the like.
  • the present invention relates to an optical semiconductor device using the same.
  • the curable silicone composition is used as a sealing material or protective coating material for an optical semiconductor element in an optical semiconductor device such as a light emitting diode (LED).
  • LED light emitting diode
  • the cured product of the curable silicone composition has high gas permeability, when used in a high-brightness LED with strong light intensity and large heat generation, discoloration of the sealing material due to corrosive gas, LED Decrease in brightness due to corrosion of silver plated on the substrate is a problem. This is because the emission efficiency of the optical semiconductor device is attenuated.
  • Patent Document 1 and Patent Document 2 propose a curable silicone composition
  • a curable silicone composition comprising a branched organopolysiloxane having a methylphenylvinylsiloxane unit, an organohydrogenpolysiloxane, and a catalyst for addition reaction.
  • These compositions are disclosed to give cured products with low gas permeability.
  • these curable silicone compositions have insufficient curability and thermal shock resistance of the resulting cured product, and further improvement has been demanded.
  • An object of the present invention is to provide a curable silicone composition that provides a cured product having high hydrosilylation reactivity, excellent curability and thermal shock resistance, and low gas permeability. Moreover, the objective of this invention is providing the optical semiconductor device etc. which are excellent in thermal shock resistance and by which high luminous efficiency continues by using the said curable silicone composition.
  • the present invention contains an organopolysiloxane containing an alkylphenylvinylsiloxane unit, and 1,3-divinyl-1,3-diphenyl-1,3-dimethyldi
  • the present inventors have found that the above problems can be solved by a curable silicone composition characterized in that the siloxane content range is greater than 0.0 mass% and less than 3.0 mass%, and the present invention has been achieved.
  • 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane remains in the organopolysiloxane during the synthesis of the branched or resinous organopolysiloxane containing alkylphenylvinylsiloxane units.
  • the said subject can be solved by using the curable silicone composition controlled so that this content may exist in said range.
  • the curable silicone composition of the present invention is An alkylphenylalkenylsiloxane unit (R 2 R 3 R 4 SiO 1/2 ; R 2 is an alkyl group having 1 to 12 carbon atoms; R 3 is a phenyl group; R 4 is an alkenyl group having 2 to 12 carbon atoms) Comprising an organopolysiloxane having, and The content of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane is greater than 0.0% by mass and less than 3.0% by mass with respect to the entire composition And
  • the curable silicone composition of the present invention comprises (A) Average unit formula: (R 1 3 SiO 1/2 ) a (R 2 R 3 R 4 SiO 1/2 ) b (R 5 2 SiO 2/2 ) c (R 3 SiO 3/2 ) d (Wherein R 1 is the same or different, an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms, provided that at least one R 1 in one molecule is an alkenyl group having 2 to 12 carbon atoms) R 2 is an alkyl group having 1 to 12 carbon atoms; R 3 is a phenyl group; R 4 is an alkenyl group having 2 to 12 carbon atoms; R 4 is an alkenyl group having 2 to 12 carbon atoms; R 5 is the same or different; , An alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a phenyl group; a, b,
  • the cured product of the present invention is obtained by curing the above curable silicone composition.
  • the optical semiconductor device of the present invention is characterized in that an optical semiconductor element is sealed with a cured product of the curable silicone composition described above.
  • the curable silicone composition of the present invention is characterized by forming a cured product having high hydrosilylation reactivity, excellent curability and thermal shock resistance, and low gas permeability. Furthermore, the cured product of the present invention is characterized by low gas permeability and excellent thermal shock resistance, and the optical semiconductor device of the present invention provided with the cured product is excellent in reliability and maintains high luminous efficiency. There is a feature.
  • the curable silicone composition of the present invention comprises an alkylphenylalkenylsiloxane unit (R 2 R 3 R 4 SiO 1/2 ;
  • R 2 is an alkyl group having 1 to 12 carbon atoms;
  • R 3 is a phenyl group;
  • R 4 is a carbon number.
  • the organopolysiloxane is characterized by containing an organopolysiloxane having 2 to 12 alkenyl groups), and the organopolysiloxane forms a cured product having excellent hydrosilylation reactivity and low gas permeability. be able to.
  • the organopolysiloxane may contain other siloxane units, and particularly preferably has a branched or resinous molecular structure.
  • Such organopolysiloxane is preferably Average unit formula: (R 1 3 SiO 1/2 ) a (R 2 R 3 R 4 SiO 1/2 ) b (R 5 2 SiO 2/2 ) c (R 3 SiO 3/2 ) d It is represented by
  • R 1 is the same or different and is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms.
  • alkyl group for R 1 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. It is a methyl group.
  • Examples of the alkenyl group for R 1 include vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, and dodecenyl group. It is a group. However, at least one R 1 in one molecule is an alkenyl group having 2 to 12 carbon atoms. R 2 is an alkyl group having 1 to 12 carbon atoms, and examples thereof are the same alkyl groups as those described above for R 1 , preferably a methyl group. R 3 is a phenyl group.
  • R 4 is an alkenyl group having 2 to 12 carbon atoms, and examples thereof include the same alkenyl groups as those described above for R 1 , preferably a vinyl group.
  • R 5 is the same or different and is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a phenyl group. Examples of the alkyl group for R 5 include the same alkyl groups as those described above for R 1 . Examples of the alkenyl group for R 5 include the same alkenyl groups as those described above for R 1 .
