TW200839324A - Polarizing plate and method of manufacturing the same - Google Patents

Polarizing plate and method of manufacturing the same Download PDF

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Publication number
TW200839324A
TW200839324A TW097101655A TW97101655A TW200839324A TW 200839324 A TW200839324 A TW 200839324A TW 097101655 A TW097101655 A TW 097101655A TW 97101655 A TW97101655 A TW 97101655A TW 200839324 A TW200839324 A TW 200839324A
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Taiwan
Prior art keywords
polarizing plate
film
component
mass
composition
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TW097101655A
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Chinese (zh)
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Tetsuya Yamamura
Masashi Okamoto
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Jsr Corp
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Priority claimed from JP2007062694A external-priority patent/JP4816515B2/en
Priority claimed from JP2007069667A external-priority patent/JP2008233279A/en
Priority claimed from JP2007080423A external-priority patent/JP2008241946A/en
Priority claimed from JP2007080422A external-priority patent/JP4816533B2/en
Application filed by Jsr Corp filed Critical Jsr Corp
Publication of TW200839324A publication Critical patent/TW200839324A/en

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/06—Coating with compositions not containing macromolecular substances
    • C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/08—Copolymers of ethene
    • C08L23/0807—Copolymers of ethene with unsaturated hydrocarbons only containing more than three carbon atoms
    • C08L23/0815—Copolymers of ethene with aliphatic 1-olefins
    • C08L23/0823—Copolymers of ethene with aliphatic cyclic olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/02—Homopolymers or copolymers of unsaturated alcohols
    • C08L29/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J169/00—Adhesives based on polycarbonates; Adhesives based on derivatives of polycarbonates
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3025—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state
    • G02B5/3033—Polarisers, i.e. arrangements capable of producing a definite output polarisation state from an unpolarised input state in the form of a thin sheet or foil, e.g. Polaroid
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/04—Homopolymers or copolymers of ethene
    • C08J2323/08—Copolymers of ethene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2329/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • C08J2329/02—Homopolymers or copolymers of unsaturated alcohols
    • C08J2329/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Nonlinear Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Materials Engineering (AREA)
  • Polarising Elements (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

This invention is to provide a polarizing plate which can be manufactured in a short period of time with a simple process and has excellent film-cutting endurance. The polarizing plate 1 is formed by layering protective films 5 and 6 composed of a norbornene based resin film on both surfaces of a polyvinyl alcohol based polarizing film 2 via adhesive layers 3 and 4. The adhesive layers 3 and 4 are composed of a cured product of a radiation curing composition, including: (A) an alicyclic epoxy compound; (B) a compound having a number average molecular weight equal to or higher than500 and containing at least one hydroxyl group; and (C) a photoacid generator.

Description

200839324 九、發明說明 【發明所屬之技術領域】 本發明係有關於一種偏光板及其製造方法。 【先前技術】 近年，顯示文字、圖像等之顯示裝置已被廣泛利用來 作爲液晶顯示裝置。如此之液晶顯示裝置一般係含有2片 之偏光板、與配置於其間之玻璃基板、透明電極、濾色片 、配光膜、液晶等所構成之液晶胞。 一般，於液晶顯示裝置所使用之偏光板係於已延伸配 向之聚乙烯醇（以下，亦稱爲PVA)系薄片吸附碘或二色系 染料之偏光膜（偏光器）的單面或雙面，介由黏著劑層貼合 三乙醯基纖維素（以下，亦稱爲TAC)系薄膜等之保護膜而 構成者。 如此之偏光板係已提出一種偏光板，其特徵在於：於 聚乙烯醇系偏光膜之至少單面介由聚乙烯醇系黏著劑層貼 合保護膜之偏光板中，黏著劑層爲由含有水性環氧化合物 之聚乙烯醇系黏著劑所構成，黏著劑中之水溶性環氧化合 物與聚乙烯醇系樹脂之比爲（5〜5 0)/ 1 00(固形分重量比）（參 照特開平09-2 5 8 023號公報）。又，於此文獻中係亦記載著 上述保護膜鹼化處理表面之三乙醯基纖維素。 若依使用水系黏著劑及TAC系保護膜之上述文獻記 載之技術，可使上述黏著劑之水分介由透濕性高之TAC 系保護膜而蒸發，使黏著劑硬化。因此，可藉由比較簡易 -5- 200839324 的製造步驟而得到偏光板。又，水系黏著劑與TAC系保 護膜係黏著性高，故可得到具有優異之黏著強度的偏光板 〇 但’ TAC系保護膜爲高的透濕性之故，有耐濕熱性低 之問題。亦即，在如車輛時等之高溫高濕的環境下，有時 產生變形等，有很難維持高的偏光性能之問題。 是故，已提出一種使用具有低的透濕性之環狀烯烴系 樹脂薄膜（環烯烴系樹脂薄膜；以下，亦稱爲COP系樹脂 薄膜）取代TAC系保護膜之方法。 例如，已提出一種偏光板，其特徵在於：於聚乙烯醇 系樹脂所構成之偏光膜的一者之面，介由從含有聚酯系離 子單體型胺基甲酸樹脂與具有縮水甘油基之化合物的水性 組成物之第一黏著劑層而層合環烯烴系樹脂薄膜，於另一 面係介由與前述第一黏著劑層相異之水性組成的第二黏著 劑層而層合醋酸纖維素系薄膜（參照特開2005-20845 6號公 報)。 又，已提出一種偏光板之製造方法，其係使偏光器與 偏光器之保護膜進行黏著層合，其特徵在於：至少含有水 性乳化液與聚乙烯醇與聚異氰酸酯化合物，使用被調整成 B型黏度計之黏度（2(TC)爲0.03〜lPa_ s之水性胺基甲酸 酯系黏著劑，而使上述偏光器與保護膜進濕式積層（參照 特開2004-3 7 84 1號公報）。又，於此文獻中係亦記載著由 上述保護膜由熱塑性飽和降冰片烯系樹脂所構成。 200839324 【發明內容】 (發明之揭示） 若依特開2005-208456號公報記載之技術，因可介由 透濕性高之醋酸纖維素系薄膜而使水系黏著劑之水分蒸散 ，故與特開平09-2 5 8 023號公報記載之技術同樣地，可以 比較簡單的步驟得到偏光板。 但，因於單側具有透濕性高之醋酸纖維素系薄膜，故 有耐濕熱性尙不充分之問題，或水系黏著劑之第一黏著劑 層與環烯烴系樹脂薄膜之黏著性不充分之問題。 若依特開2004-37841號公報記載之技術，因偏光器之 雙面的保護膜由熱塑性飽和降冰片烯系樹脂所構成，故可 得到耐濕熱性良好之偏光板。 但，因使用透濕性低之保護膜，使水系黏著劑之水性 胺基甲酸酯系黏著劑的水分蒸發而硬化需要長時間，與使 用TAC系薄膜之情形相比而製造步驟變繁雜之問題仍存 在。又，由熱塑性飽和降冰片烯系樹脂所構成之保護膜係 疏水性，故與水系黏著劑之黏著性不充分之問題仍存在。 另外，當製造偏光板時，尋求優異之耐晶片切割性。 亦即，偏光板一般係使偏光板用之層合片切割成所希望之 大小而得到，但此截切時，有於裁切部分（裁切後之端部） 產生剝離（黏著劑層之缺角）之問題。此剝離係不僅降低剝 離部分之偏光性能，恐促進偏光板之吸濕，引起在高溫高 濕下等之變形。 又，偏光板係於液晶顯示面板介由黏著劑而貼黏。其 200839324 時，於偏光板與液晶顯示面板之問存在氣泡，於偏光板會 出現變形。此時，爲再利用液晶顯示面板，可使偏光板從 液晶顯示面板剝離，採取貼合新的偏光板之步驟（再製步 驟）。但’形成偏光板之保護膜與偏光器之黏著力弱之情 形，係剝離此偏光板時，有時保護膜與偏光器會剝離。其 時’於液晶顯示面板會殘留保護膜，因附加剝離保護膜之 步驟，製造效率會降低。 因此’於偏光板之製造時所使用之用以使保護膜與偏 光器黏著之黏著劑的特性，於再製造時，亦尋求發揮偏光 器與保護膜之間的強固黏著強度（剝離強度）。 又，偏光板係尋求翹曲少者。亦即，偏光板係爲防止 液晶胞受紫外線損傷，使用於偏光板之保護膜的一者外， 必須添加紫外線吸收劑或設置紫外線吸收層。因此，於偏 光板之製造中使黏著劑硬化時，實質，從未添加紫外線吸 收劑之保護膜側只進行光照射，而於具有2層之黏著劑層 的照射強度產生差。其結果，於層合形成之偏光板產生翹 曲，有時對其後之加工性會造成影響。 本發明係有鑑於上述之背景而成者，製造步驟可以簡 單且短時間進行製造，目的在於提供一種耐晶片切割性（ 裁切時未產生剝離）、耐濕熱性優之偏光板及其製造方法 。又，本發明之目的在於提供一種保護膜-黏著劑層間之 黏著性（剝離強度）高、翹曲變形少之偏光板及其製造方法 〇 本發明人係爲解決上述課題，經專心硏究之結果’發 -8- 200839324 現使用含有特定成分之輻射線硬化性組成物而黏著偏光膜 與保護膜，俾可以簡單之製造步驟且短時間進行製造耐晶 片切割性、耐濕熱性等優之偏光板，終完成本發明。 亦即，本發明係提供以下[1]〜[10]者。 [1] 一種偏光板，其係於聚乙烯醇系偏光膜的至少單面， 介由黏著劑層而層合保護膜所構成，其特徵在於：上述黏 著劑層由含有如下之輻射線硬化性組成物的硬化物所構成 ，即（A)脂環式環氧化合物、（B)具有至少—個羥基且數目 平均分子量爲5 00以上之化合物、及（C)光酸產生劑。 [2] 如上述[1]之偏光板’其中上述成分（A)爲具有（人”於！ 分子中具有2個以上脂環式環氧基之化合物、及/或（A2)以 下述式（1)所示之具有1個脂環式環氧基之化合物。200839324 IX. Description of the Invention [Technical Field] The present invention relates to a polarizing plate and a method of manufacturing the same. [Prior Art] In recent years, display devices for displaying characters, images, and the like have been widely used as liquid crystal display devices. Such a liquid crystal display device generally includes two polarizing plates, a liquid crystal cell composed of a glass substrate disposed therebetween, a transparent electrode, a color filter, a light distribution film, and a liquid crystal. Generally, a polarizing plate used in a liquid crystal display device is one-sided or double-sided on a polarizing film (polarizer) in which an extended aligning polyvinyl alcohol (hereinafter, also referred to as PVA)-based sheet adsorbs iodine or a two-color dye. A protective film such as a triethylenesulfonated cellulose (hereinafter also referred to as TAC)-based film is bonded to the adhesive layer. In such a polarizing plate, a polarizing plate has been proposed, in which a polarizing plate is bonded to a protective film of at least one side of a polyvinyl alcohol-based polarizing film via a polyvinyl alcohol-based adhesive layer, and the adhesive layer is contained. a polyvinyl alcohol-based adhesive of a water-based epoxy compound, wherein the ratio of the water-soluble epoxy compound to the polyvinyl alcohol-based resin in the adhesive is (5 to 50) / 100 (solid weight ratio) (refer to Kaiping 09-2 5 8 023). Further, in this document, the triacetyl cellulose which is alkalized on the surface of the protective film is also described. According to the technique described in the above document using a water-based adhesive and a TAC-based protective film, the moisture of the above-mentioned adhesive can be evaporated by a TAC-based protective film having a high moisture permeability to cure the adhesive. Therefore, the polarizing plate can be obtained by a relatively simple manufacturing process of -5-200839324. Further, since the water-based adhesive has high adhesion to the TAC-based protective film, a polarizing plate having excellent adhesive strength can be obtained. However, the TAC-based protective film has a high moisture permeability and has a problem of low moist heat resistance. In other words, in an environment of high temperature and high humidity such as a vehicle, deformation or the like may occur, and it is difficult to maintain high polarization performance. Therefore, a method of using a cyclic olefin-based resin film (cycloolefin-based resin film; hereinafter, also referred to as a COP-based resin film) having a low moisture permeability in place of the TAC-based protective film has been proposed. For example, a polarizing plate has been proposed which is characterized in that one of the polarizing films composed of a polyvinyl alcohol-based resin contains a polyester-based ionic monomer-type urethane resin and a glycidyl group. Laminating a olefin-based resin film on the first adhesive layer of the aqueous composition of the compound, and laminating the cellulose acetate on the other side via a second adhesive layer having an aqueous composition different from the first adhesive layer A film (refer to Japanese Laid-Open Patent Publication No. 2005-20845-6). Further, a method for producing a polarizing plate has been proposed in which a polarizer and a protective film of a polarizer are adhesively laminated, characterized in that at least an aqueous emulsion and a polyvinyl alcohol and a polyisocyanate compound are contained, and the use is adjusted to B. The viscosity of the viscometer (2 (TC) is an aqueous urethane-based adhesive of 0.03 to 1 Pa_s, and the polarizer and the protective film are wet-laid (refer to Japanese Patent Publication No. 2004-3 7 84 1 Further, in this document, it is described that the protective film is composed of a thermoplastic saturated norbornene-based resin. 200839324 [Disclosure of the Invention] The technique described in Japanese Patent Laid-Open Publication No. 2005-208456, Since the moisture of the water-based adhesive can be evaporated by the cellulose acetate-based film having a high moisture permeability, the polarizing plate can be obtained in a relatively simple manner, similarly to the technique described in JP-A-H09-2 58 023. However, since the cellulose acetate-based film having a high moisture permeability on one side has a problem that moisture-heat resistance is insufficient, or the adhesion between the first adhesive layer of the water-based adhesive and the cycloolefin-based resin film is not high. According to the technique described in Japanese Laid-Open Patent Publication No. 2004-37841, since the protective film on both sides of the polarizer is made of a thermoplastic saturated norbornene-based resin, a polarizing plate having good moist heat resistance can be obtained. When a protective film having a low moisture permeability is used, it takes a long time to evaporate the water of the aqueous urethane-based adhesive of the water-based adhesive, and the manufacturing process becomes complicated compared with the case of using a TAC-based film. Further, since the protective film composed of the thermoplastic saturated norbornene-based resin is hydrophobic, the problem of insufficient adhesion to the aqueous adhesive is still present. Further, when manufacturing a polarizing plate, an excellent resistance to wafer cutting is sought. That is, the polarizing plate is generally obtained by cutting the laminated sheet for the polarizing plate into a desired size, but when the cutting is performed, peeling occurs at the cut portion (the end portion after cutting) (adhesive agent) The problem of the lack of corners of the layer. This peeling system not only reduces the polarizing performance of the peeling portion, but also promotes the moisture absorption of the polarizing plate, causing deformation under high temperature and high humidity, etc. Further, the polarizing plate is exposed to liquid crystal display. The panel is adhered by an adhesive. When it is 200839324, there are bubbles in the polarizing plate and the liquid crystal display panel, and the polarizing plate may be deformed. At this time, in order to reuse the liquid crystal display panel, the polarizing plate can be removed from the liquid crystal display panel. Peeling, take the step of bonding a new polarizing plate (reproduction step). However, when the adhesion between the protective film forming the polarizing plate and the polarizer is weak, when the polarizing plate is peeled off, the protective film and the polarizer may be peeled off. At this time, the protective film remains on the liquid crystal display panel, and the manufacturing efficiency is lowered by the step of peeling off the protective film. Therefore, the adhesive used to bond the protective film to the polarizer is used in the manufacture of the polarizing plate. In terms of remanufacturing, it is also sought to exert a strong adhesive strength (peel strength) between the polarizer and the protective film. Moreover, the polarizing plate is intended to be less warped. That is, the polarizing plate is for preventing the liquid crystal cell from being damaged by ultraviolet rays, and it is necessary to add an ultraviolet absorber or an ultraviolet absorbing layer in addition to one of the protective films of the polarizing plate. Therefore, when the adhesive is cured in the production of the polarizing plate, substantially only the side of the protective film from which the ultraviolet absorbing agent is not applied is irradiated with light, and the irradiation strength of the adhesive layer having two layers is inferior. As a result, the polarizing plate formed by lamination generates warpage, which may affect the subsequent workability. The present invention has been made in view of the above-described background, and the manufacturing steps can be easily and quickly manufactured, and the object of the invention is to provide a polarizing plate which is resistant to wafer cutting property (no peeling at the time of cutting) and excellent in moist heat resistance, and a method for producing the same . Moreover, an object of the present invention is to provide a polarizing plate having a high adhesiveness (peeling strength) between the protective film and the adhesive layer, and a method for producing the same, and the method for producing the same, and the present inventors have focused on the above problems. RESULTS 'Fa-8-200839324 The polarizing film and the protective film are adhered to each other using a radiation curable composition containing a specific component, and the polarizing film and the protective film can be manufactured in a short period of time, and the polarizing resistance such as wafer cutting property and moisture heat resistance can be manufactured in a short time. The board finally completes the invention. That is, the present invention provides the following [1] to [10]. [1] A polarizing plate comprising at least one surface of a polyvinyl alcohol-based polarizing film and laminated with a protective film via an adhesive layer, wherein the adhesive layer contains radiation curable properties as follows The cured product of the composition comprises (A) an alicyclic epoxy compound, (B) a compound having at least one hydroxyl group and having a number average molecular weight of 500 or more, and (C) a photoacid generator. [2] The polarizing plate of the above [1] wherein the component (A) is a compound having two or more alicyclic epoxy groups in the molecule, and/or (A2) is represented by the following formula ( 1) A compound having one alicyclic epoxy group as shown.

(式中，R1、R2及R3係分別獨立地爲氫原子或甲基）。 [3] 如上述[1]或[2]之偏光板，其中上述成分（B)之數目平 均分子量爲以上。 [4] 如上述[1]〜[3]項中任一項的偏光板，其中上述成分（B) 爲以下述式（2)所示之化合物。 200839324 H0-(R4-0-C0-0)m-(R5-0-C0-0)n-R6-0H (2) (式中，R4及R5係分別獨立地表示碳數2〜12的2價烴基， R6係表示與R4與R5之任一者相同的構造；m爲2〜150，η 爲0〜150，且m + n爲2〜200)。 [5]如上述[1]〜[4]中任一項的偏光板，其中上述（C)成分爲 以下述式（4)所示之鑰鹽。(wherein R1, R2 and R3 are each independently a hydrogen atom or a methyl group). [3] The polarizing plate according to the above [1] or [2] wherein the number of the above components (B) is more than the average molecular weight. [4] The polarizing plate according to any one of the above [1], wherein the component (B) is a compound represented by the following formula (2). 200839324 H0-(R4-0-C0-0)m-(R5-0-C0-0)n-R6-0H (2) (wherein R4 and R5 each independently represent a carbon number of 2 to 12; The valent hydrocarbon group, R6 represents the same structure as any of R4 and R5; m is 2 to 150, η is 0 to 150, and m + n is 2 to 200). [5] The polarizing plate according to any one of the above [1], wherein the component (C) is a key salt represented by the following formula (4).

