TW201211094A - Low moisture permeability resin composition and cured product thereof - Google Patents

Low moisture permeability resin composition and cured product thereof Download PDF

Info

Publication number
TW201211094A
TW201211094A TW100128662A TW100128662A TW201211094A TW 201211094 A TW201211094 A TW 201211094A TW 100128662 A TW100128662 A TW 100128662A TW 100128662 A TW100128662 A TW 100128662A TW 201211094 A TW201211094 A TW 201211094A
Authority
TW
Taiwan
Prior art keywords
compound
resin composition
low moisture
electronic device
ether
Prior art date
Application number
TW100128662A
Other languages
Chinese (zh)
Other versions
TWI591089B (en
Inventor
Ryo Itaya
Original Assignee
Daicel Chem
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 Daicel Chem filed Critical Daicel Chem
Publication of TW201211094A publication Critical patent/TW201211094A/en
Application granted granted Critical
Publication of TWI591089B publication Critical patent/TWI591089B/en

Links

Classifications

    • 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
    • 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
    • C08G59/36Epoxy compounds containing three or more epoxy groups together with mono-epoxy compounds
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00Details of semiconductor or other solid state devices
    • H01L23/28Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293Organic, e.g. plastic
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L31/00Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L31/04Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
    • H01L31/042PV modules or arrays of single PV cells
    • H01L31/048Encapsulation of modules
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/01Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013Fillers, pigments or reinforcing additives
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/0008Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025Crosslinking or vulcanising agents; including accelerators
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/54Silicon-containing compounds
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001Technical content checked by a classifier
    • H01L2924/0002Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10Details of semiconductor or other solid state devices to be connected
    • H01L2924/11Device type
    • H01L2924/12Passive devices, e.g. 2 terminal devices
    • H01L2924/1204Optical Diode
    • H01L2924/12044OLED
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10KORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00Organic light-emitting devices
    • H10K50/80Constructional details
    • H10K50/84Passivation; Containers; Encapsulations
    • H10K50/842Containers
    • H10K50/8426Peripheral sealing arrangements, e.g. adhesives, sealants
    • 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy

Landscapes

  • Chemical & Material Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Computer Hardware Design (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Power Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Electromagnetism (AREA)
  • Electroluminescent Light Sources (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The present invention provides a low moisture permeability resin composition for electronic devices which can be used as sealing agent of organic electroluminescent devices, electronic papers or solar cells and can form cured product having excellent low moisture permeability. The present invention provides a low moisture permeability resin composition for electronic devices requiring low moisture permeability and characterized by comprising compound (A), compound (B) and polymerization initiator (C). The compound (A) has more than two reactive functional groups(a) in one molecule. The compound (B) has one reactive functional group (b) in one molecule and its molecular weight is 50-1000.

Description

201211094 六、發明說明: 【發明所屬之技術領域】 本發明係關於一插古+ η ~ 種有機電致發光元件、電子紙、女 陽能電池等被要求有彳氏读、、甚丨 虿低透濕性的電子裝置用之低透渴柯 樹脂組成物及其硬化物、 - ",、眭 閉劑、用以形成低透渴性密 封 之有機電致發光元件、電 使用此4 r L 宅于紙及太陽能電池。 【先前技術】 本發明係尋求—插At & 種此夠用於有機電致發光元 子紙、太陽能電池等之妯 牛 电 之低透濕性封閉材及密電子裝置用 樹脂組成物。有人提荦二:賦予低透濕性之硬化物的 8。重量份之:有Λ;種樹脂組成物,其含有至 至2〇番^ 矢環狀骨架的環氧化合物、及80 :2〇重…具有芳香族環的環 聚合起始劑作為有機電致 /、先%離子 文獻υ。具體而言,且件用封閉劑(參閱專利 ^^ . . .八有知肪私環狀骨架之環氧化合物、 具有方香杈%之環氧化合物 之化合物。然而,在85t8二二在兩末端具有環氧基 C 8 5 /〇 R Η條件下,直輝化 濕度係55g/m2· 24h以上 ,、更化物之透 上 尚未旎夠符合。 且古另外’有人提案一種組成物,其含有:⑷!分子中 具有至少2個以上環氣丙 中 氧樹脂;(B)1分子中复右$ ,子里為200至7_之環 ϊ為20000至1〇〇〇〇〇之 土刀子 活化、““ 氧樹月曰’(C)藉能量線照射而 Γ產生酉文的之潛在性光酸觸媒;及(D)分子中含有产 軋丙基之矽烷偶合劑;—種 衣 頁機EL 7C件密封用光硬化性 201211094 樹脂組成物,其含有:相對於100重量份之該成分, 含有30至150重量份之該(B)成分’還有,並且相對於 100重量份之該(A)成分及(B)成分的合計,含有〇]至1〇 重量份之該(C)成分、含有〇.1至1〇重量份之該(…成分 (參閱專利文獻2)。然而,針對其硬化物的透濕度則未被 探討。 另外’也有人知^案一種樹脂組成物,其含有(八)環氧 化合物、(B)酚醛清漆樹脂、(c)光陽離子聚合起始劑、 及(D)填料作為有機EL等元件封裝用接著劑(參閱專利 文獻3)。然而,為了獲得低透濕性,必須要有填料在 不含填料之情形下’於60°c 9〇%RH條件下,其硬化物之 透濕度為60 g/m2 · 24h,並不充分。 先前技術文獻 專利文獻 專利文獻1日本特開2007-46035號公報 專利文獻·2日本特開2010-126699號公報 專利文獻3曰本專利第2010-24364號公報 【發明内容】 [务明所欲解決之問題] 本毛明之目的係在於提供一種樹脂組成物,直能夠 ::有機電致發光元件、電子紙、太陽能電池等:被要 伟低透濕性之電子裝置用低透濕性封閉材及密封材等 之賦予具優越之低透濕性的硬化物。 化物1纟七明之其他目的係於提供—種低透濕性硬 ,/、係使上述低透濕性樹脂組成物硬化所獲得。 -5- 的係於提供一種密封劑,其 低透/愚性封閉材及密封材之 他目的係於提供一種有機電 能電池,其係藉由利用上述 閉或密封電子裝置而減低濕 述課題而鑽研的結果,發現 由將具有特定構造且具有工 合於具有2個以上反應性官 ,來使樹脂硬化物之交聯密 物中之具有1個該特定構造 填塞自由體積之效果;也藉 反應性官能之樹脂所構成的 ,特別有用於有機電致發光 等之被要求有低透濕性之電 種被要求有低透濕性的電子 其特徵為含有:1分子中 ⑷之化合物(A)、1分子中具 子置為5〇至1000之化合物 滚化合物(B)較佳為具有i個 201211094 還有,本發明之其他目 形成具有優異的低透濕性之 封閉劑及密封劑。 另外還有,本發明之其 致發光元件、電子紙、太陽 低透濕性封閉材或密封材封 氣之影響。 [用以解決問題之手段] 本發明人等為了解決上 下列事實而完成本發明:藉 個反應性官能基之化合物掺 能基之化合物中而使其聚合 度變小,另一方面源自聚合 反應性基的材料之側鏈展現 由硬化僅由具有該2個以上 樹脂之硬化物而改善透濕度 元件、電子紙、太陽能電池 子裝置用。 亦即’本發明係提供一 裝置用低透濕性樹脂組成物 具有2個以上反應性官能基 有1個反應性官能基(1))且分 (B)、與聚合起始劑(c)。 上述該化合物(A)與/或Ί 以上環狀骨架。 201211094 另外, 己烷環。 上述環狀骨架較佳為相 同或不同的苯環或環 合物(A),上述化合物(B) 進一步較佳為10至250 相對於1 0 0重量份之上述化 之含量較佳為1至1000重量份, 重量份。 上述電子裝置用低透濕性樹脂組成物也可以進—步 含有無機填料(D)。 另外上述電子裝置用低透濕性樹脂組成物也可以 進一步含有矽烷偶合劑。 上述聚合起始劑(C)較佳為光或熱陽離子聚合起始 劑、或是光或熱自由基聚合起始劑。 另外’在上述電子裝置用低電子裝置用低透濕性樹 脂組成物中之電子裝置較佳為有機電致發光元件、電子 紙或太陽能電池。 另外本發明係提供一種硬化物,其係將上述電子 裝置用低透濕性樹脂組成物硬化而成。 另外’本發明係提供一種封閉劑,其含有上述電子 裝置用低透濕性樹脂組成物。 另外’本發明係提供一種密封劑,其含有上述電子 裝置用低透濕性樹脂組成物。 另外’本發明係提供一種有機電致發光元件,其含 有上述硬化物。 另外’本發明係提供一種電子紙,其含有上述硬化 物。 201211094 另外’本發明係提供一種太陽能電池,其含有上述 硬化物。 [發明之效果] 若根據本發明,則可以獲得一種樹脂組成物及其硬 化物,該樹脂組成物改善有機電致發光元件、電子紙、 太陽能電池等之被要求有低透濕性之電子裝置用的透濕 度’並賦予具有1 〇 〇至2 0 〇 °c之耐熱性的硬化物。另外, 右根據本發明,則可以獲得一種封閉劑及密封劑,能夠 开^成有機電致發光元件 '電子紙、太陽能電池等之被要 求有低透濕性之電子裝置用的具有優異之低透濕性的硬 =物(封閉材、密封材)。含有有關本發明之低透濕性樹 脂組成物硬化物之有機電致發光元件、電子紙、太陽能 電^係將濕度之影響抑制至最小限度。 【實施方式】 [用於實施發明之形態] <電子裝置用低透濕性樹脂組成物> 發明之f子裝置用低透濕性樹脂組成物,其特& 物(1)有广1分子中具有2個以上反應性官能基⑷之化合 50 1分子中具有1個反應性官能基(b)且分子量為 一之^化合物(B)、與聚合起始劑(C)作為必要成分。 硬化物(般二言’硬化含有交聯性多官能基之樹脂材料的 濕度,通?曰在硬化物)係具有來自於材料骨架之固有的透 於上述謂稀釋劑之含有1官能基的材料捧合 聯點矩離形’由於使共聚合之聚合物的交 I長,一般也較在樹脂單體t之透濕度變得更 -8- 201211094 门另外〜為料脂硬化物係通常藉由將聚合起始劑摻 〇於具有2個以上反應性官能基之樹脂中,利用熱或光 士使聚合起始劑活化而使其交聯硬化後製得,但主要水 洛氣係從進打材料交聯之際所形成的自由體積而穿透 出。 於本1明中,藉由使1分子中具有1個反應性官能 基(b)且分子直為50至1000之化合物(Β)摻合於1分子中 具有2個以上反應性官能基(a)之化合物(A)中來使其聚 合’而使付樹脂硬化物之交聯密度變小,另一方面,聚 合物中之源自該化合物(B)的單體單位展現聚合物之側 鏈填塞自由體積之效果,也較硬化僅由該化合物(A)所構 成的樹脂之硬化物更能夠改善透濕度。 以下’不意顯示在本發明之聚合物的自由體積的填 塞構造。標記A之橢圓係源自化合物(A)之單體單位(2 B旎之情形)、標記B之橢圓係源自化合物(B)之單體單 位、兩側之波狀線係表示聚合物之主鏈。認為源自化合 物(B)之單體單位填埋源自化合物之單體單位的間隙 而將自由體積予以填塞。201211094 VI. Description of the Invention: [Technical Field] The present invention relates to an organic electroluminescent device, an electronic paper, a female solar battery, etc., which are required to have a reading, and a low Low-thirsty ketone resin composition for use in moisture permeable electronic devices and cured products thereof, - ", clogging agents, organic electroluminescent elements for forming a low-thirsty seal, electrically using this 4 r L Housed in paper and solar cells. [Prior Art] The present invention seeks to insert and at least a low-moisture-permeable sealing material and a resin composition for a dense electronic device which are sufficient for use in an organic electroluminescence element paper, a solar battery, or the like. It has been suggested that two: a hardened substance with low moisture permeability. Parts by weight: bismuth; a resin composition containing an epoxy compound up to a 2 fluorene ring skeleton, and a weight of 80:2 ...... a cyclic polymerization initiator having an aromatic ring as an organic electrophoresis /, first % ion literature υ. Specifically, the sealant is used for the part (see Patent ^^..8) which has an epoxy compound of a private ring skeleton, a compound having an epoxy compound of a square scent. However, at 85t8 two in two Under the condition of having an epoxy group C 8 5 /〇R 末端 at the end, the direct-purification humidity system is 55 g/m 2 · 24 h or more, and the permeation of the compound is not yet sufficient. Moreover, a new composition has been proposed, which contains: (4)! There are at least two or more epoxides in the molecule; (B) in the molecule of 1 remake right, and the ring of 200 to 7 _ is 20,000 to 1 土 soil knife activation, "Oxygen tree 曰" (C) is a potential photoacid catalyst that is irradiated by energy rays to produce sputum; and (D) a decane coupling agent containing propyl groups; 7C-block photocurable 201211094 resin composition containing: 30 to 150 parts by weight of the component (B) with respect to 100 parts by weight of the component, and relative to 100 parts by weight of the (A) The total amount of the component and the component (B), containing 〇] to 1 part by weight of the component (C), containing 〇.1 to 1 The component (see Patent Document 2). However, the moisture permeability of the cured product has not been examined. In addition, a resin composition containing (VIII) epoxy compound (B) is also known. a novolak resin, (c) a photocationic polymerization initiator, and (D) a filler are used as an adhesive for encapsulating an element such as an organic EL (see Patent Document 3). However, in order to obtain low moisture permeability, a filler must be present. In the case of no filler, the moisture permeability of the cured product is 60 g/m 2 · 24 h under the condition of 60 ° c 9 〇 % RH. The prior art document patent document 1 Japanese special open 2007-46035 Japanese Laid-Open Patent Publication No. 2010-126699 (Patent Document 3) Patent No. 2010-24364 [Draft of the Invention] [Problem to be Solved] The purpose of the present invention is to provide a resin composition. , can be:: organic electroluminescent elements, electronic paper, solar cells, etc.: low moisture permeability sealing materials and sealing materials for electronic devices that are required to be low in moisture permeability, giving excellent hardening and low moisture permeability Material The other purpose of the 纟七明 is to provide a low moisture permeability hardness, which is obtained by hardening the above low moisture permeable resin composition. The -5- is provided with a sealant, which is low in transparency/stupidity. The purpose of the closure material and the sealing material is to provide an organic electric energy battery, which is studied by using the above closed or sealed electronic device to reduce the problem of wetness, and finds that it will have a specific structure and has a workmanship with two The above reactive officer has the effect of having one of the specific structures to fill the free volume in the crosslinked compact of the cured resin; and also consisting of a reactive functional resin, particularly for organic electroluminescence or the like. An electron having a low moisture permeability is required to have a low moisture permeability electron characterized by containing: a compound (A) in one molecule (4), and a compound rolling compound having a molecular weight of 5 to 1000 in one molecule (B) It is preferable to have i 201211094. Further, the other object of the present invention is to form a sealant and a sealant which have excellent low moisture permeability. Further, the effect of the light-emitting element, the electronic paper, the solar low moisture permeability sealing material or the sealing material of the present invention is also affected. [Means for Solving the Problem] The present inventors have completed the present invention in order to solve the above facts: a compound having a reactive functional group is incorporated into a compound of a compound to make the degree of polymerization small, and on the other hand, from polymerization. The side chain of the material of the reactive group exhibits improvement of the moisture permeable element, the electronic paper, and the solar cell sub-device by hardening only the cured product having the two or more resins. That is, the present invention provides a device having a low moisture permeable resin composition having two or more reactive functional groups having one reactive functional group (1), and a component (B) and a polymerization initiator (c). . The above compound (A) and/or oxime or more cyclic skeleton. 201211094 In addition, a hexane ring. The cyclic skeleton is preferably the same or different benzene ring or cyclized compound (A), and the compound (B) is further preferably 10 to 250. The content of the above-mentioned compound is preferably 1 to 100 parts by weight. 1000 parts by weight, parts by weight. The low moisture permeable resin composition for the above electronic device may further contain an inorganic filler (D). Further, the low moisture permeable resin composition for an electronic device may further contain a decane coupling agent. The above polymerization initiator (C) is preferably a photo or thermal cationic polymerization initiator or a photo or thermal radical polymerization initiator. Further, the electronic device in the low moisture permeability resin composition for a low electronic device for an electronic device is preferably an organic electroluminescence device, an electronic paper or a solar cell. Further, the present invention provides a cured product obtained by hardening the above electronic device with a low moisture permeable resin composition. Further, the present invention provides a blocking agent comprising the above-mentioned low moisture permeable resin composition for an electronic device. Further, the present invention provides a sealant comprising the above-mentioned low moisture-permeable resin composition for an electronic device. Further, the present invention provides an organic electroluminescence element comprising the above-mentioned cured product. Further, the present invention provides an electronic paper containing the above hardened material. Further, the present invention provides a solar cell comprising the above-mentioned cured product. [Effect of the Invention] According to the present invention, it is possible to obtain a resin composition which is improved in an organic electroluminescent device, an electronic paper, a solar cell, or the like, which is required to have low moisture permeability, and a cured product thereof. The moisture permeability used is 'and a hardened material having a heat resistance of 1 Torr to 20 〇 ° C is imparted. Further, according to the present invention, it is possible to obtain a sealant and a sealant which can be used to form an organic electroluminescence device, which is excellent in electronic devices requiring low moisture permeability, such as electronic paper and solar cells. Moisture-permeable hard material (closed material, sealing material). The organic electroluminescence device, the electronic paper, and the solar cell system containing the cured product of the low moisture permeability resin composition of the present invention minimize the influence of humidity. [Embodiment] [Form of the invention for carrying out the invention] <Low moisture permeable resin composition for electronic device> The low moisture permeable resin composition for the sub-device of the invention has a wide range of special & a compound having two or more reactive functional groups (4) in one molecule, having a reactive functional group (b) and having a molecular weight of one compound (B) and a polymerization initiator (C) as essential components . A cured product (generally, 'hardening the moisture of a resin material containing a crosslinkable polyfunctional group, which is cured in a hardened material) has a 1-functional group-containing material which is inherently derived from the material skeleton and which penetrates the above-mentioned diluent. By holding the joint moment away from the shape 'Because the length of the copolymerized polymer is long, it is generally more than the moisture permeability of the resin monomer t -8 - 201211094 The polymerization initiator is doped into a resin having two or more reactive functional groups, and the polymerization initiator is activated by heat or light to be cross-linked and hardened, but the main water gas system is made from The free volume formed by the cross-linking of the material penetrates. In the present invention, a compound having one reactive functional group (b) in one molecule and having a molecular weight of from 50 to 1,000 is blended in one molecule to have two or more reactive functional groups (a) The compound (A) is polymerized to reduce the crosslinking density of the cured resin. On the other hand, the monomer unit derived from the compound (B) in the polymer exhibits a side chain of the polymer. The effect of packing the free volume is also to improve the moisture permeability more than hardening of the resin composed only of the compound (A). The following 'not intended to show the free volume packing configuration of the polymer of the present invention. The ellipsoid of the label A is derived from the monomer unit of the compound (A) (in the case of 2 B )), the ellipsoid of the label B is derived from the monomer unit of the compound (B), and the wavy line on both sides represents the polymer. Main chain. It is considered that the monomer unit derived from the compound (B) is filled with a gap derived from the monomer unit of the compound to fill the free volume.

