WO2006077862A1 - Composition de résine époxy et matériau optique l’utilisant - Google Patents

Composition de résine époxy et matériau optique l’utilisant Download PDF

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Publication number
WO2006077862A1
WO2006077862A1 PCT/JP2006/300608 JP2006300608W WO2006077862A1 WO 2006077862 A1 WO2006077862 A1 WO 2006077862A1 JP 2006300608 W JP2006300608 W JP 2006300608W WO 2006077862 A1 WO2006077862 A1 WO 2006077862A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
optical
resin composition
resins
fluorine
Prior art date
Application number
PCT/JP2006/300608
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English (en)
Japanese (ja)
Inventor
Hironobu Morishita
Original Assignee
Idemitsu Kosan 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 Idemitsu Kosan Co., Ltd. filed Critical Idemitsu Kosan Co., Ltd.
Priority to JP2006553919A priority Critical patent/JPWO2006077862A1/ja
Publication of WO2006077862A1 publication Critical patent/WO2006077862A1/fr

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Classifications

    • 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
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/40—Macromolecules 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 curing agents used
    • C08G59/62—Alcohols or phenols
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
    • G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
    • G02B6/122—Basic optical elements, e.g. light-guiding paths
    • G02B6/1221—Basic optical elements, e.g. light-guiding paths made from organic materials
    • 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
    • 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
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