[R7aR8bR9cR10dZ] + PF6' (4) (式中’ IW離子爲鐵離子，Z表不S、Se、Te、P、As、Sb 、Bi、Ο、I、Br、Cl 或 Νξ N，R7、R8、R9及 R10係表示 互爲相同或相異之有機基；a、b、c及d分別爲〇〜3之螯 數，（a + b + c + d-Ι)係相等於z之價數）。 [6]如上述[1]〜[5]中任一項的偏光板，其中上述輻射線硬 化性組成物進一步含有（D)以下述式（5 )所示之化合物。[R7aR8bR9cR10dZ] + PF6' (4) (wherein IW ion is iron ion, Z is not S, Se, Te, P, As, Sb, Bi, Ο, I, Br, Cl or Νξ N, R7, R8 , R9 and R10 represent organic groups which are identical or different from each other; a, b, c and d are the chelate numbers of 〇~3, respectively, and (a + b + c + d-Ι) is equivalent to the valence of z ). [6] The polarizing plate according to any one of the above [1], wherein the radiation-hardening composition further contains (D) a compound represented by the following formula (5).

12^ (5)12^ (5)

R (式中，R11、R12及R13係分別獨立地爲一價之有機基，而 Rll〜Rl3之中至少2個爲-R14〇C〇CR15 = CH2，R14係碳數2〜8 -10- 200839324 之2價有機基，R15爲氫原子或甲基）。 [7] —種偏光板，其係於聚乙烯醇系偏光膜的至少單面’ 介由黏著劑層而層合保護膜，其特徵在於：上述黏著齊1 ® 由含有如下之輻射線硬化性組成物的硬化物所構成’即 (A)脂環式環氧化合物、及（C)以下述式（4)所示之光酸產生 劑。 [R7aR8bR9cR10dZ] + PF6_ (4) (式中，陽離子爲銷離子，Z表示S、Se、Te、P、As、Sb 、Bi、Ο、I、Br、Cl 或 N 三 N，R7、R8、R9及 R10係表示 互爲相同或相異之有機基；a、b、c及d分別爲〇〜3之整 數，（a + b + c + d-1)係相等於Z之價數）。 [8] 如上述[1]〜[7] φ任一項的偏光板，其中上述輻射線硬 化性組成物當形成厚度200μιη之硬化物時，波長5 5 0tim之 光的透過率爲70%以上。 [9] 如上述[1]〜[8]中任一項的偏光板，其中上述保護膜由 環狀烯烴系樹脂所構成。 [10] —種偏光板之製造方法，係如上述[1]〜[9]中任一項的 偏光板之製造方法，包含如下步驟：於偏光膜之至少單面 ’介由上述輻射線硬化性組成物而層合保護膜之步驟；與 光照射該輻射線硬化性組成物而硬化，得到偏光板之硬化 步驟。 本發明之偏光板係因黏著劑層爲由具有特定之成分組 -11 - 200839324 成的輻射線硬化性組成物之硬化物所構成，故具有優異之 耐晶片切割性（裁切時，不產生黏著劑層之剝離）等。 本發明之偏光板係因黏著劑層爲由具有特定之成分組 成的非水系之輻射線硬化性組成物之硬化物所構成，即使 使用非透濕性之環狀烯系樹脂薄膜作爲保護膜，亦不須要 水分之蒸發，而可以短時間得到良好之黏著性。又，亦可 於偏光膜之雙面適用環狀烯烴系樹脂薄膜作爲保護膜。此 時’可得到特優之耐濕熱性，即使在高溫高濕之環境下亦 可維持高的偏光性能。 若依本發明之偏光板的製造方法，藉於偏光膜之單面 或雙面’介由黏著劑層形成用之輻射線硬化性組成物而層 合保護膜，使該輻射線硬化性組成物進行輻射線照射而硬 化之簡易操作，俾可製造偏光板。因此，如使用水系黏著 劑之情形，不須進行水分之除去。又，即使使用非透濕性 之環狀烯系樹脂薄膜作爲保護膜，亦如使用水性之黏著劑 情形，製造步驟不會煩雜化及長時間化，而且，可得到各 層間之黏著性優的層合薄膜的偏光板。 (用以實施發明之最佳形態） 本發明之偏光板係於聚乙烯醇系偏光膜的單面或雙面 ’介由黏著劑層而層合保護膜所構成。 首先，詳細地說明有關形成黏著劑層之輻射線硬化性 組成物的各成分。 •12- 200839324 [成分（A)] 構成輻射線硬化性黏著劑用組成物之成分（A)係於1分 子中含有1個以上脂環式環氧基的脂環式環氧化合物。成 分（A)係可舉例如（A1)於1分子中具有2個以上脂環式環氧 基之化合物、（A2)於1分子中具有1個脂環式環氧基之化合 物。在本發明中，就成分（A)而言，可使成分（A1)及成分 (A2)之任一者單獨或倂用此等而使用。 成分（A)中，若含有成分（A1)(於1分子中具有2個以上 脂環式環氧基之脂環式環氧化合物）5 0質量％以上，可得到 更良好之硬化速度或機械強度。又，就成分（A)而言，藉 由使用成分（A2)，可提昇輻射線硬化性黏著劑用組成物之 硬化性（硬化速度），可使該組成物低黏度化。 可使用來作爲成分（A 1)之脂環式環氧化合物的具體例 ，可舉例如3,4-環氧基環己基甲基-3’，4’-環氧基環己烷羧 酸酯、2-(3,4-環氧基環己基-5,5-螺-3,4-環氧基）環己烷-間-二噁烷、雙（3，4-環氧基環己基甲基）己二酸酯、雙（3,4-環氧基-6-甲基環己基甲基）己二酸酯、（3,4-環氧基-6-甲基 環己基- 3’，4’-環氧基- 6’-甲基環己烷羧酸酯、ε -己內酯改 性3，4-環氧基環己基甲基-3’，4’·環氧基環己烷羧酸酯、三 甲基己內酯改性3,4-環氧基環己基甲基-3’，4’-環氧基環己 烷羧酸酯、/3-甲基- (5-戊內酯改性3,4-環氧基環己基甲 基-3’，4’-環氧基環己烷羧酸酯、亞甲基雙（3，4·環氧基環己 烷）、己二醇之二（3，4-環氧基環己基甲基）醚、亞甲基雙 (3,4-環氧基環己烷羧酸酯）、環氧基環六氫酞酸二辛酯、 -13- 200839324 環氧基環六氫酞酸二-2-乙基己酯等。 此等之脂環式環氧化合物之中，宜爲3,4-環氧基環己 基甲基·3’，4’-環氧基環己烷羧酸酯、雙（3,4-環氧基環己基 甲基）己二酸酯、ε-己內酯改性3，4-環氧基環己基甲基-3’，4’-環氧基環己烷羧酸酯、三甲基己內酯改性3,4-環氧 基環己基甲基-3’，4’-環氧基環己烷羧酸酯、甲基-5-戊 內酯改性3,4-環氧基環己基甲基-3，，4，-環氧基環己烷羧酸 酯’更宜爲3,4-環氧基環己基甲基-3，，4，-環氧基環己烷羧 酸酯、雙（3，4-環氧基環己基甲基）己二酸酯。 此等之市售品可舉例如 Celloxide 202 1、Celloxide 202 1 P、Celloxide 208 1、Celloxide 2083、Celloxide 2085 、Epolid GT-300、Epolid GT-301、Epolid GT-3 02、 Epolid GT-400、Epolid 401、Epolid 403(以上，Daicel 化 學工業公司製）、KRM2199(Adeka公司製）等。 成分（A2)之較佳例可舉例如以下述式（1)所示之化$ 物（脂環式二環氧化合物）。R (wherein R11, R12 and R13 are each independently a monovalent organic group, and at least two of R11 to Rl3 are -R14〇C〇CR15 = CH2, and R14 is a carbon number of 2 to 8 -10- 200839324 A divalent organic group, R15 is a hydrogen atom or a methyl group). [7] A polarizing plate which is formed by laminating a protective film on at least one side of a polyvinyl alcohol-based polarizing film via an adhesive layer, wherein the adhesion is 1 + contains radiation hardening as follows The cured product of the composition constitutes the (A) alicyclic epoxy compound and (C) a photoacid generator represented by the following formula (4). [R7aR8bR9cR10dZ] + PF6_ (4) (wherein the cation is a pin ion, Z represents S, Se, Te, P, As, Sb, Bi, Ο, I, Br, Cl or N N N, R7, R8, R9 And R10 represents an organic group which is the same or different from each other; a, b, c and d are integers of 〇~3, respectively, and (a + b + c + d-1) is equivalent to the valence of Z). [8] The polarizing plate according to any one of [1] to [7], wherein, in the radiation curable composition, when a cured product having a thickness of 200 μm is formed, a transmittance of light having a wavelength of 550 tim is 70% or more. . [9] The polarizing plate according to any one of [1] to [8] wherein the protective film is composed of a cyclic olefin resin. [10] The method for producing a polarizing plate according to any one of the above [1] to [9], comprising the step of: hardening at least one side of the polarizing film by the radiation. a step of laminating a protective film with a composition; and curing the radiation curable composition with light to obtain a hardening step of the polarizing plate. The polarizing plate of the present invention is excellent in resistance to wafer cutting because the adhesive layer is composed of a cured product of a radiation curable composition having a specific composition group -11 - 200839324 (when cutting, no generation occurs) Peeling of the adhesive layer). In the polarizing plate of the present invention, the adhesive layer is composed of a cured product of a non-aqueous radiation curable composition having a specific composition, and even if a non-hygroscopic cyclic olefinic resin film is used as a protective film, There is no need for evaporation of water, but good adhesion can be obtained in a short time. Further, a cyclic olefin resin film may be applied as a protective film on both sides of the polarizing film. At this time, excellent heat and humidity resistance can be obtained, and high polarization performance can be maintained even in a high temperature and high humidity environment. According to the method for producing a polarizing plate of the present invention, the radiation curable composition is laminated by laminating a protective film with a radiation curable composition for forming an adhesive layer on one side or both sides of the polarizing film. It is easy to harden by radiation irradiation, and a polarizing plate can be manufactured. Therefore, if a water-based adhesive is used, removal of moisture is not required. Further, even if a non-hygroscopic cyclic olefinic resin film is used as the protective film, as in the case of using an aqueous adhesive, the production steps are not complicated and prolonged, and adhesion between the layers can be excellent. A polarizing plate of a laminated film. (Best Mode for Carrying Out the Invention) The polarizing plate of the present invention is constituted by laminating a protective film on one side or both sides of a polyvinyl alcohol-based polarizing film via an adhesive layer. First, each component of the radiation curable composition forming the adhesive layer will be described in detail. • 12-200839324 [Component (A)] The component (A) constituting the composition for a radiation curable adhesive is an alicyclic epoxy compound containing one or more alicyclic epoxy groups in one molecule. The component (A) is, for example, a compound having two or more alicyclic epoxy groups in one molecule and (A2) a compound having one alicyclic epoxy group in one molecule. In the present invention, as the component (A), either one of the component (A1) and the component (A2) can be used singly or in combination. In the component (A), if the component (A1) (an alicyclic epoxy compound having two or more alicyclic epoxy groups in one molecule) is contained in an amount of 50% by mass or more, a more excellent curing rate or mechanical property can be obtained. strength. In addition, the component (A) can improve the hardenability (hardening rate) of the radiation curable adhesive composition by using the component (A2), and the composition can be made low in viscosity. Specific examples of the alicyclic epoxy compound which can be used as the component (A 1) include, for example, 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate. , 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane-m-dioxane, bis(3,4-epoxycyclohexyl Adipate, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, (3,4-epoxy-6-methylcyclohexyl-3', 4'-Epoxy-6'-methylcyclohexanecarboxylate, ε-caprolactone modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexane Carboxylate, trimethyl caprolactone modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, /3-methyl-(5-pentyl) Lactone-modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, methylenebis(3,4.epoxycyclohexane), Di(3,4-epoxycyclohexylmethyl)ether, methylene bis(3,4-epoxycyclohexanecarboxylate), dioctyl epoxide hexahydrophthalate , -13- 200839324 Epoxycyclohexahydrofuric acid di-2-ethylhexyl ester, etc. Among the cyclic epoxy compounds, 3,4-epoxycyclohexylmethyl·3',4'-epoxycyclohexanecarboxylate, bis(3,4-epoxycyclohexyl) Modified by adipate, ε-caprolactone, modified 3,4-epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, trimethylcaprolactone 3,4-Epoxycyclohexylmethyl-3',4'-epoxycyclohexanecarboxylate, methyl-5-valerolactone modified 3,4-epoxycyclohexylmethyl- 3,4,-epoxycyclohexanecarboxylate' is more preferably 3,4-epoxycyclohexylmethyl-3,4,-epoxycyclohexanecarboxylate, bis (3) , 4-epoxycyclohexylmethyl) adipate. Such commercially available products include, for example, Celloxide 202 1 , Celloxide 202 1 P, Celloxide 208 1, Celloxide 2083, Celloxide 2085, Epolid GT-300, Epolid. GT-301, Epolid GT-3 02, Epolid GT-400, Epolid 401, Epolid 403 (above, manufactured by Daicel Chemical Industry Co., Ltd.), KRM2199 (made by Adeka Co., Ltd.), etc. Preferred examples of the component (A2) include, for example, the following The compound (alicyclic diepoxide) represented by the formula (1).