-9 - 201211094 若該化合物(A)及/或該化合物(B)(化合物(a)及化合 物(B)中任一種或兩種)具有1個以上環狀骨架時,聚合 物中之自由體積容易減少,更能夠改善透濕度而較佳。 認為環狀骨架主要表示脂環式環狀骨架或芳香族環狀骨 架’相乘性地源自脂環式環狀骨架及芳香族環狀骨架之 疏水性、還有在芳香族環狀骨架之π-π堆積效果(積層芳 香族環狀骨架)而達成透濕度之改善。在該化合物(Α)與 該化合物(Β)皆具有環狀骨架之情形,各自的環狀骨架可 以相同或不同。另外,化合物(Α)或化合物(Β)具有2個 以上環狀骨架之情形,複數個環狀骨架也可以相同或不 同0 笨環、萘環、蒽環、 芳香族環;環戍烧環、 具體而言,環狀骨架可舉例: 菲環、苐環等之單環或縮合多環之 壞己烷環、十氫萘環、降莰烷環、金剛烷環等之單環或 多環之脂肪族環。還有,於本發明專利說明書中,將縮 合η個環等之多環環狀骨架的數目係 、 1尔叹馮η個。化合物 (Α)ι分子中之環狀骨架的數目例 馬1至3〇個,較佳為 1至10個,進一步較佳為1至6個,拉彳4 付佳馮1至5個。 化合物(Β) 1分子中之環狀骨架的數 ^ 妖目例如為1至10個, 較佳為1至6個,進一步較佳為1至3個 有苯環、萘環、 ’環狀骨架較隹 第 為 於化合物(Α)中,環狀骨架較佳為含 環或環己烷環。另外,於化合物(Β)中 含有苯環或環己烷環。 -10- 201211094 〈化合物(A) &gt; 〃要化合物(A)為i分子中具有2個以上反應性官能 基(a)之化合物的話,並未予以特別限定。具體而言反 應性官能基U)可舉例:環氧基、環氧丙基、乙烯基醚基 等之具有陽離子基聚合性之基;(甲基)丙烯醯基等之具 有自由基聚合性之基等。乙烯基醚基也有具有自由基聚 合性之情形。反應性官能基(a)能夠較佳使用具有陽離子 基聚合性之基,進一步較佳為環氧基,特佳為環氡丙基。 化合物(A) 1分子中之反應性官能基(a)的數目例如為2至 30個,較佳為2至1〇個,進一步較佳為2至“固,特 佳為2至3個。複數個反應性官能基⑷也戍 =雖然:合物⑷之分子量並未予以特別限制,但重 至5〇如1子里Γ如月匕夠3又為1〇0至1〇〇〇〇〇,較佳設為100 而使用。 種以上 例如’化合物(A)可舉例:1 離子I合性吕能基與芳香族環之化合 具有2個以上自由基聚合性官能基盘):1刀子中 (A-2).丨八| Λ 土,、方杳私環之化合物 时 刀子中具有2個以上陽離子聚合性官心其&amp; 肪族環之化合物f 吕此基與月曰 ^ . A_3 ,與^刀子中具有2個以上其 I合性官能基與脂肪族環之化合物(Α_4)等。自由基 具有芳香埃環與2個以上陽離子聚 合物(A - Π,你丨1土 S此基之化 “v氧:其可舉例:雙紛型二環氧丙基轉、雙紛 ! — %氧丙基醚、雙酚F型二 又埘 二環氧丙基醚、四甲基 ”:广雙紛S型 基又酚型-%氧丙基醚等之具有苯 -11- 201211094 環與2個環氧基之化合物;萘二醇二環氧丙基醚、雙盼 苐二環氧丙基醚、雙甲酚第二環氧丙基醚、雙苯氧基乙 醇苐二環氧丙基醚等之具有縮合環與2個環氧基之化合 物;具有如鹼酚醛型環氧樹脂、甲酚酚醛型環氧樹脂、 含雙酚骨架之酚醛型環氧樹脂、含萘骨架之酚醛型環氧 樹脂之重複單位的聚苯基壞氧丙基驗類等之具有苯環及 /或縮合環與2個以上環氧基之化合物;雙紛F雙(3 -乙基 環氧丙烷-3-基甲基)醚等之具有芳香族環與2個環氧丙 基之化合物;雙盼二乙稀基喊、雙紛A二乙稀基醚、雙 酚F二乙烯基醚、雙酚F雙(2-乙烯氧乙基)醚、雙酚s 二乙稀基醚、四曱基雙盼二乙烯基醚等之具有苯環與2 個乙烯基醚基之化合物;萘二醇二乙烯基醚、雙酚苐二 乙烯基醚、雙甲酚第二乙烯基醚、雙苯氧基乙醇第二乙 烯基醚等之具有縮合環與2個乙烯基醚基之化合物;及 此等之鹵化物、或此等之C丨-9烷基取代物等。在c! ·9烷 基取代物中之C I - 9炫基取代基,可舉例:曱基、乙基、 丙基、三級丁基等。鹵化物中之鹵素可舉例:F、Cl、Br 等。 .. 具有芳香族環與2個以上自由基聚合性官能基之化 合物(A - 2)’例如’可舉例:雙紛二(曱基)丙烯酸酯、雙 酚A二(曱基)丙烯酸酯、雙酚F二(甲基)丙烯酸酯、雙 酚S二(曱基)丙烯酸酯、四曱基雙酚二(甲基)丙烯酸酯等 之具有苯環與2個(曱基)丙烯醯基之化合物;萘二醇二 (曱基)丙烯酸酯、雙酚苐二(曱基)丙烯酸酯、雙甲酚苐二 (甲基)丙烯酸酯、雙苯甲氧乙醇苐二(甲基)丙烯酸醋等之 -12- 201211094 具有縮合環與2個(曱基)丙烯醯基之化合物;及此等之 鹵化物、或此等之Ci_9烧基取代物等。在Cu烧基取代 物中之Cw烷基取代基’可舉例:甲基、乙基、丙基、 二級丁基專。在_化物中之鹵素可舉例:F、Cl、Br等。 具有脂肪族環與2個以上陽離子聚合性官能基之化 合物(A-3)’例如,可舉例:氫化雙酚八二環氧丙基醚、 氫化雙酚F二環氧丙基醚、氫化雙酚§二環氧丙基醚、 二環己基二環氧丙基醚、雙(3,4_環氡環己基)曱基、3,4, _ 環氧環己基-3,4-環氧環己院等之具有環己烧環與2個環 氧基之化合物;具有環己烷環與2個環氧丙基之化合 物;及氫化雙齡A二乙烯基鍵基、氫化雙紛F:乙烯基 醚、氫化雙酚S二乙烯基醚、二環己基二乙烯基醚等之 具有環己烷環與2個乙烯基醚之化合物等。 ,具有脂肪族環與2個以上自由i聚合性官能基之化 :物(A·4)’例如’可舉例:氮化雙…(甲基)丙烯酸 自曰、氯化雙齡F二(甲基)丙烯酸醋、氣化㈣ 丙烯酸酯、二環己基二(甲其、系必 土)丙烯酸酯等之具有環己烷 辰/、2個(甲基)丙烯醯基之化合物等。 另外,化合物(A)係例如以下彳 ⑴ zH〇—Rl)m 乂下式⑴所不之化合物: [式(1)中,Z1係表示從m 夕_〜 f 7] r nu\ + 具之夕疋备基化合物 (Z (OH)m)除去爪個0Η基之基,r 可LV S女说/上《· 1乐衣不%氧丙基、也 了以具有取代基之核氧丙基甲 婦醯基。m係2以上之整數卜μ、乙席基、或(甲基)丙 骨¥ t A ^ ^ ^組 上述z較佳為具有環狀 月架之基%狀骨架可舉例前述例示之物。 201211094 m價之多元羥基化合物Z^OHh可舉例:雙酚、雙 盼A、雙酚F、雙酚8等之具有2個苯環之化合物、及 此等之_化物或此等之C丨-9烷基取代物;萘二醇、雙酚 筅、雙曱盼笫、雙苯氧基乙醇苐等之具有縮合環之化合 物、及此等之鹵化物或此等之c 烷基取代物;氫化雙 盼入、氫化雙酚F、氫化雙酚S、二環己基等之具有2個 環己烧環之化合物;甲酚酚醛清漆、酚酚醛清漆等之具 有3個以上笨環等之芳香族環化合物及此等之函化物, 或此等之Cl-9烷基取代物等。在C〗_9烷基取代物中之cKs 炫基取代基’可舉例:甲基、乙基、丙基、三级丁基等。 在齒化物中之鹵素可舉例:F、C1、B r等。 另外’化合物(A)係例如以下式⑴所示之化合物: [式(I)中’ χ係表示單鍵或連結基(具有1個以上原 :之2價的基)’上述連結基係2價之烴基、羰基、醚鍵: &amp;曰建反酸,*、醢胺鍵、或此等複數個連接而成之基]。 '式(1)所不之化合物中,作為連結基所例示的2 價煙基較^碳數1至18之直鏈狀或分枝鏈狀之伸垸 基、2價之脂環式烴基(尤其是2價之伸環烧基)等。碳^ 1至18之直鏈狀或分枝鏈狀之伸烷基,例如,可舉例: 亞曱基ψ基亞甲基、二甲基亞甲基、伸乙基、伸丙基、 三亞甲基等。2價之脂環式烴基,例如,可舉例· H 伸環戊基、1,3·伸環戊基、環亞戍基、1&gt;2伸環己基_ -14- 201211094 價之伸環己基(包 伸環己基、1,4-伸環己基、環亞己基等 含伸環亞已基)等。 代表例,可舉 式(I)所示之脂 例 以上式(I)所示之脂環式環氧化合物的 下式(1-1)至(1-7)所示之化合物等。上 %式壤氧化合物’例如,也能夠使用Cell〇xide 2〇21p、-9 - 201211094 If the compound (A) and/or the compound (B) (either or both of the compound (a) and the compound (B)) has one or more cyclic skeletons, the free volume in the polymer It is easy to reduce, and it is better to improve the moisture permeability. It is considered that the cyclic skeleton mainly means that the alicyclic cyclic skeleton or the aromatic cyclic skeleton is multiplied by the hydrophobicity of the alicyclic cyclic skeleton and the aromatic cyclic skeleton, and also in the aromatic cyclic skeleton. The π-π stacking effect (layered aromatic ring skeleton) achieves an improvement in moisture permeability. In the case where both the compound (Α) and the compound (Β) have a cyclic skeleton, the respective cyclic skeletons may be the same or different. Further, when the compound (Α) or the compound (Β) has two or more cyclic skeletons, the plurality of cyclic skeletons may be the same or different, 0, a ring, a naphthalene ring, an anthracene ring, an aromatic ring; Specifically, the cyclic skeleton may be exemplified by a monocyclic or polycyclic ring such as a monocyclic ring of a phenanthrene ring or an anthracene ring or a condensed polycyclic ring of a hexane ring, a decahydronaphthalene ring, a norbornane ring or an adamantane ring. Aliphatic ring. Further, in the patent specification of the present invention, the number of the polycyclic ring skeletons which are narrowed by η rings or the like is one by one. The number of cyclic skeletons in the compound (Α)1 molecule is 1 to 3, preferably 1 to 10, further preferably 1 to 6, and 1 to 5, 彳4. The number of the cyclic skeleton in the molecule of the compound (Β) is, for example, 1 to 10, preferably 1 to 6, more preferably 1 to 3 having a benzene ring, a naphthalene ring, or a 'cyclic skeleton. In the case of the compound (Α), the cyclic skeleton is preferably a ring-containing or cyclohexane ring. Further, the compound (Β) contains a benzene ring or a cyclohexane ring. -10-201211094 <Compound (A) &gt; The compound (A) is a compound having two or more reactive functional groups (a) in the i molecule, and is not particularly limited. Specifically, the reactive functional group U) is exemplified by a cationically polymerizable group such as an epoxy group, a glycidyl group or a vinyl ether group; and a (meth)acryl fluorenyl group having a radical polymerizable property. Base. The vinyl ether group also has a case of having a radical polymerization property. The reactive functional group (a) can preferably be a group having a cationic polymerizable group, more preferably an epoxy group, and particularly preferably a cyclopropyl group. The number of the reactive functional groups (a) in the molecule of the compound (A) is, for example, 2 to 30, preferably 2 to 1 , and more preferably 2 to "solid, particularly preferably 2 to 3. A plurality of reactive functional groups (4) are also 戍 = although the molecular weight of the compound (4) is not particularly limited, but it is as heavy as 5 〇, such as 1 Γ, such as 匕 匕 3 and 1 〇 0 to 1 〇〇〇〇〇, It is preferably used in the form of 100. For example, the compound (A) can be exemplified by: (1) The combination of an ion I-combination Lueneng group and an aromatic ring has two or more radical polymerizable functional disks): 1 in a knife (A- 2). 丨 | | Λ | | | , , , , , , 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀 刀There are two or more compounds having an I-bonding functional group and an aliphatic ring (Α_4), etc. The radical has an aromatic ring and two or more cationic polymers (A - Π, you 丨1 soil S) v Oxygen: It can be exemplified by: double-type diepoxypropyl conversion, double-dissolved! - % oxypropyl ether, bisphenol F-type di-p-ethylene oxide propyl ether, tetramethyl": wide a compound having a benzene-11-201211094 ring and two epoxy groups, such as a S-type group and a phenol type-% oxypropyl ether; a naphthalenediol diepoxypropyl ether, a double-pregnant diglycidyl ether a compound having a condensed ring and two epoxy groups, such as biscresol second epoxy propyl ether, bisphenoxyethanol hydrazine diepoxypropyl ether; and having, for example, an alkali novolac type epoxy resin or a cresol novolac a type of epoxy resin, a phenolic epoxy resin containing a bisphenol skeleton, a polyphenyl hydroxypropyl group of a repeating unit containing a naphthyl skeleton, and a benzene ring and/or a condensed ring and the like a compound having more than one epoxy group; a compound having an aromatic ring and two epoxy propyl groups such as F bis(3-ethyl propylene oxide-3-ylmethyl) ether; Shout, double A diethylene ether, bisphenol F divinyl ether, bisphenol F bis (2-vinyl oxyethyl) ether, bisphenol s diethyl ether ether, tetradecyl double expectation divinyl a compound having a benzene ring and two vinyl ether groups such as ether; naphthalenediol divinyl ether, bisphenol quinone divinyl ether, biscresol second vinyl ether, bisphenoxyethanol second a compound having a condensed ring and two vinyl ether groups, such as an alkenyl ether; and such a halide, or a C丨-9 alkyl substituent thereof, etc., in a c! The CI-9 thiol substituent can be exemplified by a mercapto group, an ethyl group, a propyl group, a tributyl group, etc. The halogen in the halide can be exemplified by F, Cl, Br, etc. .. having an aromatic ring and 2 The above radical polymerizable functional group compound (A-2) 'e.g. can be exemplified by: bis(indenyl) acrylate, bisphenol A bis(indenyl) acrylate, bisphenol F di(meth)acrylic acid a compound having a benzene ring and two (fluorenyl) acrylonitrile groups, such as an ester, bisphenol S bis(indenyl) acrylate, tetrakisyl bisphenol di(meth) acrylate, or the like; Acrylate, bisphenol quinone di(indenyl) acrylate, biscresol bismuth (meth) acrylate, bisbenzyl methoxy hydrazine di(meth) acrylate vinegar, etc. -12-201211094 has a condensed ring and a compound of two (fluorenyl) acrylonitrile groups; and such halides, or such Ci_9 alkylate substituents, and the like. The Cw alkyl substituent in the Cu alkyl substituent may be exemplified by methyl, ethyl, propyl or secondary butyl. The halogen in the compound can be exemplified by F, Cl, Br, and the like. The compound (A-3) having an aliphatic ring and two or more cationically polymerizable functional groups can be exemplified by hydrogenated bisphenol octadecyl propyl ether, hydrogenated bisphenol F diglycidyl ether, hydrogenated double Phenol § diglycidyl ether, dicyclohexyl diepoxypropyl ether, bis(3,4-cyclohexylcyclohexyl)fluorenyl, 3,4, _epoxycyclohexyl-3,4-epoxy ring a compound having a cyclohexane ring and two epoxy groups; a compound having a cyclohexane ring and two epoxy propyl groups; and a hydrogenated double-aged A divinyl bond group, hydrogenated double F: ethylene A compound having a cyclohexane ring and two vinyl ethers, such as a base ether, hydrogenated bisphenol S divinyl ether, and dicyclohexyl divinyl ether. , having an aliphatic ring and two or more free i-polymerizable functional groups: (A·4) 'for example, for example: nitriding double... (meth)acrylic acid, chlorinated double-aged F (a) A compound having cyclohexane ketone/two (meth) acrylonitrile groups, such as acryl vinegar, vaporized (iv) acrylate, dicyclohexyl bis(methyl ketone, bismuth) acrylate. Further, the compound (A) is, for example, the following 彳(1) zH〇-Rl)m 化合物 a compound of the formula (1): [in the formula (1), the Z1 system represents from m ̄ ̄~ f 7] r nu\ + Xifu prepared base compound (Z(OH)m) removes the base of the Η Η , , , , , , , LV LV LV LV 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上 上A woman 醯 base. The m-series 2 or more integers of Bu, Ethyl, or (Methyl)-C-B-A A ^ ^ ^ group The above-mentioned z is preferably a basal skeleton having a cyclic structure, and the above-exemplified ones can be exemplified. The 201211094 m-valent polyhydroxy compound Z^OHh can be exemplified by a compound having two benzene rings such as bisphenol, bisphenol A, bisphenol F, bisphenol 8, etc., and these compounds or such C丨- a 9-alkyl substituted compound; a compound having a condensed ring such as naphthalene diol, bisphenol oxime, bisphenol oxime, bisphenoxyethanol oxime or the like, and such a halide or a c alkyl substituent thereof; hydrogenation a compound having two cyclohexane rings, such as bisphenol F, hydrogenated bisphenol S, and dicyclohexyl group; an aromatic ring having three or more stupid rings, such as a cresol novolak or a phenol novolak Compounds and such compounds, or such Cl-9 alkyl substituents, and the like. The cKs hydryl substituent in the C -9 alkyl substituent may, for example, be a methyl group, an ethyl group, a propyl group, a tertiary butyl group or the like. The halogen in the toothing can be exemplified by F, C1, B r and the like. In addition, the compound (A) is, for example, a compound represented by the following formula (1): [In the formula (I), "anthracene means a single bond or a linking group (having one or more original: a divalent group)" The hydrocarbon group, carbonyl group, and ether bond of the valence: &amp; building a reverse acid, *, a guanamine bond, or a plurality of such linked bases]. In the compound of the formula (1), the divalent smog group exemplified as the linking group is a linear or branched chain thiol group having a carbon number of 1 to 18, and a divalent alicyclic hydrocarbon group ( In particular, it is a divalent ring-forming base). A linear or branched chain alkyl group having 1 to 18 carbon atoms, for example, anthracene fluorenyl methylene group, dimethylmethylene group, ethyl group, propyl group, and trimethylene group Base. The divalent alicyclic hydrocarbon group may, for example, be an exocyclopentyl group, a 1,3·cyclopentyl group, a cycloarylene group, a 1&gt;2 cyclohexyl group _14-201211094 valence cyclohexyl group ( Examples include a cyclohexyl group, a 1,4-cyclohexylene group, a cyclohexylene group, and the like, and a ring-containing hexylene group. Representative examples are the compounds represented by the formula (I), and the compounds represented by the following formulas (1-1) to (1-7) of the alicyclic epoxy compound represented by the above formula (I). Upper % soil oxygen compound ' For example, Cell〇xide 2〇21p can also be used,

Celloxide 208 1、Celloxide 8 0 00(Daicel 化學工業股份有 限公司製)等之市售品。還有下式中,n係表示i至3 〇 之整數。若使用此等之脂環式環氧化合物時,也能夠期 待對硬化物之透明性或玻璃轉移溫度提高的影響。Celloxide 208 1. Commercial products such as Celloxide 8 0 00 (made by Daicel Chemical Industry Co., Ltd.). Further, in the following formula, n represents an integer from i to 3 〇. When such an alicyclic epoxy compound is used, the influence on the transparency of the cured product or the increase in the glass transition temperature can also be expected.