Definitions

  • the present invention relates to an optical waveguide, an LED sealing resin, a sealant for display, an adhesive for electronic circuits, a reflector, an epoxy resin composition used for an optical communication device, and an optical material using the same.
  • thermosetting or UV curable siloxane resins containing epoxy groups or acrylic groups, or amorphous properties because they are superior in transparency in the ultraviolet and near infrared regions.
  • Application of fluororesin is being studied.
  • thermosetting resins As described above, various thermosetting resins, photo-curing resins, or thermoplastic resins are used as coating materials for optical and electronic parts and encapsulating materials, and these resins are resistant to heat alone. Applied according to properties such as transparency, solubility, and adhesion
  • Acrylic acid esters and methacrylic acid esters having an adamantane skeleton are excellent in heat resistance by polymerizing them, and are excellent in mechanical strength and optical characteristics such as impact resistance and surface hardness. It is known that a polymer can be obtained (for example, see Patent Document 1).
  • Patent Document 1 Japanese Patent Application Laid-Open No. 63-307844
  • Patent Document 2 JP 2004-123687 A
  • the present invention is suitable as an optical waveguide, an LED sealing resin, a display material, a reflective material, an optical resin such as an optical communication device, or a coating agent for an electronic circuit.
  • Another object of the present invention is to provide an epoxy resin composition that provides a cured resin excellent in optical properties, heat resistance, electrical properties, and mechanical strength.
  • the present inventors have maintained the heat resistance and strength, which are the above-mentioned problems, by substituting fluorine with adamantane having excellent heat resistance and strength. It can be further improved in transparency and light resistance, and the dielectric constant can be lowered by replacing the adamantane structure with fluorine.
  • a resin that supports higher frequency and integration of electrical circuits, etc. Alternatively, it is useful as an adhesive, a substrate film, and the like.
  • fluorine-substituted adamantane with a diol it can be reacted and cured with an epoxy resin. By blending the dioli in an epoxy resin, It was found that an epoxy resin composition giving a cured resin excellent in heat resistance, optical properties, electrical properties and mechanical strength can be obtained.
  • the present invention has been completed on the basis of force and knowledge.
  • the present invention provides the following epoxy resin composition, optical material, optical waveguide, electronic circuit, and LED member.
  • An epoxy resin composition comprising a fluorine-substituted adamantanediol represented by the general formula (1) as a curing agent.
  • the epoxy resin composition of the present invention is characterized by containing a fluorine-substituted adamantanediol represented by the general formula (1) as a curing agent.
  • the fluorine-substituted adamantanediol represented by the above general formula (1) is a force obtained by fluorinating 1,3-adamantanediol, and n is 14 in the general formula (1). Fluoroadamantanediol is the most common. [0011] As the epoxy resin, known ones can be applied.
  • bisphenol A type epoxy resin bisphenol F type epoxy resin, phenol novolac type epoxy resin and cresol novolac type epoxy resin, novolac type epoxy resin, alicyclic epoxy resin, triglycidyl isocyanurate
  • Nitrogen-containing heterocyclic epoxy resin such as hydantoin epoxy resin, hydrogenated bisphenol A type epoxy resin, aliphatic epoxy resin, glycidyl ether type epoxy resin, bisphenol S type epoxy resin, low water absorption cured type
  • Mainly used are biphenyl type epoxy resins, dicyclo ring type epoxy resins, naphthalene type epoxy resins and the like. These may be used alone or in combination of two or more.
  • epoxy resins are selected according to the intended use because of their transparency, light resistance, heat resistance, and mechanical strength.
  • the epoxy resin may be solid or liquid at room temperature, but it is generally preferred that the epoxy resin used has an average epoxy equivalent of 90 to 1000. In addition, when it is solid, it has a softening point. A temperature of 160 ° C. or lower is preferable. If the epoxy equivalent is less than 90, the cured product of the epoxy resin composition may become brittle. If the epoxy equivalent exceeds 1000, the cured product may have a low glass transition temperature (Tg).
  • Tg glass transition temperature
  • the fluorine-substituted adamantanediol represented by the general formula (1) may be used alone, but other hardeners may be used depending on the purpose.
  • An acid anhydride curing agent, a phenol curing agent, an amine curing agent, or the like may be used in combination as the agent.
  • Examples of the acid anhydride-based curing agent include phthalic anhydride, maleic anhydride, trimellitic anhydride, pyromellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methyl nadic anhydride, nadic anhydride, anhydrous Examples include glutaric acid, methylhexahydrophthalic anhydride, and methyltetrahydrophthalic anhydride.
  • phenolic curing agent examples include phenol novolak resin, cresol novolak resin, bisphenol A novolak resin, and triazine-modified phenol novolak resin.
  • amine curing agents examples include dicyandiamide, m-phenylenediamine, 4, 4 And aromatic diamines such as diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, and m-xylylenediamine.
  • acid anhydride curing agents and phenol curing agents are preferred from the viewpoint of the physical properties of the cured resin.
  • the blending ratio of the epoxy resin and the curing agent is such that the active group capable of reacting with the epoxy group in the curing agent (such as an acid anhydride group or a hydroxyl group) is 0 with respect to 1 equivalent of the epoxy group in the epoxy resin. It is preferable that the ratio is 5 to 1.5 equivalents, more preferably 0.7 to 1.2 equivalents.
  • the epoxy resin composition of the present invention is conventionally used as necessary, for example, a curing accelerator, a deterioration preventing agent, a modifier, a silane coupling agent, a defoaming agent, an inorganic
  • a curing accelerator for example, a curing accelerator, a deterioration preventing agent, a modifier, a silane coupling agent, a defoaming agent, an inorganic
  • Various known additives such as powders, leveling agents, mold release agents, dyes and pigments may be appropriately blended.
  • curing accelerator examples include, but are not limited to, for example, 1,8 diazabicyclo (5,4,0) undecene 7, triethylenediamine, trie 2,4,6 dimethylaminomethylphenol.