(式中，R1、R2及R3係分別獨立地爲氫原子或甲基）° 以式（1)所示之化合物的具體例可舉例如1，2 : 8，9 •14- 200839324 環氧基棒橡儲等。此市售品可舉例如Celloxide3000(Daicel 化學工業公司製）等。 輻射線硬化性黏著劑用組成物係含有成分（A 1 )及/或 成分（A2)作爲成分（A)。 輻射線硬化性黏著劑用組成物含有成分（A1)時，輻射 線硬化性黏者劑用組成物中之成分（A 1)的含有率係當輸射 線硬化性黏著劑用組成物之全量（該組成物含有有機溶劑 Φ 時’係除去有機溶劑的全量）爲100質量％，爲20〜80質量％ ’宜爲25〜78質量％，更宜爲30〜75質量％。該含有率未達 20質量％時’有黏著劑層之機械強度及耐濕熱性不充分的 傾向。若上述含有率超過80質量％，使輻射線硬化性黏著 劑用組成物硬化而成之黏著劑層的翹曲等之變形有變大之 傾向。又’後述之成分（B)係使用以式（2)所示之聚碳酸酯 二醇以外之化合物（例如聚酯二醇等）時係成分（A1)之含有 率係宜爲30〜70質量％，尤宜爲30〜60質量％。 φ 輻射線硬化性黏著劑用組成物含有成分（A2)時，輻射 線硬化性黏著劑用組成物中之成分（A2)的含有率係當輻射 線硬化性黏著劑用組成物之全量（該組成物含有有機溶劑 時’係除去有機溶劑的全量）爲1〇〇質量％，爲3〜90質量％ ，宜爲5〜80質量％，更宜爲7〜70質量％。成分（A2)之含有 率未達3質量％，有時光照射後之硬化性不充分，若超9 〇 質量％，有時與PVA系成形體之黏著強度差。 [成分（B)] -15- 200839324 構成輻射線硬化性黏著劑用組成物之成分（B)係含有 至少1個羥基，數目平均分子量爲5 0 0以上之化合物。 成分（B)之羥基的數目（1分子中之數目）係1個以上， 宜爲1〜4個。 成分（B)之數目平均分子量係5 00以上，宜爲1 000以上 。該數目平均分子量之上限値並無特別限疋’但從防止黏 著劑用組成物之黏度過度增大之觀點，宜爲20000，更宜 爲1〇〇〇〇。若該數目平均分子量未達500，無法充分提昇耐 晶片切割性（耐裁切性），故不佳。 又，成分（B)之數目平均分子量係依 ASTM D2 5 03， 所測定之値（具體上係使用HPC-8220 GPC(T〇S〇h製）、管 柱 TFKgel、G4000HXL G3 000HXL G2000HXL 各 2根，以 四氫呋喃作爲展開溶劑，流量Ice/分，以40 °C所測定之聚 苯乙烯換算的數目平均分子量）。 藉由使用成分（B)，可得到耐晶片切割性優之層合薄 膜。 可適宜使用來作爲成分（B)之化合物，可舉例如聚碳 酸酯二醇、聚己內酯二醇、聚醚二醇、聚酯二醇、其他之 多元醇等。 聚碳酸酯二醇係可舉例如聚四氫呋喃之聚碳酸酯、 1，6-己二醇之聚碳酸酯等’其中’適宜使用以下述通式（2) 所不之聚碳酸酯二醇。若使用如此之聚碳酸酯二醇，可對 黏著劑硬化物賦予柔軟性與膜強度，裁切性（晶片切割性） 與剝離強度可倂存。 -16- 200839324 HO-(R4-〇-C〇.〇)m.(R5.〇-CO-0)n-R6-〇H (2) (式中，R4及R5係分別獨立地表示碳數2〜12的2價烴基， R6係表示與R4與R5之任一者相同的構造；m爲2〜150，η 爲0〜150，且m + n爲2〜200)。 以上述式（2)所示之聚碳酸酯二醇之製造方法並無特 別限定，可舉例如二醇化合物與聚碳酸酯化合物之酯交換 反應、二醇化合物與光氣之聚合反應等已知之方法。於此 聚碳酸酯二醇之製造所使用的二醇化合物可舉例如1，4-丁 二醇、1，6-己二醇、3-甲基-1，5-戊二醇、1，9-壬二醇、2-甲基-1，8 -辛二醇等。又，爲得到適度的耐晶片切割性（耐 裁切性）及剝離強度，更宜爲含有1，6-己二醇、3-甲基-1，5-戊二醇等碳數6的脂肪族烴基之聚碳酸酯二醇。 可適宜使用來作爲聚碳酸酯二醇之化合物的市售品， 可舉例如 DN-980、981、982、983(以上，日本 Polyurethane 公司製）、PC-8000(PPG 公司製）、PC-PHF-CD(BASF 公司 製）、Kura ray 多元醇 C-590、C-109 0、C-2050、C-2090、 C-3 090、C-2065N、C-2015N(以上，Kuraray 公司製）、 Placcel CD CD210PL、Placel CD 220PL(以上，Daicel 化 學工業公司製）等。 聚己內酯二醇可舉例如使ε -己內酯與二醇反應所得 到之聚己內酯二醇等。此處所使用之二醇可舉例如乙二醇 、聚乙二醇、丙二醇、聚丙二醇、四亞甲基甘醇、聚四亞 -17- 200839324 甲基甘醇、1，2 -聚丁二醇、1，6·己二醇、新戊二醇、1，4-環己烷二甲醇、1，4-丁二醇等。此等之聚己內酯二醇的市 售品可舉例如 Placcel 205、205H、205AL、212、212AL 、220、220AL(以上，Daicel化學工業公司製）等。 聚醚二醇宜爲脂肪族聚醚二醇可舉例如聚乙二醇、聚 丙二醇、聚四亞甲基甘醇、聚六亞甲基甘醇、聚七亞甲基 甘醇、聚十亞甲基甘醇等。此等之聚醚二醇的市售品可舉 例如 PEG#600、#1〇〇〇、# 1 500、# 1 540、#4000(以上 Lion 公司製）、Excenol 720、1 020、2020、3020 > 510 > Preminol PPG4000(以上，旭硝子公司製）等。 聚酯二醇宜爲脂肪族二醇化合物與脂肪族二羧酸化合 物之共聚物。脂肪族二醇化合物可舉例如〗，4- 丁二醇、 1，6-己二醇、l，8 -辛二醇、i，9 -壬二醇、2 -甲基-1,8 -辛二 醇、3 -甲基-1，5 -戊二醇等，脂肪族二羧酸化合物可舉例如 馬來酸、琥珀酸、戊二醇、己二酸、癸二醇等。脂肪族二 醇化合物係可使用1種或2種以上，又脂肪族二羧酸化合物 亦可使用1種或2種以上，此等之聚酯二醇的市售品可舉例 如 Kuraray 多元醇]^-2010、0-2010、？-510、？-1010、？-1050 、 P-2010 、 P-2050 、 P-3010 、 P-3050(以上，Kuraray 公司製）等。 其他之多元醇可舉例如三羥甲基丙烷、甘油、季戊四 酉#、山梨糖醇、庶糖、二氯二胺基苯化甲院（Qu〇(J〇r〇le)等 之3價以上的多元醇以環氧乙烷（E〇)、環氧丙烷（p〇)、環 » T ；)：完' 四氫呋喃等之環狀醚化合物進行改性所得到之聚 -18- 200839324 醚多元醇。如此之化合物的具體例係可例示Ε Ο改性三經 甲基丙烷、Ρ 〇改性三羥甲基丙烷、四氫呋喃改性三羥甲 基丙烷、ΕΟ改性甘油、Ρ〇改性甘油、四氫呋喃改性甘油 、Ε Ο改性季戊四醇、？0改性季戊四醇、四氫呋喃改性季 戊四醇、Ε Ο改性山梨糖醇、Ρ ◦改性山梨糖醇、Ε Ο改性 蔗糖、ΡΟ改性蔗糖、ΕΟ改性蔗糖、ΕΟ改性二氯二胺基 苯化甲烷等，此等之中，宜爲Ε〇改性三羥甲基丙烷、Ρ〇 改性三羥甲基丙烷、ΡΟ改性甘油、Ρ〇改性山梨糖醇等。 此等之市售品可舉例如 Sannix TP-700、Sannix GP-1 000、Sannix SP-7 5 0、Sannix GP-600(以上，三洋化成公 司製）等。 又，可適宜使用來作爲成分（B)之多元醇，可舉例如 含羥基不飽和化合物之聚合物。該含羥基不飽和化合物之 聚合物可舉例如含羥基之（甲基）丙烯酸酯，具體上可舉例 如2-羥乙基（甲基）丙烯酸酯、2-羥丙基（甲基）丙烯酸酯、 2-羥丁基（甲基）丙烯酸酯、2-羥基-3-苯基氧丙基（甲基）丙 烯酸酯、1，4-丁二醇單（甲基）丙烯酸酯、2-羥基烷基（甲基 )丙烯醯基磷酸酯、4-羥基環己基（甲基）丙烯酸酯、1，6-己 二醇單（甲基）丙烯酸酯、新戊二醇單（甲基）丙烯酸酯、三 羥甲基丙烷二（甲基）丙烯酸酯、三羥甲基乙烷二（甲基）丙 烯酸酯、季戊四醇三（甲基）丙烯酸酯、二季戊四醇五（甲 基）丙烯酸酯等。進一步，可舉例如烷基縮水甘油基醚、 烯丙基縮水甘油基醚、縮水甘油基（甲基）丙烯酸酯等之含 有縮水甘油基的化合物與（甲基）丙烯酸酯之加成反應所得 -19- 200839324 到之化合物。 輻射線硬化性黏著劑用組成物中，成份（B)的含有率 係輻射線硬化性黏著劑用組成物之全量（該組成物含有有 機溶劑時，係除去有機溶劑的全量）爲100質量％，爲3〜50 質量％，宜爲5〜45質量％，更宜爲7〜40質量％，尤宜爲 7〜3 0質量％。若該含有率未達3質量％，因黏著劑層之耐晶 片切割性差，故不佳。另外，若上述含有率超過50質量％ ，輻射線硬化性黏著劑用組成物之黏度太高而塗佈性差， 黏著劑層與被黏體之黏著強度差，故不佳。又，使用以上 述式（2)所示之化合物以外之化合物（例如聚酯二元醇等）作 爲成分（B)時，成分（B)之含有率宜爲7〜20質量％，尤宜爲 7〜1 5質量％。 [成分（C)] 構成輻射線硬化性黏著劑用組成物之成分（C)爲光酸 產生劑。 光酸產生劑係藉接受光以釋出路易士酸之光陽離子聚 合起始劑。 上述光酸產生劑之例可舉例如具有以下述式（3)所示 之構造的鑰鹽。此鐵鹽係於未達400 nm具有實質上之光吸 收波長。 [R7aR8bR9cR10dZ]”[MXq + p]p- (3) -20- 200839324 z 表示 S 、 Se 、 Te 、 P 、 As 、 Sb (式中’ 1½離子爲鐵離子，2 、Bi、Ο、I、Br、C1 或 互爲相同或相異之有機基；£ Νξ Ν，R7、R8、R9 及 R1G係表示 、b、c及d分別爲0〜3之整 數’（a + b + c + d-p)係相等於z之價數；％係表示構成鹵化(wherein R1, R2 and R3 are each independently a hydrogen atom or a methyl group). Specific examples of the compound represented by the formula (1) include, for example, 1,2:8,9:14-200839324 epoxy group. Bar oak storage and so on. Such a commercially available product may, for example, be Celloxide 3000 (manufactured by Daicel Chemical Industry Co., Ltd.). The composition for a radiation curable adhesive contains the component (A 1 ) and/or the component (A2) as the component (A). When the composition for the radiation curable adhesive contains the component (A1), the content of the component (A1) in the radiation curable adhesive composition is the total amount of the composition for the radiation curable adhesive ( When the composition contains the organic solvent Φ, the total amount of the organic solvent is 100% by mass, and it is preferably 20 to 80% by mass, and is preferably 25 to 78% by mass, more preferably 30 to 75% by mass. When the content is less than 20% by mass, the mechanical strength and the moist heat resistance of the adhesive layer tend to be insufficient. When the content is more than 80% by mass, the deformation of the pressure-sensitive adhesive layer such as the radiation-curable adhesive composition tends to be large. Further, when the component (B) to be described later is a compound other than the polycarbonate diol represented by the formula (2) (for example, a polyester diol or the like), the content of the component (A1) is preferably 30 to 70% by mass. %, particularly preferably 30 to 60% by mass. When the composition for the radiant curable adhesive contains the component (A2), the content of the component (A2) in the composition for the radiation curable adhesive is the total amount of the composition for the radiation curable adhesive (this When the composition contains an organic solvent, the total amount of the organic solvent to be removed is 1% by mass, preferably 3 to 90% by mass, preferably 5 to 80% by mass, more preferably 7 to 70% by mass. The content of the component (A2) is less than 3% by mass, and the hardenability after light irradiation may be insufficient. When the content is more than 9% by mass, the adhesion strength to the PVA-based molded article may be inferior. [Component (B)] -15- 200839324 The component (B) constituting the composition for a radiation curable adhesive contains a compound having at least one hydroxyl group and a number average molecular weight of 5,000 or more. The number of hydroxyl groups (the number in one molecule) of the component (B) is one or more, and preferably from 1 to 4. The number average molecular weight of the component (B) is 500 or more, preferably 1,000 or more. The upper limit of the number average molecular weight is not particularly limited, but from the viewpoint of preventing an excessive increase in the viscosity of the adhesive composition, it is preferably 20,000, more preferably 1 Torr. If the number average molecular weight is less than 500, the wafer cutting resistance (cutting resistance) cannot be sufficiently improved, which is not preferable. Further, the number average molecular weight of the component (B) is determined according to ASTM D2 5 03 (specifically, HPC-8220 GPC (manufactured by T〇S〇h), column TFKgel, G4000HXL G3 000HXL G2000HXL each 2 Using tetrahydrofuran as a developing solvent, a flow rate of Ice/min, a polystyrene-equivalent number average molecular weight measured at 40 ° C). By using the component (B), a laminated film excellent in chip cutting resistance can be obtained. The compound which can be suitably used as the component (B) may, for example, be a polycarbonate diol, a polycaprolactone diol, a polyether diol, a polyester diol or another polyol. The polycarbonate diol may, for example, be a polycarbonate of polytetrahydrofuran or a polycarbonate of 1,6-hexanediol. The polycarbonate diol which is not used in the following formula (2) is suitably used. When such a polycarbonate diol is used, flexibility and film strength can be imparted to the cured product of the adhesive, and the cutting property (wafer cutting property) and peeling strength can be prevented. -16- 200839324 HO-(R4-〇-C〇.〇)m.(R5.〇-CO-0)n-R6-〇H (2) (wherein R4 and R5 each independently represent the carbon number A divalent hydrocarbon group of 2 to 12, and R6 represents the same structure as any of R4 and R5; m is 2 to 150, η is 0 to 150, and m + n is 2 to 200). The method for producing the polycarbonate diol represented by the above formula (2) is not particularly limited, and examples thereof include a transesterification reaction of a diol compound with a polycarbonate compound, and a polymerization reaction of a diol compound and phosgene. method. The diol compound used in the production of the polycarbonate diol may, for example, be 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,9 - decanediol, 2-methyl-1,8-octanediol, and the like. Further, in order to obtain appropriate wafer cut resistance (cut resistance) and peel strength, it is more preferable to contain a carbon number 6 fat such as 1,6-hexanediol or 3-methyl-1,5-pentanediol. A hydrocarbon group-based polycarbonate diol. A commercially available product of a compound of a polycarbonate diol, such as DN-980, 981, 982, 983 (above, manufactured by Polyurethane Co., Ltd.), PC-8000 (manufactured by PPG Co., Ltd.), PC-PHF, may be used. -CD (manufactured by BASF Corporation), Kura ray polyol C-590, C-109 0, C-2050, C-2090, C-3 090, C-2065N, C-2015N (above, Kuraray), Placcel CD CD210PL, Placel CD 220PL (above, manufactured by Daicel Chemical Industry Co., Ltd.), and the like. The polycaprolactone diol may, for example, be a polycaprolactone diol obtained by reacting ε-caprolactone with a diol. The diol used herein may, for example, be ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetrazol-17-200839324 methyl glycol, 1,2-polybutylene glycol. 1,6·hexanediol, neopentyl glycol, 1,4-cyclohexanedimethanol, 1,4-butanediol, and the like. Commercial products of such polycaprolactone diols include, for example, Placcel 205, 205H, 205AL, 212, 212AL, 220, 220AL (above, manufactured by Daicel Chemical Industry Co., Ltd.). The polyether diol is preferably an aliphatic polyether diol, and examples thereof include polyethylene glycol, polypropylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptylene glycol, and polydura. Methyl glycol and the like. Commercial products of such polyether diols include, for example, PEG #600, #1〇〇〇, #1 500, #1 540, #4000 (manufactured by Lion Corporation), Excenol 720, 1 020, 2020, 3020. > 510 > Preminol PPG4000 (above, manufactured by Asahi Glass Co., Ltd.). The polyester diol is preferably a copolymer of an aliphatic diol compound and an aliphatic dicarboxylic acid compound. Examples of the aliphatic diol compound include 4-butanediol, 1,6-hexanediol, 1,8-octanediol, i,9-nonanediol, and 2-methyl-1,8-octane. The diol, 3-methyl-1,5-pentanediol, etc., and the aliphatic dicarboxylic acid compound may, for example, be maleic acid, succinic acid, pentanediol, adipic acid or decanediol. The aliphatic diol compound may be used singly or in combination of two or more kinds, and the aliphatic dicarboxylic acid compound may be used singly or in combination of two or more kinds, and commercially available polyester diols such as Kuraray polyols may be mentioned. ^-2010, 0-2010, ? -510,? -1010,? -1050, P-2010, P-2050, P-3010, P-3050 (above, Kuraray). Other polyols include, for example, trimethylolpropane, glycerin, pentaerythritol #, sorbitol, sucrose, dichlorodiamine benzoic acid (J〇r〇le), etc. The polyhydric alcohol obtained by modifying the above polyol with ethylene oxide (E〇), propylene oxide (p〇), ring»T;): a cyclic ether compound such as tetrahydrofuran, etc. alcohol. Specific examples of such a compound are exemplified by hydrazine-modified trimethylolpropane, hydrazine-modified trimethylolpropane, tetrahydrofuran-modified trimethylolpropane, hydrazine-modified glycerin, hydrazine-modified glycerin, tetrahydrofuran. Modified glycerin, hydrazine modified pentaerythritol, ? 0 modified pentaerythritol, tetrahydrofuran modified pentaerythritol, Ε Ο modified sorbitol, Ρ ◦ modified sorbitol, Ε Ο modified sucrose, ΡΟ modified sucrose, ΕΟ modified sucrose, ΕΟ modified dichlorodiamine Among them, benzoic acid methane, etc., are preferably hydrazine-modified trimethylolpropane, hydrazine-modified trimethylolpropane, hydrazine-modified glycerin, hydrazine-modified sorbitol, and the like. Such commercially available products include, for example, Sannix TP-700, Sannix GP-1 000, Sannix SP-7 50, and Sannix GP-600 (above, Sanyo Chemical Co., Ltd.). Further, as the polyol of the component (B), a polymer containing a hydroxyl group-unsaturated compound can be suitably used. The polymer of the hydroxyl group-containing unsaturated compound may, for example, be a hydroxyl group-containing (meth) acrylate, and specific examples thereof include 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate. , 2-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, 1,4-butanediol mono (meth) acrylate, 2-hydroxyalkane (meth) propylene decyl phosphate, 4-hydroxycyclohexyl (meth) acrylate, 1,6-hexane diol mono (meth) acrylate, neopentyl glycol mono (meth) acrylate, Trimethylolpropane di(meth)acrylate, trimethylolethane di(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, and the like. Further, for example, an addition reaction of a glycidyl group-containing compound such as an alkyl glycidyl ether, an allyl glycidyl ether or a glycidyl (meth) acrylate with a (meth) acrylate may be mentioned - 19-200839324 The compound to which. In the composition for a radiation curable adhesive, the content of the component (B) is 100% by mass of the total amount of the composition for the radiation curable adhesive (when the composition contains an organic solvent, the total amount of the organic solvent is removed). It is 3 to 50% by mass, preferably 5 to 45% by mass, more preferably 7 to 40% by mass, particularly preferably 7 to 30% by mass. If the content is less than 3% by mass, the sheet resistance of the adhesive layer is poor, which is not preferable. In addition, when the content is more than 50% by mass, the viscosity of the composition for a radiation curable adhesive is too high, the coatability is poor, and the adhesion strength between the adhesive layer and the adherend is poor, which is not preferable. In addition, when a compound other than the compound represented by the above formula (2) (for example, a polyester diol or the like) is used as the component (B), the content of the component (B) is preferably 7 to 20% by mass, particularly preferably 7 to 1 5 mass%. [Component (C)] The component (C) constituting the composition for a radiation curable adhesive is a photoacid generator. The photoacid generator is a photocationic polymerization initiator which receives light to release Lewis acid. An example of the above-mentioned photoacid generator is a key salt having a structure represented by the following formula (3). This iron salt has a substantial light absorption wavelength of less than 400 nm. [R7aR8bR9cR10dZ]"[MXq + p]p- (3) -20- 200839324 z denotes S, Se, Te, P, As, Sb (where '11⁄2 ions are iron ions, 2, Bi, Ο, I, Br , C1 or an organic group which is the same or different from each other; £ Νξ Ν, R7, R8, R9 and R1G are represented by, and b, c and d are each an integer of 0 to 3' (a + b + c + dp) The valence of z is equal to the number of z;