(1-3)(1-3)

-15- 201211094 化合物(A)較佳為具有各2個環氧基、環氧丙基、乙 烯基醚基、或(甲基)丙烯醯基、苯環或環己烷環之化合 物具體而5,化合物(A)較佳能夠使用雙酚F二環氧丙 基醚0四甲基雙酚二環氧丙基醚、或雙酚苯氧基乙醇第 二環氧丙基醚等之具有2至4個苯環之二環氧丙基醚; 又酚F(3 -乙基環氧丙烷_3_基曱基)醚等之具有2至4個 苯環之二環氧丙基醚;雙酚F二乙烯基醚等之具有2至 4個苯環之二乙烯基醚;或雙酚?二(曱基)丙烯酸酿等之 具有2至4個苯環之(曱基)丙烯酸酯等。化合物(a)特佳 為具有各2個環氧丙基與苯環之化合物。 本發明之電子紙用低透濕性樹脂組成物中之化合物 (A)之含量例如為5至95wt%,較佳為1〇至9〇wt%,進 :步較佳為20至85wt%。若化合物(A)之含量為如此之 靶圍内,能夠提供一種硬化物,其係使樹脂組成物之塗 布性提高,具有優異之低透濕性、硬度。 〈化合物(B) &gt; 、化合物(B)係在1分子中具有1個反應性官能基(b), 分子5為50至1000〇若化合物(B)之分子量為5〇至1〇〇〇 時,使其硬化之情形下,能夠有效地發現聚合物之側鏈 填塞自由體積的效杲。化合物(B)之分子量較佳為5〇至 5〇〇。化合物(B)係在1分子中例如為具有1個以上,較 =為具有1至4個、進一步較佳為具有2至4個之環狀 月采複數個環狀骨架可以相同或不同。在化合物(B) 之環狀骨架可舉例:以上述化合物(A)例示之物。其中, j佳為苯環、環己烷環。還有,化合物(B)能夠使用單獨 —種或組合二種以上而使用。 -16- 201211094 反應性官能基(b)可舉例以上述反應‘1: 示之物。上述反應性官能基(a)具有陽離子 之情形下,反應性官能基(b)也為陽離子聚 上述反應性官能基(a)為自由基聚合性1 下,反應性官能基(b)也較佳為自由基聚合 應性官能基(a)與反應性官能基(b)的組合 基,同時特佳皆為環氧丙基。 例如,化合物(B)可舉例:具有芳香族 合性官能基之化合物(B-1);具有芳香族環 性官能基之化合物(B-2);具有脂肪族環與 官能基之化合物(B-3);具有脂肪族環與自 能基之化合物(B-4);具有烷基與陽離子聚 化合物(B-5);及具有烷基與自由基聚合性 物(B-6)等。 具有芳香族環與陽離子聚合性官倉I (B -1 ),例如,可舉例:環氧丙基苯基醚、 基醚、二苯基酚環氧丙基醚、三苯基酚環 具有苯環與環氧基之化合物;環氧丙基甲 氧丙基乙基苯基醚、環氧丙基丙基苯基醚 丁基苯基醚、環氧丙基三級丁基苯基醚等 代苯環與環氧基之化合物(例如,具有Cu 與環氧基之化合物);曱基笨基酚環氧丙基 酚環氧丙基醚、丙基苯基酚環氧丙基醚、 環氧丙基醚、三級丁基苯基酚環氧丙基醚 苯基酚環氧丙基醚(例如,C!_9烷基取代苯 t官能基(a)例 聚合性官能基 合性官能基; Γ能基之情形 性官能基。反 较佳皆為環氧 環與陽離子聚 與自由基聚合 陽離子聚合性 由基聚合性官 合性官能基之 官能基之化合 L基之化合物 苯基酚環氧丙 氧丙基醚等之 基苯基醚、環 、環氧丙基正 之具有烷基取 烷基取代苯環 醚、乙基苯基 正丁基苯基酚 等之烷基取代 基酚環氧丙基 -17- 201211094 趟);苄基(R)-(-)-環氧丙基醚 '笨基苄基 之苄基環氧丙基醚化合物;笨基苄基環氧 基環氧丙基醚化合物;苯基乙烯基醚、苯基 笨氧基甲基乙烯基醚、(苯基苯氧基)甲基Z 苯氧基)乙基乙烯基醚、(2-苯基苯氧基)乙 之具有1或2個苯環之乙烯基醚化合物;笨 苯基紛環氧丙烷、苯氧基曱基環氧丙烷、 甲基環氧丙烷、(2-苯氧基)乙基環氧丙烷 基)乙基環氧丙烷等之具有丨或2個苯環之 物及此等之鹵化物等。上述c ^ 9烷基取代 基、乙基、丙基、三級丁基等。 具有芳香族環與自由基聚合性官能 (B-2),例如,可舉例:(曱基)丙烯酸苯酯 酸苯基紛酯、(甲基)丙烯酸苯氧基甲酯、(甲 基苯氧基)曱酯、(甲基)丙烯酸(2-苯氧基) 丙烤酸(2-苯基苯氧基)乙酯等之具有1個〗 (甲基)丙烯醯基之化合物;及此等之鹵化 Cu9炫《基取代基等。在a —烷基取代物之 基可舉例:甲基、乙基、丙基、三級丁基 中之_素可舉例:F、Cl、Br等。 具有脂肪族環與陽離子聚合性官射 (B-3) ’例如’可舉例:環己基環氧丙基醚 氧丙基喊、三環己基環氧丙基醚等之C5_20 基鱗化合物;環己基環氧丙基醚、二環己基 三環己基環氧丙基醚等之C5.2Q環烷基環 物’環己基乙烯基醚、二環己基乙烯基醚 缚基謎等之C5-2〇環烷基乙烯基醚化合物等 環氡丙基醚等 丙基峻等之节 酚乙烯基醚、 二稀基驗、(2_ 基乙稀基醚等 :基環氧丙烷、 (苯基苯氧基) ' (2-苯基笨氧 環氧丙烷化合 基可舉例:甲 L基之化合物 、(曱基)丙烯 基)丙稀酸(苯 乙酯、(曱基) 获2個苯環與 物、或此等之 C 1 . 9炫*基取代 等。在鹵化物 i基之化合物 、二環己基環 環烷基環氧丙 -環氧丙基醚、 氧丙基醚化合 、三環己基乙 -18- 201211094 性官能基之化合物 醆環己酯、(甲基)丙 己略等之(甲基)c5.2( 具有脂肪族環與自由基聚合 (B-4),例如’可舉例:(甲基)丙缔 烯酸二環己酯、(曱基)丙烯酸三環 環烧S旨化合物等。 具有烧基與陽離子聚合性官能基之化合物(B_5),例 如’可舉例:環氧丙基甲基醚、環氧丙基乙基麵、環氧 丙基丙基醚、丁基環氧丙基驗、2_乙基己基環氧丙基醚 等之C,-9烧基環氧丙基醚化合物;甲基環氧丙基趟、乙 基環氧丙基醚、丙基環氧丙基醚、丁基環氧丙基鱗等之 C!_9烷基環氧丙基醚化合物;曱基乙烯基醚、乙美乙稀 基醚、丙基乙烯基醚、丁基乙烯基醚等之C19燒基乙稀 基醚化合物等。 具有烷基與自由基聚合性官能基之化合物,例 如’可舉例:(甲基)丙烯酸甲酯、(曱基)丙烯酸乙酿、(甲 基)丙烯酸丙酯、(甲基)丙烯酸丁酯等之(曱基)丙埽酸c19 炫·酯化合物等。 另外’化合物(B)係例如以下式(2)所示之化合物: Z2- OR2 (2) [式(2)中’ Z2係表示從1價之羥基合物(Z2OH)除去 OH基之基,R2係與前述R1相同]。上述Z2較佳為具有 環狀骨架之基。環狀骨架可舉例:前述例示之物。 經基化合物Z2 〇 Η,例如’可舉例:酴、苯基酴、二 苯基酚、三苯基酚等之具有1至3個苯環之紛類;曱基 酚、乙基酚、丙基酚、正丁基酴、三級丁基酴等之烧基 取代酚(例如’ C〗-9烷基取代酚);曱基苯基紛、乙基苯基 201211094 酚、丙基笨基酚、正丁基苯基酚、三級丁基笨基酚等之 烷基取代笨基酚(例如,C ! _9烷基取代笨基酚). /,T酵、乙 醇、丙醇、丁醇等之烷醇(例如,Cl-9烷醇);苄醇、苯美 节醇等之节醇類;環己醇、二環己醇、三環己醇等之具 有脂肪族環之醇類;及此等之齒化物等。在 ^^工迷 C 1 9烧 基取代基可舉例:甲基、乙基、丙基、三級丁基等。在 鹵化物中之鹵素可舉例:F、C1、B r等。 化合物(B)較佳為環氧基、環氧丙基、乙烯基醚基、 或具有(甲基)丙烯醯基與苯環或環己烷環之化合物。具 體而言,化合物(B)係環氧丙基苯基醚、或鄰笨基酚環氧 丙基醚等之具有1至2個苯環之環氧丙基醚;(甲基j丙 烯酸-2-(苯基笨氧基)乙酯等之具有i至2個苯環之f甲基 丙烯酸酯等。 1 相對於100重量份之該化合物(A),化合物之含 量較佳為1至1000重量份,進一步較佳為至250重 量份。若化合物(B)之含量在於如此之銘 % 、如此I乾圍内時,能夠有-15- 201211094 The compound (A) is preferably a compound having two epoxy groups, a glycidyl group, a vinyl ether group, or a (meth)acrylonitrile group, a benzene ring or a cyclohexane ring, and specifically 5 The compound (A) can preferably be used with bisphenol F diglycidyl ether 0 tetramethyl bisphenol diepoxypropyl ether or bisphenol phenoxyethanol second epoxy propyl ether having 2 to Diphenylepoxy propyl ether having 2 to 4 benzene rings, such as bisphenol epoxy propyl ether of benzene ring; bisphenol, F (3-ethyl propylene oxide _3_ fluorenyl) ether; a divinyl ether having 2 to 4 benzene rings such as F divinyl ether; or bisphenol? A (fluorenyl) acrylate having 2 to 4 benzene rings, such as bis(indenyl)acrylic acid. The compound (a) is particularly preferably a compound having two epoxypropyl groups and a benzene ring. The content of the compound (A) in the low moisture-permeable resin composition for electronic paper of the present invention is, for example, 5 to 95% by weight, preferably 1 to 9 % by weight, more preferably 20 to 85% by weight. When the content of the compound (A) is within such a target range, it is possible to provide a cured product which improves the coating property of the resin composition and has excellent low moisture permeability and hardness. <Compound (B) &gt; The compound (B) has one reactive functional group (b) in one molecule, and 50 to 1000 in molecular molecule 5, and the molecular weight of the compound (B) is from 5 to 1〇〇〇. In the case where it is hardened, the effect of the side chain packing free volume of the polymer can be effectively found. The molecular weight of the compound (B) is preferably from 5 Å to 5 Å. The compound (B) has, for example, one or more in one molecule, and has a ring shape of 1 to 4, and more preferably 2 to 4 in a single molecule. The plurality of cyclic skeletons may be the same or different. The cyclic skeleton of the compound (B) can be exemplified by the above compound (A). Among them, j is preferably a benzene ring or a cyclohexane ring. Further, the compound (B) can be used singly or in combination of two or more. -16- 201211094 The reactive functional group (b) can be exemplified by the above reaction '1: shown. When the reactive functional group (a) has a cation, the reactive functional group (b) is also cationically polymerized. The reactive functional group (a) is a radical polymerizable property 1, and the reactive functional group (b) is also It is preferably a combination of a radical polymerizable functional group (a) and a reactive functional group (b), and particularly preferably a glycidyl group. For example, the compound (B) can be exemplified by a compound (B-1) having an aromatic functional group; a compound (B-2) having an aromatic cyclic functional group; and a compound having an aliphatic ring and a functional group (B) -3); a compound having an aliphatic ring and an energy group (B-4); having an alkyl group and a cationic poly compound (B-5); and having an alkyl group and a radical polymerizable substance (B-6). The aromatic ring and the cationically polymerizable official compartment I (B -1 ), for example, may be exemplified by epoxy phenyl ether, alkyl ether, diphenyl phenol epoxy propyl ether, and triphenyl phenol ring having benzene. a compound of a ring and an epoxy group; an epoxy propyl methoxypropyl ethyl phenyl ether, a glycidyl propyl phenyl ether butyl phenyl ether, a glycidyl propyl tertiary phenyl ether, and the like a compound of a benzene ring and an epoxy group (for example, a compound having Cu and an epoxy group); a mercapto-based phenol propyl acrylate epoxy propyl ether, a propyl phenyl phenol epoxy propyl ether, an epoxy a propyl ether, a tertiary butyl phenol phenol propyl propyl phenol phenol propyl propyl ether (for example, a C! -9 alkyl substituted benzene t functional group (a) exemplified polymerizable functional group functional group; a functional functional group of a fluorenyl group. The reverse is preferably a compound of a epoxide group which is an epoxy ring and a cationically polymerized and radically polymerized cationically polymerizable functional group based on a functional group of a polymerizable functional group. a phenyl ether such as propoxypropyl ether, a ring, or a propylene group having an alkyl group, an alkyl group-substituted benzene ring ether, an ethyl phenyl n-butyl phenyl phenol, or the like Alkyl-substituted phenol epoxypropyl-17- 201211094 趟); benzyl (R)-(-)-epoxypropyl ether benzylidene benzyl epoxide propyl propyl ether compound; Epoxy-epoxy propyl ether compound; phenyl vinyl ether, phenyl phenoxymethyl vinyl ether, (phenylphenoxy) methyl Z phenoxy) ethyl vinyl ether, (2 -Phenylphenoxy)divinyl ether compound having 1 or 2 benzene rings; stupid phenyl propylene oxide, phenoxy decyl propylene oxide, methyl propylene oxide, (2-phenoxy) A compound having hydrazine or two benzene rings, such as ethyl epoxide oxide) ethyl propylene oxide, and the like, and the like. The above c ^ 9 alkyl substituent, ethyl, propyl, tert-butyl or the like. The aromatic ring and the radical polymerizable functional group (B-2), for example, may be exemplified by (phenyl) phenyl phenyl acrylate, phenoxymethyl (meth) acrylate, (methyl phenoxy) a compound having one (meth)acryl fluorenyl group such as an oxime ester or (2-phenoxy)propanol (2-phenylphenoxy)ethyl ester; and the like Halogenated Cu9 Hyun "based substituents and the like. The base of the a-alkyl substituent may, for example, be a methyl group, an ethyl group, a propyl group or a tertiary butyl group, and examples thereof include F, Cl, Br and the like. An aliphatic ring and a cationically polymerizable (B-3) 'for example' may be exemplified by a C5_20 squaring compound such as cyclohexylepoxypropyloxypropyl propyl hydride or tricyclohexyl epoxypropyl ether; cyclohexyl group; C5-2 anthracene ring of C5.2Q cycloalkyl ring compound such as epoxidized propyl ether or dicyclohexyltricyclohexyl epoxypropyl ether, cyclohexyl vinyl ether or dicyclohexyl vinyl ether a phenolic vinyl ether such as a cyclopropyl propyl ether such as an alkyl vinyl ether compound, or a dilute base test, (2-ethylidene ether, etc.: propylene oxide, (phenylphenoxy) '(2-Phenyloxy propylene oxide compound can be exemplified by a compound of a methyl group L, a (fluorenyl) propylene group) acrylic acid (phenethyl ester, (fluorenyl), 2 benzene rings, or Such a C 1 .9 * * group substitution, etc. in the halide i-based compound, dicyclohexylcyclocycloalkyl epoxide-epoxypropyl ether, oxypropyl ether compound, tricyclohexylethyl-18 - 201211094 The functional group of the compound 醆cyclohexyl ester, (meth) propylene, etc. (methyl) c5.2 (having an aliphatic ring and a radical polymerization (B-4), for example ' Examples: (meth) propionate dicyclohexyl ester, (mercapto)acrylic acid tricyclic ring-burning S compound, etc. Compound (B_5) having a burnt group and a cationically polymerizable functional group, for example, 'exemplification: ring C, -9 alkyl ring of oxypropyl methyl ether, epoxy propyl ethyl face, glycidyl propyl ether, butyl epoxy propyl test, 2-ethylhexyl epoxypropyl ether Oxypropyl propyl ether compound; methyl epoxypropyl hydrazine, ethyl epoxidized propyl ether, propyl epoxidized propyl ether, butyl epoxy propyl scale, etc. C! _ alkyl alkyl propyl ether compound a C19 alkyl ether compound such as mercapto vinyl ether, ethylene glycol ether, propyl vinyl ether or butyl vinyl ether, etc. a compound having an alkyl group and a radical polymerizable functional group, For example, 'exemplified by: (meth) methacrylate, (mercapto) acrylic acid, propyl (meth) acrylate, butyl (meth) acrylate, etc. Further, 'compound (B) is a compound represented by the following formula (2): Z2-OR2 (2) [In the formula (2), the Z2 system represents a hydroxyl group derived from a monovalent group. (Z2OH) The group of the OH group is removed, and the R2 is the same as the above R1. The Z2 is preferably a group having a cyclic skeleton. The cyclic skeleton may, for example, be the one exemplified above. The base compound Z2 〇Η, for example, For example: hydrazine, phenyl hydrazine, diphenyl phenol, triphenyl phenol, etc. having 1 to 3 benzene rings; nonylphenol, ethyl phenol, propyl phenol, n-butyl fluorene, tertiary butyl Substituted phenols (eg, 'C -9 alkyl substituted phenols); mercapto phenyl, ethyl phenyl 201211094 phenol, propyl streptophenol, n-butyl phenyl phenol, tertiary butyl An alkyl group substituted with a streptophenol or the like (for example, a C? -9 alkyl substituted streptophenol). An alcohol such as T-fermentation, ethanol, propanol or butanol (for example, a Cl-9 alkanol) An alcohol having an aliphatic ring such as benzyl alcohol or phenylhydrin; a alcohol having an aliphatic ring such as cyclohexanol, dicyclohexanol or tricyclohexanol; and a tooth such as these. The substituent of the C 1 9 alkyl group can be exemplified by a methyl group, an ethyl group, a propyl group, a tertiary butyl group or the like. The halogen in the halide can be exemplified by F, C1, Br and the like. The compound (B) is preferably an epoxy group, a glycidyl group, a vinyl ether group, or a compound having a (meth)acryl fluorenyl group and a benzene ring or a cyclohexane ring. Specifically, the compound (B) is a glycidyl phenyl ether or an epoxy propyl ether having 1 to 2 benzene rings, such as o-phenylphenol epoxypropyl ether; (methyl j-acrylic acid-2) - phenyl methacrylate having i to 2 benzene rings, etc., such as (phenylphenyloxy)ethyl ester, etc. 1 The compound is preferably contained in an amount of 1 to 1000 by weight based on 100 parts by weight of the compound (A). Further, it is preferably preferably 250 parts by weight. If the content of the compound (B) is such that it is so in the range of