  • the organopolysiloxane according to the present invention is represented by the above average unit formula, but is a siloxane unit represented by the formula: R 2 2 R 3 SiO 1/2 within the range not impairing the object of the present invention, the formula: Siloxane unit represented by R 2 R 3 2 SiO 1/2 , siloxane unit represented by formula: R 3 3 SiO 1/2 , siloxane unit represented by formula: R 2 SiO 3/2 , formula: R It may have a siloxane unit represented by 4 SiO 3/2 or a siloxane unit represented by the formula: SiO 4/2 .
  • R 2 is an alkyl group having 1 to 12 carbon atoms
  • R 3 is an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms
  • R 4 is an alkyl group having 2 to 12 carbon atoms.
  • the same groups as described above are exemplified.
  • the organopolysiloxane of the present invention may have a silicon atom-bonded alkoxy group such as a methoxy group, an ethoxy group, or a propoxy group, or a silicon atom-bonded hydroxyl group as long as the object of the present invention is not impaired.
  • the method of hydrolyzing and condensing the silane compound represented by these in presence of an acid or an alkali is mentioned.
  • R 3 Six 3 Is a raw material for introducing a siloxane unit represented by the formula: R 3 SiO 3/2 into an organopolysiloxane.
  • R 3 is an aryl group having 6 to 20 carbon atoms or an aralkyl group having 7 to 20 carbon atoms, and examples thereof are the same as those described above, and preferably a phenyl group or a naphthyl group.
  • X represents an alkoxy group, an acyloxy group, a halogen atom, or a hydroxyl group. Examples of the alkoxy group for X include a methoxy group, an ethoxy group, and a propoxy group. An example of the acyloxy group for X is an acetoxy group. Examples of the halogen atom for X include a chlorine atom and a bromine atom.
  • silane compounds include alkoxysilanes such as phenyltrimethoxysilane and phenyltriethoxysilane; acyloxysilanes such as phenyltriacetoxysilane; halosilanes such as phenyltrichlorosilane; hydroxysilanes such as phenyltrihydroxysilane.
  • alkoxysilanes such as phenyltrimethoxysilane and phenyltriethoxysilane
  • acyloxysilanes such as phenyltriacetoxysilane
  • halosilanes such as phenyltrichlorosilane
  • hydroxysilanes such as phenyltrihydroxysilane.
  • R 1 3 SiOS iR 1 3 Is a raw material for introducing a siloxane unit represented by the formula: R 1 3 SiO 1/2 into the organopolysiloxane.
  • R 1 is the same or different and is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms.
  • Examples of the alkyl group for R 1 include the same groups as described above, and a methyl group is preferable.
  • Examples of the alkenyl group for R 1 include the same groups as described above, and a vinyl group is preferable.
  • Such disiloxanes include 1,1,1,3,3,3-hexamethyldisiloxane, 1,1,1,3,3,3-hexaethyldisiloxane, 1,3-divinyl-1, 1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,1,3,3-tetraethyldisiloxane, 1,1,3,3-tetravinyl-1,3-dimethyldisiloxane, 1,1,3,3,3-hexavinyldisiloxane is exemplified.
  • Two or more such disiloxanes can be used in combination, but at least 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3-divinyl-1,1,3, It is necessary to include 1,3-dialkenyl-1,1,3,3-tetraalkyldisiloxane such as 3-tetraethyldisiloxane.
  • R 1 3 SiX Is also a raw material for introducing a siloxane unit represented by the formula: R 1 3 SiO 1/2 into the organopolysiloxane.
  • R 1 is the same or different and is an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms.
  • Examples of the alkyl group for R 1 include the same groups as described above, and a methyl group is preferable.
  • Examples of the alkenyl group for R 1 include the same groups as described above, and a vinyl group is preferable.
  • X represents an alkoxy group, an acyloxy group, a halogen atom, or a hydroxyl group, and examples thereof include the same groups as described above.
  • silane compounds include alkoxysilanes such as trimethylmethoxysilane, trimethylethoxysilane, dimethylvinylmethoxysilane, diethylvinylmethoxysilane, dimethylvinylethoxysilane, diethylvinylethoxysilane, divinylmethylmethoxysilane, and trivinylmethoxysilane; Acyloxysilanes such as dimethylvinylacetoxysilane, diethylvinylacetoxysilane, divinylmethylacetoxysilane, and trivinylacetoxysilane; halosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, diethylvinylchlorosilane, divinylmethylchlorosilane, and trivinylchlorosilane; dimethylvinylhydroxy Silane, diethylvinylhydroxysilane, divinylmethylhydroxysilane
  • silane compounds Two or more such silane compounds can be used in combination, but it is necessary to include at least an alkenyldialkylsilane compound such as divinylmethylmethoxysilane, divinylmethylacetoxysilane, divinylmethylchlorosilane, divinylmethylhydroxysilane, and the like.
  • alkenyldialkylsilane compound such as divinylmethylmethoxysilane, divinylmethylacetoxysilane, divinylmethylchlorosilane, divinylmethylhydroxysilane, and the like.
  • R 2 R 3 R 4 SiOSiR 2 R 3 R 4 Is a raw material for introducing a siloxane unit represented by the formula: R 2 R 3 R 4 SiO 1/2 into the organopolysiloxane.
  • R 2 is an alkyl group having 1 to 12 carbon atoms, and examples thereof are the same groups as described above, preferably a methyl group.
  • R 3 is a phenyl group.
  • R 4 is an alkenyl group having 2 to 12 carbon atoms, and examples thereof are the same groups as described above, preferably a vinyl group.
  • Examples of such disiloxane include 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane.
  • R 2 R 3 R 4 SiX Is also a raw material for introducing a siloxane unit represented by the formula: R 2 R 3 R 4 SiO 1/2 into the organopolysiloxane.
  • R 2 is an alkyl group having 1 to 12 carbon atoms, and examples thereof are the same groups as described above, preferably a methyl group.
  • R 3 is a phenyl group.
  • R 4 is an alkenyl group having 2 to 12 carbon atoms, exemplified by the same groups as described above, and preferably a vinyl group.
