WO2014069610A1 - Curable silicone composition, cured product thereof, and optical semiconductor device - Google Patents

Curable silicone composition, cured product thereof, and optical semiconductor device Download PDF

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Publication number
WO2014069610A1
WO2014069610A1 PCT/JP2013/079653 JP2013079653W WO2014069610A1 WO 2014069610 A1 WO2014069610 A1 WO 2014069610A1 JP 2013079653 W JP2013079653 W JP 2013079653W WO 2014069610 A1 WO2014069610 A1 WO 2014069610A1
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WO
WIPO (PCT)
Prior art keywords
groups
group
carbons
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/JP2013/079653
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English (en)
French (fr)
Inventor
Tomohiro Iimura
Michitaka Suto
Kazuhiro Nishijima
Kasumi Takeuchi
Haruhiko Furukawa
Yoshitsugu Morita
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 US14/438,695 priority Critical patent/US9312196B2/en
Priority to EP13792111.0A priority patent/EP2914664B1/en
Priority to CN201380060840.0A priority patent/CN104812841B/zh
Priority to KR1020157013088A priority patent/KR101704425B1/ko
Publication of WO2014069610A1 publication Critical patent/WO2014069610A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • 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
    • 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
    • C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
    • 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
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • 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

Definitions

  • Examples of this type of disiloxane include l,3-divinyl-l,l ,3,3- tetramethyldisiloxane, l ,3-divinyl-l ,3-diphenyl-l,3-dimethyldisiloxane, 1 ,3-divinyl- 1 ,1 ,3,3-tetraethyldisiloxane, l ,l ,3,3-tetravinyl-l ,3-dimethyldisiloxane, and 1 ,1,1 ,3,3,3- hexavinyldisiloxane.
  • R 1 are the same or different, are each an alkenyl group having from 2 to 12 carbons, and examples thereof are the same as the groups described above.
  • R 2 are the same or different, are each an alkyl group having from 1 to 12 carbons, an alkenyl group having from 2 to 12 carbons, an aryl group having from 6 to 20 carbons, or an aralkyl group having from 7 to 20 carbons, and examples thereof are the same as the groups described above.
  • X is an alkoxy group, an acyloxy group, a halogen atom, or a hydroxyl group; and examples thereof are the same as the groups described above.
  • organic solvents able to be used include aromatic hydrocarbons, aliphatic hydrocarbons, and mixtures of 2 or more types thereof.
  • examples of preferred organic solvents include toluene and xylene.
  • Me, Ph, and Naph in the formulae below denote a methyl group, a phenyl group, and a naphthyl group respectively, n' is a number from 1 to 100, n" and n"' are each numbers of 1 or higher, and n" + n"' is a number of 100 or lower.
  • the molecular weight of this type of component (C 2 ) is not particularly limited, but from the perspectives of the handling/workability of the composition and the mechanical strength of the cured product, the mass average molecular weight in terms of standard polystyrene, as measured by gel permeation chromatography, is preferably from 500 to 10,000, and more preferably from 500 to 2,000.
  • R 5 is an alkyl group having from 1 to 12 carbons, and examples thereof are the same as the groups described above.
  • An example of a method for producing the surface mounted type LED illustrated in Figure 1 is a method comprising die-bonding the LED chip 1 to the lead frame 2, wire-bonding this LED chip 1 and the lead frame 3 by means of metal bonding wire 4, filling inside the frame material 5 provided around the LED chip 1 with the curable silicone composition of the present invention, and then curing the curable silicone composition by heating to 50 to 200°C.
  • a cured product is produced by heating the curable silicone composition at 150°C for 2 hours in a circulating hot air oven.
  • the refractive index of this cured product at 25 °C and a wavelength of 633 nm was measured using a refractometer.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Silicon Polymers (AREA)
  • Sealing Material Composition (AREA)
PCT/JP2013/079653 2012-10-30 2013-10-25 Curable silicone composition, cured product thereof, and optical semiconductor device Ceased WO2014069610A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US14/438,695 US9312196B2 (en) 2012-10-30 2013-10-25 Curable silicone composition, cured product thereof, and optical semiconductor
EP13792111.0A EP2914664B1 (en) 2012-10-30 2013-10-25 Curable silicone composition, cured product thereof, and optical semiconductor device
CN201380060840.0A CN104812841B (zh) 2012-10-30 2013-10-25 可固化有机硅组合物、其固化产物及光学半导体器件
KR1020157013088A KR101704425B1 (ko) 2012-10-30 2013-10-25 경화성 실리콘 조성물, 이의 경화물, 및 광반도체 장치