效地填塞聚合物(硬化物)之自由* M 曰田二間(自由體積),故能夠 獲得低透濕性更優異的聚合物。 化合物(A)與化合物(b)之鲂 v J &lt;钗佳的組合,例如,可舉 例:化合物(A)具有2個環狀骨牟 月木、化合物(B)具有1個 環狀骨架的組合;化合物(A)具有9彳田Α ★ 胥2個裱狀骨架、化合物 (Β)具有2個環狀骨架的組合;彳卜人 化合物(Α)具有5個環狀 骨架、化合物(Β)具有1個環狀骨趣从。人 么队月系的組合;及化合物 具有5個環狀骨架、化合物(Bn 士 Λ β 具有2個環狀骨架的組 合。藉由作成如此的組合,可以從。 , J以獲得賦予具優越之更低 -20- 201211094 透濕性之硬化物的電子裝置用低透濕性樹脂組成物。認 為於如此組合中,因而更為有效地進行硬化物中之自由 體積的填塞。 尤其’於本發明之電子裝置用低透濕性樹脂組成物 中二在有效地使硬化物之透濕性降低之觀點,相對於1〇〇 重量份之化合物(A),化合物(A)具有2個環狀骨架、化 口 : (B)具有1個環狀骨架的組合之情形的化合物⑻之 合ΐ並未予以特別限定,較佳為i至25〇重量份,更佳 為10至200重量份’進一步較佳為2〇至15〇重量份, 特佳為25至1〇〇重量份。 另外’於本發明之電子裝置用低透濕性樹脂組成物 ,化合物(A)具有2個環狀骨架、化合物(B)具有2個 壤狀f架的組合之情形的化合物(B)之含量並未予以特 别限疋’但在有效地使硬化物之透濕性降低之觀點相 =00重量份之化合物㈧’較佳為…5。重量份, 、為1〇至250重量份,進-步較佳為20至2〇〇重量 伤’特佳為3 0至15 〇重量份。 化合物(A)與化合物(B)之較佳的組合,具體而言, :舉例.雙酚F二環氧丙基醚與環氧丙基苯基醚之組 : '雙酚F二環氧丙基醚與鄰苯基酚環氧丙基醚的組合 /組合雙酉分F ^環氧丙基喊與環、氧丙基苯基喊之情 形,相對於100重量份之作為化合物(A)之雙酚F二環氧 土蜒作為化合物(B)之環氧丙基苯基醚之含量特佳為 … 里伤另外,雙酌'F二環氧丙基喊與鄰笨基g分 …基越的組合之情形’相對於1〇〇重量份之作為化 -21 - 201211094 合物(A)之雙酚F二環氧丙基醚,作為化合物(B)之鄰苯 基紛環氧丙基醚之含量特佳為1至25〇重量份。 〈聚合物起始劑(c) &gt; 於本發明之電子紙低透濕性樹脂組成物中,含有聚 合物起始劑(C)。聚合物起始劑(C)並未予以特別限定, 能夠使用習知慣用之聚合起始劑,較佳能夠使用光或熱 陽離子聚合起始劑、或是光或熱自由基聚合起始劑。聚 合起始劑能夠使用單獨一種’或是能夠組合二種以上而 使用。 &lt;光陽離子聚合起始劑&gt; 例如’光1¾離子聚合起始劑能夠使用C y r a c u r e UVI-6970、Cyracure UVI-6974、Cyracure UVI-6990、 Cyracure UVI-950(以上,美國 Union Carbide 公司製、商 品名);Irgacure 250、Irgacure 261、Irgacure 264(Ciba Specialty Chemicals 公司製、商品名);SP-150、SP-1 51、 SP-170、Optomer SP-1 7 1(以下,旭電化工業股份有限公 司製、商品名);CG-24-61(Ciba Specialty Chemicals 公 司製、商品名);DAICATII(Daicel化學工業股份有限公 司製、商品名);UVAC1590、UVAC1591(Daicel Cytec 公司製、商品名);CI-2064、CI-2639、CI-2624、CI-248 1、 CI-2734、CI-2855、CI-2823、CI-2758、CIT-1682(以上, 曰本曹達股份有限公司製品、商品名);PI-2074(Rhodia 公司製、商品名、五氟苯基硼酸鹽甲苯醯對異丙基苄錤 鹽);FFC5 09(3M 公司製品、商品名);BBI-102、BBI-101、 BBI-103、MPI-103、TPS-103、MDS-103、DTS-103、 -22- 201211094 NAT-1 03、NDS-103 (Midori化學股份有限公司製、商品 名);CD-1010、CD-1011、CD-1012(美國、Sartomer 公 司製、商品名);CPI-100P、CPI-101 A(Sun Apro 股份有 限公司製、商品名)等之市售品所代表之二重氮鏽鹽、鐫 鹽、鎏鹽、鎸鹽、硒鹽、鲜鹽、銨鹽等。 &lt;熱陽離子聚合起始劑&gt; 例如,熱陽離子聚合起始劑能夠使用San Aid SI-45 ' San Aid SI-47 ' San Aid SI-60 ' San Aid SI-60L 'Effectively packing the free *M 曰田 (free volume) of the polymer (hardened material), it is possible to obtain a polymer with better low moisture permeability. The combination of the compound (A) and the compound (b), and preferably, the compound (A) has two cyclic skeletons, and the compound (B) has one cyclic skeleton; The compound (A) has 9 彳田Α ★ 胥 2 裱-like skeletons, and the compound (Β) has a combination of two cyclic skeletons; the 彳 human compound (Α) has 5 cyclic skeletons, and the compound (Β) has 1 A ring of bones is interesting. The combination of the human team and the moon; and the compound has five cyclic skeletons and a compound (Bn glyph β has a combination of two cyclic skeletons. By making such a combination, it is possible to obtain a superiority from J. Lower-20-201211094 A low moisture permeability resin composition for electronic devices of a moisture permeable cured product. It is considered that in such a combination, the free volume of the hardened material is more effectively filled. In the low moisture permeability resin composition for an electronic device, the compound (A) has two cyclic skeletons with respect to 1 part by weight of the compound (A) from the viewpoint of effectively lowering the moisture permeability of the cured product. (B) The compound of the compound (8) having a combination of one cyclic skeleton is not particularly limited, and is preferably from i to 25 parts by weight, more preferably from 10 to 200 parts by weight. It is preferably from 2 to 15 parts by weight, particularly preferably from 25 to 1 part by weight. In addition, in the low moisture permeability resin composition for an electronic device of the present invention, the compound (A) has two cyclic skeletons and compounds. (B) The combination of two soil f frames The content of the compound (B) is not particularly limited, but in view of effectively reducing the moisture permeability of the cured product, 00 parts by weight of the compound (VIII) is preferably ... 5 parts by weight, and 1 part by weight. 〇 to 250 parts by weight, preferably 20 to 2 Torr, and particularly preferably 30 to 15 parts by weight. A preferred combination of the compound (A) and the compound (B), specifically, : Example. Group of bisphenol F diglycidyl ether and epoxy propyl phenyl ether: 'combination/combination of bisphenol F diglycidyl ether with o-phenylphenol epoxidopropyl ether F ^Ethoxypropyl group and ring, oxypropyl phenyl group, in the case of 100 parts by weight of the bisphenol F diepoxide as the compound (A) as the epoxy propylbenzene of the compound (B) The content of the ether is particularly good for... In addition, the combination of 'F diepoxypropyl group and the o-stupyl group g... the combination of the base of the case' relative to 1 part by weight of the act-21 - 201211094 The bisphenol F diglycidyl ether of the compound (A) is particularly preferably used in an amount of from 1 to 25 parts by weight as the ortho-phenyl epoxide propyl ether of the compound (B). c) &gt; The electronic paper low moisture permeable resin composition of the invention contains a polymer initiator (C). The polymer initiator (C) is not particularly limited, and a conventional polymerization initiator can be preferably used. A photo or thermal cationic polymerization initiator or a photo or thermal radical polymerization initiator can be used. The polymerization initiator can be used alone or in combination of two or more. <Photocationic polymerization initiator &gt; For example, 'light cation polymerization initiator can use Cyracure UVI-6970, Cyracure UVI-6974, Cyracure UVI-6990, Cyracure UVI-950 (above, manufactured by Union Carbide, USA); Irgacure 250, Irgacure 261, Irgacure 264 (manufactured by Ciba Specialty Chemicals Co., Ltd., trade name); SP-150, SP-1 51, SP-170, Optomer SP-1 7 1 (hereinafter, manufactured by Asahi Kasei Kogyo Co., Ltd., trade name); CG -24-61 (manufactured by Ciba Specialty Chemicals Co., Ltd., trade name); DAICATII (manufactured by Daicel Chemical Industry Co., Ltd., trade name); UVAC 1590, UVAC 1591 (manufactured by Daicel Cytec Co., Ltd., trade name); CI-2064, CI-2 639, CI-2624, CI-248 1, CI-2734, CI-2855, CI-2823, CI-2758, CIT-1682 (above, Sakamoto Soda Co., Ltd. products, trade names); PI-2074 (Rhodia Company, trade name, pentafluorophenyl borate toluene oxime isopropyl benzyl hydrazine salt; FFC5 09 (3M company products, trade names); BBI-102, BBI-101, BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, -22- 201211094 NAT-1 03, NDS-103 (Midori Chemical Co., Ltd., trade name); CD-1010, CD-1011, CD-1012 (USA, Sodium rust salt, strontium salt, strontium salt, strontium salt, etc. represented by commercially available products such as CPI-100P and CPI-101 A (manufactured by Sun Apro Co., Ltd., trade name) Selenium salt, fresh salt, ammonium salt, etc. &lt;Thermal cationic polymerization initiator&gt; For example, the thermal cationic polymerization initiator can use San Aid SI-45 'San Aid SI-47 ' San Aid SI-60 ' San Aid SI-60L '

San Aid SI-80、San Aid SI-80L、San Aid SI-100、San Aid SI-100L、San Aid SI-110L、San Aid SI-145、San Aid SI-150、San Aid SI-160、San Aid SI-170L、San Aid SI-180L(以上,三新化學工業股份有限公司製品、商品 名)’ CI-2921、CI-2920、CI-2946、CI-3128、CI-2624、 CI-263 9、CI-2〇64(以上,日本曹達股份有限公司製品、 商品名)、PP-33、CP-66、CP-77(旭電化工業公司製品、 商品名)、FC-509、FC-520(3M公司製品、商品名)等所 代表之二重氮鑌鹽、鎭鹽、鎏鹽、鱗鹽、硒鹽、銲鹽、 銨鹽等。還有’也可以與鋁或鈦等之金屬與乙醯乙酸或 是二酮類之螯合物與三笨基矽烷醇等之矽烷醇的化合 物,或是鋁或鈦等之金屬與乙醯乙酸或是二酮類之螯合 物與雙酚S等之酚類的化合物。 0.05 例如,相對於100重量份之在電子裝置用低透渴性 樹脂組成物中所含之化合物(A)與化合物(b)的全部聚a 性化合物’光或熱陽離子聚合起始劑之用量例如約二i 至15重罝份,較佳為〇 〇1至12重量份,特佳為 -23- 201211094 至10重量份,最好為〇」至10重量份左右。藉由於此 範圍内使用而能夠獲得具優越之低透濕性的硬化物。 &lt;硬化加速劑&gt; 本發明之電子裝置用低透濕性樹脂組成物係於藉光 或熱陽離子聚合起始劑而硬化聚合性化合物之際,也可 以含有具有加速硬化速度之機能的硬化加速劑。能夠使 用習知慣用之硬化加速劑做為硬化加速劑,例如,可舉 例:1,8-二。丫雙環[5·4 0]_7_十一烯(DBU)、及其鹽(例如, 紛鹽、辛酸鹽、對曱苯續酸鹽、曱酸鹽、四苯基爛酸鹽); 1,5-二外雙環[4·3.〇]-5-壬烯(DBN)及其鹽(例如,鐫鹽、San Aid SI-80, San Aid SI-80L, San Aid SI-100, San Aid SI-100L, San Aid SI-110L, San Aid SI-145, San Aid SI-150, San Aid SI-160, San Aid SI-170L, San Aid SI-180L (above, Sanshin Chemical Industry Co., Ltd. products, trade name) ' CI-2921, CI-2920, CI-2946, CI-3128, CI-2624, CI-263 9. CI-2〇64 (above, Japan Soda Co., Ltd. product, trade name), PP-33, CP-66, CP-77 (Asahi Chemical Industry Co., Ltd. product, trade name), FC-509, FC-520 (3M The company's products, trade names, etc. represent the diazo sulfonium salts, strontium salts, strontium salts, scale salts, selenium salts, solder salts, ammonium salts, and the like. There is also a compound which can also be used with a metal such as aluminum or titanium, a chelate compound of acetonitrile or a diketone, a decyl alcohol such as trisyl decyl alcohol, or a metal such as aluminum or titanium and acetonitrile. It is a compound of a ketone of a diketone and a phenol of a bisphenol S or the like. 0.05. For example, the amount of the total polya compound 'light or thermal cationic polymerization initiator' of the compound (A) and the compound (b) contained in the low-transparent resin composition for electronic devices is 100 parts by weight. For example, about two to fifteen parts by weight, preferably from 1 to 12 parts by weight, particularly preferably from -23 to 201211094 to 10 parts by weight, preferably from about 〇 to about 10 parts by weight. By using it in this range, it is possible to obtain a cured product having superior low moisture permeability. &lt;hardening accelerator&gt; The low moisture permeability resin composition for an electronic device of the present invention may be hardened by a function of accelerating hardening speed when the polymerizable compound is cured by a light or thermal cationic polymerization initiator. Accelerator. A hardening accelerator which is conventionally used can be used as the hardening accelerator, and for example, 1,8-two can be exemplified.丫bicyclo[5·4 0]_7_undecene (DBU), and salts thereof (for example, salt, octanoate, p-benzoate, citrate, tetraphenyl sulphonate); 5-di-bicyclo[4.3.〇]-5-pinene (DBN) and its salts (eg, sulfonium salts,

婆鹽、4級錢鹽、鐫鹽);苄基二曱基胺、2,4,6_三(二甲 胺基曱基)齡、Ν,Ν-二曱基環己基胺等之3級胺;2_乙基 -4-曱基啼唾、1_氰乙基-2_乙基_4_甲基咪唑等之咪唑;磷 酸醋、三苯基膦等之膦類;四苯基鳞四(對曱苯基)硼酸 鹽等之鱗化合物;辛酸錫、辛酸辞等之有機金屬鹽;金 屬整合物等。此等能夠單獨使用或混合二種以上而使用。 另外’硬化加速劑也能夠使用U-CAT SA 506、U-CAT SA 102、U-CAT 5003、U-CAT 18X、12XD(開發品)(任一 種皆為Sun Apro股份有限公司製);τρρ-κ、TPP-MK(任 一種皆為北興化學工業股份有限公司製);ρχ_4ΕΤ(曰本 化學工業股份有限公司製)等之市售品。 例如’相對於丨〇〇重量份之在電子裝置用低透濕性 树月曰組成物中所含之全部聚合性化合物,硬化加速劑之 用ΐ:例如為0_05至5重量份,較佳為〇丨至3重量份, 特佳為0.2至3重量份,最好為〇 25至2 5重量份左右。 -24- 201211094 4 ‘ 逮劑之用量低於〇. 〇 5重量份時,有硬化加速效 果變得不充公々丨主, 刀之,U形;另一方面,若硬化加速劑之用量 超過5畲I + , 里知時,有硬化物將著色而色調將變差之情形。 &lt;光自由基聚合起始劑〉 J 士 光自由基聚合起始劑可舉例:二笨曱酮、苯 丙3篮笨^、牟甘 卞|二甲基酮、苯偶因、苯偶因甲基醚、苯偶 因乙基醚、苯偶因異丙基醚、二曱氧基苯基笨乙酮、二 基苯基苯乙酮、二乙氧基苯乙_、二苯基二硫醚、 p笨曱醯文息香酸甲酯、4 _二曱胺基安息香酸乙酯(日本 化藥舨伤有限公司製Kayacure EPA等)、2,4-二乙基氧硫 °山11星(曰本化藥股份有限公司製Kayacure DETX等)、2-甲基1 [4-(甲基)笨基]_2咮琳基丙酮— yciba 股份 $限公司製Irgacure 907等)、2_二甲胺基_2 (4咪啉基) 笨曱醯-1-笨基丙烷等之2_胺基_2_苯曱醯_丨_笨基烷化合 物,四(二級丁過氧羰基)二苯曱酮、二苯曱醯、2-羥基-2-甲基-1-苯基-丙烷_丨_酮、4,4_雙二乙胺基二苯曱酮等之胺 基苯衍生物;2,2,-雙(2·氯苯基)_4,5,4,,5,_四苯基qj,· 聯咪唑(保土谷化學股份有限公司製B_CIM等)等之咪唑 化合物;2,6-雙(三氣曱基)_4_(4_甲氧基萘· 三畊等之_曱基化三听化合物;2_三氣曱基·5_(2苯并呋 喃-2-基-乙烯基)噚二唑合物等之鹵曱基嘮二唑化 合物等。此等之光自由基聚合起始劑能夠單獨使用,或 混合二種以上而使用。另外,必要時能夠添加光增感劑。 從感度及耐藥品性等之觀點,光自由基聚合起始劑較佳 為咪唑化合物與胺基苯衍生物之組合、2_胺基_2_苯曱醯 -25- 201211094 -i-苯基烷化合物、鹵 化合物等。 甲基化二听合物、_甲基化噚二唑 &lt;熱自由基聚合起始劑〉 例如熱自由基聚合起始劑可舉例.右媳g ^ &amp; 類。有機過氧化物類能夠使用氡=過氧化物 _ 迥氧化物、酮過氧化物、過氧化酯#。右 機過氧化物之且俨彻n 、虱化S日尊。有 過軋-2-乙基己酯、2 —級丁 化己ρ _ , 一 土·,5_二(2_乙基己醯基)過氧 :氧:显 基過氧苯甲酸醋、過氧化三級丁基、氣 k氧化異丙本、氫過《化-好 基)、2 5-二甲装 氧化―一丙本基、二(過氧化三級丁 2 4 _ i +Γ 土 _2,5·二(過氧化三級丁基)己烷、過氧化 雔(,两气几 一(過軋化二級丁基)異丙基苯、 =過氧化三級丁基)-3,3,…基環己院、過氧化甲基乙 土 .、丨,1,3,3·過氧化四甲基丁基-2-乙基己酸酯等。 $還有,與上述熱自由基聚合起始劑一起,也能夠併 用環烷酸鈷、環烷酸錳、環烷酸鋅、辛烯酸鈷等之環烷 S夂或辛烯酸之鈷、錳、錯、鋅、鈀等之金屬鹽。同樣地, 也能夠使用二甲基苯胺等之3級胺。 光或熱自由基聚合起始劑可以使用單獨一種,也可 以任意之比例混合二種以上而使用。相對力ι〇〇重量份 之樹脂組成物,通常其用量例如為〇」重量份至5重量 份’較佳為0 _ 5重量份至4重量份。 〈無機填料(D)&gt; 本發明之電子裝置用低透濕性樹脂組成物也可以進 —步含有無機填料(D)。無機填料(D)並未予以特別限 -26- 201211094 定’可舉例匕氧化石夕、氧化紹、雲母、合成雲母、滑 石、氧化妈、碳酸妈、氧化錯、氧化欽、欽酸鎖、高^ 土、膨土、矽藻土、氮化硼、氮化鋁、碳化矽、氧化鋅\ 氧化鈽、氧化鉋、氧化鎂、玻璃珠、玻璃纖維、石墨、 虱氧化舞、氫氧化鎂 '氫氧化銘、纖維素等。無機填料 (D)能夠使用單獨一種,也能夠組合二種以上而使用 此等之無機填料(D)能夠利用例如國際公開專利第 96/3 1 572號所記載之火焰水解法或火焰熱分解法、電激 法等之習知方法而製造。較佳的無機填料⑼能夠使用經 ^定化的膠體狀無機粒子之奈米分散溶膠類等,市售品 忐夠購自BAYER公司製之矽膠、G〇ldschmidt公司製之 ㈣2溶膠類、MERCK公司製之Ti〇2溶膠類、购則婆 盐 salt, 4 grade money salt, strontium salt); benzyl dimercaptoamine, 2,4,6-tris(dimethylamino fluorenyl) age, hydrazine, fluorenyl-didecylcyclohexylamine, etc. An amine; an imidazole such as 2-ethyl-4-mercaptopurine, 1-cyanoethyl-2-ethyl-4-methylimidazole; a phosphine such as phosphoric acid vinegar or triphenylphosphine; tetraphenyl scale a scaly compound such as tetrakis(p-phenyl)borate; an organic metal salt such as tin octylate or octanoic acid; a metal integrator or the like. These can be used alone or in combination of two or more. In addition, 'hardening accelerators can also use U-CAT SA 506, U-CAT SA 102, U-CAT 5003, U-CAT 18X, 12XD (developed products) (any one is made by Sun Apro Co., Ltd.); τρρ- κ, TPP-MK (any one is manufactured by Kitakatsu Chemical Industry Co., Ltd.); commercially available products such as χ χ ΕΤ ΕΤ ΕΤ 制 。 。 。 。 。 。 。 。 。 。 For example, 'all of the polymerizable compounds contained in the low moisture permeability tree sap composition for electronic devices relative to the 丨〇〇 part by weight, 硬化 for the accelerator; for example, 0 to 05 parts by weight, preferably It is preferably from 0.2 to 3 parts by weight, more preferably from about 25 to 25 parts by weight, based on 3 parts by weight. -24- 201211094 4 ' The amount of the agent is less than 〇. 〇 5 parts by weight, the hardening acceleration effect becomes unsatisfactory, the knife, the U shape; on the other hand, if the amount of the hardening accelerator exceeds 5 When 畲I + , I know, there is a case where the hardened material will be colored and the color tone will be deteriorated. &lt;Photoradical polymerization initiator> J. Photo-radical polymerization initiator can be exemplified by dicuminone, phenylpropanoid 3 baskets, 牟 卞 卞 dimethyl ketone, benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, dimethoxy phenyl acetophenone, diphenyl phenyl acetophenone, diethoxy phenyl ethane, diphenyl disulfide Ether, p abbreviated methyl benzoate, ethyl 4-diamine benzoate (Kayacure EPA, manufactured by Nippon Kasaku Co., Ltd.), 2,4-diethyloxysulfate (Kayacure DETX, manufactured by Sakamoto Chemical Co., Ltd.), 2-methyl 1 [4-(methyl) phenyl] 咮 基 基 丙酮 — y y y I I I I I I I I I I I I I I I I I I I I I I I I Amino-2 (4 morpholinyl) alkaloid-1-phenylpropane, etc. 2-amino-2 benzoquinone-indole-alkyl compound, tetrakis(di-butylperoxycarbonyl)diphenyl An aminobenzene derivative such as anthrone, diphenyl hydrazine, 2-hydroxy-2-methyl-1-phenyl-propane fluorenyl ketone or 4,4-diethylaminodibenzophenone; , 2,-bis(2·chlorophenyl)_4,5,4,,5,_tetraphenyl qj, ·biimidazole Imidazole compound such as B_CIM, etc.; 2,6-bis(trimethylsulfonyl)_4_(4-methoxynaphthalene, tri-farming, etc. 曱 化 三 三 三 listening compound; 2_三气曱基·5_ a halogenated oxadiazole compound such as (2 benzofuran-2-yl-vinyl) oxadiazole compound, etc. These photoradical polymerization initiators can be used singly or in combination of two or more. Further, a photo sensitizer can be added as necessary. From the viewpoints of sensitivity, chemical resistance, etc., the photoradical polymerization initiator is preferably a combination of an imidazole compound and an aminobenzene derivative, and 2-amino group_2_ Phenylhydrazine-25- 201211094 -i-phenylalkane compound, halogen compound, etc. Methylated di-hinder, _methylated oxadiazole &lt;thermal radical polymerization initiator> For example, thermal radical polymerization The starting agent can be exemplified by the right 媳g ^ &amp; class. The organic peroxide can use 氡 = peroxide 迥 迥 oxide, ketone peroxide, peroxyester #.虱化S日尊. There have been rolling 2-ethylhexyl ester, 2-tert-butylation ρ _ , a soil ·, 5 bis (2-ethylhexyl) peroxy: oxygen: ankyl Peroxybenzoic acid Acid vinegar, tertiary butyl peroxide, gas oxidized isopropyl, hydrogen over "chemical-good", 2 5- dimethyl oxidized - one propyl base, two (peroxidized tertiary butyl 2 4 _ i +Γ土_2,5·2 (tributylbutyl peroxide) hexane, ruthenium peroxide (two gas (one over-rolled secondary butyl) cumene, = tertiary butyl peroxide) )-3,3,...Base ring home, methyl ethyl peroxide, hydrazine, 1,3,3, tetramethylbutyl-2-ethylhexanoate peroxide, and the like. Further, together with the above-mentioned thermal radical polymerization initiator, it is also possible to use a combination of a naphthenic sulfonium or a octenoic acid such as cobalt naphthenate, manganese naphthenate, zinc naphthenate or cobalt octylate. a metal salt of manganese, wrong, zinc, palladium or the like. Similarly, a tertiary amine such as dimethylaniline can also be used. The light or thermal radical polymerization initiator may be used singly or in combination of two or more kinds in any ratio. The resin composition is usually used in an amount of, for example, from 5% by weight to 5 parts by weight, preferably from 0 to 5 parts by weight to 4 parts by weight. <Inorganic filler (D)&gt; The low moisture permeable resin composition for an electronic device of the present invention may further contain an inorganic filler (D). Inorganic filler (D) is not specifically limited -26- 201211094 定' can be exemplified by oxidized stone sulphate, oxidized sulphate, mica, synthetic mica, talc, oxidized mother, carbonic acid mother, oxidized error, oxidized chin, acidified lock, high ^ Soil, bentonite, diatomaceous earth, boron nitride, aluminum nitride, tantalum carbide, zinc oxide, cerium oxide, oxidized planer, magnesia, glass beads, glass fiber, graphite, cerium oxide dance, magnesium hydroxide 'hydrogen Oxidation, cellulose, etc. The inorganic filler (D) can be used alone or in combination of two or more kinds. The inorganic filler (D) can be used, for example, by the flame hydrolysis method or the flame thermal decomposition method described in International Patent Publication No. 96/3 1 572. It is manufactured by a known method such as an electric shock method. A preferred inorganic filler (9) can be a nano-dispersed sol of colloidal inorganic particles, and a commercially available product is commercially available from BAYER Co., Ltd., G〇ldschmidt Co., Ltd. (4) 2 Sol, MERCK Ti〇2 sols, purchase