  • X represents an alkoxy group, an acyloxy group, a halogen atom, or a hydroxyl group, and examples thereof include the same groups as described above.
  • silane compounds include alkoxysilanes such as methylphenylvinylmethoxysilane and methylphenylvinylethoxysilane; acetoxysilanes such as methylphenylvinylacetoxysilane; chlorosilanes such as methylphenylvinylchlorosilane; hydroxy such as methylphenylvinylhydroxysilane.
  • alkoxysilanes such as methylphenylvinylmethoxysilane and methylphenylvinylethoxysilane
  • acetoxysilanes such as methylphenylvinylacetoxysilane
  • chlorosilanes such as methylphenylvinylchlorosilane
  • hydroxy such as methylphenylvinylhydroxysilane.
  • a silane compound or a silane oligomer for introducing the siloxane unit represented by 2 can be reacted.
  • R 5 is the same or different and is an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or a phenyl group.
  • Examples of the alkyl group for R 5 include the same alkyl groups as those described above for R 1 .
  • Examples of the alkenyl group for R 5 include the same alkenyl groups as those described above for R 1 .
  • silane compounds include dimethyldimethoxysilane, methylethyldimethoxysilane, methylphenyldimethoxysilane, diphenyldimethoxysilane, tetramethoxysilane, dimethyldiethoxysilane, methylethyldiethoxysilane, methylphenyldiethoxysilane, and diphenyldiethoxy.
  • Alkoxysilanes such as silane, tetramethoxysilane, tetraethoxysilane; acetoxysilanes such as dimethyldiacetoxysilane, methylphenyldiacetoxysilane, diphenyldiacetoxysilane, tetraacetoxysilane; dimethyldichlorosilane, methylphenyldichlorosilane, diphenyldichlorosilane , Halosilanes such as tetrachlorosilane; dimethyldihydroxysilane, methylphenyldihydroxysilane, di Hydroxy silanes such as E sulfonyl dihydroxysilane are exemplified.
  • cyclic silicone compounds examples include cyclic dimethylsiloxane oligomers, cyclic phenylmethylsiloxane oligomers, and cyclic diphenylsiloxane oligomers. Furthermore, as a silane oligomer, the partial hydrolyzate of tetramethoxysilane and the partial hydrolyzate of tetraethoxysilane are illustrated.
  • Examples of the acid that can be used include hydrochloric acid, acetic acid, formic acid, nitric acid, oxalic acid, sulfuric acid, phosphoric acid, polyphosphoric acid, polyvalent carboxylic acid, trifluoromethanesulfonic acid, and ion exchange resin.
  • alkalis examples include inorganic alkalis such as potassium hydroxide and sodium hydroxide; triethylamine, diethylamine, monoethanolamine, diethanolamine, triethanolamine, aqueous ammonia, tetramethylammonium hydroxide, alkoxysilane having an amino group, Examples include organic base compounds such as aminopropyltrimethoxysilane.
  • an organic solvent can be used.
  • the organic solvent that can be used include ethers, ketones, acetates, aromatic or aliphatic hydrocarbons, ⁇ -butyrolactone, and mixtures of two or more thereof.
  • Preferred organic solvents include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol mono-t-butyl ether, ⁇ -butyrolactone, toluene and xylene. Illustrated.
  • Such an organopolysiloxane of the present invention has good hydrosilylation reactivity. Therefore, the organopolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule as a main component, and for hydrosilylation reaction.
  • a hydrosilylation reaction-curable silicone composition can be prepared by adding a catalyst.
  • the curable silicone composition of the present invention comprises 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane and comprises 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane.
  • the second feature is that the content of siloxane in the composition is greater than 0.0 mass% and less than 3.0 mass%. 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane remains in the organopolysiloxane during the synthesis of the branched or resinous organopolysiloxane containing alkylphenylvinylsiloxane units.
  • the thermal shock resistance is improved by using a curable silicone composition whose content is controlled to be in the above range.
  • the content of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the composition is 0.05 mass% to 2.50 mass. % Range is more preferred.
  • the thermal shock resistance is lowered as shown in the comparative example of the present specification.
  • the said content exceeds the said upper limit, it may become a cause of sclerosis
  • the curable silicone composition of the present invention contains the above-mentioned components (A) to (D), and optionally contains the component (E).
  • the organopolysiloxane of component (A) is as described above.
  • the content of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the composition is 0.05 mass% to 2.50 mass. % Range is particularly preferred.
  • Component (B) is an optional component for imparting flexibility, extensibility, and flexibility to the cured product, and has at least two alkenyl groups in one molecule and silicon-bonded hydrogen atoms. It is a linear organopolysiloxane that does not.
  • the alkenyl group in the component (B) includes 2 to 12 carbon atoms such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group and dodecenyl group.
  • the alkenyl group is exemplified, and a vinyl group is preferable.
  • Propyl, anthracenylethyl, phenanthrylethyl, pyrenylethyl, and their aralkyls An alkyl group such as a methyl group or an ethyl group; an alkoxy group such as a methoxy group or an ethoxy group; an aralkyl group having 7 to 20 carbon atoms such as a group substituted with a halogen atom such as a chlorine atom or a bromine atom; or chloro Examples thereof include a halogenated alkyl group having 1 to 12 carbon atoms such as a methyl group and a 3,3,3-trifluoropropyl group, and examples thereof are the same groups as those described above, preferably a methyl group and a phenyl group.
  • Examples of such a component (B) include a trimethylsiloxy group-capped dimethylsiloxane / methylvinylsiloxane copolymer with both molecular chain terminals, a trimethylsiloxy group-capped methylvinylpolysiloxane with both molecular chain terminals, and a trimethylsiloxy group-capped dimethyl group with both molecular chains.