  • Tertiary amines such as 2-ethyl 4-methylimidazole, imidazoles such as 2-methinoreimidazole, triphenylphosphine, tetraphenylphosphonium tetraphenolevoleate, tetra-n-butinorephosphonium o, o
  • Examples include phosphorus compounds such as tinole phosphorodithioate, quaternary ammonium salts, organometallic salts, and derivatives thereof. These may be used alone or in combination.
  • tertiary amines, imidazoles, and phosphorus compounds are preferably used.
  • the content of the curing accelerator is preferably 0.01 to 8.0% by mass, more preferably 0.0 :! to 3.0% by mass with respect to the epoxy resin.
  • Examples of the deterioration preventing agent include phenolic compounds, amine compounds, and organic sulfur. Conventionally known deterioration inhibitors such as yellow compounds and phosphorus compounds can be used.
  • phenolic compounds include Irganox 1010 (Irganoxl010, Ciba 'Specialty' Chemicals, Trademark), Inoreganox 1076 (Irganoxl076, Chinoku 'Specialty' Chemikanorez, Trademark), Inoreganox 1330 (Irganoxl330, Chino's Specialty 'Chemica Norez, Trademark), Inoreganox 3114 (Irganox 3114, Chinoku' Specialty 'Chemicals, Trademark), Inoreganox 3125 (Irganox3125, Chinoku' Specialty 'Chemicals, Trademark), Inoreganox 3790 (Irganox3790 , Chinoku 'Specialty' Chemicals, Inc., Trademark) BHT, Cyanox 1790 (Cyanoxl790, Cyanamide, Trademark), Sumilizer GA-8 0 (SumilizerGA_80, Sumitomo Chemical, Trade
  • Examples of amine compounds include Irgastab FS042 (Tinoku 'Specialty' Chemicals, Trademark), GENOX EP (Crimpton, Trademark, Compound Name; Dialkyl_N_methylamino oxide), and hindered amines.
  • organic sulfur compounds examples include DSTP (Yoshitomi, Trademark), DLTP (Yoshitomi, Trademark), DLTOIB (Yoshitomi, Trademark), DMTP (Yoshitomi, Trademark), Seeno X412S (Cypro Kasei Co., Ltd., trademark), Cyanox 1212 (Cyanamide Co., Ltd., trademark) and other commercial products can be listed.
  • Examples of the modifying agent include conventionally known modifying agents such as glycols, silicones, and alcohols.
  • Examples of the silane coupling agent include conventionally known silane coupling agents such as silane and titanate.
  • Examples of the defoaming agent include known defoaming agents such as silicones.
  • Examples of the inorganic powder include conventionally known inorganic powders such as glass powder and silica powder.
  • the epoxy resin composition of the present invention may contain a solvent as necessary. As a solvent, when the epoxy resin is a powder, or as a diluent solvent for coating, toluene is used. Aromatic solvents such as xylene, and ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone can be used.
  • the epoxy resin composition of the present invention mixes the above-mentioned epoxy resin component and curing agent with various additives, and injects them into a mold (resin mold) to be molded, or a desired film or the like by coating. After making into a shape, it is cured by heating.
  • the curing temperature is 50 to 200 ° C, preferably 100 to 150 ° C. Setting it to 50 ° C or higher does not cause poor curing. Setting it to 200 ° C or lower eliminates coloring and the like.
  • the curing time varies depending on the epoxy resin used, the curing accelerator, and the curing temperature, but is preferably 0.5 to 6 hours.
  • the cured product has excellent characteristics such as optical characteristics, heat resistance, electrical characteristics and mechanical strength, and is used for optical waveguides, LED sealing resins and electronic circuits. It can be suitably used for various optical materials such as optical resins such as adhesives, reflective materials and optical communication devices.
  • the present invention also provides an optical material, an optical waveguide, an LED member, and an electronic circuit obtained using the above epoxy resin composition.
  • the sample was heated from 25 ° C to 350 ° C under a nitrogen stream (20 ml / min) at a heating rate of 10 ° C / min. Immediately cool to remove the thermal history of the sample, and JIS K7121 The glass transition temperature was measured according to the above. As a result, the glass transition temperature was 70 ° C.
  • a test piece having a length of 40 mm and a width of 40 mm was cut out from the obtained sheet, and haze was measured on the test piece by a haze meter (manufactured by Suga Test Instruments Co., Ltd .; HGM-2DP type). As a result, the haze is 0.2. /. Met.
  • a test piece having a length of 20 mm and a width of 10 mm was cut out from the obtained sheet, and the refractive index was measured with an Abbe refractometer (manufactured by Atago Co., Ltd.). As a result, the refractive index was 1.50.
  • a transparent thin film layer having a thickness of 0.01 mm was formed on a 10.2 cm (4 inch) silicon substrate by thermosetting (film formation) under the same conditions as in Example 1.
  • light of a predetermined wavelength (830 nm, 1300 nm) was incident using a prism force bra, and the light was propagated in the thin film.
  • the detector was scanned along the propagation light to detect the scattered light from the sample, and the light loss of the thin film propagation light was calculated from the attenuation of the intensity.
  • the optical loss when 830 nm light was incident was 1.0 dB / cm (TM direction)
  • the optical loss when 1300 nm light was incident was 1.3 dB / cm (TM direction).
  • the epoxy resin composition containing the fluorine-substituted adamantanediol of the present invention as a curing agent, the cured product has excellent characteristics such as optical characteristics, heat resistance, electrical characteristics and mechanical strength, It can be suitably used for various optical materials such as optical waveguides, LED members, and display sealants.
  • the epoxy resin composition of the present invention since the epoxy resin composition of the present invention has such excellent characteristics, it can be used for optical semiconductors (LEDs, etc.), flat panel displays (organic EL elements, etc.), electronic circuits, It can be suitably used for optical electronic members such as resin (sealing agent, adhesive) for circuit (optical waveguide), optical communication lens, and optical film.
  • the epoxy resin composition of the present invention is used as a semiconductor element / integrated circuit (IC, etc.), individual semiconductor (diode, transistor, thermistor, etc.), LED (LED lamp, chip LED, light receiving element, optical semiconductor lens).
  • Sensors temperature sensors, optical sensors, magnetic sensors
  • passive components high-frequency devices, resistors, capacitors, etc.
  • mechanical components connectors, switches, relays, etc.
  • automotive components circuit systems, control systems, sensors
  • adhesives optical components, optical discs, pickup lenses, etc.
  • surface coatings optical films such as antireflection films and sealing films.