原子’ P係齒化物錯合物離子之正電荷、^爲Μ之原子價 )° 在前述式（3)中，鑰離子之具體例可舉例如二苯基碘 鑰、4-甲氧基二苯基碘鑰、雙（4-甲基苯基）碘鑰、雙（4_第 二丁基苯基）碗鑰、雙（十二烷基苯基）碘鑰等之二芳基碘 鐵、或三苯基硫鍚、二苯基硫代苯氧基苯基硫鑰等之 三芳基硫鑰或雙[4-(二苯基硫鑰）_苯基]硫醚、雙[4_(二（4-(2-羥乙基）苯基）硫鏺）_苯基]硫醚、環戊二烯 )[1，2,3,4,5,6 - ??]-(甲基乙基）-苯]-鐵（1+)等。 在前述式（3)中，陰離子[MXq + p]之具體例可舉例如四 氟硼酸鹽（BF〇、六氟磷酸鹽（PF〇、六氟銻酸鹽（SbF〇 、六氟砷酸鹽（AsF〇、六氯銻酸鹽（SbCl6_)等，但尤宜爲 六氟磷酸鹽（PF，）。 亦即，在本發明中尤佳之（C)成分（光酸產生劑）可舉 例如以下述式（4)所示之鐵鹽。 (4) [R7aR8bR9cR10dZ] + PF6· -21 - 200839324 (式中’陽離子爲鐵離子，Z表示s、Se、Te、P、As、Sb 、：Bi、Ο、I、Br、Cl 或 Νξ N，R7、R8、R9及 R10係表示 互爲相同或相異之有機基；a、b、c及d分別爲0〜3之整 數，（a + b + c + d-1)係相等於z之價數）。 就（C)成分而言’若使用式（4)所示之鑰鹽，相較於使 用SbF’等之其他陰離子種者時，可得到翹曲更小的偏光 板。又’就（C)成分而言’若使用式（4)所示之鐵鹽，不使 用上述（B)成分而調製輻射線硬化性組成物，亦可得到翹 曲小的偏光板。 在偏光板之製造中，於一者之保護膜係因具有吸收紫 外線之性質，黏著劑之硬化係以來自偏光板之單側的光照 射進行。使用SbF6_等之其他的陰離子種之光酸產生劑的 黏著劑，係可得到充分的黏著力，但硬化速度快。因此， 使用來作爲偏光板之黏著劑時，藉偏光器吸收光等的理由 ’於2層之黏著層的硬化速度易產生差。然而，認爲使用 以PF6_作爲陰離子之光酸產生劑時，係適度的硬化速度， 故具有2層之黏著層之硬化速度的差變小，結果，翹曲變 小。 又，可用具有以通式[MXq(OHK]所示之陰離子的鑰鹽 。進一步，亦可使用具有過氯酸離子（cl0，）、三氟甲烷磺 酸離子（CF3S03·)、氟磺酸離子（FSO〇、甲烷磺酸離子、 三硝基苯磺酸離子、三亞硝基甲苯磺酸離子等之其他陰離 子的鏺鹽。 -22- 200839324 可使用來作爲成分（C)之鑰鹽的例子可舉例如特開昭 50- 1 5 1 996號公報、特開昭50- 1 58680號公報等之芳香族鹵 素鍚鹽、特開昭50- 1 5 1 997號公報、特開昭52-3 0899號公 報、特開昭56-55420號公報、特開昭5 5- 1 25 1 05號公報等 之VIA族芳香族鏺鹽、特開昭50- 1 5 8698號公報等之VIA 族芳香族鐵鹽、特開昭56-8428號公報、特開昭56-1 49402 號公報、特開昭57- 1 92429號公報記載等之氧化亞硫鑰鹽 、特開昭49- 1 7 040號公報等之芳香族二偶氮鑰鹽、美國專 利第4 1 3 9 6 5 5號說明書記載之硫代吡啶鑰鹽等。又，亦可 舉例如鐵/芳香烴錯合物、鋁錯合物/光分解矽化合物系起 始劑等。較宜使用來作爲成分（C)之光酸產生劑係二芳基 碘鑰鹽、三芳基硫鑰鹽等之芳香族鐵等，更佳係三芳基硫 鐵鹽。 (C)光酸產生劑之市售品的例子，可舉例如UVI-695 0 、UVI-6970、UVI-6974、UVI-6990、UVI-6992(以上， Union Carbide 公司製）、Adecaoptomer-SP-150、SP-151、 SP-152、SP-170、SP-172(以上，旭電化工業公司製）、 Irgacure 260、Irgacure 261(以上，Ciba Specialty Chemicals 公司製）、CI-248 1、CI-2624、CI-263 9、CI-2064、Cl-5 1 02( 以上，日本曹達公司製）、CD-1010、CD-1011、CD-1012( 以上，Sartomer 公司製）、DTS-102、DTS-103、NAT-103 、NDS-103、TPS-103、MDS-103、MPI-103、BBI-103(以 上，綠的化學公司製）、PCI-061T、PCI-062T、PCI-020T、 PCI-022T(以上，日本化藥公司製）、CPI-1 10A、CPI-101 A、 -23- 200839324 CPI-100P(以上，San-apro公司製）等。此等之中，υνΐ-6970 、UVI-697 4、Adecaoptomer SP-170、SP-172、CD-1012、 MPI-10 3、CPI-110A、CPI-101A就含有此等而構成之黏著 劑用組成物可顯現高的光硬化感度，故佳。又，此等之中 ，若使用 UVI-6950、UVI-6990、UVI-6992(以上，Union Carbide 公司製）、Adecaoptomer-SP-150、SP-151、SP-152(以上 ，旭電化工業公司製）、Irgacure 260(Ciba Specialty Chemicals 公司製）、CI-5102(日本曹達公司製）、CPI-100P(San-apro公司 製）等，因可得到翹曲變形小之偏光板，故佳。 上述光酸產生劑係可1種單獨或組合2種以上而使用。 又，爲促進以光酸產生劑所產生之酸的發生，亦可倂 用增感劑。增感劑之例，可舉例如二羥基苯、三羥基苯、 羥基乙醯苯、二羥基二苯基甲烷等。 輻射線硬化性黏著劑用組成物中，成分（C)之含有率 係輻射線硬化性黏著劑用組成物之全量（該組成物含有有 機溶劑時，係除去有機溶劑的全量）爲1 〇〇質量％，爲 0 · 1〜1 0質量％，更宜爲0 · 2〜5質量％，尤宜爲〇 · 3〜3質量％。 若上述含有率未達〇. 1質量％，因輻射線硬化性黏著劑用組 成物之輻射線硬化性降低’無法形成具有充分機械強度之 黏著劑層，故不佳。另外，若上述含有率超過1 〇質量％， 光酸產生劑有可能對黏著劑層之長期特性有不良影嚮，不 佳。 [成分（D)] -24- 200839324 輻射線硬化性黏著劑用組成物係進一步可含有具有以 下述式（5)所示之聚合性不飽和基之三聚異氰酸衍生物（成 分（D))。藉由使用成分（D)，可提昇輻射線硬化性黏著劑 用組成物之硬化性（硬化速度）。In the above formula (3), specific examples of the key ion include, for example, diphenyl iodine and 4-methoxy bis. a phenyl iodide, a bis(4-methylphenyl) iodine, a bis(4_t-butylphenyl) iodine, a bis(dodecylphenyl) iodine, etc. Or triphenylsulfonium, diphenylthiophenoxyphenylsulfide, etc., triarylsulfide or bis[4-(diphenylsulfonyl)phenyl]thioether, bis[4_(di( 4-(2-hydroxyethyl)phenyl)thioindole)-phenyl] sulfide, cyclopentadienyl) [1,2,3,4,5,6 - ??]-(methylethyl) -Benzene]-iron (1+) and the like. In the above formula (3), specific examples of the anion [MXq + p] include, for example, tetrafluoroborate (BF〇, hexafluorophosphate (PF〇, hexafluoroantimonate (SbF〇, hexafluoroarsenate) (AsF〇, hexachloroantimonate (SbCl6_), etc., but particularly preferably hexafluorophosphate (PF,). That is, in the present invention, the component (C) (photoacid generator) is preferably, for example, An iron salt represented by the following formula (4): (4) [R7aR8bR9cR10dZ] + PF6· -21 - 200839324 (wherein the cation is an iron ion, and Z represents s, Se, Te, P, As, Sb, :Bi , Ο, I, Br, Cl or Νξ N, R7, R8, R9 and R10 represent the same or different organic groups; a, b, c and d are each an integer of 0 to 3, (a + b + c + d-1) is equivalent to the valence of z.) For the component (C), 'if the key salt shown by the formula (4) is used, compared to the other anion species such as SbF', A polarizing plate having a smaller warpage can be obtained. Further, in the case of the component (C), if the iron salt represented by the formula (4) is used, the radiation curable composition can be prepared without using the component (B). Obtain a polarizing plate with a small warpage. In the polarizing plate In manufacturing, the protective film of one of them has the property of absorbing ultraviolet rays, and the curing of the adhesive is performed by light irradiation from one side of the polarizing plate. Adhesion of photoacid generator using other anionic species such as SbF6_ The agent has sufficient adhesion, but the curing speed is fast. Therefore, when the adhesive is used as a polarizing plate, the reason why the polarizing layer absorbs light or the like is that the curing speed of the adhesive layer of the two layers is likely to be poor. When a photoacid generator using PF6_ as an anion is used, it is an appropriate hardening rate, so that the difference in the hardening speed of the adhesive layer having two layers becomes small, and as a result, the warpage becomes small. a key salt of an anion represented by the formula [MXq(OHK]. Further, it may also be used with a perchloric acid ion (cl0,), a trifluoromethanesulfonate ion (CF3S03·), a fluorosulfonic acid ion (FSO〇, methanesulfonate). An anthracene salt of another anion such as an acid ion, a trinitrobenzenesulfonic acid ion or a trinitrosotosylate ion. -22- 200839324 An example of a key salt which can be used as the component (C) is, for example, a special opening 50. - 1 5 1 996 bulletin Japanese Laid-Open Patent Publication No. SHO-50-58 58 pp., JP-A-H05-1501, pp. In the case of the Group VIA aromatic sulfonium salt, such as the publication of the Japanese Patent Publication No. 55-1250, and the VIA group aromatic iron salt, etc., JP-A-56-8428, JP-A-56-8428 An arsenic sulfoxide salt such as oxidized sulfite salt, and the like, and an aromatic diazo salt of JP-A-49-107040, and U.S. Patent No. 4 1 The thiopyridyl key salt described in the specification of 3 9 6 5 5 is used. Further, examples thereof include an iron/aromatic hydrocarbon complex, an aluminum complex/photodecomposition ruthenium compound initiator, and the like. The photoacid generator which is preferably used as the component (C) is an aromatic iron such as a diaryl iodine salt or a triarylsulfonium salt, and more preferably a triarylsulfite salt. (C) Examples of commercially available photoacid generators include, for example, UVI-695 0 , UVI-6970, UVI-6974, UVI-6990, UVI-6992 (above, manufactured by Union Carbide), and Adecaoptomer-SP- 150, SP-151, SP-152, SP-170, SP-172 (above, manufactured by Asahi Kasei Kogyo Co., Ltd.), Irgacure 260, Irgacure 261 (above, manufactured by Ciba Specialty Chemicals Co., Ltd.), CI-248 1, CI-2624 , CI-263 9, CI-2064, Cl-5 1 02 (above, manufactured by Japan Soda Co., Ltd.), CD-1010, CD-1011, CD-1012 (above, Sartomer), DTS-102, DTS-103 , NAT-103, NDS-103, TPS-103, MDS-103, MPI-103, BBI-103 (above, manufactured by Green Chemical Co., Ltd.), PCI-061T, PCI-062T, PCI-020T, PCI-022T ( The above is manufactured by Nippon Kayaku Co., Ltd., CPI-1 10A, CPI-101 A, -23-200839324 CPI-100P (above, manufactured by San-apro Co., Ltd.). Among these, υνΐ-6970, UVI-697 4, Adecaoptomer SP-170, SP-172, CD-1012, MPI-10 3, CPI-110A, and CPI-101A contain these adhesive compositions. The object can exhibit high light hardening sensitivity, so it is good. In addition, UVI-6950, UVI-6990, UVI-6992 (above, manufactured by Union Carbide), Adecaoptomer-SP-150, SP-151, and SP-152 (above, manufactured by Asahi Kasei Kogyo Co., Ltd.) are used. ), Irgacure 260 (manufactured by Ciba Specialty Chemicals Co., Ltd.), CI-5102 (manufactured by Nippon Soda Co., Ltd.), CPI-100P (manufactured by San-apro Co., Ltd.), etc., are preferable because a polarizing plate having a small warpage deformation can be obtained. These photoacid generators can be used alone or in combination of two or more. Further, in order to promote the generation of an acid generated by the photoacid generator, a sensitizer may be used. Examples of the sensitizer include dihydroxybenzene, trihydroxybenzene, hydroxyacetamidine, dihydroxydiphenylmethane, and the like. In the composition for a radiation curable adhesive, the content of the component (C) is the total amount of the composition for the radiation curable adhesive (when the composition contains an organic solvent, the total amount of the organic solvent is removed) is 1 〇〇 The mass % is 0 · 1 to 1 0% by mass, more preferably 0 · 2 to 5 % by mass, particularly preferably 〇 · 3 to 3 % by mass. When the content rate is less than 0.1% by mass, the radiation curability of the composition for a radiation curable adhesive is lowered, and the adhesive layer having sufficient mechanical strength cannot be formed, which is not preferable. Further, when the content is more than 1% by mass, the photoacid generator may have an adverse effect on the long-term characteristics of the adhesive layer, which is not preferable. [Component (D)] -24- 200839324 The radiation curable adhesive composition may further contain a trimeric isocyanic acid derivative having a polymerizable unsaturated group represented by the following formula (5) (ingredient (D) )). By using the component (D), the hardenability (hardening rate) of the composition for the radiation curable adhesive can be improved.