  • the content of the component (B) is in the range of 0 to 70% by weight, preferably in the range of 0 to 50% by weight, particularly preferably, based on the present composition. It is in the range of 0 to 40% by mass.
  • the content of the component (B) is below the upper limit of the above range, the cured product can be given flexibility, extensibility, and flexibility without increasing the gas permeability of the cured product. As a result, it is because the reliability of the optical semiconductor device produced using this composition can be improved.
  • Component is a cross-linking agent of the present composition, and is an organopolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule.
  • Examples of the bonding position of silicon atom-bonded hydrogen atoms in component (C) include molecular chain terminals and / or molecular chain side chains.
  • Other groups bonded to the silicon atom in the component include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, An alkyl group having 1 to 12 carbon atoms such as dodecyl group; a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, and a hydrogen atom of these aryl groups such as a methyl group, an ethyl group, etc.
  • An alkyl group such as a methyl group or an ethyl group; an alkoxy group such as a methoxy group or an ethoxy group; an aralkyl group having 7 to 20 carbon atoms such as a group substituted with a halogen atom such as a chlorine atom or a bromine atom; or a chloromethyl group, Examples thereof include halogenated alkyl groups having 1 to 12 carbon atoms such as
  • component (C) examples include molecular chain both ends trimethylsiloxy group-blocked methylhydrogenpolysiloxane, molecular chain both ends trimethylsiloxy group-blocked dimethylsiloxane / methylhydrogensiloxane copolymer, molecular chain both ends trimethylsiloxy group Blocked dimethylsiloxane / methylhydrogensiloxane / methylphenylsiloxane copolymer, molecular chain both ends dimethylhydrogensiloxy group blocked dimethylpolysiloxane, molecular chain both ends dimethylhydrogensiloxy group blocked dimethylsiloxane / methylphenylsiloxane copolymer, Methylphenylpolysiloxane blocked with a dimethylhydrogensiloxy group blocked at both ends of the molecular chain, a siloxane unit represented by the general formula: R ′ 3 SiO 1/2 and a siloxy represented by the general formula:
  • R ′ in the formula is an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or a halogenated alkyl group having 1 to 12 carbon atoms, Examples are the same as those described above.
  • the content of the component (C) is such that the silicon-bonded hydrogen atoms in this component are 0.1 to 0.1 mol in total for 1 mol of the alkenyl groups in the component (A) and the component (B).
  • the amount is in the range of 5 moles, preferably the amount in the range of 0.5 to 2 moles. This is because if the content of the component (C) is not less than the lower limit of the above range, the composition is sufficiently cured. On the other hand, if it is not more than the upper limit of the above range, the heat resistance of the cured product is improved. As a result, the reliability of the optical semiconductor device manufactured using this composition is improved.
  • the component (D) is a hydrosilylation catalyst for accelerating the curing of the composition, and examples thereof include platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts.
  • the component (D) is preferably a platinum-based catalyst because the curing of the composition can be remarkably accelerated.
  • the platinum-based catalyst include platinum fine powder, chloroplatinic acid, an alcohol solution of chloroplatinic acid, a platinum-alkenylsiloxane complex, a platinum-olefin complex, and a platinum-carbonyl complex, preferably a platinum-alkenylsiloxane complex. is there.
  • 1,3-divinyl-1,1,3,3-tetramethyldisiloxane is preferred because the platinum-alkenylsiloxane complex has good stability.
  • stimulates hydrosilylation reaction you may use non-platinum type metal catalysts, such as iron, ruthenium, and iron / cobalt.
  • the content of the component (D) is an effective amount for accelerating the curing of the present composition.
  • the catalyst metal in the component (D) is 0.01 by mass unit with respect to the composition.
  • the amount is preferably in the range of ⁇ 500 ppm, more preferably in the range of 0.01 to 100 ppm, and particularly in the range of 0.01 to 50 ppm. It is preferable.
  • the composition may contain (E) an adhesion-imparting agent in order to improve the adhesion of the cured product to the substrate that is in contact with the curing process.
  • the component (E) is preferably an organosilicon compound having at least one alkoxy group bonded to a silicon atom in one molecule. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a methoxyethoxy group, and a methoxy group is particularly preferable.
  • the group other than the alkoxy group bonded to the silicon atom of the organosilicon compound includes a substituted or unsubstituted monovalent hydrocarbon group such as an alkyl group, an alkenyl group, an aryl group, an aralkyl group, and a halogenated alkyl group; 3 Glycidoxyalkyl groups such as glycidoxypropyl group and 4-glycidoxybutyl group; epoxies such as 2- (3,4-epoxycyclohexyl) ethyl group and 3- (3,4-epoxycyclohexyl) propyl group Cyclohexyl alkyl group; epoxy group-containing monovalent organic group such as oxiranylalkyl group such as 4-oxiranylbutyl group, 8-oxiranyloctyl group; acrylic group-containing monovalent organic group such as 3-methacryloxypropyl group Group; a hydrogen atom is exemplified.
  • This organosilicon compound preferably has a silicon atom-bonded alkenyl group or a silicon atom-bonded hydrogen atom. Moreover, since it can provide favorable adhesiveness to various types of substrates, the organosilicon compound preferably has at least one epoxy group-containing monovalent organic group in one molecule.
  • organosilicon compounds include organosilane compounds, organosiloxane oligomers, and alkyl silicates. Examples of the molecular structure of the organosiloxane oligomer or alkyl silicate include linear, partially branched linear, branched, cyclic, and network, particularly linear, branched, and network. Preferably there is.