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  • Physics & Mathematics (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Power Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Optical Integrated Circuits (AREA)

Abstract

La présente invention concerne une composition de résine époxy qui comprend un adamantanediol substitué par du fluor représenté par la formule générale (1) ci-dessous. L’invention décrit également un matériau optique, un guide d’ondes optiques, un élément DEL et un circuit électronique qui utilisent une telle composition de résine époxy. Un produit durci d’une telle composition de résine époxy qui comprend de l’adamantanediol substitué par du fluor comme agent de durcissement présente d'excellentes propriétés optiques, électriques, de résistance thermique, de résistance mécanique et similaires, et peut ainsi être utilisé de façon appropriée pour divers matériaux optiques tels que des guides d’ondes optiques, des résines d'étanchéité pour DEL, des agents d’étanchéité pour des affichages et des adhésifs pour les circuits électroniques. (Dans la formule, n représente un nombre entier de 1 à 14.)
PCT/JP2006/300608 2005-01-24 2006-01-18 Composition de résine époxy et matériau optique l’utilisant WO2006077862A1 (fr)

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JP2006553919A JPWO2006077862A1 (ja) 2005-01-24 2006-01-18 エポキシ樹脂組成物及びそれを用いた光学材料

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009260194A (ja) * 2008-04-21 2009-11-05 Sharp Corp 発光デバイスおよび発光デバイスの製造方法
US7649065B2 (en) * 2005-10-28 2010-01-19 Asahi Glass Company, Limited Fluoroadamantane derivative, fluorine-containing polymer and production method
JP2010163566A (ja) * 2009-01-16 2010-07-29 Three M Innovative Properties Co エポキシ樹脂組成物
KR101090382B1 (ko) 2011-08-22 2011-12-07 (주)디오코리아 일체형 ｕｖ 몰딩 패키징 모듈
WO2014069273A1 (fr) * 2012-11-01 2014-05-08 三菱瓦斯化学株式会社 Agent de durcissement de résine époxyde
JP2017034137A (ja) * 2015-08-03 2017-02-09 パナソニックＩｐマネジメント株式会社 Ｌｅｄモジュール
WO2017130849A1 (fr) * 2016-01-29 2017-08-03 日東電工株式会社 Composition de résine époxyde photosensible de formation de guide d'ondes optique et film photosensible de formation de guide d'ondes optique, guide d'ondes optique l'utilisant, et carte de câblage imprimé souple mixte de transmission optique/électrique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7192796B2 (ja) * 2017-12-19 2022-12-20 Jsr株式会社 硬化性樹脂組成物、積層体、光学フィルターおよび化合物