(5) (式中，R11、R12及R13係分別獨立地爲一價之有機基，而 R11〜R13之中至少2個爲-R14OCOCR15 = CH2，R14係碳數2〜8 之2價有機基，R15爲氫原子或甲基）。 成分（D)係宜於分子中具有聚合性不飽和基2個以上。 聚合性不飽和基並無特別限制，但宜爲（甲基）丙烯酸酯。 藉具有聚合性不飽和基2個以上俾交聯密度高，可減 少因添加此所造成之硬度降低。 在本發明中可使用之成分（D)的具體例可舉例如三[2-( 甲基）丙烯醯氧乙基]三聚異氰酸酯、雙[2-(甲基）丙烯醯氧 乙基](2-羥乙基）三聚異氰酸酯、雙[2 _(甲基）丙烯醯氧乙基 ]三聚異氰酸酯、及此等之起始醇類的環氧乙烷（EO)、環 氧丙烷、或己內醯胺加成物之（甲基）丙烯酸酯等。此等之 中’尤宜爲三[2-(甲基）丙烯醯氧乙基]三聚異氰酸酯、雙 [2-(甲基）丙烯醯氧乙基](2-羥乙基）三聚異氰酸酯。 -25- 200839324 可適宜使用來作爲成分（D)之市售品可舉例如Aronix Μ - 2 1 5、Μ - 3 1 3、Μ - 3 1 5、Μ - 3 2 5、Μ - 3 2 6、Μ - 3 2 7 (以上東 亞合成化學工業公司製）、SR-3 68(Sartomer公司製）等。 上述之化合物係可1種單獨或組合2種以上而使用。 輻射線硬化性黏著劑用組成物含有成份（D)之情形， 成份（D)之含有率係輻射線硬化性黏著劑用組成物之全量（ 該組成物含有有機溶劑時，係除去有機溶劑的全量）爲1 00 質量％，爲3〜40質量％，宜爲5〜35質量％，更宜爲7〜30質 量％。若上述含有率未達3質量％，有時光照射後之硬化性 不充分，若超過40質量％，有時與PVA系成形體之黏著強 度差。 [成分（E)] 輻射線硬化性黏著劑用組成物係可進一步含有脂肪族 環氧化合物（成分（E))。成分（E)之脂肪族環氧化合物係用 以控制黏著劑層之機械強度等所添加之任意成分。 上述脂肪族環氧化合物的具體例可舉例如1，4-丁二醇 二縮水甘油基醚、1，6-己二醇二縮水甘油基醚、新戊二醇 二縮水甘油基醚、三羥甲基丙烷三縮水甘油基醚、聚乙二 醇二縮水甘油基醚、甘油三縮水甘油基醚、聚丙二醇二縮 水甘油基醚類；乙二醇、丙二醇、甘油等之脂肪族多元醇 加成1種或2種以上之環氧烷所得到之聚醚多元醇的聚縮水 甘油基醚類；脂肪族長鏈二鹼酸的二縮水甘油基酯類；脂 肪族高級醇之單縮水甘油基醚類；高級脂肪酸之縮水甘油 -26- 200839324 基酯類；環氧基化大豆油；環氧基硬脂酸丁酯；環氧基硬 脂酸辛酯；環氧化亞麻油；環氧基化聚丁二烯等。 輻射線硬化性黏著劑用組成物含有成份（E)之情形， 成份（E)之含有率係輻射線硬化性黏著劑用組成物之全量（ 該組成物含有有機溶劑時，係除去有機溶劑的全量）爲1 00 質量％，宜爲〇〜50質量。/◎，更宜爲〇〜45質量％，尤宜爲 0〜40質量％。若上述含有率未達5 0質量％，必須成分之（A) 脂環式環氧化合物等之含有率變小，無法得到本發明之效 果，故不佳。又，使用以上述式（2)所示之聚碳酸酯二醇 以外的化合物作爲成分（B)時，成分（E)之含有率宜爲 15〜45質量％，尤宜爲30〜40質量％。 又，在本發明所使用之輻射線硬化性黏著劑用組成物 中係在無損本發明之目的、效果之範圍中，可調配各種添 加劑作爲其他之任意成分。如此之添加劑係可舉例如環氧 樹脂、聚醯胺、聚醯胺醯亞胺、聚胺基甲酸酯、聚丁二烯 、聚氯丁二烯、聚醚、聚酯、苯乙烯-丁二烯嵌段共聚物 、石油樹脂、二甲苯樹脂、酮樹脂、纖維素樹脂、氟系寡 聚物、聚矽氧系寡聚物、聚硫醚系寡聚物等之聚合物或寡 聚物；吩噻嗪、2,6·二第三丁基-4-甲基酚等之聚合抑制劑 ;聚合起始助劑；流平劑；潤濕改良劑；界面活性劑；可 塑劑；紫外線吸收劑；矽烷偶合劑；無機塡充劑；顏料； 染料等。 將本發明之輻射線硬化性黏著劑用組成物中的成分組 成之例係表示於以下。又以下之各成分的含有率係輻射線 -27- 200839324 硬化性黏著劑用組成物之全量（該組成物含有有機溶劑時 ，係除去有機溶劑的全量）爲100質量％時的含有率。 [成分組成1 :含有成分（A1)、且不含有成分（A2)之情形] 成分（A1)之含有率宜爲20〜80質量％，更宜爲25〜70質 量％，尤宜爲3〇〜60質量％。 成分（B)之含有率宜爲3〜30質量％，更宜爲5〜20質量％ ，尤宜爲7〜15質量％。 成分（C)之含有率宜爲0.1〜10質量％，更宜爲0.2〜5質 量％，尤宜爲〇·3〜3質量°/〇。 成分（E)之含有率宜爲〇〜50質量％，更宜爲15〜45質量 %，尤宜爲30〜40質量％。 成分（A1)之含有率未達20質量％時，黏著劑層之機械 強度及耐濕熱性有不充分之傾向。若該含有率超過8〇質量 %，使輻射線硬化性黏著劑用組成物硬化而成之黏著劑層 的翹曲等變形有變大之傾向。 若成分（B)之含有率未達3質量％，黏著劑層之晶片切 割性差，故不佳。另外’若該含有率超過3 〇質量％ ’輪射 線硬化性黏著劑用組成物之黏度太高而塗佈性差’黏著劑 層與被黏體之黏著強度差，故不佳。 若成分（C )之含有率未達G · 1質量％ ’輻射線硬化性黏 著劑用組成物之輻射線硬化性降低’無法形成具有充分機 械強度之黏著劑層’故不佳。另外’若含有率超過1〇質量 %，光酸產生劑有可能對黏著劑層之長期特性有不良影嚮 •28- 200839324 ，故不佳。 若成分（E)之含有率超過50質量％，必須成分之（A)脂 環式環氧化合物等之含有率變小，無法得到本發明之效果 ，故不佳。 [成分組成2 :含有成分（A1)或不含有且含有成分（A2)之情形] 成分（A1)之含有率宜爲2 0〜80質量％，更宜爲25〜75質 量％，尤宜爲30〜70質量％。 成分（A2)之含有率宜爲3〜90質量％，更宜爲5〜80質量 %，尤宜爲7〜7〇質量％。 成分（B)之含有率宜爲3〜50質量％，更宜爲5〜45質量％ ，尤宜爲7〜40質量％。 成分（C)之含有率宜爲0.1〜10質量％，更宜爲0.2〜5質 量％，尤宜爲〇.3〜3質量％。 成分（E)之含有率宜爲〇〜50質量％，更宜爲15〜45質量 %，尤宜爲30〜40質量％。 成分（A1)、成分（B)、成分（C)及成分（E)之含有率的上 限値、下限値係從與前述之成分組成1同樣之觀點來決定 〇 若成分（A2)之含有率未達3質量％，有時光照射後之 硬化性不充分，若超過90質量％，有時與PVA系成形體之 黏著強度差。 [成分組成3 :含有成分（A1)，且成分（B)爲以式（2)所示之 -29 - 200839324 聚碳酸酯二醇之情形] 成分（A1)之含有率宜爲20〜80質量％，更宜爲25〜70質 量％，尤宜爲30〜60質量％。 成分（B)之含有率宜爲3〜30質量％，更宜爲5〜20質量％ ，尤宜爲7〜15質量％。 成分（C)之含有率宜爲0.1〜10質量％，更宜爲0.2〜5質 量％，尤宜爲〇 · 3〜3質量％。 成分（E)之含有率宜爲0〜50質量％，更宜爲0〜45質量％ ，尤宜爲0〜40質量％。 成分（A1)、成分（8)、成分（〇及成分斤）之含有率的上 限値、下限値係從與前述之成分組成1同樣之觀點來決定 [成分組成4:含有成分（A1)且含有成分（D)之情开夕] 成分（A1)之含有率宜爲20〜80質量％，更宜爲25〜75質 量％，尤宜爲30〜70質量％。 成分（B)之含有率宜爲3〜50質量％ ’更宜爲5〜45質量％ ，尤宜爲7〜40質量％。 成分（C)之含有率宜爲〇·1〜1〇質量％，更宜爲〇.2〜5質 量％，尤宜爲0.3〜3質量％。 成分（D)之含有率宜爲3〜40質量％ ’更宜爲5〜35質量％ ，尤宜爲7〜30質量％。 成分（Ε)之含有率宜爲〇〜50質量％，更宜爲0〜45質量％ ，尤宜爲〇〜40質量％。 -30- 200839324 成分（A1)、成分（B)、成分（C)及成分（E)之含有率的上 限値、下限値係從與前述之成分組成1同樣之觀點來決定 〇 若成分（D)未達3質量％，有時光照射後之硬化性不充 分，若超過40質量％，有時與PVA系成形體之黏著強度差 [成分組成5 :含有成分（A1)，且含有以式（4)所示之光酸產 生劑（成分（C))之情形] 成分（A1)之含有率宜爲20〜80質量％，更宜爲25〜7 0質 量％，尤宜爲30〜70質量％。 成分（B)之含有率宜爲3〜50質量％，更宜爲5〜45質量％ ，尤宜爲7〜40質量％。 成分（C)之含有率宜爲0.1〜10質量％，更宜爲0.2〜5質 量％，尤宜爲〇·3〜5質量％。 成分（D)之含有率宜爲0〜40質量％，更宜爲5〜35質量％ ，尤宜爲7〜30質量％。 成分（E)之含有率宜爲0〜50質量％，更宜爲〇〜45質量％ ，尤宜爲〇〜40質量％。 成分（A1)、成分（B)、成分（C)及成分（E)之含有率的上 限値、下限値係從與前述之成分組成1同樣之觀點來決定 〇 成分（D)之含有率的上限値、下限値係從與前述之成 分組成4同樣之觀點來決定。 -31 - 200839324 輻射線硬化性組成物係可藉由均一地混合上述成分而 調製。如此做法所得到之輻射線硬化性組成物的黏度（25 t：)係一般爲2000mPa · s以下，宜爲550mPa · s以下，更宜 爲300mPa · s以下。 又’於輻射線硬化性組成物中係依需要而可添加有機 溶劑等之溶劑。但，在本發明中，即使無溶劑，亦可調製 輻射線硬化性組成物。在本發明中，從作業環境之維持、 環境負荷等之方面，宜不含有溶劑。 又，輻射線硬化性黏著劑組成物係厚度2 0 0 μιη之硬化 物時的波長5 5 0 nm之光的透過率宜爲70%以上，更宜爲 80 %以上者。若上述之透過率未達70%，偏光板本身之透 過率亦降低，故不佳。 又’輻射線硬化性組成物亦宜使用以過濾器等進行過 濾者。 · 其次，一面適宜參照圖面，一面說明有關本發明之偏 光板及其製造方法。 圖1係模式地表示本發明之偏光板的一例之截面圖， 圖2係表示本發明之偏光板的製造方法一例之流程圖。 圖1中，偏光板1係由聚乙烯醇系偏光膜2、形成於此 偏光膜2之雙面（下面及上面）之黏著劑層3,4、與層合於此 等黏著劑層3,4之各單面（具體上係黏著劑層3之下面及黏 著劑層4之上面）所形成之保護膜5,6所構成。 [偏光膜] -32- 200839324 偏光膜係可使用聚乙烯醇系偏光膜（以下亦稱爲PVA 系偏光膜）。PVA系偏光膜係一般可使用來作爲偏光膜者 ，於聚乙烯醇系薄膜吸附碘或二色染料而延伸配向者。 偏光膜之厚度並無特別限定，但限定於例如〗〇〜4〇μιη [黏著劑層] φ 黏著劑層係使上述輻射線硬化性組成物輻射線硬化而 構成之硬化物層。 使用上述輻射線硬化性組成物而形成黏著劑層，可得 到優異之耐晶片切割性，又，保護膜即使爲COP系、 TAC系之任一者，亦可使保護膜與黏著劑層之黏著強度爲 優異者。 黏著劑層之厚度並無特別限制，但限定於例如 0 · 0 1 〜5.0 μιη 〇 [保護膜] 保護膜係可使用例如由三乙醯基纖維素之乙酸酯系樹 脂' 聚對苯二甲酸乙二酯樹脂等之聚酯系樹脂、聚醚颯系 樹脂、聚碳酸酯系樹脂、聚醯胺系樹脂、聚醯亞胺系樹脂 、聚烯烴系樹脂、環狀烯煙系樹脂、丙燦酸系樹脂等之光 學上透明的樹脂所構成的薄膜。其中，宜爲環狀烯烴系樹 脂薄膜（COP系薄膜）、三乙醯基纖維素系樹脂薄膜（T A C 系薄膜）。 -33- 200839324 偏光板之構成可舉例如以下之（1)〜（3)。 (1) TAC系薄膜/黏著劑層/PVA系偏光膜/黏著劑層/TAC系 薄膜 (2) TAC系薄膜/黏著劑層/PVA系偏光膜/黏著劑層/COP系 薄膜 (3) COP系薄膜/黏著劑層/PVA系偏光膜/黏著劑層/COP系 薄膜 在本發明中宜至少一個的保護膜爲COP系薄膜。亦 即’偏光板之構成宜爲上述（2)、（3)，更宜爲上述（3)。若 依上述（2)、（3)之構成，可使用透濕性低之COP系薄膜作 爲保護膜，故可得到耐濕熱性優之偏光板。 在本發明中，上下之保護膜中，一者之保護膜係抗紫 外線吸收劑之保護膜，另一者之保護膜係必須爲紫外線透 過性的保護膜。 上述抗紫外線性之保護膜係當偏光板配置於液晶胞之 雙面時’來自外部之紫外線可發揮保護液晶胞的角色者。 抗紫外線性之保護膜係可適當調配紫外線吸收劑。抗紫外 線性之保護膜之波長380nm之光的透過率例如爲10%以下 〇 i：述紫外線透過性之保護膜係藉從該保護膜之側進行 _射線照射（光照射），以使輻射線硬化性組成物硬化者。 紫外線透過性之保護膜係不含有紫外線吸收劑，或即使含 有’亦含有介由該保護膜而照射光以使輻射線硬化性組成 物硬化之程度’紫外線透過性之保護膜之波長38〇nm的光 -34- 200839324 之透過率例如爲60%以上。 保護膜中亦可設有相位差。 又，保護膜之厚度係無特別限制，但限定於例如 1 0〜200μχη ° 保護膜係亦可於輻射線硬化性組成物之塗佈前進行各 種表面處理。 (環狀烯烴系樹脂薄膜） 又，上述環狀烯烴系樹脂薄膜係使含有至少一種環狀 烯烴系化合物之單體組成物，又，依需要而進一步添加氫 所得到之樹脂所構成的薄膜。 上述環狀烯烴系化合物係可舉例如以下述通式（6)所 示之環狀烯烴系化合物。(5) (wherein R11, R12 and R13 are each independently a monovalent organic group, and at least two of R11 to R13 are -R14OCOCR15 = CH2, and R14 is a divalent organic group having 2 to 8 carbon atoms; , R15 is a hydrogen atom or a methyl group). The component (D) is preferably one or more polymerizable unsaturated groups in the molecule. The polymerizable unsaturated group is not particularly limited, but is preferably a (meth) acrylate. By having two or more polymerizable unsaturated groups, the crosslink density is high, and the reduction in hardness due to the addition can be reduced. Specific examples of the component (D) which can be used in the present invention include, for example, tris[2-(methyl)propenyloxyethyl]trimeric isocyanate, bis[2-(methyl)acryloyloxyethyl]( 2-Hydroxyethyl)trimeric isocyanate, bis[2-(methyl)acryloyloxyethyl]trimeric isocyanate, and the starting alcohols of ethylene oxide (EO), propylene oxide, or A (meth) acrylate or the like of a caprolactam adduct. Among these, 'especially tris[2-(methyl)acryloyloxyethyl]trimeric isocyanate, bis[2-(methyl)acryloyloxyethyl](2-hydroxyethyl)trimeric isocyanate . -25- 200839324 A commercially available product which can be suitably used as the component (D) is, for example, Aronix Μ - 2 1 5, Μ - 3 1 3, Μ - 3 1 5, Μ - 3 2 5, Μ - 3 2 6 Μ - 3 2 7 (manufactured by Toagosei Chemical Co., Ltd.), SR-3 68 (manufactured by Sartomer Co., Ltd.), etc. The above compounds may be used alone or in combination of two or more. In the case where the composition for the radiation curable adhesive contains the component (D), the content of the component (D) is the total amount of the composition for the radiation curable adhesive (when the composition contains an organic solvent, the organic solvent is removed) The total amount is 100% by mass, and is 3 to 40% by mass, preferably 5 to 35% by mass, more preferably 7 to 30% by mass. When the content is less than 3% by mass, the hardenability after light irradiation may be insufficient, and if it exceeds 40% by mass, the adhesion strength to the PVA-based molded body may be inferior. [Component (E)] The radiation curable adhesive composition may further contain an aliphatic epoxy compound (ingredient (E)). The aliphatic epoxy compound of the component (E) is used to control any component added by mechanical strength or the like of the adhesive layer. Specific examples of the aliphatic epoxy compound include, for example, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, neopentyl glycol diglycidyl ether, and trishydroxyl Methylpropane triglycidyl ether, polyethylene glycol diglycidyl ether, glycerol triglycidyl ether, polypropylene glycol diglycidyl ether; aliphatic polyol addition of ethylene glycol, propylene glycol, glycerin, etc. Polyglycidyl ethers of polyether polyols obtained by one or more kinds of alkylene oxides; diglycidyl esters of aliphatic long-chain dibasic acids; monoglycidyl ethers of aliphatic higher alcohols ; higher fatty acid glycidyl -26- 200839324 base ester; epoxidized soybean oil; butyl epoxide stearate; octyl octyl stearate; epoxidized linseed oil; epoxylated polybutane Alkene and the like. In the case where the composition for the radiation curable adhesive contains the component (E), the content of the component (E) is the total amount of the composition for the radiation curable adhesive (when the composition contains the organic solvent, the organic solvent is removed) The full amount) is 100% by mass, preferably 〇~50 mass. / ◎, more preferably 〇 ~ 45% by mass, particularly preferably 0 to 40% by mass. When the content is less than 50% by mass, the content of the component (A) alicyclic epoxy compound or the like is small, and the effect of the present invention cannot be obtained, which is not preferable. In addition, when a compound other than the polycarbonate diol represented by the above formula (2) is used as the component (B), the content of the component (E) is preferably 15 to 45% by mass, particularly preferably 30 to 40% by mass. . Further, in the composition for a radiation curable adhesive used in the present invention, various additives may be added as other optional components insofar as the object and effect of the present invention are not impaired. Such additives may, for example, be epoxy resins, polyamines, polyamidiamines, polyurethanes, polybutadienes, polychloroprenes, polyethers, polyesters, styrene-butenes. Polymer or oligomer of a diene block copolymer, a petroleum resin, a xylene resin, a ketone resin, a cellulose resin, a fluorine-based oligomer, a polyoxymethylene oligomer, a polythioether oligomer, or the like Polymerization inhibitors such as phenothiazine, 2,6·di-tert-butyl-4-methylphenol; polymerization initiator; leveling agent; wetting improver; surfactant; plasticizer; Agent; decane coupling agent; inorganic cerium filling agent; pigment; dye, etc. The examples of the components in the composition for a radiation curable adhesive of the present invention are shown below. In addition, the content ratio of each of the following components is the content of the radiation -27-200839324 when the total amount of the composition for a curable adhesive (the total amount of the organic solvent is removed when the composition contains an organic solvent) is 100% by mass. [Component 1] When the component (A1) is contained and the component (A2) is not contained] The content of the component (A1) is preferably 20 to 80% by mass, more preferably 25 to 70% by mass, particularly preferably 3〇. ~60% by mass. The content of the component (B) is preferably from 3 to 30% by mass, more preferably from 5 to 20% by mass, particularly preferably from 7 to 15% by mass. The content of the component (C) is preferably from 0.1 to 10% by mass, more preferably from 0.2 to 5% by mass, particularly preferably from 3% to 3 parts by mass. The content of the component (E) is preferably from 〇 50% by mass, more preferably from 15 to 45% by mass, particularly preferably from 30 to 40% by mass. When the content of the component (A1) is less than 20% by mass, the mechanical strength and the moist heat resistance of the adhesive layer tend to be insufficient. When the content is more than 8% by mass, deformation such as warpage of the adhesive layer which is cured by the radiation curable adhesive composition tends to become large. If the content of the component (B) is less than 3% by mass, the wafer of the adhesive layer is inferior in cutting property, which is not preferable. In addition, if the content is more than 3% by mass, the viscosity of the composition for a radiation curable adhesive is too high and the coating property is poor, and the adhesive strength between the adhesive layer and the adherend is poor, which is not preferable. When the content of the component (C) is less than G·1 mass%, the radiation hardenability of the composition for a radiation curable adhesive is lowered, and the adhesive layer having sufficient mechanical strength cannot be formed, which is not preferable. In addition, if the content rate exceeds 1% by mass, the photoacid generator may have a bad influence on the long-term characteristics of the adhesive layer. 28-200839324, which is not preferable. When the content of the component (E) is more than 50% by mass, the content of the component (A) alicyclic epoxy compound or the like is small, and the effect of the present invention cannot be obtained, which is not preferable. [Component 2: When component (A1) is contained or does not contain component (A2)] The content of component (A1) is preferably 20 to 80% by mass, more preferably 25 to 75% by mass, particularly preferably 30 to 70% by mass. The content of the component (A2) is preferably from 3 to 90% by mass, more preferably from 5 to 80% by mass, particularly preferably from 7 to 7% by mass. The content of the component (B) is preferably from 3 to 50% by mass, more preferably from 5 to 45% by mass, particularly preferably from 7 to 40% by mass. The content of the component (C) is preferably from 0.1 to 10% by mass, more preferably from 0.2 to 5% by mass, particularly preferably from 3% to 3% by mass. The content of the component (E) is preferably from 〇 50% by mass, more preferably from 15 to 45% by mass, particularly preferably from 30 to 40% by mass. The upper limit 値 and the lower limit of the content ratio of the component (A1), the component (B), the component (C), and the component (E) are determined from the same viewpoint as the component composition 1 described above, and the content of the component (A2) is determined. When it is less than 3% by mass, the hardenability after light irradiation may be insufficient, and if it exceeds 90% by mass, the adhesion strength to the PVA-based molded body may be inferior. [Component composition 3: contains the component (A1), and the component (B) is in the case of the -29 - 200839324 polycarbonate diol represented by the formula (2)] The content of the component (A1) is preferably 20 to 80% by mass. %, more preferably 25 to 70% by mass, particularly preferably 30 to 60% by mass. The content of the component (B) is preferably from 3 to 30% by mass, more preferably from 5 to 20% by mass, particularly preferably from 7 to 15% by mass. The content of the component (C) is preferably from 0.1 to 10% by mass, more preferably from 0.2 to 5% by mass, particularly preferably from 3% to 3% by mass. The content of the component (E) is preferably from 0 to 50% by mass, more preferably from 0 to 45% by mass, particularly preferably from 0 to 40% by mass. The upper limit 値 and the lower limit 含有 of the content ratio of the component (A1), the component (8), and the component (〇 and the component jin) are determined from the same viewpoint as the component composition 1 described above. [Component composition 4: component (A1) is contained. The content of the component (D) is preferably from 20 to 80% by mass, more preferably from 25 to 75% by mass, even more preferably from 30 to 70% by mass. The content of the component (B) is preferably from 3 to 50% by mass, more preferably from 5 to 45% by mass, particularly preferably from 7 to 40% by mass. The content of the component (C) is preferably 〇·1 to 1% by mass, more preferably 〇. 2 to 5% by mass, particularly preferably 0.3 to 3% by mass. The content of the component (D) is preferably from 3 to 40% by mass, more preferably from 5 to 35% by mass, particularly preferably from 7 to 30% by mass. The content of the component (Ε) is preferably 〇 50% by mass, more preferably 0 to 45% by mass, particularly preferably 〇 40% by mass. -30- 200839324 The upper limit 値 and the lower limit of the content ratio of the component (A1), the component (B), the component (C), and the component (E) are determined from the same viewpoint as the component composition 1 described above. When the amount is less than 3% by mass, the hardenability after light irradiation may be insufficient, and if it exceeds 40% by mass, the adhesion strength to the PVA-based molded body may be inferior [component composition 5: component (A1) is contained, and 4) In the case of the photoacid generator (component (C)) shown] The content of the component (A1) is preferably 20 to 80% by mass, more preferably 25 to 70% by mass, particularly preferably 30 to 70% by mass. %. The content of the component (B) is preferably from 3 to 50% by mass, more preferably from 5 to 45% by mass, particularly preferably from 7 to 40% by mass. The content of the component (C) is preferably from 0.1 to 10% by mass, more preferably from 0.2 to 5% by mass, particularly preferably from 3% to 5% by mass. The content of the component (D) is preferably from 0 to 40% by mass, more preferably from 5 to 35% by mass, particularly preferably from 7 to 30% by mass. The content of the component (E) is preferably from 0 to 50% by mass, more preferably from 〇 to 45% by mass, particularly preferably from 〇 to 40% by mass. The upper limit 値 and the lower limit of the content ratio of the component (A1), the component (B), the component (C), and the component (E) are determined from the same viewpoint as the component composition 1 described above, and the content of the component (D) is determined. The upper limit 値 and the lower limit 决定 are determined from the same viewpoint as the above-described component composition 4. -31 - 200839324 The radiation curable composition can be prepared by uniformly mixing the above components. The viscosity (25 t:) of the radiation curable composition obtained in this manner is generally 2000 mPa·s or less, preferably 550 mPa·s or less, more preferably 300 mPa·s or less. Further, a solvent such as an organic solvent may be added to the radiation curable composition as needed. However, in the present invention, the radiation curable composition can be prepared even without a solvent. In the present invention, it is preferred that the solvent is not contained in terms of maintenance of the working environment, environmental load, and the like. Further, the transmittance of the light having a wavelength of 550 nm in the case of the radiation curable adhesive composition having a thickness of 200 μm is preferably 70% or more, more preferably 80% or more. If the above transmittance is less than 70%, the transmittance of the polarizing plate itself is also lowered, which is not preferable. Further, the radiation curable composition is preferably filtered by a filter or the like. Next, a polarizing plate and a method of manufacturing the same according to the present invention will be described with reference to the drawings. Fig. 1 is a cross-sectional view showing an example of a polarizing plate of the present invention, and Fig. 2 is a flow chart showing an example of a method for producing a polarizing plate of the present invention. In FIG. 1, the polarizing plate 1 is composed of a polyvinyl alcohol-based polarizing film 2, an adhesive layer 3, 4 formed on both sides (bottom surface and upper surface) of the polarizing film 2, and an adhesive layer 3 laminated thereon. The protective films 5 and 6 formed on each of the single faces of 4 (specifically, the lower surface of the adhesive layer 3 and the upper surface of the adhesive layer 4). [Polarizing film] -32- 200839324 A polyvinyl alcohol-based polarizing film (hereinafter also referred to as a PVA-based polarizing film) can be used as the polarizing film. The PVA-based polarizing film system can be generally used as a polarizing film, and the polyvinyl alcohol-based film adsorbs iodine or a dichroic dye to extend the alignment. The thickness of the polarizing film is not particularly limited, but is limited to, for example, 〇 〇 4 〇 ι η [adhesive layer] φ The adhesive layer is a cured layer formed by curing the radiation curable composition by radiation. When the adhesive layer is formed by using the radiation curable composition, excellent wafer cut resistance can be obtained, and even if the protective film is either COP or TAC, the protective film and the adhesive layer can be adhered. The strength is excellent. The thickness of the adhesive layer is not particularly limited, but is limited to, for example, 0 · 0 1 to 5.0 μm 〇 [Protective film] The protective film may be, for example, an acetate resin of triethyl fluorenyl cellulose. Polyester resin such as formic acid formate resin, polyether oxime resin, polycarbonate resin, polyamine resin, polyimide resin, polyolefin resin, cyclic olefin resin, and C A film made of an optically transparent resin such as a succinic resin. Among these, a cyclic olefin-based resin film (COP-based film) and a triethylene-based cellulose-based resin film (T A C-based film) are preferable. -33- 200839324 The configuration of the polarizing plate is, for example, the following (1) to (3). (1) TAC film/adhesive layer/PVA polarizing film/adhesive layer/TAC film (2) TAC film/adhesive layer/PVA polarizing film/adhesive layer/COP film (3) COP Film/Adhesive Layer/PVA-Based Polarizing Film/Adhesive Layer/COP-Based Film In the present invention, at least one of the protective films is preferably a COP-based film. That is, the configuration of the polarizing plate is preferably the above (2) and (3), and more preferably the above (3). According to the configuration of the above (2) and (3), a COP-based film having a low moisture permeability can be used as a protective film, so that a polarizing plate excellent in moisture-heat resistance can be obtained. In the present invention, one of the upper and lower protective films is a protective film against the ultraviolet absorber, and the other protective film is an ultraviolet-permeable protective film. In the above-mentioned ultraviolet ray protective film, when the polarizing plate is disposed on both sides of the liquid crystal cell, ultraviolet rays from the outside can function to protect the liquid crystal cell. The UV-resistant protective film can be suitably formulated with an ultraviolet absorber. The transmittance of light having a wavelength of 380 nm of the ultraviolet ray protective film is, for example, 10% or less. 保护i: The protective film of the ultraviolet ray permeability is irradiated with _ ray (light illuminating) from the side of the protective film to illuminate the ray. The hardening composition is hardened. The ultraviolet ray-permeable protective film does not contain an ultraviolet ray absorbing agent, or has a wavelength of 38 〇 nm of a protective film that contains 'the degree of hardening of the radiation curable composition by the protective film. The transmittance of light-34-200839324 is, for example, 60% or more. A phase difference can also be provided in the protective film. Further, the thickness of the protective film is not particularly limited, but is limited to, for example, 10 to 200 μm χ °. The protective film system can also be subjected to various surface treatments before application of the radiation curable composition. (Cyclic olefin-based resin film) The above-mentioned cyclic olefin-based resin film is a film comprising a monomer composition containing at least one cyclic olefin compound, and a resin obtained by further adding hydrogen as needed. The cyclic olefin compound is, for example, a cyclic olefin compound represented by the following formula (6).