  • organosilicon compounds examples include silane compounds such as 3-glycidoxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and 3-methacryloxypropyltrimethoxysilane; A siloxane compound having at least one silicon atom-bonded alkenyl group or silicon atom-bonded hydrogen atom and silicon atom-bonded alkoxy group, and a silane compound or siloxane compound having at least one silicon atom-bonded alkoxy group and silicon in one molecule.
  • silane compounds such as 3-glycidoxypropyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, and 3-methacryloxypropyltrimethoxysilane
  • a siloxane compound having at least one silicon atom-bonded alkenyl group or silicon atom-bonded hydrogen atom and silicon atom-bonded alkoxy group and
  • Examples thereof include a mixture of a siloxane compound having at least one atom-bonded hydroxy group and at least one silicon atom-bonded alkenyl group, methyl polysilicate, ethyl polysilicate, and epoxy group-containing ethyl polysilicate.
  • the content of the component (E) is not limited, but it adheres favorably to the base material that is in contact with the curing process, so that a total of 100 masses of the components (A) to (D) is included.
  • the content is preferably in the range of 0.01 to 10 parts by mass with respect to parts.
  • the present composition includes 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, 2-phenyl-3-butyne-2- Alkyne alcohols such as all; Enyne compounds such as 3-methyl-3-penten-1-yne and 3,5-dimethyl-3-hexen-1-yne; 1,3,5,7-tetramethyl-1,3 , 5,7-tetravinylcyclotetrasiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane, and a reaction inhibitor such as benzotriazole.
  • the content of the reaction inhibitor is not limited, but is within the range of 0.0001 to 5 parts by mass with respect to 100 parts by mass in total of the components (A) to (D). preferable.
  • the present composition can contain a fluorescent material as other optional components.
  • the phosphor include oxide phosphors, oxynitride phosphors, nitride phosphors, sulfide phosphors, and oxysulfide phosphors that are widely used in light emitting diodes (LEDs). Examples thereof include yellow, red, green, and blue light emitting phosphors.
  • oxide phosphors include yttrium, aluminum, and garnet-based YAG green-yellow light-emitting phosphors containing cerium ions, terbium, aluminum, garnet-based TAG yellow light-emitting phosphors containing cerium ions, and Examples include silicate green to yellow light emitting phosphors containing cerium and europium ions.
  • oxynitride phosphors include silicon, aluminum, oxygen, and nitrogen-based sialon-based red to green light-emitting phosphors containing europium ions.
  • nitride-based phosphors include calcium, strontium, aluminum, silicon, and nitrogen-based casoon-based red light-emitting phosphors containing europium ions.
  • sulfide type include ZnS type green coloring phosphors including copper ions and aluminum ions.
  • oxysulfide phosphors include Y 2 O 2 S red light-emitting phosphors containing europium ions.
  • These fluorescent materials may be used singly or as a mixture of two or more.
  • the content of the fluorescent material is not particularly limited, but in the present composition is in the range of 0.1 to 70% by mass, and further in the range of 1 to 20% by mass. preferable.
  • inorganic fillers such as silica, glass, alumina and zinc oxide; fine organic resin powders such as polymethacrylate resin; You may contain dye, a pigment, a flame-retarding agent, a solvent, etc.
  • the curable silicone composition of the present invention cures at room temperature or by heating, but is preferably heated to cure quickly.
  • the heating temperature is preferably in the range of 50 to 200 ° C.
  • the curable silicone composition of the present invention is suitable for a sealant for an optical semiconductor device, and can provide an optical semiconductor device in which an optical semiconductor element is sealed with a cured product of the curable silicone composition.
  • the cured product of the present invention is obtained by curing the above curable silicone composition.
  • the shape of the cured product is not particularly limited, and examples thereof include a sheet shape and a film shape.
  • the cured product can be handled alone, but can also be handled in a state where the optical semiconductor element or the like is covered or sealed.
  • the optical semiconductor device of the present invention is characterized in that an optical semiconductor element is sealed with a cured product of the above curable silicone composition.
  • an optical semiconductor device of the present invention include a light emitting diode (LED), a photocoupler, and a CCD.
  • the optical semiconductor element include a light emitting diode (LED) chip and a solid-state imaging element.
  • the use of the curable silicone composition of the present invention is not limited to these.
  • FIG. 1 shows a cross-sectional view of a single surface-mounted LED that is an example of the optical semiconductor device of the present invention.
  • an LED chip 1 is die-bonded on a lead frame 2, and the LED chip 1 and the lead frame 3 are wire-bonded by a bonding wire 4.
  • a frame member 5 is provided around the LED chip 1, and the LED chip 1 inside the frame member 5 is sealed with a cured product 6 of the curable silicone composition of the present invention.
  • the LED chip 1 is die-bonded to the lead frame 2, the LED chip 1 and the lead frame 3 are wire-bonded by a gold bonding wire 4, and then
  • An example is a method in which the inside of the frame member 5 provided around the LED chip 1 is filled with the curable silicone composition of the present invention and then cured by heating at 50 to 200 ° C.
  • the curable silicone composition of the present invention the cured product thereof, and the optical semiconductor device will be described in detail with reference to examples.
  • the viscosity is a value at 25 ° C.
  • Me, Vi, Ph, and Ep represent a methyl group, a vinyl group, a phenyl group, and a 3-glycidoxypropyl group, respectively.