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012-239671 2012-10-30
JP2012239671A JP6081774B2 (ja) 2012-10-30 2012-10-30 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

Publications (1)

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WO2014069610A1 true WO2014069610A1 (en) 2014-05-08

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PCT/JP2013/079653 Ceased WO2014069610A1 (en) 2012-10-30 2013-10-25 Curable silicone composition, cured product thereof, and optical semiconductor device

Country Status (7)

Country Link
US (1) US9312196B2 (enExample)
EP (1) EP2914664B1 (enExample)
JP (1) JP6081774B2 (enExample)
KR (1) KR101704425B1 (enExample)
CN (1) CN104812841B (enExample)
TW (1) TWI635138B (enExample)
WO (1) WO2014069610A1 (enExample)

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Publication number Priority date Publication date Assignee Title
WO2016022332A1 (en) * 2014-08-06 2016-02-11 Dow Corning Corporation Organosiloxane compositions and uses thereof
WO2016060831A1 (en) * 2014-10-16 2016-04-21 Dow Corning Corporaiton Silicone composition and a pressure sensitive adhesive film having a pressure sensitive adhesive layer made from the composition
US9683084B2 (en) 2012-10-24 2017-06-20 Dow Corning Toray Co., Ltd. Curable silicone composition, cured product thereof, and optical semiconductor device
US9688822B2 (en) 2012-10-24 2017-06-27 Dow Corning Toray Co., Ltd. Organopolysiloxane, curable silicone composition, cured product thereof, and optical semiconductor
US10927278B2 (en) 2017-02-27 2021-02-23 Dupont Toray Specialty Materials Kabushiki Kaisha Curable organopolysiloxane composition and semiconductor device

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TWI653295B (zh) * 2014-02-04 2019-03-11 日商道康寧東麗股份有限公司 硬化性聚矽氧組合物、其硬化物及光半導體裝置
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WO2018235491A1 (ja) 2017-06-19 2018-12-27 東レ・ダウコーニング株式会社 硬化性粒状シリコーン組成物、それからなる半導体用部材、およびその成型方法
JP6863878B2 (ja) * 2017-11-02 2021-04-21 信越化学工業株式会社 付加硬化型シリコーン組成物、硬化物、及び光学素子
JP6823578B2 (ja) * 2017-11-02 2021-02-03 信越化学工業株式会社 付加硬化型シリコーン組成物、硬化物、光学素子
JP7021046B2 (ja) * 2018-10-22 2022-02-16 信越化学工業株式会社 付加硬化型シリコーン組成物、シリコーン硬化物、及び、光学素子
EP3663346B1 (de) * 2018-12-04 2023-11-15 Evonik Operations GmbH Reaktivsiloxane
CN113874454B (zh) * 2019-05-21 2023-05-23 美国陶氏有机硅公司 聚有机硅氧烷防粘涂层及其制备和用途
US12139634B2 (en) 2020-04-14 2024-11-12 Shin-Etsu Chemical Co., Ltd. Silylated isocyanurate compound, metal corrosion inhibitor, curable organosilicon resin composition, and semiconductor apparatus
CN114058326B (zh) * 2021-11-22 2023-05-23 烟台德邦科技股份有限公司 一种粘接及可靠性优异的有机聚硅氧烷组合物及其制备方法
CN114181535B (zh) * 2021-12-08 2023-04-25 东莞市贝特利新材料有限公司 一种可固化的有机聚硅氧烷组合物及其制备方法
CN119192854A (zh) * 2024-11-06 2024-12-27 江西贝特利新材料有限公司 一种可固化有机聚硅氧烷组合物及其制备方法

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9683084B2 (en) 2012-10-24 2017-06-20 Dow Corning Toray Co., Ltd. Curable silicone composition, cured product thereof, and optical semiconductor device
US9688822B2 (en) 2012-10-24 2017-06-27 Dow Corning Toray Co., Ltd. Organopolysiloxane, curable silicone composition, cured product thereof, and optical semiconductor
EP3191549A4 (en) * 2014-08-06 2018-03-28 Dow Corning Corporation Organosiloxane compositions and uses thereof
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JP2014088513A (ja) 2014-05-15
US9312196B2 (en) 2016-04-12
TWI635138B (zh) 2018-09-11
CN104812841B (zh) 2017-08-29
CN104812841A (zh) 2015-07-29
EP2914664A1 (en) 2015-09-09
TW201420686A (zh) 2014-06-01
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US20150252221A1 (en) 2015-09-10
JP6081774B2 (ja) 2017-02-15

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