Chenucals公司製之Si〇2、Zr〇2、Al2〇3及§卜〇3溶膠或 EGUSSA公司製之Aerosil分散物類等之市售品。 —無機填料(D)能夠藉由表面之改質而使此等之黏度 ^為改變。粒子之表面改質能夠使用習知之表面改質 劑。例如,如此之表面改質劑能夠使用與存在於無機填 料(D)之表面的官能基能夠形成共價鍵或錯合物等之相 互作用的化合物、或能夠與聚合物陣列相互作用的化合 物。例如,如此之表面改質劑能夠使用分子内具有羧基、 (第1級、第2級、第3級)胺基、4級銨基、羰基、環氧 丙基、乙烯基、(甲基)丙烯醯氧基、酼基等之官能基的 化合物等。如此之表面改質劑,通常在標準溫度及壓力Commercial products such as Si〇2, Zr〇2, Al2〇3, and §Bu 3 Sol, manufactured by Chenucals Co., Ltd., or Aerosil dispersions manufactured by EGUSSA. - The inorganic filler (D) can be modified by the modification of the surface. The surface modification of the particles can use conventional surface modifiers. For example, such a surface modifying agent can use a compound which can interact with a functional group present on the surface of the inorganic filler (D) to form a covalent bond or a complex or the like, or a compound capable of interacting with the polymer array. For example, such a surface modifying agent can have a carboxyl group in the molecule, a (first, second, third) amine group, a 4- to ammonium group, a carbonyl group, a glycidyl group, a vinyl group, a (meth) group. A compound having a functional group such as an acryloxy group or a fluorenyl group. Such surface modifiers, usually at standard temperature and pressure

條件下為液體,分子内之碳數係例如為1 5以下,較佳為 1 Q ’特佳為8以下之低分子有機化合物所構成。該 -27- 201211094 低分子有機化合物之分子量例如 以下,特佳為200以下。 以下,較佳為350 較佳的表面改質韌可舉例:甲酸 &amp; &amp;、丁酸、戊酸、己酸、丙歸酸-乙酸、丙 檸檬酸、己二酸、伽、甲基丙•、巴豆酸、 及反丁烯二酸等之碳數1至12之二馱、順丁烯二酸 酸類(較佳為單m酸類广&amp; ° 5 =和單或聚羧 酸甲醋等之cjc…魅 類(較佳為甲基丙烯 己1同Η I );酿胺類;乙酿丙酮、24- :二:、乙醯乙酸及Cl…基乙醯乙酸 專β·一七基化合物等。另外,並未予 也能夠使用習用之石夕烧偶合劑作為表面改質劑。 1無機填料⑼之粒徑通常為〇 〇lnm至2〇〇_左右, 較佳為O.lrnn至100μιη,特佳為〇 Um至左右 若將化合物(A)及化合物(B)之合計含量設為1〇〇° 量份時,無機填料(D)之含量較佳為2至2〇〇〇重量份, 進一步較佳為1〇至1000重量份。另外,相對於裝 置用低透濕性樹脂組成物之全部量,無機填料(D)之含量 例如為5至95wt%,較佳為1〇至9〇wt〇/。。 &lt;矽烷偶合劑(E)&gt; 本發明之電子裝置用低透濕性樹脂組成物為了要使 與基板等之被接著物之接著性提高,進一步也可以含有 矽烷偶合劑(E)。矽烷偶合劑(E)並未予以特別限定,能 夠使用習知慣用之石夕烧偶合劑。例如,石夕烧偶合劑(E)係 由下列矽烷等之水溶液中較安定者之中所選出:四甲氧 基石夕烧、四乙氧基石夕烧、甲基三乙氧基石夕燒、二甲基二 -28- 201211094 乙氧基碎院、曱基r乙翁其 土一乙虱基矽烷、乙烯基三乙氧基矽烷、 乙烯基三甲氧基矽烷、Γ、法其会 沉乙烯基參(甲氧基乙氧基矽烷)、 笨基三甲氧基矽烷、-芏其_田^ —本基一甲乳基矽烷、乙烯基三乙 醯乳基㈣、γ_(甲基)丙烯醯氧丙基三乙氧基钱、丫(甲 基)丙烯醯氧丙基三甲氧基·、γ_(曱基)丙稀醯氧丙基 曱基 甲氧基碎燒&gt;甲y \ 3C, γ (曱基)丙烯醯氧丙基.曱基二乙氧基 石夕烧、3-環氧丙基丙基=甲4其 m ^ 甲巩基矽烷、3-環氧丙基丙基 甲基二曱氧基矽烷、3裏氧 〇 〕%軋丙基丙基三乙氧基矽烷、3_In the case of a liquid, the number of carbon atoms in the molecule is, for example, 15 or less, and preferably 1 Q' is preferably a low molecular organic compound having 8 or less. The molecular weight of the low molecular organic compound of the -27-201211094 is, for example, the following, and particularly preferably 200 or less. Hereinafter, preferably 350 preferred surface modification toughness can be exemplified by formic acid &amp;&amp;, butyric acid, valeric acid, caproic acid, acryl-acetic acid, propionic acid, adipic acid, gamma, methyl propyl • crotonic acid, fumaric acid, etc., carbon number 1 to 12, maleic acid (preferably single m acid wide & ° 5 = and mono or polycarboxylic acid methyl vinegar, etc. Cjc... charm class (preferably methacrylic 1 Η I); brewing amines; B-brewed acetone, 24-: 2:, acetamidine acetic acid and Cl... In addition, it is not possible to use a conventional ceramsite coupling agent as a surface modifier. 1 The inorganic filler (9) usually has a particle diameter of from about 1 nm to about 2 Å, preferably from 0.1 nm to 100 μm. When the total content of the compound (A) and the compound (B) is 1 part by weight, the content of the inorganic filler (D) is preferably 2 to 2 parts by weight. Further, it is preferably from 1 to 1000 parts by weight. Further, the content of the inorganic filler (D) is, for example, from 5 to 95% by weight, preferably 1 based on the total amount of the low moisture-permeable resin composition for the apparatus. 〇 〇 〇 。 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 矽 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低 低The decane coupling agent (E). The decane coupling agent (E) is not particularly limited, and a conventionally used sulphur coupling agent can be used. For example, the sulphur coupling agent (E) is obtained from an aqueous solution of the following decane or the like. Selected among the stabilizers: tetramethoxy zephyr, tetraethoxy zebra, methyl triethoxy zebra, dimethyl di-28-201211094 ethoxy ash, 曱 r 乙Tert-Ethyl decane, vinyl triethoxy decane, vinyl trimethoxy decane, hydrazine, ruthenium hexamethylene (methoxy methoxy decane), stupyl trimethoxy decane, - hydrazine _田^ - Benyl 1-methyl decyl decane, vinyl triethyl hydrazide (IV), γ_(methyl) propylene oxypropyl triethoxy ketone, 丫 (meth) propylene 醯 methoxy propyl trimethoxy Base ·, γ_(indenyl) propylene oxime propyl methoxy methoxy calcination &gt; A y \ 3C, γ (mercapto) propylene oxypropyl . Mercapto diethoxy zephyr, 3-epoxypropyl propyl = methyl 4, m ^ methyl sulfhydryl, 3-epoxypropyl propyl dimethoxy decane, 3 oxime % rolled propyl propyl triethoxy decane, 3_

氧丙基丙基甲基二7 宜· rA 一 乳基矽烷、2-(3,4-環氧環己基)乙 基二甲氧基梦燒、對笨△嫌其-田岛* τ本乙烯基二甲氧基矽烷' 3_丙烯醯 氧丙基三曱氧基石夕烧、·甘、 Ν (β_胺乙基)-γ-胺丙基甲基二甲 氧基妙:^、Ν-(β -胺 γ ηΛ» Ρ妝乙基)-γ_胺丙基甲基二乙氧基矽烷、 Ν - ( β -胺乙基)-γ _胺丙其__田祭# a y妝内基二曱氧基矽烷、N_(卜胺乙基)_γ_ 胺丙基三乙氧基石夕烧、且 ^ N-本基_丫_胺丙基三曱氧基矽烷、 γ-胺丙基三甲氧基矽烷、γ_胺丙基三乙氧基石夕烷、3_疏丙 基二甲氧基矽烷、3_巯丙基三乙氧基矽烷、3·巯丙基甲 基二甲氧基矽烷、四硫化雙(三乙氧基矽烷丙基)、3_里氰 酸酯丙基三乙氧基矽烷等。 相對於1 00重量份之無機填料之 劑(Ε)之用量較佳為〇1至2〇曹晉ρ尤女争杜: 主2^)重1份左右,更佳為❹^至 8重量:’進-步較佳$ 〇.5至5重量份之範圍。若低於 重量知,缺乏因矽烷偶合劑(E)所造成的樹脂之交聯 效果j因而無法獲得緻密之薄膜,另外缺乏對金屬基材 s政果緊貼性差,難以獲得所欲之财驗性與防鐵 力較20重量份為多之情形,因水解所造成的耐水、耐 -29- 201211094 驗性等各種性能顯著降低,製膜性上舍路*时as s讨王問《ι ,另外 在經濟性之點,也容易變得不利。 〈其他添加劑&gt; 於本發明之電子裝置用低透濕性樹脂組成物中,依 照所需,能夠使用聚合抑制劑、抗氧化劑、光安定劑'&quot; 可塑劑、平坦劑、消泡劑 '顏料、有機溶劑、m及 收劑、離子吸附物、顏料、螢光體、脫模劑等之習用六 加劑。 + &lt;電子裝置用低透濕性樹脂組成物之製造法〉 .本發明之電子裝置用低透濕性樹脂組成物係藉由均 勻混合上述各成分所獲得。為了獲得本發明之電子裝置 用低透濕性樹脂組成物’宜使用自公轉式攪拌脫:裝 置、均質機、行星式攪拌器、3輥磨機、珠磨機等之二 史已知之混合用機器而盡可能地使各成分成為均一的方 式來進行攪拌、溶解、混合、分散等。 &lt;硬化物&gt; 本發明之電子裝置用低透濕性樹脂組成物能夠藉光 〜而使其硬化。藉光而使其硬化之情幵&gt;,例如,能夠 :用水銀燈等進行1 000mJ/cm2以上之光照射。另外,藉 …而使其硬化之情形,能夠以例如溫度為5〇 較佳為50至1Q〇〇r 90 C,進一步較佳為50至l8〇t;;例如硬 佳曰10至600分鐘’較佳為10至480分鐘,進一步 :為15至360分鐘之條件下使其硬化。硬化溫 分;杈上述範圍之下限值為低之情形,硬化變得不充 刀相反地,較上述範圍之上限值為高之情形,因為有 -30- 201211094 引起樹脂成分分解之情形’有任一種皆為不佳之情形。 硬化溫度高之情形係縮短硬化時間;硬化溫度低之情形 係拉長硬化時間等而能夠進行適當調整。藉由使本發明 之電子裝置用低透濕性樹脂組成物硬化而可以獲得具優 越之低透濕性的硬化物。 由硬化本發明之電子裝置用低透濕性樹脂組成物而 成之硬化物係低透濕性,且具優越之防濕性。硬化物之 透濕度係依照JIS L1099及JIS Z0208,藉由在 60°C90%RH條件下測定調整成厚度ι〇〇 μιη之樹脂硬化 物的透濕量而能夠獲得。本發明之硬化物係利用上述方 法所測出的透濕度例如為5 0 g / m2 . a t m · d a y以下(例 如,0 至 50g/m2 . atm · day),較佳為 3〇g/m2 · atm · day 以下(例如,0至3〇g/m2 · atm · day),進一步較佳為 25g/m2 · atm · day 以下(例如,〇 至 25g/m2 · atm ·心幻。 另外’藉由添加無機填料(D),若例如為2〇g/m2 · atm · day 以下(例如〇至20g/m2 · atm . day),特佳為 15g/m2 · atm · day 以下(例如 〇 至 15g/m2 · atin · day)時, 能夠進一步使透濕度提高 &lt;有機電致發光元件、電子紙、或太陽能電池&gt; 作為在本發明之電子裝置用低透濕性樹脂組成物中 之電子裝置較佳可舉例〔有機電致發光元件、電子紙或 太陽能電池。若根據本發明之電子裝置用低透濕性樹脂 組成物,則能夠使在此等電子裝置中之濕度影響成為最 小限度。 -31- 置用低透濕性樹脂組成 蒸氣障壁性的有機電致 池等之以低透濕性為必 材等使用。具體而言, 透濕性樹脂組成物作為 之電子裝置用低透濕姓 密封劑硬化而能夠形成 化之際的條件能夠採用 外,本發明之電子裝置 為接著劑使用。 201211094 &lt;封閉材、密封材&gt; 本發明之電子裝 能夠作為具優越之水 電子紙、或太陽能電 件用之封閉材、密封 發明之電子裝置用低 含之封閉劑、本發明 作為必要成分所含之 封閉材、密封材。硬 化物之際的條件β另 樹脂組成物也能夠作 實施例 以下,根據實施例而更詳細地說明本發 受此等實施例所限定。 製造例1 [氫化雙酚Α二乙烯基醚之合成] 具備附Dean &amp; Stark之冷卻管、授拌器 2L的4 口燒瓶中,添加碳酸鈉(31.8g、300. 苯(537.2g)、丙酸乙婦醋(199.9.g、2.00mol) A(62.0g、257.7mmol)、及[IrCI(cod)]2(5.04g、 安裝至130°C之油浴中而加熱回流。一邊將由 生成出的水向反應系統外抽離’且一邊攪拌 後,將反應液放冷直到室溫’加水後移入分 利用乙酸乙酯而萃取水層,將飽和食鹽水加 而洗淨。其後,分離有機層,利用無水硫酸 物之硬化物 發光元件、 要的電子構 藉由使以本 必要成分所 樹脂組成物 低透濕性之 獲得上述硬 用低透濕性 明,但並不 及溫度計之 Ommol)、甲 、氫化雙酚 7.5Ommol), 反應進行而 4小時。其 液漏斗中。 入有機層中 鎂脫水後, -32- 201211094 蒸餾去除溶劑而獲得液狀之粗生成物。利用減壓蒸德而 精製此粗生成物(160°C、30Pa),獲得以下式(3)所示之氫 化雙酚A二乙烯基醚的無色透明液體7l.6g(產率95%、 純度99%)。 'H-NMR(500 MHz, CDC13) '· δ0.72-〇.76(ϊη, 6Η) ' 1.01-l_46(m,12Η)、1.70-1.76(m,3Η)、2·〇〇_2.12(m,3Η)、 3 · 6 0 - 3.6 6 (m,1 H)、3 · 9 7 - 4.0 4 (m,3 H)、4 · 2 7 - 4.3 〇 (d, J = 1 5 〇 Hz, 2H) ' 6.31-6.34(m, 2H)Oxypropyl propylmethyl 2 y · rA monolacyl decane, 2-(3,4-epoxycyclohexyl)ethyldimethoxy dream, idiot △ 其 - - Tajima * τ 本 ethylene Dimethoxy oxane ' 3 _ propylene oxypropyl tri methoxy oxalate, · Gan, Ν (β_amine ethyl)-γ-aminopropyl methyl dimethoxy: ^, Ν - (β-amine γ ηΛ» Ρethyl)-γ_aminopropylmethyldiethoxy decane, Ν-(β-aminoethyl)-γ _amine propyl __田祭# ay makeup base Dimethoxydecane, N_(iamineethyl)_γ_aminopropyltriethoxylate, and N-benyl-丫-aminopropyltrimethoxy decane, γ-aminopropyltrimethoxy矽, γ-aminopropyltriethoxy oxacyclohexane, 3- propyl propyl dimethoxy decane, 3- propyl propyl triethoxy decane, 3 · propyl propyl methyl dimethoxy decane, four Sulfurized bis(triethoxydecanepropyl), 3-cyanoic acid propyl triethoxy decane, and the like. The amount of the agent (Ε) relative to 100 parts by weight of the inorganic filler is preferably 〇1 to 2 〇Cao Jin ρ 尤 争 : Du: Main 2^) weighs about 1 part, more preferably ❹^ to 8 weight: The 'step-step is better than $ 〇. 5 to 5 parts by weight. If it is lower than the weight, there is a lack of cross-linking effect of the resin caused by the decane coupling agent (E), so that a dense film cannot be obtained, and the lack of adhesion to the metal substrate is poor, and it is difficult to obtain the desired economy. When the sex and anti-ironing power are more than 20 parts by weight, the water resistance and the resistance to -29-201211094 due to hydrolysis are significantly reduced, and when the film-forming property is on the road*, the s In addition, at the point of economy, it is easy to become disadvantageous. <Other Additives> In the low moisture-permeable resin composition for an electronic device of the present invention, a polymerization inhibitor, an antioxidant, a light stabilizer, a plasticizer, a flat agent, and a defoaming agent can be used as needed. Conventional six-additives for pigments, organic solvents, m and collectors, ion adsorbents, pigments, phosphors, mold release agents, and the like. + &lt;Manufacturing method of low moisture-permeable resin composition for electronic device> The low moisture-permeable resin composition for an electronic device of the present invention is obtained by uniformly mixing the above respective components. In order to obtain the low moisture permeability resin composition for an electronic device of the present invention, it is preferable to use a self-revolving stirring device: a homogenizer, a homogenizer, a planetary agitator, a 3-roll mill, a bead mill, etc. The machine is stirred, dissolved, mixed, dispersed, and the like in such a manner that the components are as uniform as possible. &lt;Cured product&gt; The low moisture permeable resin composition for an electronic device of the present invention can be cured by light. In the case of hardening by light, for example, it is possible to irradiate light of 1 000 mJ/cm 2 or more with a mercury lamp or the like. Further, the case where it is hardened by, for example, the temperature is 5 Torr, preferably 50 to 1 Q 〇〇r 90 C, further preferably 50 to 18 〇t;; for example, a hard 曰 10 to 600 minutes' It is preferably from 10 to 480 minutes, and further: it is hardened under conditions of from 15 to 360 minutes. Hardening temperature; if the lower limit of the above range is low, the hardening becomes not the opposite of the knife, and the upper limit is higher than the upper limit of the above range, because there is a case where the resin component is decomposed by -30-201211094' Any situation is not good. When the hardening temperature is high, the hardening time is shortened; and the hardening temperature is low, and the curing time can be appropriately adjusted. By curing the low moisture permeability resin composition of the electronic device of the present invention, a cured product having excellent low moisture permeability can be obtained. The cured product obtained by curing the low moisture permeable resin composition for an electronic device of the present invention has low moisture permeability and superior moisture resistance. The moisture permeability of the cured product can be obtained by measuring the moisture permeability of the cured resin of the thickness ι〇〇 μηη under conditions of 60 ° C and 90% RH in accordance with JIS L1099 and JIS Z0208. The cured product of the present invention has a moisture permeability measured by the above method, for example, 50 g / m 2 . atm · day or less (for example, 0 to 50 g / m 2 . atm · day), preferably 3 〇 g / m 2 · Atm · day or less (for example, 0 to 3 〇 g / m 2 · atm · day), further preferably 25 g / m 2 · atm · day or less (for example, 〇 to 25 g / m 2 · atm · heart illusion. The inorganic filler (D) is added, for example, 2 〇g/m2 · atm · day or less (for example, 〇 to 20 g/m 2 · atm . day), particularly preferably 15 g/m 2 · atm · day or less (for example, 〇 to 15 g / When m2 · atin · day), it is possible to further increase the moisture permeability &lt;organic electroluminescence device, electronic paper, or solar cell&gt; as an electronic device in the low moisture permeability resin composition for an electronic device of the present invention. For example, an organic electroluminescence device, an electronic paper, or a solar cell can reduce the influence of humidity in such an electronic device according to the low moisture permeability resin composition for an electronic device of the present invention. - Use a low-moisture-permeable resin to form a vapor barrier organic cell, etc. The low moisture permeability is used as a material or the like. Specifically, the moisture permeable resin composition can be used as a condition that the electronic device can be formed by curing with a low moisture permeability sealant, and the electronic device of the present invention can be used. 201211094 &lt;Closed material, sealing material&gt; The electronic device of the present invention can be used as a sealing material for a superior water-electronic paper or a solar electric component, and a low-containing sealing agent for an electronic device of the invention. The sealing material and the sealing material contained in the essential component of the invention. The conditions of the cured product and the resin composition can also be exemplified below, and the present invention will be described in more detail by way of examples. Example 1 [Synthesis of hydrogenated bisphenol quinone divinyl ether] Sodium carbonate (31.8 g, 300. benzene (537.2 g), C) was added to a 4-neck flask equipped with a Dean &amp; Stark cooling tube and a 2 L stirrer. Acid ethyl vinegar (199.9.g, 2.00mol) A (62.0g, 257.7mmol), and [IrCI(cod)]2 (5.04g, installed in an oil bath of 130 ° C and heated to reflux. Water is pumped away from the reaction system and one side After the mixture is stirred, the reaction solution is allowed to cool to room temperature. After adding water, the aqueous layer is extracted with ethyl acetate, and the aqueous layer is extracted and washed with saturated brine. Thereafter, the organic layer is separated, and the light-emitting element is cured with anhydrous sulfuric acid. The desired electron structure is obtained by making the resin composition of the present essential component low in moisture permeability and obtaining the above-mentioned hard use low moisture permeability, but not as good as the thermometer (Ommol), and the hydrogenated bisphenol (7.5 mmol), and the reaction proceeds. And 4 hours. In its liquid funnel. After the magnesium was dehydrated in the organic layer, the solvent was distilled off at -32 - 201211094 to obtain a liquid crude product. The crude product (160 ° C, 30 Pa) was purified by vacuum distillation to obtain a colorless transparent liquid of the hydrogenated bisphenol A divinyl ether represented by the following formula (3), 7.16 g (yield 95%, purity). 99%). 'H-NMR (500 MHz, CDC13) '· δ0.72-〇.76(ϊη, 6Η) ' 1.01-l_46(m,12Η), 1.70-1.76(m,3Η), 2·〇〇_2.12( m,3Η), 3 · 6 0 - 3.6 6 (m,1 H), 3 · 9 7 - 4.0 4 (m,3 H), 4 · 2 7 - 4.3 〇(d, J = 1 5 〇Hz, 2H) ' 6.31-6.34(m, 2H)