(6) (式中，R16〜R19係分別獨立地表示氫原子；鹵原子；亦可 具有氧、氮、硫或矽之連結基的取代或非取代之碳原子數 1~15的烴基或其他之1價的有機基。或亦可爲R16與R17或 R18與R19相互地鍵結而形成亞烷基，亦可R16與R17、R18 與R1 9或R17與R18相互地鍵結而形成碳環或雜環（此等之 -35- 200839324 碳環或雜環亦可爲單環構造，其他之環亦可進行縮合而形 成多環構造）。所形成之碳環或雜環係可爲芳香環，亦可 爲非芳香環。又，X係表示〇或1〜3之整數，y係表示〇或i ’但X爲〇時係y亦爲〇)。 以式（6)所示之環狀烯烴系化合物的具體例，例如例 示於以下之化合物，但不限定於此等之例示物。 •雙環[2·2.1]庚-2-烯（降冰片烯） • 5-甲基-雙環[2.2.1]庚-2-烯 • 5-乙基-雙環[2·2·1]庚-2-烯 • 5-環己基-雙環[2·2,1]庚-2-烯 • 5-苯基·雙環[2.2.1]庚-2-烯 • 5-(4-聯苯基雙環[221]庚-2_靖 • 5-甲氧基羰基-雙環[2.2.1]庚-2-烯 • 5-苯氧基羰基_雙環[2.21]庚_2_烯 • 5-苯氧基乙基羰基-雙環[221]庚·2_烯 • 5-苯基鐵基氧-雙環[2·21]庚-2_烯 · • 5 -甲基_ 5 —甲氧基羰基-雙環[2 · 2 · 1 ]庚-2 -烯 • 5-甲基-5-苯氧基羰基_雙環[221]庚_2_烯 • 5·甲基苯氧基乙基羰基_雙環2 ―基-雙環[2·2.·_2, • 5_叉乙烯基_雙環[2·2·1]庚·2_烯 • 5,5-一甲基·雙環[2 21]庚_2•烯 • 5,6-二甲基-雙環[221]庚_2_烯 • %氟-雙環[2·2·1]庚-2-烯 -36 - 200839324 • 5-氯-雙環[2.2.1]庚-2-烯 • 5-溴-雙環[2·2·1]庚-2-燏 • 5,6-二氟-雙環[2·2·1]庚-2-烯 • 5,6-二氯-雙環[2.2.1]庚-2-烯 • 5,6-二溴-雙環[2.2.1]庚-2-烯 • 5-羥基-雙環[2.2.1]庚-2-烯 • 5-羥基乙基-雙環[2.2.1]庚-2·烯 • 5-氰基-雙環[2.2.1]庚-2-烯 • 5-胺基-雙環[2.2.1]庚-2-烯 •三環[4.3.0.I2,5]癸-3-烯 •三環[4.4.0.I2,5]十一碳基-3-烯 • 7-甲基-三環[4.3.0.I2,5]癸-3-烯 • 7-乙基-三環[4.3.0.12,5]癸-3·烯 • 7-環己基-三環[4·3.0·12,5]癸-3·烯 • 7-苯基-三環[4.3.0.I2,5]癸-3-烯 • 7-(4-聯苯基）-三環[4.3.0.I2,5]癸-3-烯 • 7,8·二甲基-三環[4.3.0.12,5]癸-3-烯 • 7,8，9-三甲基-三環[4.3.0. I2,5]癸-3-烯 • 8-甲基-三環[4.4.0.I2’5]十一碳基-3-烯 • 8-苯基-三環[4.4.0.I2,5]十一碳基-3-烯 • 7-氟-三環[4.3.0.12,5]癸-3-烯 • 7-氯-三環[4.3.0.I2,5]癸-3-烯 • 7,8- • 7-溴-三環[4.3.0.12,5]癸-3-烯 二氯-三環[4·3.0.12,5]癸-3-烯 -37- 200839324 • 7,8，9-三氯-三環[4.3.0.12,5 ]癸-3 ·烯 • 7-氯甲基-三環[4.3.0.12,5]癸-3-烯 • 7-二氯甲基-三環[4.3.0.12’5]癸-3-烯 • 7-三氯甲基-三環[4.3.0.I2,5]癸-3-烯 • 7-羥基-三環[4.3.0.12,5]癸-3-烯 • 7-氰-三環[4.3.0.12,5]癸-3-烯 • 7-胺基-三環[4.3.0.12,5]癸-3-烯 •四環[4.4·0.12’5.Γ’1()]十二碳基-3·烯 •五環[7.4.0.115.1^.0^12]十五碳基-3-烯 •六環[8.4.0·12’5·17’14·19’12·08，13]十七碳基-3-烯 • 8-甲基-四環[4.4.0」2,5.17，1()]十二碳基-3-烯 • 8-乙基-四環[4.4·0·12,5.Γ，1()]十二碳基-3-烯 •8-環己基-四環[4.4.0.12’5.17，1()]十二碳基-3-烯 • 8-苯基-四環[4·4.0.12,5·Γ，1()]十二碳基-3-烯 • 8-(4-聯苯基）-四環[4.4.0.12,5.17，1G]十二碳基-3-烯 • 8-甲氧基羰基-四環[4.4.0. 1 2’5.1 7’1Q]十二碳基-3-烯 • 8-苯氧基羰基-四環[4.4.0.1 2’5.17’1G]十二碳基-3-烯 • 8·苯氧乙基羰基-四環[4.4.0.12’5.17’1()]十二碳基-3-烯 • 8-苯基羰氧基-四環[4.4.0.12’5.17’1G]十二碳基-3-烯 • 8 -甲基-8-甲氧基鑛基-四環[4.4.〇.12’5.17’10]十—·碳基-3-傭 • 8-甲基-8-苯氧羰基-四環[4.4.0.12’5.17’1D]十二碳基-3-烯 • 8-甲基-8-苯氧基乙基羰基-四環[4.4.0.1 2,5.17’1G]十二碳 基-3 -錄 • 8-乙烯基-四環[4.4.0. I2,5. 17，1G]十二碳基-3·烯 -38- 200839324 "-叉乙烯基-四環^^”十^’十二碳基^一矯 •8,8-二甲基_四環[4.4 〇.12,517，10]十二碳基_3-烯 •8,9-二甲基-四環[4.4.〇.12,5.17，1〇]十二碳基-3_燦 • 8-氟-四環[4.4.0.12,5」7，1。]十二碳基-3-矯 •8-氯-四環[4.4.0.12,5.17，1〇]十二碳基_3_烯 • 8-溴 _四環[4.4.0· l2,5·;^，！。]十二碳基 _3一烯 • 8,8-一氯_四環[4.4.〇.12,5.17，1〇]十二碳基_3_烯 • 8,9-二氯-四環[4·4.〇·12,5·ι7，ι ❹]十二碳基·3-烯 •8,8,9,9-四氯_四環[4.4.〇.12,517，1()]十二碳基_3_烯 • 8-經基-四環[4·4·〇·12,5·ι7，ι。]十二碳基-3-烯 •8-羥乙基-四環[4.4.〇.12,5.17，1。]十二碳基_3-燃 • 8 -甲基-8 -經乙基-四環[4 · 4 . 〇 . 1 2，5 · 17，10 ]十二碳基-3 -烯 • 8-氰-四環[4.4.0.12,5.17，1〇]十二碳基-3-烯 •8-胺基-四環[4.4.0.12,5.17，1”十二碳基_3_稀 又’此等環狀烯煙系化合物係可1種單獨使用，亦可 倂用2種以上。 上述環狀烯烴系化合物之種類及量係依所得到之樹脂 所尋求的特性適當選擇。 就環狀烯烴系化合物而言，若使用於其分子內具有至 少一個含有選自氮原子、硫原子或矽原子的至少一種原子 之構造（以下稱爲「極性構造」）的化合物，因與其他材料 之黏著性或密著性優，故佳。尤其前述式（6)，R16及R18 爲氫原子、或碳數1〜3之烴基、宜爲氫原子、或甲基’ Rl 7 或R19之任一者爲具有極性構造之基，其他爲氫原子或碳 -39- 200839324 數1〜3之烴基的化合物，係樹脂之吸水（濕）性低，佳。進 一步，具有極性構造之基爲以下述式（7)所示之基的環狀 烯烴系化合物，係易取得所得到之樹脂的耐熱性與吸水（ 濕）性之平衡，可適宜使用。 -(CH2)zCOOR20 (7) (式中，R2()係表示取代或非取代之碳原子數1〜15的烴基， z表示0或1〜10之整數）。 在（7)中，z之値愈小，所得到之氫添加物的玻璃轉移 溫度愈高，耐熱性優，故宜z爲0〜3之整數。進一步，z 爲〇之單體係其合成很容易，故佳。又，在前述式（7)中之 R2Q係碳數愈多，所得到之聚合物的氫添加物之吸水（濕） 性有降低之傾向，但，亦有玻璃轉移溫度降低之傾向，故 從保持耐熱性之觀點，宜爲碳數1〜1 0的烴基，尤宜爲碳數 1〜6之烴基。 又’於前述式（6)中，若於以前述式（7)所示之基鍵結 的碳原子上鍵結碳數1〜3之烷基，尤其甲基，則就耐熱性 與吸水（濕）性之均衡而言，佳。進一步，於前述式（6)中， X爲〇或1，y爲0之化合物係從反應性高、可以高效率得到 聚合物，又可得到耐熱性高之聚合物氫添加物，進而工業 上易取得性上適宜使用。 於上述環狀烯烴系樹脂中，可使能與上述環狀烯烴系 化合物共聚合之其他單體包含於單體組成物中而進行聚合 -40- 200839324 上述可共聚合之其他單體可舉例如環丁烯、環戊烯、 環庚烯、環辛烯、環十二碳烯等之環狀烯烴或1，4-環辛二 烯、二環戊二烯、環十二碳三烯等之非共軛環狀聚烯。 此等可共聚合之其他的單體係亦可1種單獨使用，亦 可併用2種以上。 含有上述環狀烯烴系化合物之單體組成物的聚合方法 ，可使用例如特開2006-201 736號公報、特開2005- 1 64632 號公報記載之復分解開環聚合或加成聚合之公知的方法。 又，即使有關所得到之（共）聚合物的氫添加之方法， 亦可使用上述文獻記載之公知方法。 氫添加聚合物的氫添加率係以500 MHz、j-NMR所 測定之値，宜爲50%以上，更宜爲70%以上，更宜爲90% 以上，尤宜爲99%以上。氫添加率應高，對熱或光之安定 性愈優者，可得到長期間安定之特性。 環狀烯烴系樹脂的固有黏度[7? ]inh宜爲0.2〜2.0 dl/g ，更宜爲 〇·35 〜1.0 dl/g，尤宜爲 〇·4 〜0.85 dl/g。 以環狀烯烴系樹脂之凝膠滲透色層分析（GPC)所測定 之聚苯乙烯換算的數目平均分子量（Μη)宜爲5000〜100萬， 更宜爲1萬〜50萬，尤宜爲1.5萬〜25萬。 環狀燦煙系樹脂之重量平均分子量（Mw)宜爲1萬〜2 0 0 萬，更宜爲2萬〜100萬，尤宜爲3萬〜50萬。 環狀烯烴系樹脂之玻璃轉移溫度（Tg)宜爲120以上。C ，更宜爲130以上°C，尤宜爲150以上°C。 -41 - 200839324 環狀烯烴系樹脂之飽和吸水率宜爲1質量％以下，更 宜爲0.1〜0.8質量％。 飽和吸水率超過1質量％時，從該樹脂所得到之保護 膜受所使用之環境係經時地吸水（濕）而變形等耐久性上產 生問題。另外，未達0 · 1質量％時，有時於黏着性上產生問 題。又，前述飽和吸水率依A STM D 570，在23 °c之水中 浸漬1週而測定增加質量所得到之値。 在本發明中，於無損本發明之效果的範圍中，進一步 可添加抗氧化劑、紫外線吸收劑等之添加劑。 抗氧化劑可舉例如2,6-二第三丁基-4-甲基酣、2,2，-二 氧-3，3’-二第三丁基-5，5’-二甲基二苯基甲烷、四[亞甲基· 3- (3,5-二第三丁基-4-羥基苯基）丙酸酯]甲烷等。 紫外線吸收劑可舉例如2,4-二羥基二苯甲酮、2-羥基- 4- 甲氧基二苯甲酮等。 (環狀烯烴系樹脂薄膜之製造方法） 環狀烯烴系樹脂薄膜之製造方法係可使用特開2006-20 1 73 6號公報、特開2005-1 64632號公報等記載之公知的 方法。亦即，環狀烯烴系樹脂薄膜係藉由使前述環狀烯烴 系樹脂直接熔融成形，或溶解於溶劑，進行澆鑄（澆鑄成 形）之方法俾可適當地成形。 其次，說明有關偏光板之製造方法。 本發明之偏光板的製造方法係於偏光膜之至少單面（ 具體上係單面或雙面）使保護膜介由液狀之輻射線硬化性 -42- 200839324 組成物而層合後，使此液狀之輻射線硬化性組成物進行輻 射線（例如紫外線）照射而硬化者。 圖2中，偏光板1之製造方法係含有如下步驟，即準備 聚乙烯醇系偏光膜2之步驟（a);於保護膜5,6之各單面塗佈 黏著劑層形成用之輻射線硬化性組成物，得到保護膜5,6 與輻射線硬化性組成物層3’，4’之層合體5’，6’之步驟（b); 於聚乙烯醇系偏光膜2之上面及下面的各別，使層合體 $ 5、6’以組成物層3’，4’對峙於偏光膜2之面的方式進行層合 之步驟（c);藉光照射使組成物層3’，4’硬化，而形成黏著 劑層3，4之步驟（d)。 以下說明每一步驟。 [步驟（a)] 步驟（a)係準備聚乙烯醇系偏光板2之步驟（a)(參照圖2 中之（a))。 [步驟（b)] 步驟（b)係於保護膜5(6)之單面塗佈黏著劑層形成用之 ^ 輻射線硬化性組成物，得到具有組成物層3’（4，）之保護膜 5’（6’）之步驟（參照圖2中之（a))。 具體上，係於保護膜5,6之各單面塗佈黏著劑層形成 用之輻射線硬化性組成物，依需要而進行乾燥等，而形成 由輻射線硬化性組成物所構成之層3 ’，4’。 輻射線硬化性組成物之塗佈方法並無特別限定，但可 -43- 200839324 舉例如模塗法、輥塗法、凹版塗佈法、旋塗法等。 [步驟（c)] 具體上係於聚乙烯醇系偏光膜2之上面及下面之各面 層合保護膜5,6與輻射線硬化性組成物層3’，4’之層合體 5’，6’之步驟（參照圖2中之（c))。層合體5’係以組成物層3’ 對峙於偏光膜2之面的方式進行層合。層合體6 ’係以組成 物層4’對峙於偏光膜2之面的方式進行層合。 [步驟（d )] 步驟（d)藉照射輻射線7以使組成物層3’，4’硬化，而形 成黏著劑層3,4之步驟（參照圖2中之（d)(e))。 具體上係從保護膜6之上面照射輻射線7。藉此，完成 偏光板1，該偏光板1係使輻射線硬化性組成物層3 ’，4 ’硬化 而形成黏著劑層3,4，偏光膜2與保護膜5,6介由黏著劑層 3,4而黏着構成者。（參照圖1、圖2中之（e))。 輻射線之照射量並無特別限定，但波長200〜450 nm、 照度1〜5 00 mW/cm2之光，以照射量成爲1〇〜1〇〇〇〇 mj/cm2 之方式進行照射而曝光。 進行照射之輻射線的種類係可使用可見光、紫外線、 紅外線、X線、α線、Θ線、τ線等，但尤宜爲紫外線。 光之照射裝置宜使用例如高壓水銀燈、低壓水銀燈、金屬 鹵素燈、準分子燈等。 又’在本發明中’輻射線係從紫外線透過性之保護膜 -44 - 200839324 的側面照射。於圖2中係表示保護膜6爲紫外線透過性保護 膜之情形。 所得到之偏光板一般係實施裁切等加工而使用。 【實施方式】 [實施例] 以下，藉實施例具體地說明本發明。 ^ [實施例1] (輻射線硬化性黏著劑用組成物之調整） 於附帶擾泮裝置之容器中以表1所不之調配比率，投 入成分（A)〜（C)及任意成分，攪拌4小時，均一地混合。停 止攪拌，靜置24小時，得到黏著劑層形成用之輻射線硬化 性組成物1。 φ (偏光板之製造） 利用絲線塗佈器# 3而使所得到之輻射線硬化性組成 物1塗佈於下述之TAC薄膜2(保護膜1)上，於其上貼合下 述之PVA薄膜以免氣泡等之缺陷出現。其次，於下述之 ' TAC薄膜1(保護膜2)上，使輻射線硬化性組成物1利用絲 線塗佈器# 3而塗佈，貼合於上述之貼合的薄膜之PVA上 以免氣泡等之缺陷出現。於玻璃板上，以保護膜2成爲上 面之方式，以膠帶固定保護膜2之四角，以金屬鹵素燈（照 度220 mW/cm2、照射光量1 000 mJ/cm2)從保護膜2之側進 -45- 200839324 行光照射，製作偏光板。 又，使用如以下所示之薄膜而進行同樣之操作，製作 表1所示之各種的偏光板。 PVA薄膜：使硼酸20質量份、碘〇.2質量份、碘化鉀 〇 · 5質量份溶解於水4 8 0質量份而調製成染色液，於此染色 液中浸漬PVA薄膜（維尼綸薄膜#40、Aicello公司製）3〇 秒後，使薄膜朝一方向延伸成2倍，乾燥，而製作膜厚 30μιη之PVA薄膜。 TAC薄膜1 :使纖維素乙酸酯（氧化度60.8%)1〇〇質量 份、三苯基磷酸酯1 2質量份、二氯甲烷3 〇 〇質量份、甲醇 5 0質量份投入於密閉容器內，在加壓下保溫至80°C，一邊 攪拌一邊完全溶解。其次，過濾此溶液，冷卻而保持於3 0 °C，在貼有玻璃基板之PET薄膜上以1 5 mil之薄塗器進 行塗佈。以此狀態靜置5分鐘後，進一步以1 〇 〇 °c之烘箱終 止乾燥1小時，得到膜厚80μιη之TAC薄膜1(無紫外線吸 收劑）。 TAC薄膜2:富士照片薄膜公司製「Fujitech 80D」（ 商品名）(6) (wherein R16 to R19 each independently represent a hydrogen atom; a halogen atom; or a substituted or unsubstituted hydrocarbon group having 1 to 15 carbon atoms or other substituents having a linking group of oxygen, nitrogen, sulfur or hydrazine; a monovalent organic group. Alternatively, R16 and R17 or R18 and R19 may be bonded to each other to form an alkylene group, or R16 and R17, R18 and R1 9 or R17 and R18 may be bonded to each other to form a carbocyclic ring. Or a heterocyclic ring (these -35-200839324 carbocyclic or heterocyclic ring may also be a monocyclic structure, and other rings may be condensed to form a polycyclic structure). The formed carbocyclic or heterocyclic ring may be an aromatic ring. It may also be a non-aromatic ring. Further, X represents 〇 or an integer of 1 to 3, and y represents 〇 or i ', but when X is 系, y is also 〇). Specific examples of the cyclic olefin compound represented by the formula (6) are, for example, the following compounds, but are not limited to the examples. • Bicyclo[2·2.1]hept-2-ene (norbornene) • 5-Methyl-bicyclo[2.2.1]hept-2-ene • 5-ethyl-bicyclo[2·2·1]g- 2-ene• 5-cyclohexyl-bicyclo[2·2,1]hept-2-ene• 5-phenyl·bicyclo[2.2.1]hept-2-ene• 5-(4-biphenylbicyclo[ 221]Geng-2_ Jing• 5-methoxycarbonyl-bicyclo[2.2.1]hept-2-ene• 5-phenoxycarbonyl-bicyclo[2.21]hept-2-ene• 5-phenoxy Alkylcarbonyl-bicyclo[221]hept-2-ene • 5-phenylironyloxy-bicyclo[2·21]hept-2-ene · 5 -methyl-5-methoxycarbonyl-bicyclo[2 · 2 · 1 ]heptane-2-ene • 5-methyl-5-phenoxycarbonyl-bicyclo [221]hept-2-ene • 5·methylphenoxyethylcarbonyl _bicyclo 2 -yl-bicyclo[ 2·2.·_2, • 5_ forked vinyl_bicyclo[2·2·1]hept-2-ene • 5,5-monomethylbicyclo[2 21]hept-2-ene • 5,6 - dimethyl-bicyclo[221]hept-2-ene • % fluoro-bicyclo[2·2·1]hept-2-ene-36 - 200839324 • 5-Chloro-bicyclo[2.2.1]heptan-2- Alkene 5-bromo-bicyclo[2·2·1]hept-2-indole 5,6-difluoro-bicyclo[2·2·1]hept-2-ene • 5,6-dichloro-bicyclo[ 2.2.1]hept-2-ene • 5,6-dibromo-bicyclo[2.2.1]hept-2-ene • 5-hydroxy-bicyclo[2.2.1]g- 2-ene • 5-hydroxyethyl-bicyclo[2.2.1]heptan-2-ene • 5-cyano-bicyclo[2.2.1]hept-2-ene• 5-amino-bicyclo[2.2.1] Hept-2-ene•Tricyclo[4.3.0.I2,5]indole-3-ene•tricyclo[4.4.0.I2,5]undecyl-3-ene•7-methyl-tricyclic [4.3.0.I2,5]癸-3-ene • 7-ethyl-tricyclo[4.3.0.12,5]癸-3·ene • 7-cyclohexyl-tricyclo[4·3.0·12,5 ]癸-3·ene • 7-phenyl-tricyclo[4.3.0.I2,5]indole-3-ene • 7-(4-biphenylyl)-tricyclo[4.3.0.I2,5]癸-3-ene • 7,8· dimethyl-tricyclo[4.3.0.12,5]non-3-ene • 7,8,9-trimethyl-tricyclo[4.3.0. I2,5]癸-3-ene • 8-methyl-tricyclo[4.4.0.I2'5]undecyl-3-ene• 8-phenyl-tricyclo[4.4.0.I2,5]undecene 3--3-ene • 7-fluoro-tricyclo[4.3.0.12,5]non-3-ene • 7-chloro-tricyclo[4.3.0.I2,5]indole-3-ene • 7,8- • 7-Bromo-tricyclo[4.3.0.12,5]non-3-endichloro-tricyclo[4.3.0.12,5]indole-3-ene-37- 200839324 • 7,8,9-three Chloro-tricyclo[4.3.0.12,5 ]癸-3 · alkene • 7-chloromethyl-tricyclo[4.3.0.12,5]non-3-ene • 7-dichloromethyl-tricyclo[4.3. 0.12'5] indole-3-ene • 7-trichloromethyl-tricyclo[4.3.0.I2,5]indole-3-ene • 7-hydroxy-tricyclo[4.3 .0.12,5]non-3-ene • 7-cyano-tricyclo[4.3.0.12,5]non-3-ene • 7-amino-tricyclo[4.3.0.12,5]indole-3-ene Tetracycline [4.4·0.12'5.Γ'1()]dodecyl-3·ene •pentacyclo[7.4.0.115.1^.0^12]pentadecyl-3-ene•hexacyclo[ 8.4.0·12'5·17'14·19'12·08,13]heptadecen-3-ol•8-methyl-tetracyclo[4.4.0”2,5.17,1()]10 Dicarbyl-3-ene• 8-ethyl-tetracyclo[4.4·0·12,5.Γ,1()]dodecyl-3-ene•8-cyclohexyl-tetracyclo[4.4.0.12 '5.17,1()]dodecyl-3-ene•8-phenyl-tetracyclo[4·4.0.12,5·Γ,1()]dodecyl-3-ene• 8-( 4-biphenyl)-tetracyclo[4.4.0.12,5.17,1G]dodecyl-3-ene•8-methoxycarbonyl-tetracyclo[4.4.0. 1 2'5.1 7'1Q] Dicarbyl-3-ene•8-phenoxycarbonyl-tetracyclo[4.4.0.1 2'5.17'1G]dodecyl-3-ene•8·phenoxyethylcarbonyl-tetracyclo[4.4.0.12 '5.17'1()]Dodecyl-3-ene• 8-phenylcarbonyloxy-tetracyclo[4.4.0.12'5.17'1G]dodecyl-3-ene•8-methyl-8 -Methoxy-based-tetracyclic [4.4.〇.12'5.17'10] 十-·Carbonyl-3-Buly • 8-Methyl-8-phenoxycarbonyl-tetracyclo[4.4.0.12'5.17' 1D]dodecyl-3-ene•8-methyl-8-phenoxyethylcarbonyl-tetracyclo[4.4.0.1 2,5.17'1G]dodecyl-3-recorded•8-vinyl -tetracyclo[4.4.0. I2,5. 17,1G]dodecyl-3·ene-38- 200839324 "-cross-vinyl-tetracyclic ^^"10^' twelve carbon base ^ one correction • 8,8-Dimethyl-tetracyclo[4.4 〇.12,517,10]dodecyl-3-ene-8,9-dimethyl-tetracyclo[4.4.〇.12,5.17,1〇] Dodecyl-3_can• 8-fluoro-tetracyclo[4.4.0.12,5” 7,1. ]Dodecyl-3-ortho-8-chloro-tetracyclo[4.4.0.12, 5.17,1〇]dodecyl_3_ene• 8-bromo-tetracyclic [4.4.0· l2,5· ;^,! . ]Dodecyl _3-ene • 8,8-monochloro-tetracyclo[4.4.〇.12,5.17,1〇]dodecyl _3_ene • 8,9-dichloro-tetracyclo[ 4·4.〇·12,5·ι7,ι ❹]Dodecyl·3-ene•8,8,9,9-tetrachloro-tetracyclic [4.4.〇.12,517,1()]12 Carbon-based _3_ene • 8-yl-based-tetracyclic [4·4·〇·12,5·ι7, ι. ]Dodecyl-3-ene •8-Hydroxyethyl-tetracyclo[4.4.〇.12,5.17,1. ] 12-carbon _3-burning • 8-methyl-8-ethyl-tetracyclo[4 ·4 . 