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55115423A (en) * 1979-02-28 1980-09-05 Mitsubishi Electric Corp Manufacture of adamantane-epoxy resin
JPH10130371A (ja) * 1996-11-01 1998-05-19 Nippon Kayaku Co Ltd アダマンタン類、これらを含有する熱可塑性樹脂及びこれらを含有する熱硬化性樹脂組成物
JP2004123687A (ja) * 2001-12-25 2004-04-22 Idemitsu Petrochem Co Ltd パーフルオロアダマンチルアクリル酸エステル類及びその中間体
WO2004052832A1 (fr) * 2002-12-11 2004-06-24 Asahi Glass Company, Limited Derives fluores de l'adamantane

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS55115423A (en) * 1979-02-28 1980-09-05 Mitsubishi Electric Corp Manufacture of adamantane-epoxy resin
JPH10130371A (ja) * 1996-11-01 1998-05-19 Nippon Kayaku Co Ltd アダマンタン類、これらを含有する熱可塑性樹脂及びこれらを含有する熱硬化性樹脂組成物
JP2004123687A (ja) * 2001-12-25 2004-04-22 Idemitsu Petrochem Co Ltd パーフルオロアダマンチルアクリル酸エステル類及びその中間体
WO2004052832A1 (fr) * 2002-12-11 2004-06-24 Asahi Glass Company, Limited Derives fluores de l'adamantane

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7649065B2 (en) * 2005-10-28 2010-01-19 Asahi Glass Company, Limited Fluoroadamantane derivative, fluorine-containing polymer and production method
JP2009260194A (ja) * 2008-04-21 2009-11-05 Sharp Corp 発光デバイスおよび発光デバイスの製造方法
JP2010163566A (ja) * 2009-01-16 2010-07-29 Three M Innovative Properties Co エポキシ樹脂組成物
KR101090382B1 (ko) 2011-08-22 2011-12-07 (주)디오코리아 일체형 ｕｖ 몰딩 패키징 모듈
WO2014069273A1 (fr) * 2012-11-01 2014-05-08 三菱瓦斯化学株式会社 Agent de durcissement de résine époxyde
CN104755526A (zh) * 2012-11-01 2015-07-01 三菱瓦斯化学株式会社 环氧树脂固化剂
US9605110B2 (en) 2012-11-01 2017-03-28 Mitsubishi Gas Chemical Company, Inc. Epoxy resin curing agent
TWI623581B (zh) * 2012-11-01 2018-05-11 Mitsubishi Gas Chemical Co 環氧樹脂硬化劑
JP2017034137A (ja) * 2015-08-03 2017-02-09 パナソニックＩｐマネジメント株式会社 Ｌｅｄモジュール
WO2017130849A1 (fr) * 2016-01-29 2017-08-03 日東電工株式会社 Composition de résine époxyde photosensible de formation de guide d'ondes optique et film photosensible de formation de guide d'ondes optique, guide d'ondes optique l'utilisant, et carte de câblage imprimé souple mixte de transmission optique/électrique
JP2017134319A (ja) * 2016-01-29 2017-08-03 日東電工株式会社 光導波路形成用感光性エポキシ樹脂組成物および光導波路形成用感光性フィルム、ならびにそれを用いた光導波路、光・電気伝送用混載フレキシブルプリント配線板
US11377550B2 (en) 2016-01-29 2022-07-05 Nitto Denko Corporation Photosensitive epoxy resin composition for formation of optical waveguide, photosensitive film for formation of optical waveguide, optical waveguide produced by using the epoxy resin composition or the photosensitive film, and hybrid flexible printed wiring board for optical/electrical transmission

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JPWO2006077862A1 (ja) 2008-06-19

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