WO2006137884A3 - Curable high refractive index resins for optoelectronic applications - Google Patents

Curable high refractive index resins for optoelectronic applications Download PDF

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Publication number
WO2006137884A3
WO2006137884A3 PCT/US2005/034270 US2005034270W WO2006137884A3 WO 2006137884 A3 WO2006137884 A3 WO 2006137884A3 US 2005034270 W US2005034270 W US 2005034270W WO 2006137884 A3 WO2006137884 A3 WO 2006137884A3
Authority
WO
WIPO (PCT)
Prior art keywords
high refractive
refractive index
compositions
vinyl ethers
include aromatic
Prior art date
Application number
PCT/US2005/034270
Other languages
French (fr)
Other versions
WO2006137884A2 (en
Inventor
Ramil-Marcelo L Mercado
Robert V Morford
Curtis Planje
Willie Perez
Tony D Flaim
Taylor R Bass
Original Assignee
Brewer Science Inc
Ramil-Marcelo L Mercado
Robert V Morford
Curtis Planje
Willie Perez
Tony D Flaim
Taylor R Bass
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 Brewer Science Inc, Ramil-Marcelo L Mercado, Robert V Morford, Curtis Planje, Willie Perez, Tony D Flaim, Taylor R Bass filed Critical Brewer Science Inc
Priority to JP2007533680A priority Critical patent/JP2008514764A/en
Priority to EP20050858173 priority patent/EP1815273A2/en
Publication of WO2006137884A2 publication Critical patent/WO2006137884A2/en
Publication of WO2006137884A3 publication Critical patent/WO2006137884A3/en

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    • 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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22Di-epoxy compounds
    • C08G59/24Di-epoxy compounds carbocyclic
    • C08G59/245Di-epoxy compounds carbocyclic aromatic
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • 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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22Di-epoxy compounds
    • C08G59/226Mixtures of di-epoxy compounds
    • 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
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32Epoxy compounds containing three or more epoxy groups
    • C08G59/38Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • 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
    • C08G65/00Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16Cyclic ethers having four or more ring atoms
    • C08G65/18Oxetanes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/04Epoxynovolacs
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/08Epoxidised polymerised polyenes
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/10Epoxy resins modified by unsaturated compounds
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80Constructional details
    • H10K59/875Arrangements for extracting light from the devices
    • H10K59/879Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/80Constructional details
    • H10K50/85Arrangements for extracting light from the devices
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31511Of epoxy ether

Abstract

Novel compositions and methods of using those compositions to form high refractive index coatings are provided. The compositions preferably comprise both a reactive solvent and a high refractive index compound. Preferred reactive solvents include aromatic resins that are functionalized with one or more reactive groups (e.g., epoxides, vinyl ethers, oxetane), while preferred high refractive index compounds include aromatic epoxides, vinyl ethers, oxetanes, phenols, and thiols. An acid or crosslinking catalyst is preferably also included. The inventive compositions are stable under ambient conditions and can be applied to a substrate to form a layer and cured via light and/or heat application. The cured layers have high refractive indices and light transmissions.
PCT/US2005/034270 2004-09-28 2005-09-26 Curable high refractive index resins for optoelectronic applications WO2006137884A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2007533680A JP2008514764A (en) 2004-09-28 2005-09-26 Curable high refractive index resin for optoelectronic applications
EP20050858173 EP1815273A2 (en) 2004-09-28 2005-09-26 Curable high refractive index resins for optoelectronic applications

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61401704P 2004-09-28 2004-09-28
US60/614,017 2004-09-28

Publications (2)

Publication Number Publication Date
WO2006137884A2 WO2006137884A2 (en) 2006-12-28
WO2006137884A3 true WO2006137884A3 (en) 2007-06-28

Family

ID=37570879

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/034270 WO2006137884A2 (en) 2004-09-28 2005-09-26 Curable high refractive index resins for optoelectronic applications

Country Status (7)