  • Methylglycidoxypropyldimethoxysilane (314 g), water (130 g), and potassium hydroxide (0.50 g) were added to the toluene solution layer washed with water, and the mixture was heated to reflux for 1 hour. Subsequently, methanol was distilled off and excess water was removed by azeotropic dehydration. After heating at reflux for 4 hours, the toluene solution was cooled, neutralized with 0.55 g of acetic acid, and then washed with water three times.
  • silicone resins A to C containing methylphenylvinylsiloxane units having different contents of 1,3-divinyl-1,3-diphenyldimethyldisiloxane were obtained.
  • Synthesis Example 2 Silicone Resin B
  • Example 1 6.83 parts by mass of silicone resin B prepared in Synthesis Example 2, 0.82 parts by mass of methylphenylpolysiloxane blocked with dimethylvinylsiloxy group-blocked dimethylvinylsiloxy group having a viscosity of 3,000 mPa ⁇ s, formula: H (CH 3) 2 SiO (C 6 H 5 ) Organotrisiloxane represented by 2SiOSi (CH3) 2H 2.10 parts by mass (the silicon atom-bonded hydrogen atom in this component is contained in 1 mol of the total vinyl group in the silicone resin and methylphenylpolysiloxane) 1), 0.25 parts by mass of the adhesion-imparting agent of Reference Example 1, 0.02 parts by mass of 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, And 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane solution
  • a silicone composition was prepared. When this composition was cured at 150 ° C. for 1 hour, a cured product of Shore-D 73 was obtained. The surface of the cured product was smooth with no tack. The characteristics are shown in Table 1. The amount of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the curable silicone composition was 0.10% by mass.
  • Example 2 A curable silicone composition having a viscosity of 6,200 mPa ⁇ s was prepared in the same manner as in Example 1 except that the amount of 1,3-divinyl-1,3-diphenyldimethyldisiloxane added was 0.10 parts by mass. Prepared. When this composition was cured at 150 ° C. for 1 hour, a cured product of Shore-D 69 was obtained. The surface of the cured product was smooth with no tack. The characteristics are shown in Table 1. The amount of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the curable silicone composition was 0.99% by mass.
  • Example 3 In the same manner as in Example 1, except that the amount of 1,3-divinyl-1,3-diphenyldimethyldisiloxane added was 0.20 parts by mass, a curable silicone composition having a viscosity of 5,000 mPa ⁇ s was prepared. Prepared. When this composition was cured at 150 ° C. for 1 hour, a cured product of Shore-D 64 was obtained. The surface of the cured product was smooth with no tack. The characteristics are shown in Table 1. The 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the curable silicone composition was 1.96% by mass.
  • a curable silicone composition having a viscosity of 2300 mPa ⁇ s was prepared in the same manner as in Example 1, except that the amount of 1,3-divinyl-1,3-diphenyldimethyldisiloxane added was 0.50 parts by mass. .
  • this composition was cured at 150 ° C. for 1 hour, a cured product of Shore-D 44 was obtained. The surface of the cured product was smooth with no tack.
  • the characteristics are shown in Table 1.
  • the 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the curable silicone composition was 4.75% by mass.
  • a curable silicone composition having a viscosity of 1100 mPa ⁇ s was prepared in the same manner as in Example 1, except that the amount of 1,3-divinyl-1,3-diphenyldimethyldisiloxane added was 0.91 part by mass. .
  • This composition was cured at 150 ° C. for 1 hour, but the surface of the cured product was sticky and Shore-D measurement was not possible. The characteristics are shown in Table 1.
  • the 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane in the curable silicone composition was 8.33% by mass.
  • Example 4 The content of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane is 0.47% by mass, 5.95 parts by mass of a silicone resin containing a vinylmethylphenylsiloxy group, a viscosity of 3, 000 mPa ⁇ s molecular chain both ends dimethylvinylsiloxy group-blocked methylphenylpolysiloxane 1.80 parts by mass, organotrisiloxane represented by the formula: H (CH 3) 2 SiO (C 6 H 5) 2 SiOS i (CH 3) 2 H 1.98 parts by mass (The amount of silicon atom-bonded hydrogen atoms in this component is 1 with respect to a total of 1 mol of vinyl groups in the silicone resin and methylphenylpolysiloxane), 0.25 part by mass of the adhesion-imparting agent of Reference Example 1 0.02, part by weight of 1,3,5,7-tetramethyl-1,3,5,7-t
  • a curable silicone composition containing a silicone resin containing a methylphenylvinylsiloxane unit, comprising 1,3-divinyl-1,3-diphenyldimethyldisiloxane When the content is 0.10% by mass, 0.99% by mass, or 1.96% by mass, the number of defects is 2 or less even at 401 cycles, and excellent thermal shock resistance is exhibited.
  • Comparative Examples 1 to 3 the same curable silicone composition having a 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane content of 0
  • the number of defects becomes 8 or more even at 401 cycles, and the thermal shock resistance is clearly inferior.
  • the content is 8.33% by mass, the curability is clearly inferior.
  • an optical semiconductor device using the curable silicone composition of Example 4 (content of 1,3-divinyl-1,3-diphenyl-1,3-dimethyldisiloxane is 0.28% by mass) Compared to Comparative Example 4 (the same content of 3.51% by mass), the light emission efficiency after 566 hours and 997 hours is excellent.
  • the curable silicone composition of the present invention can be used as an electric / electronic adhesive, potting agent, protective agent, coating agent, and underfill agent, and has particularly high reactivity and gas permeability. Since it can form a cured product that is low and has high thermal shock resistance, it is suitable as a sealing material or protective coating material for optical semiconductor elements in optical semiconductor devices such as light emitting diodes (LEDs), and light that maintains high luminous efficiency.
  • a semiconductor device or the like can be provided.