〇. 1 2,5 · 17,10 ]dodecyl-3-ene • 8- Cyan-tetracyclo[4.4.0.12, 5.17,1〇]dodecyl-3-ene•8-amino-tetracyclo[4.4.0.12,5.17,1”12-carbonyl_3_稀稀' The cyclic olefinic compound may be used singly or in combination of two or more kinds. The type and amount of the cyclic olefin-based compound are appropriately selected depending on the properties sought for the obtained resin. The compound is used in a compound having at least one structure containing at least one atom selected from a nitrogen atom, a sulfur atom or a ruthenium atom (hereinafter referred to as "polar structure") in its molecule, because of adhesion to other materials or Good adhesion, so good. In particular, in the above formula (6), R16 and R18 are a hydrogen atom or a hydrocarbon group having 1 to 3 carbon atoms, preferably a hydrogen atom, or a methyl group, R'7 or R19, which is a group having a polar structure, and the others are hydrogen. Atom or carbon-39-200839324 A compound having a hydrocarbon group of 1 to 3, which is preferably low in water absorption (wet). Further, the cyclic olefin compound having a polar structure is a group represented by the following formula (7), and the balance between heat resistance and water absorption (wet) of the obtained resin can be easily obtained, and can be suitably used. -(CH2)zCOOR20 (7) (wherein R2() represents a substituted or unsubstituted hydrocarbon group having 1 to 15 carbon atoms, and z represents 0 or an integer of 1 to 10). In (7), the smaller the z is, the higher the glass transition temperature of the obtained hydrogen additive is, and the heat resistance is excellent, so z is preferably an integer of 0 to 3. Further, z is a single system, and its synthesis is easy, so it is good. Further, as the carbon number of the R2Q system in the above formula (7) increases, the water absorption (wet) property of the hydrogen additive of the obtained polymer tends to decrease, but the glass transition temperature tends to decrease, so that the glass transition temperature tends to decrease. From the viewpoint of maintaining heat resistance, a hydrocarbon group having 1 to 10 carbon atoms is preferable, and a hydrocarbon group having 1 to 6 carbon atoms is particularly preferable. Further, in the above formula (6), when an alkyl group having 1 to 3 carbon atoms, particularly a methyl group, is bonded to a carbon atom bonded to a group represented by the above formula (7), heat resistance and water absorption ( In terms of the balance of wetness, it is good. Further, in the above formula (6), a compound in which X is ruthenium or 1, y is 0 is a polymer hydrogen additive which is high in reactivity, can obtain a polymer with high efficiency, and can obtain high heat resistance, and further industrially It is suitable for easy accessibility. In the above cyclic olefin-based resin, another monomer copolymerizable with the above cyclic olefin-based compound may be contained in the monomer composition to carry out polymerization -40-200839324, for example, the other monomer which can be copolymerized, for example a cyclic olefin such as cyclobutene, cyclopentene, cycloheptene, cyclooctene or cyclododecene or 1,4-cyclooctadiene, dicyclopentadiene or cyclododecatriene Non-conjugated cyclic polyene. These other single systems which can be copolymerized may be used alone or in combination of two or more. For the polymerization method of the monomer composition containing the above-mentioned cyclic olefin-based compound, a known metathesis ring-opening polymerization or addition polymerization described in JP-A-2006-201 736 method. Further, even in the method of adding hydrogen to the obtained (co)polymer, a known method described in the above literature can be used. The hydrogen addition rate of the hydrogen-added polymer is preferably 50% or more, more preferably 70% or more, more preferably 90% or more, and particularly preferably 99% or more, as measured by 500 MHz and j-NMR. The hydrogen addition rate should be high, and the better the stability to heat or light, the long-term stability characteristics can be obtained. The intrinsic viscosity [7?]inh of the cyclic olefin resin is preferably 0.2 to 2.0 dl/g, more preferably 〇·35 to 1.0 dl/g, and particularly preferably 〇·4 to 0.85 dl/g. The polystyrene-equivalent number average molecular weight (?η) measured by gel permeation chromatography (GPC) of a cyclic olefin resin is preferably 5,000 to 1,000,000, more preferably 10,000 to 500,000, and particularly preferably 1.5. Million ~ 250,000. The weight average molecular weight (Mw) of the cyclic smokable resin is preferably from 10,000 to 200,000, more preferably from 20,000 to 1,000,000, and particularly preferably from 30,000 to 500,000. The glass transition temperature (Tg) of the cyclic olefin resin is preferably 120 or more. C is more preferably 130 or more °C, and particularly preferably 150 or more °C. -41 - 200839324 The saturated water absorption of the cyclic olefin resin is preferably 1% by mass or less, more preferably 0.1 to 0.8% by mass. When the saturated water absorption ratio exceeds 1% by mass, the protective film obtained from the resin is problematic in durability such as deformation (water absorption) and deformation due to the environment to be used. On the other hand, when it is less than 0.1% by mass, there is a problem in adhesion. Further, the saturated water absorption rate was measured by immersing in water of 23 ° C for one week in accordance with A STM D 570 to measure the mass obtained by increasing the mass. In the present invention, an additive such as an antioxidant or an ultraviolet absorber may be further added to the extent that the effects of the present invention are not impaired. The antioxidant may, for example, be 2,6-di-t-butyl-4-methylindole or 2,2,-dioxy-3,3'-di-t-butyl-5,5'-dimethyldiphenyl. Methane, tetrakis[methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]methane, and the like. The ultraviolet absorber may, for example, be 2,4-dihydroxybenzophenone or 2-hydroxy-4-methoxybenzophenone. (Manufacturing method of the cyclic olefin-based resin film) The method of producing the cyclic olefin-based resin film is a known method described in JP-A-2006-20176, JP-A-2005-1 64632, and the like. In other words, the cyclic olefin resin film can be appropriately molded by directly melt-molding the above-mentioned cyclic olefin resin or by dissolving it in a solvent and casting (casting). Next, a description will be given of a method of manufacturing a polarizing plate. The method for producing a polarizing plate of the present invention is characterized in that at least one side (specifically, one side or both sides) of the polarizing film is laminated on the protective film via a liquid radiation curable property - 42 - 200839324 The liquid radiation curable composition is cured by irradiation with radiation (for example, ultraviolet rays). In Fig. 2, the method for producing the polarizing plate 1 comprises the steps of preparing the polyvinyl alcohol-based polarizing film 2 (a); and applying the radiation for forming the adhesive layer to each of the protective films 5 and 6. a curable composition, a step (b) of obtaining a laminate 5', 6' of the protective film 5, 6 and the radiation curable composition layer 3', 4'; above and below the polyvinyl alcohol-based polarizing film 2 For each of the layers, the laminates $5, 6' are laminated (c) in such a manner that the constituent layers 3', 4' are laminated on the surface of the polarizing film 2; the composition layer 3', 4 is irradiated by light. 'Step hardening to form the adhesive layer 3, 4 (d). Each step is explained below. [Step (a)] The step (a) is a step (a) of preparing the polyvinyl alcohol-based polarizing plate 2 (refer to (a) of Fig. 2). [Step (b)] The step (b) is a radiation hardening composition for forming an adhesive layer on one side of the protective film 5 (6) to obtain protection of the composition layer 3' (4,). The step of the film 5' (6') (refer to (a) in Fig. 2). Specifically, a radiation curable composition for forming an adhesive layer is applied to each of the protective films 5 and 6, and if necessary, drying or the like is performed to form a layer 3 composed of a radiation curable composition. ', 4'. The coating method of the radiation curable composition is not particularly limited, but may be, for example, a die coating method, a roll coating method, a gravure coating method, a spin coating method, or the like. [Step (c)] Specifically, the protective film 5, 6 and the laminate 5' of the radiation curable composition layer 3', 4' are laminated on the upper surface and the lower surface of the polyvinyl alcohol-based polarizing film 2, Step 6' (refer to (c) in Fig. 2). The laminate 5' is laminated such that the composition layer 3' faces the surface of the polarizing film 2. The laminate 6' is laminated such that the composition layer 4' faces the surface of the polarizing film 2. [Step (d)] Step (d) The step of forming the adhesive layer 3, 4 by irradiating the radiation 7 to harden the composition layers 3', 4' (refer to (d) (e) in Fig. 2) . Specifically, the radiation 7 is irradiated from the upper surface of the protective film 6. Thereby, the polarizing plate 1 is completed, and the radiation curable composition layer 3', 4' is hardened to form the adhesive layers 3, 4, and the polarizing film 2 and the protective film 5, 6 are adhered to the adhesive layer. 3,4 and stick to the constitutive. (Refer to (e) in Fig. 1 and Fig. 2). The amount of irradiation of the radiation is not particularly limited, but light having a wavelength of 200 to 450 nm and an illuminance of 1 to 50,000 mW/cm 2 is irradiated and exposed so that the irradiation amount is 1 〇 to 1 〇〇〇〇 mj/cm 2 . The type of the radiation to be irradiated may be visible light, ultraviolet light, infrared light, X-ray, alpha line, ridge line, τ line or the like, but is preferably ultraviolet light. As the light irradiation device, for example, a high pressure mercury lamp, a low pressure mercury lamp, a metal halogen lamp, an excimer lamp or the like is preferably used. Further, in the present invention, the radiation is irradiated from the side surface of the ultraviolet ray protective film -44 - 200839324. Fig. 2 shows a case where the protective film 6 is an ultraviolet ray transparent protective film. The obtained polarizing plate is generally used for processing such as cutting. [Embodiment] [Examples] Hereinafter, the present invention will be specifically described by way of examples. ^ [Example 1] (Adjustment of composition for radiation curable adhesive) In the container with the scrambler, the components (A) to (C) and optional components were mixed at a mixing ratio not shown in Table 1. 4 hours, uniformly mixed. Stirring was stopped and allowed to stand for 24 hours to obtain a radiation curable composition 1 for forming an adhesive layer. φ (Production of Polarizing Plate) The obtained radiation curable composition 1 was applied onto the TAC film 2 (protective film 1) described below by a wire coater #3, and the following was attached thereto. The PVA film is free from defects such as bubbles. Next, on the TAC film 1 (protective film 2) described below, the radiation curable composition 1 is applied by a wire coater #3, and bonded to the PVA of the above-mentioned bonded film to prevent bubbles. The defects appear. On the glass plate, the protective film 2 is formed as the upper surface, and the four corners of the protective film 2 are fixed by tape, and the metal halide lamp (illuminance 220 mW/cm 2 , irradiation light amount: 1 000 mJ/cm 2 ) is introduced from the side of the protective film 2 - 45- 200839324 Light beaming, making polarizing plates. Further, various polarizing plates shown in Table 1 were produced by performing the same operation using the film shown below. PVA film: 20 parts by mass of boric acid, 2 parts by mass of iodonium, and 5 parts by mass of potassium iodide were dissolved in 48 parts by mass of water to prepare a dyeing liquid, and the PVA film was immersed in the dyeing liquid (Vinyl film #40 After 3 seconds, the film was stretched twice in one direction and dried to prepare a PVA film having a film thickness of 30 μm. TAC film 1 : 1 part by mass of cellulose acetate (degree of oxidation: 60.8%), 12 parts by mass of triphenyl phosphate, 3 parts by mass of dichloromethane, and 50 parts by mass of methanol were placed in a closed container The inside was kept warm to 80 ° C under pressure, and completely dissolved while stirring. Next, the solution was filtered, cooled and kept at 30 ° C, and coated on a PET film to which a glass substrate was attached, using a thin coater of 15 mil. After standing for 5 minutes in this state, the film was further dried in an oven at 1 Torr for 1 hour to obtain a TAC film 1 having a film thickness of 80 μm (no ultraviolet absorber). TAC film 2: "Fujitech 80D" (product name) manufactured by Fuji Photo Film Co., Ltd.