[(2-苯基苯氧基)乙基乙烯基醚之合成] 具備裝設冷卻管、攪拌器及溫度計之2L的4 口燒瓶 中,添加氫化鈉(55%於礦物油中)(15.4§、352.9111111〇1)、 及DMSO(510.6g) ’冷卻至〇。〇後,將鄰苯基酚(5〇 6g、 297.3mmol)溶解於DMSO( 1 9 1.0g)而成之溶液滴入其 中。其後,安裝至6(TC之油浴中,將2•氣乙基乙烯基醚 (38.2g、358.5mm〇l)溶解於 DMSO(61.4g)而成之溶液滴 入。攪拌反應液6小時後,冷卻至〇它後慢慢地滴入水而 急冷’移入分液漏斗中。利用乙酸乙酯萃取水層,將飽 和食鹽水加入有機層中而洗淨。其後,分離有機層,利 用無水硫酸鈉脫水後,蒸餾去除溶劑而獲得液狀之粗生 成物。利用石夕膠管柱層析法而精製此粗生成物(己烧/乙 -33- 201211094 酸乙酯=10/1),獲得以下式(4)所示之(2-苯基苯氧基)乙基 乙稀基鱗的無色透明液體55.5g(產率78%、純度98%)。 H-NMR(500 MHz, CDC13) : 63.96{t, J = 5.0 Hz, 2H) ' 4.17-4.21(m,3H)、6.44(dd,J=14.1,6.5 Hz, 1H)、 6.98-7.01(m,1H)、7.04-7,07(m, 1H)、7.28-7.41(m,6H)、 7.56-7.57(m, 2H)[Synthesis of [(2-phenylphenoxy)ethyl vinyl ether] A sodium 2-hydride flask equipped with a cooling tube, a stirrer and a thermometer was added with sodium hydride (55% in mineral oil) (15.4§ , 352.9111111〇1), and DMSO (510.6g) 'cooled to 〇. After the hydrazine, a solution obtained by dissolving o-phenylphenol (5 〇 6 g, 297.3 mmol) in DMSO (1 9 1.0 g) was added dropwise thereto. Thereafter, it was placed in a 6 (TC oil bath, and a solution obtained by dissolving 2·Vethyl ethyl ether (38.2 g, 358.5 mm〇l) in DMSO (61.4 g) was dropped. The reaction solution was stirred for 6 hours. After that, it was cooled to 〇, and then slowly dripped in water and quenched and transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate, and the saturated brine was added to the organic layer to be washed. Thereafter, the organic layer was separated and used. After dehydration by anhydrous sodium sulfate, the solvent was distilled off to obtain a crude liquid product, and the crude product was purified by a sulphur column chromatography (hexane/b-33-201211094 ethyl ester = 10/1). 55.5 g (yield 78%, purity 98%) of a colorless transparent liquid of the (2-phenylphenoxy)ethylethylene group scale represented by the following formula (4). H-NMR (500 MHz, CDC13) : 63.96{t, J = 5.0 Hz, 2H) ' 4.17-4.21(m,3H), 6.44 (dd, J=14.1, 6.5 Hz, 1H), 6.98-7.01(m,1H), 7.04-7,07 (m, 1H), 7.28-7.41 (m, 6H), 7.56-7.57 (m, 2H)

(4) 製造例3 [雙酚F雙(3-乙基環氧丙烷_3_基甲基)醚之合成] 具備裝設冷卻管、攪拌器、溫度計之1L的4 口燒瓶 中’添加氫化鈉(55%於礦物油中)(13 5g、3〇9.4mmol)、 DMSO(295.0g)’ 冷卻至(TC後,將雙酚 F(25.8g、128.9mmol) 浴解於DMS0( 104· lg)而成之溶液滴入其中。其後,安裝 至80 C之油浴中,將曱烷磺酸_3_乙基-3_環氧丙烷甲酯 (5〇_〇g、257.4mmol)溶解於 DMSO(100.6g)而成之溶液滴 入°授拌反應液4小時後,冷卻至〇。〇後慢慢地滴入水而 急冷’移入分液漏斗十。利用乙酸乙酯而萃取水層,將 飽和食鹽水加入有機層中而洗淨。其後,分離有機層, 利用無水硫酸鎮脫水後’蒸餾去除溶劑而獲得液狀之粗 生成物。利用石夕膠管柱層析法而精製此粗生成物(己烷/ 乙酸乙酯=2/1—&gt;1/1),獲得以下式(5)所示之雙酚F雙(3_ •34- 201211094 乙基%氧丙烧-3-基甲基)醚的無色透明液體38.5g(產率 75% &gt; 純度 95%)。 H-NMR(500 MHz, CDC13) : δ0.85-0.94(m, 6Η) ' 1.78-1.89(m,4Η)、3.87-3.96(m,2Η)、4.03-4.05(m, 4Η)、 4.38-4.57(m,8H)、6.81-7.23(m,8H)(4) Production Example 3 [Synthesis of bisphenol F bis(3-ethyl propylene oxide _3_ ylmethyl) ether] Addition of hydrogenation in a 4-neck flask equipped with a cooling tube, a stirrer, and a thermometer Sodium (55% in mineral oil) (13 5g, 3〇9.4mmol), DMSO (295.0g)' was cooled to (after TC, bisphenol F (25.8g, 128.9mmol) was dissolved in DMS0 (104· lg The resulting solution was dropped into it. Thereafter, it was placed in an 80 C oil bath to dissolve decylsulfonic acid _3_ethyl-3 propylene oxide methyl ester (5 〇 〇 g, 257.4 mmol). The solution obtained in DMSO (100.6 g) was added dropwise to the reaction solution for 4 hours, and then cooled to hydrazine. The hydrazine was slowly added dropwise to the water and quenched and transferred to the separatory funnel. The aqueous layer was extracted with ethyl acetate. Saturated brine was added to the organic layer and washed. Thereafter, the organic layer was separated, and the residue was removed by dehydration with anhydrous sulfuric acid to obtain a liquid crude product. This was purified by Shixi rubber column chromatography. The crude product (hexane/ethyl acetate = 2/1 - &gt; 1/1) gave the bisphenol F double (3_ •34-201211094 ethyl oxypropyl -3-) represented by the following formula (5) Colorless and transparent 38.5 g (yield 75% &gt; purity 95%) H-NMR (500 MHz, CDC13): δ 0.85 - 0.94 (m, 6 Η) ' 1.78-1.89 (m, 4 Η), 3.87-3.96 (m , 2Η), 4.03-4.05 (m, 4Η), 4.38-4.57 (m, 8H), 6.81-7.23 (m, 8H)

製造例4 [ll -雙紛-2-基(3-乙基環氧丙烧_3_基甲基)醚之合成] 具備裝設冷卻管、攪拌器、溫度計之1L的4 口燒瓶 中’添加氫化納(55%於礦物油中)(6.8层'154.7111111〇1)、及 DMS〇(145.0g),冷卻至〇t:後’將鄰苯基酚(21.9g、 128:7mm〇l)溶解於DMSO(104.1g)而成之溶液滴入其 中。其後’安裝至80°C之油浴中,將甲烷磺酸_3_乙基_ J衣氧丙烷曱酯(25.0g、128.9mmol)溶解於 DMSO(50_3g) 而成之溶液滴入。攪拌反應液5小時後,冷卻至〇 °c後慢 慢地滴入水而急冷’移入分液漏斗中。利用乙酸乙酯而 萃取水層,將飽和食鹽水加入有機層中而洗淨。其後’ 刀離有機層,利用無水硫酸鎂脫水後,蒸餾去除溶劑而 獲得液狀之粗生成物。利用矽膠管柱層析法而精製此粗 生成物(己烷/乙酸乙酯=2/1 —1/1),獲得以下式(6)所示之 工’1 -聯苯-2-基(3 -乙基環氧丙院-3-基曱基)醚的無色透 明液體29.4 g(產率85%、純度98%)。 -35- 201211094 'H-NMR(500 MHz, CDC13) : 60.85(t, J = 7.6 Hz, 3H) ' 1.75(m,2H)、4.10(s, 2H)、4.40(d, J = 6.1 Hz,2H)、4.50(d, J = 6.1 Hz, 2H) ' 7.10-7.25(m, 2H) &gt; 7.31-7.42(m, 5H) ' 7.51(d, J = 7.6 Hz, 2H)Production Example 4 [Synthesis of ll-bis-diethyl-2-yl (3-ethylepoxypropanol-3-ylmethyl)ether] In a 4-neck flask equipped with a cooling tube, a stirrer, and a thermometer 1' Add sodium hydride (55% in mineral oil) (6.8 layers '154.7111111〇1), and DMS 〇 (145.0g), cool to 〇t: after 'o-phenylphenol (21.9g, 128:7mm〇l) A solution obtained by dissolving in DMSO (104.1 g) was dropped thereinto. Thereafter, it was mounted in an oil bath of 80 ° C, and a solution obtained by dissolving methanesulfonic acid _3_ethyl_J-propoxyl oxime ester (25.0 g, 128.9 mmol) in DMSO (50_3 g) was added dropwise. After the reaction solution was stirred for 5 hours, it was cooled to 〇 °c, and water was slowly dropped and quenched and transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate, and saturated brine was added to the organic layer to be washed. Thereafter, the knives were separated from the organic layer, dehydrated with anhydrous magnesium sulfate, and the solvent was distilled off to obtain a crude liquid product. This crude product (hexane/ethyl acetate = 2/1 - 1/1) was purified by a silica gel column chromatography to obtain a '1-biphenyl-2-yl group represented by the following formula (6). A colorless transparent liquid of 3-ethylepoxypropyl-3-ylmercapto)ether (29.4 g, yield: 85%, purity 98%). -35- 201211094 'H-NMR (500 MHz, CDC13): 60.85 (t, J = 7.6 Hz, 3H) ' 1.75 (m, 2H), 4.10 (s, 2H), 4.40 (d, J = 6.1 Hz, 2H), 4.50 (d, J = 6.1 Hz, 2H) ' 7.10-7.25(m, 2H) &gt; 7.31-7.42(m, 5H) ' 7.51(d, J = 7.6 Hz, 2H)

製造例5 [雙酚F二乙烯基醚之合成] 具備附Dean &amp; Stark之冷卻管、攪拌器及溫度計之 2L的4 口燒瓶中,添加碳酸納(31.8g、300.0mmol)、曱 苯(537.2g)、丙酸乙烯酯(199.9g、2.00mol)、雙酚 F(51.6g、257.7mmol)、及[IrCI(cod)]2(5.04g、7.50mmol), 安裝至1 30°C之油浴中而加熱回流》—邊將由反應進行而 生成出的水向反應系統外抽離,且一邊授拌4小時。其 後,將反應液放冷直到室溫,加水後移入分液漏斗中。 利用乙酸乙酯而萃取水層,將飽和食鹽水加入有機層中 而洗淨。其後’分離有機層,利用無水硫酸鎂脫水後, 蒸餾去除溶劑而獲得液狀之粗生成物。利用減壓蒸餾而 精製此粗生成物(142°C、30Pa),獲得以下式(7)所示之雙 酚F二乙烯基醚的無色透明液體63.0g(產率97%、純度 9 9%) 0 -36- 201211094 »H-NMR(500 MHz, CDC13) : δ 3.9 0-4.0 1 (m} 2H) ' 4.36-4.400, 2H)、4.63-4.74(m,2H)、6.57-6.63(m, 2H)、 6.93-7.000,4H)、7.10-7.21(m,4H)Production Example 5 [Synthesis of bisphenol F divinyl ether] A 2-liter 4-liter flask equipped with a Dean &amp; Stark cooling tube, a stirrer, and a thermometer was charged with sodium carbonate (31.8 g, 300.0 mmol) and toluene ( 537.2 g), vinyl propionate (199.9 g, 2.00 mol), bisphenol F (51.6 g, 257.7 mmol), and [IrCI(cod)] 2 (5.04 g, 7.50 mmol), mounted to 1 30 ° C The water was heated and refluxed in an oil bath. The water formed by the reaction was extracted outside the reaction system and allowed to mix for 4 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and water was added and then transferred to a separating funnel. The aqueous layer was extracted with ethyl acetate, and saturated brine was added to the organic layer and washed. Thereafter, the organic layer was separated and dehydrated with anhydrous magnesium sulfate, and the solvent was evaporated to give a liquid crude product. This crude product (142 ° C, 30 Pa) was purified by distillation under reduced pressure to obtain 63.0 g of a colorless transparent liquid of bisphenol F divinyl ether represented by the following formula (7) (yield 97%, purity 9 9%). 0 -36- 201211094 »H-NMR(500 MHz, CDC13) : δ 3.9 0-4.0 1 (m} 2H) ' 4.36-4.400, 2H), 4.63-4.74 (m, 2H), 6.57-6.63 (m , 2H), 6.93-7.000, 4H), 7.10-7.21 (m, 4H)

製造例6 [鄰苯基酚乙烯基醚之合成] 具備附Dean &amp; Stark之冷卻管、攪拌器及溫度計之 2L的4 口燒瓶中,添加碳酸鈉(18.9g、178_3mmol)、曱 苯(557.2g)、丙酸乙烯醋(267.5g、2.67mol)、鄰苯基g分 (5 0.0g、293.7mmol)、及[IrCI(cod)]2(3.02 g、4.5 0 mmol), 安褒至1 3 0 C之油浴中而加熱回流。一邊將由反應進行而 生成出的水向反應系統外抽離,且一邊攪拌4小時。其 後,將反應液放冷直到室溫,加水後移入分液漏斗中。 利用乙酸乙酯而萃取水層,將飽和食鹽水加入有機層中 而洗淨。其後,分離有機層,利用無水硫酸鎂脫水後, 蒸顧去除溶劑而獲得液狀之粗生成物。利用 Kugelrohr 減壓蒸餾而精製此粗生成物(240°C、50 Pa),獲得以下式 (8)所示之鄰苯基酚乙烯基醚的無色透明液體52 3 g(產率 9 1%、純度 99%)。 'H-NMR(500 MHz, CDC13) : 84.33(d, J = 6.1 Hz, 1H) &gt; 4.59(d5 J=13.8 Hz, 1H) ' 6.56(dd, J=13.8, 6.1 Hz, 1H) ' 7.10(d, J = 7.6 Hz, lH)'7.18(t, J = 7.6 Hz, lH)'7.31-7.35(m, 2H)、7_39-7_42(m, 3H)、7.51(d,J = 7.6 Hz, 2H) -37- 201211094Production Example 6 [Synthesis of o-phenylphenol vinyl ether] A 4-liter four-necked flask equipped with a Dean &amp; Stark cooling tube, a stirrer, and a thermometer was charged with sodium carbonate (18.9 g, 178_3 mmol) and toluene (557.2). g), Vinyl propionate vinegar (267.5 g, 2.67 mol), o-phenyl g fraction (5 0.0 g, 293.7 mmol), and [IrCI(cod)] 2 (3.02 g, 4.5 0 mmol), ampoule to 1 Heat the reflux in an oil bath of 3 0 C. The water formed by the reaction was extracted outside the reaction system and stirred for 4 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and water was added and then transferred to a separating funnel. The aqueous layer was extracted with ethyl acetate, and saturated brine was added to the organic layer and washed. Thereafter, the organic layer was separated, dehydrated with anhydrous magnesium sulfate, and the solvent was evaporated to give a liquid crude product. The crude product (240 ° C, 50 Pa) was purified by Kugelrohr vacuum distillation to obtain 52 3 g of a colorless transparent liquid of o-phenylphenol vinyl ether represented by the following formula (8) (yield 91%, Purity 99%). 'H-NMR (500 MHz, CDC13): 84.33 (d, J = 6.1 Hz, 1H) &gt; 4.59 (d5 J = 13.8 Hz, 1H) ' 6.56 (dd, J = 13.8, 6.1 Hz, 1H) ' 7.10 (d, J = 7.6 Hz, lH) '7.18(t, J = 7.6 Hz, lH) '7.31-7.35(m, 2H), 7_39-7_42(m, 3H), 7.51 (d, J = 7.6 Hz, 2H) -37- 201211094

製造例7 [雙酚F雙(2-乙烯氧乙基)醚之合成] 具備裝设冷卻f、攪拌器及溫度計之2L的4 口燒瓶 中,添加氫化鈉(55%於礦物油中)(3〇 8g、7〇5 8mm〇1)、 及DMSO(5〇9.4g) ’冷卻至ye後將雙酚F(5〇 2g、 250.7nm〇1)溶解於DMS〇(m 6g)而成之溶液滴入其 中。其後,安裝至60。(:之油浴中,將2_氣乙基乙烯基醚 (58.6g、550.0mmol)溶解於DMS〇(46 〇g)而成之溶液滴 入。授拌反應液4小時後,冷卻至〇它後慢慢地滴入水而 急冷’移入分液漏斗中。利用乙酸乙酯而萃取水層,將 飽和食鹽水加入有機層中而洗淨。其後,分離有機層, 利用無水硫酸鈉脫水後,蒸餾去除溶劑而獲得液狀之粗 生成物。利用矽膠管柱層析法而精製此粗生成物(己烷/ 乙酸乙醋=10/1),獲得以下式(9)所示之雙齡F雙(2 -乙稀 氧乙基)醚的白色固體37.5g(產率44%、純度99%)。 'H-NMR(500 MHz, CDC13) : 53.85 = 4.05(m, 6Η) ^ 4.14-4.16(m,4Η)、4.22-4.25(m,2Η)、6.47-6_54(m,2Η)、 6.80-6_89(m,2H)、7.06-7,09(m,4H)、7.12-7.16(m,4H) -38- (9) 201211094Production Example 7 [Synthesis of bisphenol F bis(2-vinyloxyethyl)ether] A four-necked flask equipped with a cooling fin, a stirrer, and a thermometer was placed in a four-necked flask, and sodium hydride (55% in mineral oil) was added ( 3〇8g, 7〇5 8mm〇1), and DMSO (5〇9.4g) 'After cooling to ye, bisphenol F (5〇2g, 250.7nm〇1) is dissolved in DMS〇(m 6g) The solution was dropped into it. Thereafter, install to 60. (In the oil bath, a solution obtained by dissolving 2_gas ethyl vinyl ether (58.6 g, 550.0 mmol) in DMS 〇 (46 〇g) was added dropwise. After mixing the reaction solution for 4 hours, it was cooled to 〇. After that, the mixture was slowly poured into water and quenched and transferred to a separatory funnel. The aqueous layer was extracted with ethyl acetate, and the saturated aqueous sodium chloride was added to the organic layer to be washed. Thereafter, the organic layer was separated and dried over anhydrous sodium sulfate. After that, the solvent was distilled off to obtain a crude liquid product, and the crude product (hexane / ethyl acetate = 10/1) was purified by silica gel column chromatography to obtain a double represented by the following formula (9). 37.5 g (yield 44%, purity 99%) of white solid of F (bis-ethoxyethyl)ether (H-NMR (500 MHz, CDC13): 53.85 = 4.05 (m, 6 Η) ^ 4.14 -4.16(m,4Η), 4.22-4.25(m,2Η), 6.47-6_54(m,2Η), 6.80-6_89(m,2H), 7.06-7,09(m,4H), 7.12-7.16( m,4H) -38- (9) 201211094