Landscapes

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

Abstract

Le problème décrit par la présente invention est de préparer une composition de silicone durcissable qui présente une excellente durabilité, et fournit un produit durci qui présente une résistance élevée aux chocs thermiques et une faible perméabilité aux gaz. De plus, en appliquant la composition de silicone durcissable à un dispositif semi-conducteur optique, afin de préparer un dispositif semi-conducteur optique présentant des avantages, à savoir une excellente résistance aux chocs thermiques et un rendement soutenu d'émission de lumière élevé. La solution selon l'invention porte sur une composition de silicone durcissable et le dispositif semi-conducteur optique l'utilisant caractérisée en ce qu'elle contient un organopolysiloxane ayant un motif d'alkyl phényl vinyl siloxane (R2R3R4SiO0,5 ; R2 représentant un groupe alkyle tel qu'un groupe méthyle, R3 représentant un groupe phényle, et R4 représentant un groupe alcényle tel qu'un groupe vinyle), la quantité contenue de 1,3-divinyl-1,3-diphényl-1,3-diméthyl di-siloxane étant supérieure à 0,0 % en masse mais inférieure à 3,0 % en masse par rapport à la composition entière.
PCT/JP2017/039673 2016-11-11 2017-11-02 Composition de silicone durcissable et dispositif semi-conducteur optique l'utilisant Ceased WO2018088316A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201780080034.8A CN110088207B (zh) 2016-11-11 2017-11-02 可固化硅酮组合物和使用其的光学半导体装置
KR1020197016211A KR102498396B1 (ko) 2016-11-11 2017-11-02 경화성 실리콘 조성물 및 그것을 사용한 광반도체 장치
JP2018550171A JPWO2018088316A1 (ja) 2016-11-11 2017-11-02 硬化性シリコーン組成物およびそれを用いた光半導体装置

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2016-220218 2016-11-11
JP2016220218 2016-11-11

Publications (1)

Publication Number Publication Date
WO2018088316A1 true WO2018088316A1 (fr) 2018-05-17

Family

ID=62110666

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2017/039673 Ceased WO2018088316A1 (fr) 2016-11-11 2017-11-02 Composition de silicone durcissable et dispositif semi-conducteur optique l'utilisant

Country Status (5)

Country Link
JP (1) JPWO2018088316A1 (fr)
KR (1) KR102498396B1 (fr)
CN (1) CN110088207B (fr)
TW (1) TWI761386B (fr)
WO (1) WO2018088316A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021534295A (ja) * 2018-08-17 2021-12-09 ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG 架橋性オルガノシロキサン組成物

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102734213B1 (ko) * 2021-03-26 2024-11-25 삼성에스디아이 주식회사 유기발광소자 봉지용 조성물 및 이로부터 제조된 유기층을 포함하는 유기발광소자 표시장치
CN113549098A (zh) * 2021-07-09 2021-10-26 陕西德信祥能源科技有限公司 一种二甲基二乙烯基二苯基硅氧烷的制备方法