Country Link
US (2) US20060068207A1 (en)
EP (1) EP1815273A2 (en)
JP (1) JP2008514764A (en)
KR (1) KR20070072939A (en)
CN (1) CN101142499A (en)
TW (1) TW200619312A (en)
WO (1) WO2006137884A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8809413B2 (en) 2011-06-29 2014-08-19 Chau Ha Ultraviolet radiation-curable high refractive index optically clear resins
CN112233970B (en) * 2020-12-15 2021-03-23 度亘激光技术(苏州)有限公司 Method for manufacturing gallium arsenide-based semiconductor device

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010047043A1 (en) * 2000-03-20 2001-11-29 Okoroafor Michael O. Method of preparing a polymerizate

Family Cites Families (47)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4710557A (en) * 1985-02-01 1987-12-01 Eastman Kodak Company Polymers of thiophenyl thioacrylate and thiomethacrylate monomers
US5230906A (en) * 1986-11-24 1993-07-27 Polytex Plastic Sa Method of and apparatus for manufacturing fiber-reinforced plastics articles
US5886101A (en) * 1988-03-02 1999-03-23 E. I. Du Pont De Nemours And Company Solvent dispersible interpenetrating polymer networks
US5214116A (en) * 1989-02-07 1993-05-25 Tokuyama Soda Kabushiki Kaisha Resin derived from sulfur-containing unsaturated compound and having a high refractive index
US5132430A (en) * 1991-06-26 1992-07-21 Polaroid Corporation High refractive index polymers
CA2151834A1 (en) * 1992-12-21 1994-07-07 Alliedsignal Inc. Solvent free epoxy resin compositions
JPH06273631A (en) * 1993-03-18 1994-09-30 Nippon Telegr & Teleph Corp <Ntt> Optical waveguide
US5789039A (en) * 1994-09-06 1998-08-04 Herberts Powder Coatings, Inc. Radiation curing of powder coatings on heat sensitive substrates: chemical compositions and processes for obtaining coated workpieces
US5855983A (en) * 1995-02-03 1999-01-05 Minnesota Mining And Manufacturing Company Flame retardant ultraviolet cured multi-layered film
JP2917884B2 (en) * 1995-12-19 1999-07-12 東洋製罐株式会社 Water-based paint
EP0795788B1 (en) * 1996-03-13 2002-07-24 Ibiden Co, Ltd. Resist compositions for plating
US6521714B2 (en) * 1996-09-26 2003-02-18 Albemarle Corporation Brominated polystyrenic resins
JPH11199651A (en) * 1998-01-12 1999-07-27 Sumitomo Bakelite Co Ltd Ultraviolet light-curable adhesive resin composition for sealing hollow package for device
US6204311B1 (en) * 1998-03-13 2001-03-20 Mitsui Chemicals, Inc. Polymerizable composition
US6100007A (en) * 1998-04-06 2000-08-08 Ciba Specialty Chemicals Corp. Liquid radiation-curable composition especially for producing cured articles by stereolithography having high heat deflection temperatures
US6037096A (en) * 1998-05-26 2000-03-14 International Business Machines Corporation Film composition and method for a planar surface atop a plated through hole
US6320020B1 (en) * 1998-09-08 2001-11-20 Mitsui Chemicals, Inc. Sulfur-containing (thio)ether (co)polymer and a use thereof
US6583196B2 (en) * 1999-04-23 2003-06-24 Rodenstock North America, Inc. Curable casting compositions having a high refractive index and high impact resistance
DE19936605A1 (en) * 1999-08-04 2001-02-15 Osram Opto Semiconductors Gmbh Transparent cast resin compound for SMT-compatible LED applications with high temperature and high brightness or luminosity
CN1151186C (en) * 1999-09-07 2004-05-26 爱尔康通用有限公司 Foldable ophthalmic and otorhinolaryngological device materials
JP4122661B2 (en) * 1999-10-22 2008-07-23 Jsr株式会社 Photocurable resin composition and plastic sheet
US6288210B1 (en) * 1999-11-12 2001-09-11 Virginia Tech. Intellectual Properties, Inc. High refractive index thermoplastic polyphosphonates
JP3460820B2 (en) * 1999-12-08 2003-10-27 日本電気株式会社 Flame retardant epoxy resin composition