實施例1 將69.3重量份之雙酚F二環氧丙基醚(商品名 RE-303S ;日本化藥股份有限公司製)、29 7重量份之環 氧丙基苯基醚(商品名G〇〇98;東京化成工業股份有限公 司製)、1重量份之PI-2〇74倒入自公轉式攪拌脫泡裝置 (型式AR-250 ; Thinky股份有限公司製)内,進行攪拌、 溶解、混合、分散,調製樹脂組成物之溶液。 實施例2至4 以表1所示之量而使用矣1 _ 用表1所不之化合物(A)、化合 物(B)、聚合起始劑(C)、及益機 …、械填枓(D),與實施例1同 樣地調製樹脂組成物之溶液。還古 還有,針對作為無機填料 (D)之二氧化矽,使用藉矽烷偶 σ Μ (商品名 KBM-403 ; 信越化學工業股份有限公司萝 π…J表)將商品名Adomafine SC4500(Ad〇matechs股份有限公司制 表面改質而成者。 另外,針對作為無機填料(D)之Example 1 69.3 parts by weight of bisphenol F diglycidyl ether (trade name: RE-303S; manufactured by Nippon Kayaku Co., Ltd.), 297 parts by weight of epoxypropyl phenyl ether (trade name G〇) 〇98; manufactured by Tokyo Chemical Industry Co., Ltd.), 1 part by weight of PI-2〇74, poured into a self-revolving stirring and defoaming device (type AR-250; manufactured by Thinky Co., Ltd.), stirred, dissolved, mixed Dispersing and modulating a solution of the resin composition. Examples 2 to 4 In the amounts shown in Table 1, 矣1 _ was used as the compound (A), the compound (B), the polymerization initiator (C), the polymerization initiator (C), and the machine (not shown in Table 1). D) A solution of the resin composition was prepared in the same manner as in Example 1. Also, for the ruthenium dioxide as the inorganic filler (D), the use of decane σ Μ Μ (trade name KBM-403; Shin-Etsu Chemical Co., Ltd. π...J table) will be used under the trade name Adomafine SC4500 (Ad〇 Matechs Co., Ltd. made a surface modification. In addition, as an inorganic filler (D)

u. u π , 、』,月石,使用商品名MSTu. u π , , 』, Moonstone, use the trade name MST

Hlgh Talc;竹原化學工業股份有限公司製。 實施例5 ° 除了化合物(B)係使用鄰苯基 SY ΟΡΓ &gt; 酚娘氧丙基醚(商品名 SY-OPG,阪本樂品工業股份有 ^ , 民公司製)以取代環氧丙 基醚以外,進行相同於實施例丨 版η 方式而調製樹脂組成 物之溶液。 -39- 201211094 實施例6至8 . 以表1所示之量而使用表1所示之化合物(A)、化合 物(B)、聚合起始劑(C)、及無機填料(D),與實施例5同 樣地調製樹脂組成物之溶液。還有,針對作為無機填料 (D)之二氧化矽,使用藉矽烷偶合劑(商品名KBM_4〇3 ; 信越化學工業股份有限公司製)將商品名Adomafine SC4500(Ad〇matechS股份有限公司製)表面改質而成者。 實施例9 除了化合物(A)係使用以上式(1_3)所表示之 3,4,3,4 -一 5衣氧雙環己基(商品名「ceii〇xide 8000」、Hlgh Talc; manufactured by Takehara Chemical Industry Co., Ltd. Example 5 ° In addition to the compound (B), o-phenyl SY ΟΡΓ &gt; phenoxypropyl ether (trade name: SY-OPG, Sakamoto Music Industrial Co., Ltd., manufactured by Minku Co., Ltd.) was used in place of the epoxy propyl ether. A solution in which the resin composition was prepared in the same manner as in the Example η mode was carried out. -39-201211094 Examples 6 to 8. The compound (A), the compound (B), the polymerization initiator (C), and the inorganic filler (D) shown in Table 1 were used in the amounts shown in Table 1, and In the same manner as in Example 5, a solution of a resin composition was prepared. In addition, for the cerium oxide as the inorganic filler (D), the surface of the product name: Adomafine SC4500 (manufactured by Adhematech Co., Ltd.) was used as a surface of a ruthenium coupling agent (trade name: KBM_4〇3; manufactured by Shin-Etsu Chemical Co., Ltd.). Revised as a winner. Example 9 In addition to the compound (A), 3,4,3,4-penta-5 represented by the above formula (1-3) was used (trade name "ceii〇xide 8000",

Dai cel化學工業股份有ρ艮公司製)以取代雙齡F二環氧丙 基醚,如表1的方式來變更各成分之摻合量以外,進行 相同於實施例5之方式而調製樹脂組成物之溶液。 實施例10 除了化合物(A)係使用在製造例1所獲得之氫化雙酚 A二乙烯基醚(式(3))以取代雙酚f二環氧丙基醚,化合 物(B)係使用在製造例2所獲得之(2-苯基苯氧基)乙基乙 烯基醚(式(4))以取代環氧丙基醚,化合物(c)係使用 SI-60以取代PI-2074 ’如表1的方式來變更各成分之摻 合量以外’進行相同於實施例1之方式而調製樹脂組成 物之溶液。 實施例11 除了化合物(A)係使用在製造例3所獲得之雙酚F雙 (3 -乙基環氧丙烧-3-基曱基)謎(式(5))以取代在製造例1 所獲得之氫化雙酚A二乙烯基醚,化合物(b)係使用在製 -40- 201211094 造例4所獲得之U、聯苯-2_ 基)醚(式(6))以取代在製造例:;乙:環氧丙烧-3 -基甲 乙基乙稀基鍵,如表i的方氧基)Modification of the resin composition was carried out in the same manner as in Example 5 except that the amount of the blending of the components was changed in the manner of Table 1 in place of the double-aged F diglycidyl ether. a solution of the substance. Example 10 In addition to the compound (A), the hydrogenated bisphenol A divinyl ether (formula (3)) obtained in Production Example 1 was used in place of the bisphenol f diglycidyl ether, and the compound (B) was used. (2-phenylphenoxy)ethyl vinyl ether (formula (4)) obtained in Production Example 2 was substituted for epoxy propyl ether, and compound (c) was used in place of PI-2074'. In the manner of Table 1, the solution of the resin composition was prepared in the same manner as in Example 1 except that the blending amount of each component was changed. Example 11 In place of the compound (A), the bisphenol F bis(3-ethylglycidyl-3-ylindenyl) mystery (formula (5)) obtained in Production Example 3 was used instead of the production example 1. The hydrogenated bisphenol A divinyl ether obtained, and the compound (b) is substituted with the U, biphenyl-2-yl) ether (formula (6)) obtained in the preparation of the product of the preparation of -40-2012-11094, in the production example. :; B: Glycidyl-3 -ylethylethylidene bond, such as the aryloxy group of Table i)

外,進仃相同於實施例1()之方 σ里U 液0 式而調製樹脂組成物之溶 實施例1 2 ’ 除了化合物(A)係使用在赞! y , /甘 衣造例5所獲得之雙酚ρ二 乙烯基醚(式⑺)以取代在製造&lt;列i -Further, the dissolution of the resin composition was carried out in the same manner as in the case of the first embodiment (1), and the resin composition was dissolved. Example 1 2 ' In addition to the compound (A), it was used in praise! y, / bismuth 5 obtained by the bisphenol ρ divinyl ether (formula (7)) in place of the manufacturing &lt;column i

二乙烯基醚,使用在製造例6 又 ^又-A , , /ΟΛλ 所獲侍之鄰苯基酚乙烯基 醚(式(8))以取代在製造例2所霜,曰f ^ , ^ 獲得之(2_苯基苯氧基)乙 基乙烯基醚以外,進行相同於會 ^ 貫施例10之方式而調製樹 脂組成物之溶液。 實施例1 3 除了化合物(Α)係使用在制,&amp; 7 , ; 用隹裊造例7所獲得之雙酚F雙 (2 -乙烯氧基乙基)醚(式(9))以&amp;上 、叭U取代在製造例5所獲得之 雙酌· F 一乙浠基趟以外,進行相鬥狄— 订相冋於實施例12之方式而 調製樹脂組成物之溶液。 實施例1 4 除了化σ物(Α)係使用在製造例7所獲得之雙酚f雙 (2-乙稀氣基乙基)醚(式(9))以取代在製造例1所獲得之 氫化㈣Α二乙;基鱗以外’進行相同於實施例1〇之方 式而調製樹脂組成物之溶液。 實施例1 5 除了化合物(A)係使用雙酚F二丙烯酸醋(Nard研究 所股份有限公司合成品)’化合物(B)係使用2_(鄰苯基苯 -4 1- 201211094 氧基)丙烯酸乙酯(商品名hrd-o 1、曰本蒸餾工業股份有 限公司製),化合物(C)係使用1,1,3,3-過氧化四甲基丁基 -2-乙基己酸酯(商品名per〇cta 〇、日本油脂股份有限公 司製)’如表1的方式來變更各成分之摻合量以外,進行 相同於貫施例1之方式而調製樹脂組成物之溶液。 實施例1 6 除了化合物(A)係使用酚醛清漆環氧丙基醚樹脂(盼 酚醛清漆型環氧樹脂)(商品名jER-152、三菱化學股份有 限公司製)以外,進行相同於實施例1之方式而調製樹脂 組成物之溶液。 比較例1至9 以表1所示之量而使用表1所示之化合物(A)及聚合 起始劑(C),進行與實施例2同樣之方式來調製樹脂組成 物之溶液。 &lt;樹脂組成物之硬化&gt; 藉由利用水銀燈而對實施例1、2、4至9、16 '比 較例1至3、9所獲得之樹脂組成物進行5 〇 〇 〇 m j / c m 2之 光照射,接著在加熱乾燥機内,於i 00°c加熱1小時而製 得硬化物。 對貫把例3 ' 1 〇至1 5、比較例4至8所獲得之樹脂 組成物’於1 5 0 C進行2小時之加熱而製成硬化物。 &lt;透濕度之評估&gt; 硬化物之透濕度係依照JIS L1099及JIS Z0208,在 60°C 90%RH條件下’測定調整至厚度丨〇〇 _之樹脂硬 化物的透濕度。 -42- 201211094 表1中顯示針對實施例1至16、比較例1至9所獲 得之樹脂組成物之硬化物的透濕度之測定結果。 化合物(A)與化合物(B)之共聚物的實施例1至8所 獲得之樹脂組成物之硬化物與僅由任一種化合物(A)製 得的聚合物(比較例1)作一比較,可以獲得低透濕度之硬 平乂 化物。同樣地,實施例9之硬化物係較比 物、實施例1 0之硬化物係較比較例4之硬化物、實施例 1 1之硬化物係較比較例5之硬化物、實施例12之硬化 物係較比較例6之硬化物、實施作&quot;3、14之硬化 比較例7之硬化物、實施例15之硬化物係較比較例乂 硬化物、實施例16之硬化物後± , η 之 化物係較比較例9之硬化物 更低的透濕度(低透濕性)。 β不 *43- 201211094 |透濕度| η Β 'ωι 二 */Ί (N 卜 〇 CN yn (N (N ΓΟ OS CN m 〇〇 (N 00 (N m CO 〇\ m 9 〇 (N 無機填料〇D) wt% 1 s § 1 構造 1 二氧化石夕 二氧化矽 滑石 二氧化石夕 1 1 聚合起始劑(C) wt% 寸 d 〇 卜 d 1-^ 寸 〇 ι-Η 1-^ F-H 構造 PI-2074 PI-2074 SI-60 PI-2074 PI-2074 PI-2074 PI-2074 PI-2074 i PI-2074 SI-60 SI-60 ! SI-60 SI-60 1 SI-60 Perocta 0 1 PI-2074 PI-2074 PI-2074 PI-2074 SI-60 SI-60 SI-60 SI-60 Perocta Ο PI-2074 1官能之化合物(Β) wt% 29.7 11.9 On 20.8 29.7 39.6 49.5 Ο) 49.5 39.6 49.5 39.6 39.6 39.6 :39.6 29.7 1 1 1 1 1 1 1 1 1 構造 環氧丙基苯基醚 環氧丙基苯基謎 環氧丙基苯基醚 環氧丙基苯基醚 鄰苯基酚環氧丙基醚 鄰苯基酚環氧丙基醚 鄰苯基酚環氧丙基醚 鄰苯基酚環氧丙基醚 鄰苯基酚環氧丙基醚 苯基苯氧基)乙基乙烯基鍵 1,1 聯苯-2-基(3-乙基環氧丙烷-3-基甲基)醚 鄰苯基酚環氧丙基醚 鄰苯基酚環氧丙基醚 i (2-苯基笨氧基)乙基乙烯基醚 HRD-01 環氧丙基苯基醚 1 1 1 1 1 1 1 1 1 2官能以上之化合物(Α) wt% 69.3 27.7 27.7 48.5 69.3 59.4 27.7 49-5 59.4 49.5 59.4 1 59.4 59.4 L6.93 〇\ σ\ 49.5 49.5 On Os On 〇\ Os On σ\ On On 〇\ On ON On On 構造 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 雙酚F二環氧丙基醚 3,4,3’,4’-二環氧雙環己基 氫化雙酚A二乙烯基醚 雙酚F雙(3-乙基環氧丙烷-3-基曱基)醚 雙酚F二乙烯基醚 雙酚F雙(2-乙烯氧基乙基)¾ | 雙酚F雙(2-乙烯氧基乙基)醚 雙酚F二丙烯酸酯 酚酚醛清漆型環氧樹脂 雙酚F二環氧丙基醚 四甲基雙酚二環氧丙基醚 雙酚F二環氧丙基醚 3,4,3’,4’-二環氧雙環己基 氫化雙酚A二乙烯基醚 雙酚F雙(3-乙基環氧丙烷-3-基曱基)醚 雙酚F二乙烯基醚 雙酚F雙(2-乙烯氧基乙基)醚 雙酚F二丙烯酸酯 酚酚醛清漆型環氧樹脂 實施例1 實施例2 實施例3 實施例4 實施例5 實施例6 丨實施例7 |實施例8 1 |實施例9 1 實施例10 實施例11 實施例12 實施例13 實施例14 實施例15 |實施例16 I 比較例1 比較例2 比較例3 比較例4 比較例5 比較例6 比較例7 比較例8 比較例9 —寸寸丨 201211094 [產業上利用之可能性] 使本發明之電子裝置用低透濕性樹脂組成物硬化所 獲得之硬化物係具優越之水蒸氣障壁性,能夠作為有機 電致發光元件、電子紙、或太陽能電池等之需要低透渴 性的電子構件用之封閉材、密封材等使用。另外,本發 明之電子裝置用低透濕性樹脂組成物也能夠作; 使用。 … 【圖式簡單說明】 無。 【主要元件符號說明】 無。 -45-Divinyl ether, which was used in the production example 6 and -A, , /ΟΛλ to give o-phenylphenol vinyl ether (formula (8)) to replace the frost in the production example 2, 曰f ^ , ^ A solution of the resin composition was prepared in the same manner as in Example 10 except for the obtained (2-phenylphenoxy)ethyl vinyl ether. Example 1 3 In addition to the compound (Α) used in the preparation, &amp;7; bisphenol F bis(2-vinyloxyethyl)ether (Formula (9)) obtained in Preparation Example 7 &amp; The upper layer was replaced with the solution of the resin composition in the same manner as in Example 12 except for the double-prepared F-acetyl group obtained in Production Example 5. Example 1 4 The bisphenol f bis(2-ethylene ethoxyethyl)ether (formula (9)) obtained in Production Example 7 was used instead of the yttrium compound (yield) to obtain the product obtained in Production Example 1. A solution of the resin composition was prepared in the same manner as in Example 1 except that hydrogen (tetra) fluorene was used. Example 1 5 In addition to the compound (A), bisphenol F diacrylate vinegar (synthesized product of Nard Research Co., Ltd.) was used. 'Compound (B) was obtained by using 2_(o-phenylbenzene-4 1-201211094 oxy)acrylic acid B. Ester (trade name: hrd-o 1, manufactured by Sakamoto Distillation Co., Ltd.), and compound (C) using 1,1,3,3-tetramethylbutyl-2-ethylhexanoate (product) A solution of the resin composition was prepared in the same manner as in Example 1 except that the blending amount of each component was changed as shown in Table 1 in the manner of "Per 〇 cta 〇, manufactured by Nippon Oil & Fat Co., Ltd.". Example 1 6 The same procedure as in Example 1 was carried out except that the compound (A) was a novolak epoxy propyl ether resin (a novolak type epoxy resin) (trade name: jER-152, manufactured by Mitsubishi Chemical Corporation). The solution of the resin composition is prepared in the same manner. Comparative Examples 1 to 9 Using the compound (A) shown in Table 1 and a polymerization initiator (C) in the amounts shown in Table 1, a solution of a resin composition was prepared in the same manner as in Example 2. &lt;Curing of Resin Composition&gt; The resin compositions obtained in Examples 1, 2, 4 to 9, and 16 'Comparative Examples 1 to 3, 9 were subjected to 5 〇〇〇mj / cm 2 by using a mercury lamp. The light was irradiated, followed by heating in i 00 ° C for 1 hour in a heating drier to obtain a cured product. The resin composition obtained in Example 3 '1 〇 to 15 and Comparative Examples 4 to 8 was heated at 150 C for 2 hours to obtain a cured product. &lt;Evaluation of moisture permeability&gt; The moisture permeability of the cured product was measured and adjusted to the moisture permeability of the resin slab of thickness 丨〇〇 at 60 ° C and 90% RH in accordance with JIS L1099 and JIS Z0208. -42-201211094 Table 1 shows the results of measurement of the moisture permeability of the cured product of the resin compositions obtained in Examples 1 to 16 and Comparative Examples 1 to 9. The cured product of the resin composition obtained in Examples 1 to 8 of the copolymer of the compound (A) and the compound (B) was compared with the polymer obtained by only the compound (A) (Comparative Example 1). A hard flattening of low moisture permeability can be obtained. Similarly, the cured product of Example 9 is a cured product of Comparative Example 4 and the cured product of Comparative Example 1 and the cured product of Comparative Example 1 are compared with the cured product of Comparative Example 5, and Example 12 The cured product was cured as compared with the hardened material of Comparative Example 6, the cured product of Comparative Example 7 which was subjected to "3, 14 and the hardened material of Example 15, the cured product of Comparative Example, and the cured product of Example 16," The η compound was lower in moisture permeability (low moisture permeability) than the cured product of Comparative Example 9. β不*43- 201211094 | Moisture permeability | η Β 'ωι 二*/Ί (N 〇 〇 CN 〇〇 (N N CN OS CN m 〇〇 (N 00 (N m CO 〇\ m 9 〇 (N inorganic filler) 〇D) wt% 1 s § 1 structure 1 cerium dioxide cerium dioxide talc talc dioxide day 1 1 polymerization initiator (C) wt% inch d 〇卜d 1-^ inch 〇ι-Η 1-^ FH Construction PI-2074 PI-2074 SI-60 PI-2074 PI-2074 PI-2074 PI-2074 PI-2074 i PI-2074 SI-60 SI-60 ! SI-60 SI-60 1 SI-60 Perocta 0 1 PI-2074 PI-2074 PI-2074 PI-2074 SI-60 SI-60 SI-60 SI-60 Perocta Ο PI-2074 1-functional compound (Β) wt% 29.7 11.9 On 20.8 29.7 39.6 49.5 Ο) 49.5 39.6 49.5 39.6 39.6 39.6 :39.6 29.7 1 1 1 1 1 1 1 1 1 Construction of Epoxypropyl Phenyl Ether Epoxypropyl Phenyl Epoxy Propyl Phenyl Ether Epoxypropyl Phenyl Ether O-Phenylphenol Epoxy Propyl ether o-phenylphenol epoxypropyl ether o-phenylphenol epoxypropyl ether o-phenylphenol epoxypropyl ether o-phenylphenol epoxypropyl ether phenylphenoxy) ethyl vinyl bond 1,1 biphenyl-2-yl (3-ethyl epoxypropan-3-yl) Ether o-phenylphenol epoxypropyl ether o-phenylphenol epoxypropyl ether i (2-phenyl phenyloxy) ethyl vinyl ether HRD-01 epoxy propyl phenyl ether 1 1 1 1 1 1 1 1 1 Compound with more than 2 functional groups (Α) wt% 69.3 27.7 27.7 48.5 69.3 59.4 27.7 49-5 59.4 49.5 59.4 1 59.4 59.4 L6.93 〇\ σ\ 49.5 49.5 On Os On 〇\ Os On σ\ On On 〇\ On ON On On Construction bisphenol F diglycidyl ether bisphenol F diglycidyl ether bisphenol F diglycidyl ether bisphenol F diglycidyl ether bisphenol F epoxide Propyl ether bisphenol F diglycidyl ether bisphenol F diglycidyl ether bisphenol F diglycidyl ether 3,4,3',4'-diepoxy biscyclohexyl hydrogenated bisphenol A Vinyl ether bisphenol F bis(3-ethyl propylene oxide-3-ylmercapto) ether bisphenol F divinyl ether bisphenol F bis(2-vinyloxyethyl) 3⁄4 | bisphenol F double ( 2-vinyloxyethyl)ether bisphenol F diacrylate phenol novolak type epoxy resin bisphenol F diglycidyl ether tetramethyl bisphenol diepoxypropyl ether bisphenol F diepoxypropyl Ether 3,4,3',4'-diepoxybicyclohexyl hydrogenated bisphenol A divinyl ether bisphenol F bis(3-ethyl propylene oxide-3-yl Ether bisphenol F divinyl ether bisphenol F bis(2-vinyloxyethyl) ether bisphenol F diacrylate phenol novolac type epoxy resin Example 1 Example 2 Example 3 Example 4 Implementation Example 5 Example 6 丨 Example 7 | Example 8 1 | Example 9 1 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 | Example 16 I Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Comparative Example 6 Comparative Example 7 Comparative Example 8 Comparative Example 9 - inch inch 丨 201211094 [Probability of industrial use] Hardening obtained by hardening the low moisture permeable resin composition of the electronic device of the present invention The material has a superior water vapor barrier property, and can be used as a sealing material or a sealing material for an electronic component requiring low treadiness such as an organic electroluminescence device, an electronic paper, or a solar battery. Further, the low moisture permeable resin composition for an electronic device of the present invention can also be used; ... [Simple description of the schema] None. [Main component symbol description] None. -45-