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01299873A (ja) * 1988-05-26 1989-12-04 Toray Dow Corning Silicone Co Ltd オルガノポリシロキサン組成物
JPH0967440A (ja) * 1995-08-31 1997-03-11 Toray Dow Corning Silicone Co Ltd ヒドロシリル化反応用微粒子触媒およびこれを含有してなる加熱硬化性シリコーン組成物
JPH111619A (ja) * 1997-06-12 1999-01-06 Shin Etsu Chem Co Ltd 付加硬化型シリコーン樹脂組成物
JP2011517707A (ja) * 2008-03-04 2011-06-16 ダウ・コーニング・コーポレイション シリコーン組成物、シリコーン接着剤、塗装基板及び積層基板
JP2012052045A (ja) * 2010-09-02 2012-03-15 Shin-Etsu Chemical Co Ltd 低ガス透過性シリコーン樹脂組成物及び光半導体装置
JP2012052035A (ja) * 2010-09-01 2012-03-15 Shin-Etsu Chemical Co Ltd 付加硬化型シリコーン組成物、該組成物からなる光学素子封止材、及び該光学素子封止材の硬化物により光学素子が封止された半導体装置
JP2013544949A (ja) * 2010-12-08 2013-12-19 ダウ コーニング コーポレーション 封止材を形成するのに好適な二酸化チタンナノ粒子を含むシロキサン組成物
JP2014505748A (ja) * 2010-12-08 2014-03-06 ダウ コーニング コーポレーション 封止材を作成するのに好適な金属酸化物ナノ粒子を含むシロキサン組成物
JP2014506263A (ja) * 2010-12-08 2014-03-13 ダウ コーニング コーポレーション 封止材を作成するのに好適なシロキサン組成物
JP2016079320A (ja) * 2014-10-20 2016-05-16 信越化学工業株式会社 光半導体素子封止用シリコーン樹脂組成物及び光半導体装置

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009012663B3 (de) * 2009-03-13 2010-09-16 Uhde Gmbh Verfahren und Vorrichtung zur gleichmäßigen Dampferzeugung aus der Abwärme einer Alkandehydrierung
JP6084808B2 (ja) 2012-10-24 2017-02-22 東レ・ダウコーニング株式会社 オルガノポリシロキサン、硬化性シリコーン組成物、その硬化物、および光半導体装置
JP6105966B2 (ja) * 2013-02-15 2017-03-29 東レ・ダウコーニング株式会社 硬化性シリコーン組成物、その硬化物、および光半導体装置

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01299873A (ja) * 1988-05-26 1989-12-04 Toray Dow Corning Silicone Co Ltd オルガノポリシロキサン組成物
JPH0967440A (ja) * 1995-08-31 1997-03-11 Toray Dow Corning Silicone Co Ltd ヒドロシリル化反応用微粒子触媒およびこれを含有してなる加熱硬化性シリコーン組成物
JPH111619A (ja) * 1997-06-12 1999-01-06 Shin Etsu Chem Co Ltd 付加硬化型シリコーン樹脂組成物
JP2011517707A (ja) * 2008-03-04 2011-06-16 ダウ・コーニング・コーポレイション シリコーン組成物、シリコーン接着剤、塗装基板及び積層基板
JP2012052035A (ja) * 2010-09-01 2012-03-15 Shin-Etsu Chemical Co Ltd 付加硬化型シリコーン組成物、該組成物からなる光学素子封止材、及び該光学素子封止材の硬化物により光学素子が封止された半導体装置
JP2012052045A (ja) * 2010-09-02 2012-03-15 Shin-Etsu Chemical Co Ltd 低ガス透過性シリコーン樹脂組成物及び光半導体装置
JP2013544949A (ja) * 2010-12-08 2013-12-19 ダウ コーニング コーポレーション 封止材を形成するのに好適な二酸化チタンナノ粒子を含むシロキサン組成物
JP2014505748A (ja) * 2010-12-08 2014-03-06 ダウ コーニング コーポレーション 封止材を作成するのに好適な金属酸化物ナノ粒子を含むシロキサン組成物
JP2014506263A (ja) * 2010-12-08 2014-03-13 ダウ コーニング コーポレーション 封止材を作成するのに好適なシロキサン組成物
JP2016079320A (ja) * 2014-10-20 2016-05-16 信越化学工業株式会社 光半導体素子封止用シリコーン樹脂組成物及び光半導体装置

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021534295A (ja) * 2018-08-17 2021-12-09 ワッカー ケミー アクチエンゲゼルシャフトWacker Chemie AG 架橋性オルガノシロキサン組成物
JP7203196B2 (ja) 2018-08-17 2023-01-12 ワッカー ケミー アクチエンゲゼルシャフト 架橋性オルガノシロキサン組成物

Also Published As

Publication number Publication date
KR102498396B1 (ko) 2023-02-13
JPWO2018088316A1 (ja) 2019-10-03
CN110088207A (zh) 2019-08-02
TW201829629A (zh) 2018-08-16
CN110088207B (zh) 2022-10-14
KR20190078625A (ko) 2019-07-04
TWI761386B (zh) 2022-04-21

Similar Documents

Publication Publication Date Title
JP6081774B2 (ja) 硬化性シリコーン組成物、その硬化物、および光半導体装置
JP6084808B2 (ja) オルガノポリシロキサン、硬化性シリコーン組成物、その硬化物、および光半導体装置
JP6460534B2 (ja) 硬化性シリコーン組成物、その硬化物、および光半導体装置
JP6355210B2 (ja) 半導体装置および半導体素子封止用硬化性シリコーン組成物
JPWO2013005858A1 (ja) 硬化性シリコーン組成物、その硬化物、および光半導体装置
US9683084B2 (en) Curable silicone composition, cured product thereof, and optical semiconductor device
KR102498396B1 (ko) 경화성 실리콘 조성물 및 그것을 사용한 광반도체 장치
WO2019026754A1 (fr) Composition de silicone durcissable et dispositif optique à semi-conducteurs

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 17870086

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2018550171

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 20197016211

Country of ref document: KR

Kind code of ref document: A

122 Ep: pct application non-entry in european phase

Ref document number: 17870086

Country of ref document: EP

Kind code of ref document: A1