US6593388B2 (en) * 2000-04-04 2003-07-15 Renssealer Polytechnic Institute Oligomeric and polymeric photosensitizers comprising a polynuclear aromatic group
US6376704B1 (en) * 2000-06-28 2002-04-23 3M Innovative Properties Company Naphthyoxyalkyl(meth)acrylates with high refractive indices and low glass transition temperatures
KR100886689B1 (en) * 2000-07-19 2009-03-04 코닌클리케 필립스 일렉트로닉스 엔.브이. Method of manufacturing a replica as well as a replica obtained by carrying out a uv light-initiated cationic polymerization
KR100315158B1 (en) * 2000-08-02 2001-11-26 윤덕용 High reliability non-conductive adhesives for non-solder flip chip bondings and flip chip bonding method using the same
US6794058B2 (en) * 2000-09-12 2004-09-21 Shin-Etsu Chemical Co., Ltd. Flip-chip type semiconductor device
KR20030051763A (en) * 2000-11-27 2003-06-25 데이진 가부시키가이샤 Multilayered film and near-infrared-ray reflection film
US6541591B2 (en) * 2000-12-21 2003-04-01 3M Innovative Properties Company High refractive index microreplication resin from naphthyloxyalkylmethacrylates or naphthyloxyacrylates polymers
DE10100442A1 (en) * 2001-01-08 2002-07-11 Bayer Ag Transparent plastic molding compound
US20030176529A1 (en) * 2001-01-15 2003-09-18 Kenji Yamauchi Photoreactive hot-melt adhesive composition
US6733698B2 (en) * 2001-02-15 2004-05-11 Pabu Services, Inc. Mixture of mono-, bis- and tris-(hydroxyaryl) phosphine oxides useful to make polyglycidyl ethers or in epoxy compositions
TW593450B (en) * 2001-03-21 2004-06-21 Hoya Corp Transparent molded articles, optical components, plastic lenses and preparation method thereof
DE10122188B4 (en) * 2001-05-08 2007-04-12 Ems-Chemie Ag Polyamide molding compounds for the production of optical lenses
JP4857489B2 (en) * 2001-06-19 2012-01-18 三菱瓦斯化学株式会社 Aliphatic cyclic compounds for optical materials
US20030036580A1 (en) * 2001-08-17 2003-02-20 Mingxin Fan Bromine-containing radiation curable acrylates and methacrylates
EP1426392B1 (en) * 2001-08-30 2010-02-24 Mitsubishi Gas Chemical Company, Inc. Composition for optical material
AU2002367417A1 (en) * 2002-01-11 2003-07-24 Koninklijke Philips Electronics N.V. Method of manufacturing a replica as well as a replica obtained by carrying out an uv light-initiated cationic polymerization
US6924000B2 (en) * 2002-03-07 2005-08-02 Lord Corporation Environmentally preferred high solids, low viscosity flock adhesives
US20030207050A1 (en) * 2002-04-29 2003-11-06 Grant Hay Polymeric substrate for display and light emitting devices
MY139328A (en) * 2002-05-20 2009-09-30 Nitto Denko Corp Thermosetting resin composition and semiconductor device obtained with the same
KR100511100B1 (en) * 2002-07-12 2005-08-31 김미화 Perfluorostyrene compounds, Coating solution and Optical waveguide device using the same
WO2004011158A1 (en) * 2002-07-31 2004-02-05 Vision-Ease Lens, Inc. Spin application of thermally cured coatings
US6818306B2 (en) * 2002-09-27 2004-11-16 The Boeing Company Optically clear structural laminate
JP4249996B2 (en) * 2003-02-10 2009-04-08 日東電工株式会社 Lens material comprising polycarbodiimide copolymer
US6939939B2 (en) * 2003-02-24 2005-09-06 Younger Mfg. Polyurea/urethane optical material and method for making it

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010047043A1 (en) * 2000-03-20 2001-11-29 Okoroafor Michael O. Method of preparing a polymerizate

Also Published As

Publication number Publication date
CN101142499A (en) 2008-03-12
US20090087666A1 (en) 2009-04-02
JP2008514764A (en) 2008-05-08
TW200619312A (en) 2006-06-16
WO2006137884A2 (en) 2006-12-28
KR20070072939A (en) 2007-07-10
EP1815273A2 (en) 2007-08-08
US20060068207A1 (en) 2006-03-30

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