Claims (1)

201211094 七、申請專利範圍: 1. 一種被要.求有低透濕性的電子裝置用低透濕性樹脂組 成物’其特徵為含有:1分子中具有2個以上反應性官 能基(a)之化合物(A)、1分子中具有1個反應性官能基 (b)且分子量為5〇至1000之化合物(B)、與聚合起始劑 (C)。 2. 如申請專利範圍第1項之電子裝置用低透濕性樹脂組 成物’其令該化合物(A)與/或該化合物(B)具有1個以 上環狀骨架。 3 ·如申凊專利範圍第2項之電子裝置用低透濕性樹脂組 成物,其中該環狀骨架為相同或不同的苯環或環己烷 環。 4·如申請專利範圍第!至3項中任一項之電子裝置用低 透濕性樹脂組成物,其中相料1〇〇重量份之該化合 物(A)’該化合物(B)之含量為i至1000重量份。 5 ·如申請專利範圍第4 ji $發, 矛項之電子裝置用低透濕性樹脂組 成物,其_相對於1 〇〇產旦 、 重里份之該化合物(A),該化合 物(B)之含量為1〇至25〇重量份。 6·如申請專利範圍第…項二一項之電子裝置用低 透濕性樹脂組成物,其進—步含有無機填料⑼。 7.如申請專利範圍第i至6項中任一項之電子裝置用低 透濕性樹脂組成4勿,其進-步含有#偶合劑⑻。 8·如申請專利範圍第i至7項中任一項之電子裝置用低 透濕性樹脂組成物,其中該聚合起始劑(c)為光或熱陽 離子聚合起始劑、或是光或熱自由基聚合起始劑。 -46- 201211094 9.如申請專利範圍第1至8項中任一項之電子 透濕性樹脂組成物,其中該電子裝置為有. 光、電子紙或太陽能電池。 1 0 · —種硬化物,其係將如申請專利範圍第1至 一項之電子裝置用低透濕性樹脂組成物硬化ί 1 1. 一種封閉劑,其含有如申請專利範圍第1至 一項之電子裝置用低透濕性樹脂組成物。 1 2 . —種密封劑,其含有如申請專利範圍第1至 一項之電子裝置用低透濕性樹脂組成物。 1 3 . —種有機電致發光,其含有如申請專利範圍 之硬化物。 1 4. 一種電子紙,其含有如申請專利範圍第1 0 物。 1 5 . —種太陽能電池,其含有如申請專利範圍第 硬化物。 裝置用低 幾電致發 9項中任 •η成。 9項中任 9項中任 第10項 項之硬化 10項之 -47- 201211094 四、指定代表圖: (一) 本案指定代表圖為:無。 (二) 本代表圖之元件符號簡單說明: 無0 五、本案若有化學式時,請揭示最能顯示發明特徵的化學式: 201211094 修正本 第100128662號「低透濕性樹脂組成物及其硬化物」專利案 .^ (2011年12月9日修正) 七、申凊專利範圍: 1 · -種被要求有低透濕性的電子裝置用低透濕性樹脂組 成物’其特徵為含有:i分子中具有2個以上反應性官 月匕基(a)之化合物(A)、i分子中具有}個反應性官能基 (b)且分子量為5〇至1〇⑽之化合物(b)、與聚合起始劑 (C)。 Ο 2.如申請專利範圍第1項之電子裝置用低透濕性樹脂組 成物,其中該化合物(A)與/或該化合物(B)具有i個以 上環狀骨架。 3·如申請專利範圍第2項之電子裝置用低透濕性樹脂組 成物其中δ亥環狀骨架為相同或+㈣H α 環。 4 ·如申請專利範圍第1曼3 至3項中任一項之電子裝置用低 透濕性樹脂組成物’其中相對於100重量份之該化合 物(Α),該化合物(Β)之含量為1至1〇〇〇重量份。 5. 如申請專利範圍第4項之φ 、 喝t電子裝置用低透濕性樹脂組 成物,其中相封於〗on舌· 、 重里伤之該化合物(A),該化合 物(B)之含量為10至25〇重量份。 6. 如申請專利範圍第U 5項中任一項之電子裳置用低 透濕性樹脂組成物,其進—步含有無機填料⑼。 士 t α # Μ 圍第1 i 6項中任一項之電子裳置用低 透濕性樹脂組成物’其進—步含有矽烷偶合劑⑻。 8.如申請專利範圍第1 $ 7 号』粑固弟1至7項中任一項之電子裝置用低 201211094 修正本 透濕性樹脂組 成物,其中該聚合起始劑(c 、&gt; 離子聚合起始劑、或是光或熱自由基 ’&quot;、光或熱陽 9 ·如申請專利範圍第1至8項申任一項之電子 。 替先 透濕性樹脂組成物,其中該電子裝置為有機電薏用低 元件、電子紙或太陽能電池。 至欠201211094 VII. Patent application scope: 1. A low moisture permeability resin composition for electronic devices having low moisture permeability. It is characterized by containing: 2 or more reactive functional groups in one molecule (a) The compound (A), the compound (B) having one reactive functional group (b) in one molecule and having a molecular weight of from 5 Å to 1,000, and the polymerization initiator (C). 2. The low moisture permeable resin composition for an electronic device according to the first aspect of the invention, wherein the compound (A) and/or the compound (B) have one or more cyclic skeletons. 3. A low moisture permeable resin composition for an electronic device according to the second aspect of the invention, wherein the cyclic skeleton is the same or different benzene ring or cyclohexane ring. 4. If you apply for a patent scope! The low moisture permeable resin composition for an electronic device according to any one of the preceding claims, wherein the compound (A)' is contained in an amount of from 1 to 1000 parts by weight based on 1 part by weight of the compound. 5 · If the patent application scope is 4 ji $, the low moisture permeability resin composition for the electronic device of the spear, which is relative to the compound (A) which is produced in 1 liter, and the compound (B) The content is from 1 to 25 parts by weight. 6. The low moisture permeable resin composition for an electronic device according to the second aspect of the patent application, which further comprises an inorganic filler (9). 7. The low moisture permeability resin composition for an electronic device according to any one of claims 1 to 6, which further comprises a # coupling agent (8). The low moisture permeable resin composition for an electronic device according to any one of claims 1 to 7, wherein the polymerization initiator (c) is a photo or thermal cationic polymerization initiator, or light or Thermal radical polymerization initiator. The electronically permeable resin composition according to any one of claims 1 to 8, wherein the electronic device is an optical, electronic paper or solar cell. 1 0 - a hardened material which is hardened with a low moisture permeable resin composition for an electronic device according to claim 1 to 1. 1. A blocking agent containing the first to first patents as claimed The electronic device uses a low moisture permeable resin composition. A sealant comprising the low moisture permeable resin composition for an electronic device according to the first to the first aspect of the invention. An organic electroluminescence comprising a hardened material as claimed in the patent application. 1 4. An electronic paper containing the contents as claimed in the patent application. A solar cell comprising a hardened material as claimed in the patent application. The device uses a low number of electro-acceptances to generate η. Among the 9 items, 9 of them are the 10th item. The hardening of the item is 10 -47- 201211094 4. The designated representative figure: (1) The representative representative of the case is: None. (2) A brief description of the symbol of the representative figure: None 0. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 201211094 Amendment No. 100128662 "Low moisture permeable resin composition and cured product thereof Patent case.^ (Revised on December 9, 2011) VII. The scope of the patent application: 1 · A low moisture permeability resin composition for electronic devices requiring low moisture permeability' is characterized by: i a compound (A) having two or more reactive guanyl groups (a) in the molecule, a compound (b) having a reactive functional group (b) in the i molecule and having a molecular weight of 5 Å to 1 Å (10), and Polymerization initiator (C). 2. The low moisture permeability resin composition for an electronic device according to the first aspect of the invention, wherein the compound (A) and/or the compound (B) have i or more cyclic skeletons. 3. A low moisture permeable resin composition for an electronic device according to the second aspect of the invention, wherein the δH ring skeleton is the same or a +(tetra)H α ring. 4. The low moisture permeable resin composition for electronic devices of any one of claims 1 to 3, wherein the content of the compound (Β) is relative to 100 parts by weight of the compound (Α) 1 to 1 part by weight. 5. For example, in the application of patent item 4, φ, drink t, low moisture permeability resin composition for electronic devices, wherein the compound (A), the content of the compound (B) is sealed on the tongue. It is 10 to 25 parts by weight. 6. The composition of the low moisture permeable resin for electronic discharge according to any one of the claims of the invention, which further comprises an inorganic filler (9).士 t α # Μ 低 第 第 第 第 第 第 第 第 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 8. For example, the composition of the patent application No. 1 $7, the electronic device used in any of the items 1 to 7 is modified by the 201211094 modified moisture permeable resin composition, wherein the polymerization initiator (c, &gt; ion a polymerization initiator, or a light or thermal radical '&quot;, light or heat yang. 9. An electron according to any one of claims 1 to 8 of the patent application. The first moisture permeable resin composition, wherein the electron The device is a low-element, electronic paper or solar battery for organic electricity. 1〇.一種硬化物,其係將如申請專利範圍第1至〇 —項之電子裝置用低透濕性樹脂組成物硬化而成、中 1 1 · 一種封閉劑,其含有如申請專利範圍第1至9 ° —項之電子裝置用低透濕性樹脂組成物。 中 1 2. —種密封劑’其含有如申請專利範圍第1至9 一項之電子裝置用低透濕性樹脂組成物。 項中乜 1 3 · 一種有機電致發光元件,其含有如申請專利範 項之硬化物。 ㈤第1 〇 1 4 .種電子紙,其含有如申請專利範圍第丨〇項 物。 、夂噯化 15.一種太陽能電池,其含有如申請專利範圍第 硬化物。 U項史A hardened material obtained by hardening a low moisture permeability resin composition of an electronic device according to the first to third aspects of the patent application, wherein the sealing agent contains a sealing agent as claimed in the patent application. A low moisture permeable resin composition for an electronic device of 1 to 9 °. Medium 1 2. A type of sealant' which contains a low moisture-permeable resin composition for an electronic device according to the first to ninth aspects of the patent application. Item 乜 1 3 · An organic electroluminescence element containing a cured product as claimed in the patent application. (5) Article 1 1-4. An electronic paper containing the items of the scope of the patent application. 1. A solar cell comprising a cured product as claimed in the patent application. U item history
TW100128662A 2010-08-12 2011-08-11 Permeability resin composition, cured product and use thereof TWI591089B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2010180704 2010-08-12

Publications (2)

Publication Number Publication Date
TW201211094A true TW201211094A (en) 2012-03-16
TWI591089B TWI591089B (en) 2017-07-11

Family

ID=45567657

Family Applications (1)

Application Number Title Priority Date Filing Date
TW100128662A TWI591089B (en) 2010-08-12 2011-08-11 Permeability resin composition, cured product and use thereof

Country Status (3)

Country Link
JP (1) JP5812993B2 (en)
TW (1) TWI591089B (en)
WO (1) WO2012020688A1 (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105246940A (en) * 2013-05-28 2016-01-13 株式会社大赛璐 Curable composition for sealing optical semiconductor
CN105319619A (en) * 2014-06-27 2016-02-10 富士胶片株式会社 Polarizing plate protective film, polarizing plate, image display device and method of producing polarizing plate protective film
TWI614301B (en) * 2013-10-30 2018-02-11 Sekisui Chemical Co Ltd Blocking agent for organic EL display elements
CN107686714A (en) * 2016-08-04 2018-02-13 日本化药株式会社 Liquid crystal sealing agent and the liquid crystal display using the liquid crystal sealing agent
TWI636090B (en) * 2014-05-20 2018-09-21 日商積水化學工業股份有限公司 Sealant for organic electroluminescent display elements
TWI658062B (en) * 2012-11-28 2019-05-01 日商日本化藥股份有限公司 Resin composition and cured product (1) thereof
TWI833812B (en) * 2019-09-27 2024-03-01 日商積水化學工業股份有限公司 Photocurable resin composition for electronic devices

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5829856B2 (en) * 2011-07-29 2015-12-09 丸善石油化学株式会社 Method for producing aromatic vinyl ether
JP6228734B2 (en) * 2013-02-14 2017-11-08 日東電工株式会社 Resin sheet for encapsulating electronic components, resin-encapsulated semiconductor device, and method for producing resin-encapsulated semiconductor device
JP6474719B2 (en) * 2013-02-19 2019-02-27 株式会社ダイセル Curable composition, cured product thereof, optical member, and optical apparatus
JP6278624B2 (en) * 2013-07-12 2018-02-14 株式会社日本触媒 Metal oxide particle-containing composition and optical member
JP5703429B1 (en) * 2013-10-30 2015-04-22 積水化学工業株式会社 Sealant for organic EL display element
JPWO2015087807A1 (en) * 2013-12-11 2017-03-16 積水化学工業株式会社 Curable resin composition for sealing organic electroluminescence display element, curable resin sheet for sealing organic electroluminescence display element, and organic electroluminescence display element
JP6527390B2 (en) * 2014-06-03 2019-06-05 積水化学工業株式会社 Sealant for organic electroluminescent display device
WO2018052007A1 (en) * 2016-09-16 2018-03-22 積水化学工業株式会社 Sealing agent for organic electroluminescent display element
JP6228289B1 (en) * 2016-12-28 2017-11-08 株式会社ダイセル Composition for sealing an organic electroluminescence device
JP7123943B2 (en) * 2017-08-24 2022-08-23 デンカ株式会社 Encapsulants for organic electroluminescence devices
WO2021059420A1 (en) * 2019-09-26 2021-04-01 積水化学工業株式会社 Photocurable resin composition for electronic devices
KR20220069877A (en) * 2019-09-26 2022-05-27 세키스이가가쿠 고교가부시키가이샤 Photocurable resin composition for electronic devices
KR20230021827A (en) * 2021-08-06 2023-02-14 (주)이녹스첨단소재 Thermosetting liquid composition for an encapsulant of organic light emitting device

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4502367B2 (en) * 2004-02-04 2010-07-14 旭化成イーマテリアルズ株式会社 Method for manufacturing cylindrical flexographic printing plate capable of laser engraving
JP4548415B2 (en) * 2004-03-04 2010-09-22 東亞合成株式会社 UV curable composition
JP4570417B2 (en) * 2004-08-06 2010-10-27 ナミックス株式会社 Liquid sealing resin composition
JP2007277467A (en) * 2006-04-10 2007-10-25 Sony Chemical & Information Device Corp Curable resin composition
JP4999393B2 (en) * 2006-07-31 2012-08-15 旭化成ケミカルズ株式会社 Cationic photosensitive composition and cured product thereof
JP5234562B2 (en) * 2006-08-10 2013-07-10 旭化成ケミカルズ株式会社 Photosensitive composition
JP2008059945A (en) * 2006-08-31 2008-03-13 Nagase Chemtex Corp Method of manufacturing electronic device
JP2010018797A (en) * 2008-06-11 2010-01-28 Sekisui Chem Co Ltd Curable composition for optical parts, adhesive agent for optical parts, and sealing agent for organic electroluminescence element
JP5683073B2 (en) * 2009-01-20 2015-03-11 三菱化学株式会社 Epoxy resin composition for solar cell encapsulant and solar cell
JP5684460B2 (en) * 2009-04-06 2015-03-11 株式会社ダイセル Cationic polymerizable resin composition and cured product thereof

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI658062B (en) * 2012-11-28 2019-05-01 日商日本化藥股份有限公司 Resin composition and cured product (1) thereof
CN105246940A (en) * 2013-05-28 2016-01-13 株式会社大赛璐 Curable composition for sealing optical semiconductor
CN105246940B (en) * 2013-05-28 2018-09-04 株式会社大赛璐 Optical semiconductor sealing solidification compound
TWI614301B (en) * 2013-10-30 2018-02-11 Sekisui Chemical Co Ltd Blocking agent for organic EL display elements
TWI636090B (en) * 2014-05-20 2018-09-21 日商積水化學工業股份有限公司 Sealant for organic electroluminescent display elements
CN105319619A (en) * 2014-06-27 2016-02-10 富士胶片株式会社 Polarizing plate protective film, polarizing plate, image display device and method of producing polarizing plate protective film
CN107686714A (en) * 2016-08-04 2018-02-13 日本化药株式会社 Liquid crystal sealing agent and the liquid crystal display using the liquid crystal sealing agent
TWI833812B (en) * 2019-09-27 2024-03-01 日商積水化學工業股份有限公司 Photocurable resin composition for electronic devices

Also Published As

Publication number Publication date
WO2012020688A1 (en) 2012-02-16
TWI591089B (en) 2017-07-11
JPWO2012020688A1 (en) 2013-10-28
JP5812993B2 (en) 2015-11-17

Similar Documents

Publication Publication Date Title
TW201211094A (en) Low moisture permeability resin composition and cured product thereof
TW201529736A (en) Polyorganosilsesquioxane, hard coat film, adhesive sheet, and laminate
TW201202403A (en) Composition used for hard coating, hard coating film and display device
TWI582167B (en) Containing silicon hardened composition and hardened material
TW201231472A (en) Additional curable metallosiloxane compound
TW200940604A (en) Organosilicon compounds which have oxetanyl groups, and a method for the production and curable compositions of the same
TW201211160A (en) Curable composition
WO2005085317A1 (en) Ultraviolet-curing composition
TW201609851A (en) Curable resin having excellent post-curing flexibility, methacrylated curable resin, and liquid crystal sealing agent composition
TW200911887A (en) Silicon-containing compound, curable composition, and cured material
TW201522391A (en) Polymerizable composition containing reactive silicone compound
TW201504206A (en) Compound containing structural unit derived from vinyl ether compound
EP3498691B1 (en) Novel cationic photoinitiator, and preparation method therefor and applications thereof
KR20210151819A (en) Curable composition and cured product thereof
CN100462385C (en) Ultraviolet-curing composition
JP5719631B2 (en) Compound, derivative, composition, cured product, and method for producing compound and derivative
TW200806695A (en) (Meth)acrylic ester-based compound for energy ray-curable type resin
CN100558764C (en) Salt compounded of iodine of cationic photoinitiator polystyrene or its multipolymer and preparation method thereof
JP2015124286A (en) Curable composition
CN103189403A (en) Composition, moisture-capturing cured product, and electronic devices
TW201229055A (en) Liquid addition curable metallosiloxane
WO2021039480A1 (en) Cationic curing agent, method for producing same and cationically curable composition
TW202000720A (en) Cationically curable composition and cured product production method
US20190194454A1 (en) Compound, Cationic Curing Agent, and Cationic Curable Composition
TW201221541A (en) High refractive resin composition and cured resin