Artone薄膜1 : JSR公司製「Artone R5300」（商品名） Artone 薄膜 2: JSR 公司製「Artone R5300U」（帶有 紫外線吸收劑之薄膜）(商品名）。Artone film 1: Artone R5300 (product name) manufactured by JSR Corporation Artone film 2: "Artone R5300U" (film with UV absorber) manufactured by JSR Corporation (trade name).

Zeonor 薄膜:日本 Zeon 公司製「Zeonor ZF14-100」 (商品名）Zeonor film: Zeonor ZF14-100, manufactured by Zeon, Japan (trade name)

使Apelle薄膜：使三井化學公司製之「Apelle APL -46- 200839324 6013Tj (商品名）溶解於環戊烷中，形成樹脂濃度30質量％ 之樹脂溶液。將此樹脂溶液以桿塗器塗佈於聚對苯二甲酸 乙二酯薄膜上，靜置1小時後，以80 °C乾燥12小時而得到 膜厚72μπι之Apelle薄膜。Apelle film: "Apelle APL-46-200839324 6013Tj (trade name) manufactured by Mitsui Chemicals Co., Ltd. was dissolved in cyclopentane to form a resin solution having a resin concentration of 30% by mass. This resin solution was applied by a bar coater. The polyethylene terephthalate film was allowed to stand for 1 hour, and then dried at 80 ° C for 12 hours to obtain an Apelle film having a film thickness of 72 μm.

Topas 薄膜··使 Polyplastics 公司製之「TOPAS 5013 」（商品名）溶解於二氯甲烷以外，其餘係與Apelle薄膜之 製造同樣的操作，得到7 5 μιη之Topas薄膜。 又，PVA薄膜以外之薄膜係使用電暈表面處理裝置（ 春日電機公司製之 AGF-012)，以320 W·分/m2之放電量 對薄膜表面進行電暈放電處理，表面處理後1小時以內實 施黏着。 (評估） 依以下之方法評估所得到之輻射線硬化性組成物1的 硬化物之光的透過率、各偏光板之耐晶片切割性、耐濕熱 性。 [波長550 nm之光的透過率] 於玻璃板上，以黏着劑固定PET薄膜（膜厚188μιη、 表面未處理品），於PET薄膜上使用間隙15 mil之薄塗器 ，塗佈輻射線硬化性組成物。於此塗膜上，使用金屬鹵素 燈（照度220 mW/cm2、照射光量1 000 mJ/cm2)而進行光照 射，使組成物硬化，以23°C、5 0%RH靜置24小時。從 PET薄膜剝離硬化物，確認膜厚爲200±5μηι後，使用U- -47- 200839324 34 10型自記分光光度計（日立製作所製），對於硬化物’而 以空氣作爲對照而測定波長5 50 nm之光的透過率。 [耐晶片切割性] 以光照射貼合後，使以23°C、5 0%RH靜置24小時之偏光 板’使用 Supper Dumbbell Cutter(S SK-12862-06、Dumbbell 公司製）及、SD型 Level式試料裁切機（SDL-200、 Dumbbell公司製），沖切成50mmx8 0mm之大小。以目視 觀察所沖切之偏光板的周邊，使無剝離爲◎，於端部可看 到條狀模樣，但未被剝離之情形爲〇，於端部可觀察到被 剝離者作爲X。 [耐濕熱性] 以光照射貼合後，使以23°c、50%RH靜置24小時之 偏光板，曝露於60°C、90% RH(相對濕度）之環境下25 0小 時後’以與上述相同之判斷基準，進行耐晶片切割性之評 估。 [竇施例2〜9、比較例1〜3] 除以表1記載之比率調配各成分以外，其餘係與實施 例1同樣做法，而測定各種物性。結果表示於表1。 -48- 200839324 睛1] 1 單位:質置份1 分子童 實施例1 實施例2 實施例3 實施例4 K鋼 寊施例6 實施例7 實施例8 實施例9 比較例1 瞇例2 比韻3 \~ Cclloxidc2011P 霸 39.4 2PA 39.4 35.4 •孙· 一 i 39.4 S 24.0 39 0 一 39.4 ι_ - (A) 卜A!) KKM2199 — 一 - * i 一 ! 42.0 - j ! 15.0 ! - 97.5 一 - ICA2) Celloxide3000 39.4 38.4 14.4 1 24.4 ! 39.4 Kuraray 多元醇P-510 500 11.6 轉 - i 一 S.l 11.6 一 一 一 一 一 - Kuraray 多元酵ΪΜ010 I0D0 一 11.6 — - 15.4 一 11.6 一 - 一 一 • Preminol PPG400Q 4 IDO 一 一 ΙΙ.δ - • - — 11.6 一 一 秦 一 I 」 Kuraray 多元歐-2090 2000 一 - 一 η.β 一 一 - 一 1U 一 - 一 (Ο 1 CPI-ΠΟΑ 15 15 2.5 2.5 2.5 2.5 2.5 15 25 2.5 15 2.5 其他之 SR-l^G 38.4 38.4 3S.4 38.4 — 3S.4 - 24.4 14.4 一 38.4 38.4 成分 Sunnix GP-400 420 8.1 8.1 SI SI 一 8.1 S.l 8.1 ΖΛ 一 15>.7 19.7 合訊質量份） IDO 100 100 1DD 咖 1D0 100 100 100 100 100 100 I評估] II life的透過率(％>1(波長500 πιη，膜厚200 μ m> 1 87 1 1 87 1 1 86 ! 1 86 1 1 87 1 87 1 1 87 1 u ί 1 S6 1 I 57 1 1 87 1 I87I 1»晶片切割性顺濕熱性J 偏光板之構造(保護膜】)/(保護膜2) 丁六頌膜2/7六(^膜1 €>/€> ； ❽! ©/© 1 ! χ/χ | x/x i Χ/Χ TAC^M2/Arton 礎膜] 0/0 ®/<s> 0/0 0/0 ©/<§> ©/<§> Χ/Χ χ/χ χ/χ T八€^膜2/^職薄膜 0/0 ®/® i ©/© Ο/Ό 0/0 Χ/Χ χ/χ χ/χ TAC 薄膜 2/Topas 瓣 0/0 €>Χ© 0/0 0/0 ®/<s> Χ/Χ χ/χ χ/χ TAC薄肢2/Apelle薄膀 0/0 0/0 0/0 ®/© ®/© Χ/Χ χ/χ χ/χ Artoπe¾膜2/Arton^M 1 0/0 ©/© ©/© 0/0 0/0 ®/€> €>/© χ/χ χ/χ χ/χ Zeonoi#M/Zeonor 薄膜 0/0 ©/© 0/0 0/0 ©/© <§>/© €>/© χ/χ χ/χ χ/χTopas film · "TOPAS 5013" (trade name) manufactured by Polyplastics Co., Ltd. was dissolved in methylene chloride, and the same operation as in the manufacture of Apelle film was carried out to obtain a Tops film of 75 μm. In addition, a film other than the PVA film was subjected to corona discharge treatment at a discharge amount of 320 W·min/m 2 using a corona surface treatment apparatus (AGF-012, manufactured by Kasuga Electric Co., Ltd.), and within 1 hour after surface treatment. Implement adhesion. (Evaluation) The transmittance of light of the cured product of the radiation curable composition 1 obtained, the wafer cut resistance of each polarizing plate, and the moist heat resistance were evaluated by the following methods. [Transmittance of light with a wavelength of 550 nm] On a glass plate, a PET film (film thickness 188 μm, surface untreated product) was fixed with an adhesive, and a thin coater with a gap of 15 mil was applied to the PET film to apply radiation hardening. Sexual composition. On the coating film, a metal halide lamp (illuminance: 220 mW/cm2, irradiation light amount: 1 000 mJ/cm2) was used for the irradiation, and the composition was cured, and allowed to stand at 23 ° C and 50% RH for 24 hours. The cured product was peeled off from the PET film, and after confirming that the film thickness was 200±5 μηι, a U-47-200839324 34 10 self-recording spectrophotometer (manufactured by Hitachi, Ltd.) was used, and the cured product was measured with a wavelength of 5 50 using air as a control. The transmittance of light in nm. [Resistance to Wafer Cutting] After bonding with light, the polarizing plate was allowed to stand at 23 ° C and 50% RH for 24 hours. Using Supper Dumbbell Cutter (S SK-12862-06, manufactured by Dumbbell) and SD Type Level sample cutting machine (made by SDL-200, Dumbbell), punched into a size of 50mm x 8 0mm. The periphery of the punched polarizing plate was visually observed so that no peeling was observed, and a strip-like pattern was observed at the end portion, but in the case where it was not peeled off, the peeled portion was observed as X. [Heat and Heat Resistance] After bonding with light, the polarizing plate was allowed to stand at 23 ° C and 50% RH for 24 hours, and exposed to an environment of 60 ° C and 90% RH (relative humidity) for 25 hours. The wafer cut resistance was evaluated on the same basis as the above. [Sinus Examples 2 to 9 and Comparative Examples 1 to 3] Various physical properties were measured in the same manner as in Example 1 except that the components were blended in the ratios shown in Table 1. The results are shown in Table 1. -48- 200839324 Eye 1] 1 Unit: Qualification 1 Molecular Child Example 1 Example 2 Example 3 Example 4 K steel 寊 Example 6 Example 7 Example 8 Example 9 Comparative Example 1 眯 Example 2 Rhyme 3 \~ Cclloxidc2011P PA 39.4 2PA 39.4 35.4 • Sun · One i 39.4 S 24.0 39 0 A 39.4 ι_ - (A) A A!) KKM2199 — One - * i One! 42.0 - j ! 15.0 ! - 97.5 One - ICA2 Celloxide3000 39.4 38.4 14.4 1 24.4 ! 39.4 Kuraray Polyol P-510 500 11.6 Transfer - i One Sl 11.6 One 1111 - Kuraray Multiple Fermentation 010 I0D0 A 11.6 - - 15.4 A 11.6 One - One One • Preminol PPG400Q 4 IDO δ - • - - 11.6 一一秦一I ” Kuraray Multi-European-2090 2000 One-one η.β One-one-one 1U one-one (Ο 1 CPI-ΠΟΑ 15 15 2.5 2.5 2.5 2.5 2.5 15 25 2.5 15 2.5 Other SR-l^G 38.4 38.4 3S.4 38.4 — 3S.4 - 24.4 14.4 A 38.4 38.4 Composition Sunnix GP-400 420 8.1 8.1 SI SI A 8.1 Sl 8.1 ΖΛ A 15>.7 19.7 Parts by mass) IDO 100 100 1DD Coffee 1D0 100 100 100 100 100 100 I Evaluation] II Transmittance of life (% > 1 (wavelength 500 πιη, film thickness 200 μ m) 1 87 1 1 87 1 1 86 ! 1 86 1 1 87 1 87 1 1 87 1 u ί 1 S6 1 I 57 1 1 87 1 I87I 1» Wafer-cutting heat-sensitive J-polarized plate structure (protective film)) / (protective film 2) Ding Liuqi film 2/7 six (^ film 1 €>/€>; ❽! ©/ © 1 ! χ/χ | x/xi Χ/Χ TAC^M2/Arton Base Film] 0/0 ®/<s> 0/0 0/0 ©/<§>©/<§> Χ/Χ χ/χ χ/χ T8€^膜2/^膜膜0/0®/® i ©/© Ο/Ό 0/0 Χ/Χ χ/χ χ/χ TAC film 2/Topas 0/0 €>Χ© 0/0 0/0 ®/<s> Χ/Χ χ/χ χ/χ TAC Thin 2/Apelle Thin 0/0 0/0 0/0 ®/© ® /© Χ/Χ χ/χ χ/χ Artoπe3⁄4 Film 2/Arton^M 1 0/0 ©/© ©/© 0/0 0/0 ®/€>€>/© χ/χ χ/χ χ/χ Zeonoi#M/Zeonor Film 0/0 ©/© 0/0 0/0 ©/© <§>/© €>/© χ/χ χ/χ χ/χ

又，表1中之各成分的化合物名係如以下般。 [(A1)成分]Further, the compound names of the respective components in Table 1 are as follows. [(A1) ingredient]

Celloxide 202 1 P: 3,4-環氧基環己烯基甲基-3’，4’-環氧基 環己烯羧酸酯（Dai cel公司製） KRM 2 199 :雙（3,4-環氧基環己基甲基）己二酸（AdeCa公司製） [(A2)成分]Celloxide 202 1 P: 3,4-epoxycyclohexenylmethyl-3',4'-epoxycyclohexenecarboxylate (manufactured by Daicel Co., Ltd.) KRM 2 199 : Double (3,4- Epoxycyclohexylmethyl)adipic acid (manufactured by AdeCa Co., Ltd.) [(A2) component]

Celloxid 3000: 1,2: 8,9-二環氧基檸檬烯（Daicel 化學工 業公司製） [(B)成分]Celloxid 3000: 1,2: 8,9-dicyclooxy limonene (manufactured by Daicel Chemical Co., Ltd.) [(B) component]

Kuraray 多元醇 P-510:聚[(3-甲基-1,5-戊二醇）-alt-(己二 酸）](Kuraray公司製；數目平均分子量5 00)Kuraray polyol P-510: poly[(3-methyl-1,5-pentanediol)-alt-(adipate)] (manufactured by Kuraray Co., Ltd.; number average molecular weight 500)

Kuiraray 多元醇 P-1010:聚[(3-甲基-1，5-戊二醇）1^-(己 二酸）](Kuraray公司製；數目平均分子量1，〇〇〇)Kuiraray polyol P-1010: poly[(3-methyl-1,5-pentanediol) 1^-(adipate)] (manufactured by Kuraray Co., Ltd.; number average molecular weight 1, 〇〇〇)

Preminol PPG 4000 :聚丙二醇（旭硝子公司製；數目平均 -49- 200839324 分子量4100)Preminol PPG 4000: Polypropylene glycol (Asahi Glass Co., Ltd.; average number -49- 200839324 molecular weight 4100)

Kuraray 多元醇 02090:聚[(3-甲基-1,5-戊二醇；l，6-己 二醇）碳酸酯](Kuraray公司製；數目平均分子量2〇〇〇) [(C)成分] CPI-110A: 一苯基[4-(苯基硫）苯基]硫鑰六氟銻酸酯 (Sun-apro 公司製） [其他之成分] SR-NPG ··新戊二醇二縮水甘油基醚（阪本藥品工業公司製） Sunnix GP-400 :聚氧丙烯甘油基醚（三洋化成工業公司製 :數目平均分子量420) [實施例1〇〜17、比較例4、5、參考例1〜3] 除以表2記載之比率調配各成分以外，其餘係與實施 φ 例1同樣做法，得到黏著劑層用之輻射線硬化性組成物及 偏光板。 將所得到之輻射線硬化性組成物的硬化物之光的透過 ^ 率、偏光板的耐晶片切割性與實施例1同樣做法而進行評 - 估，進一步依下述之方法評估偏光板之剝離強度測定。 [剝離測定] 所製作之偏光板的剝離強度係依Jis K 6854-4黏著 劑-剝離黏着強度試驗法第4部：浮動輥法而測定。具體上 -50- 200839324 係使所製作之偏光板於金屬板（不鏽鋼製、尺寸··長度200 mm、寬25 mm、厚1.5 mm)上以雙面黏着膠帶（ST-416 P、 住友3M公司製）固定。使用切刀，剝離偏光板之長方向的 端部。依JIS法，於浮動輥上安裝試樣，使所剝離之薄膜 試樣的端部固定於抗拉試驗機之抓取具上，以抗拉試驗機 使浮動輥以300mm/分之速度上昇，測定薄膜剝離時之平 均剝離力（單位N)。 平均剝離力爲1 ·5 N以上，或偏光板破壞或無法剝離 偏光板之端時爲「◎」，平均剝離力爲〇·8 Ν以上1·5 Ν以 下時爲「〇」，平均剝離力爲未達（Κ8Ν時爲「X」。 結果表示於表2中。 又，就比較例4、5而言，對於與上述比較例1、2相同 組成之組成物，除光之透過率、耐晶片切割性外’尙測定 剝離強度之結果，就參考例1〜3而言，對於與上述實施例 1〜3相同組成之組成物，除光之透過率、耐晶片切割性外 ，尙測定剝離強度之結果，一倂表示於表2中。 200839324 [表2]Kuraray Polyol 02090: Poly[(3-methyl-1,5-pentanediol; 1,6-hexanediol) carbonate] (manufactured by Kuraray Co., Ltd.; number average molecular weight 2〇〇〇) [(C) component CPI-110A: monophenyl[4-(phenylthio)phenyl]thiol hexafluoroantimonate (manufactured by Sun-apro) [Other components] SR-NPG ··Pentyl glycol diglycidyl Sunthix GP-400: polyoxypropylene glyceryl ether (manufactured by Sanyo Chemical Industries, Ltd.: number average molecular weight 420) [Examples 1 to 17, Comparative Examples 4 and 5, Reference Example 1 3) The radiation curable composition for the adhesive layer and the polarizing plate were obtained in the same manner as in Example 1 except that the components were blended in the ratios shown in Table 2. The transmittance of the light of the cured product of the radiation curable composition and the wafer cut resistance of the polarizing plate were evaluated in the same manner as in Example 1, and the peeling of the polarizing plate was further evaluated by the following method. Strength measurement. [Peeling Measurement] The peeling strength of the polarizing plate produced was measured in accordance with the Visa 6 6-6 Adhesive-Peel Adhesion Test Method Part 4: Floating Roll Method. Specifically -50-200839324 made the polarizing plate made of double-sided adhesive tape on stainless steel (stainless steel, size, length 200 mm, width 25 mm, thickness 1.5 mm) (ST-416 P, Sumitomo 3M Fixed). Using a cutter, the end portion of the polarizing plate in the longitudinal direction is peeled off. According to the JIS method, the sample is mounted on the floating roller, the end of the peeled film sample is fixed on the gripper of the tensile tester, and the floating roller is raised at a speed of 300 mm/min by the tensile tester. The average peel force (unit: N) at the time of film peeling was measured. The average peeling force is 1. 5 N or more, or "◎" when the polarizing plate is broken or the end of the polarizing plate cannot be peeled off, and the average peeling force is "〇" when the average peeling force is 〇·8 Ν or more and 1·5 Ν or less, and the average peeling force is When it is less than Κ8Ν, it is "X". The results are shown in Table 2. In addition, in Comparative Examples 4 and 5, the composition of the same composition as those of Comparative Examples 1 and 2 except for light transmittance and resistance. As a result of measuring the peeling strength of the wafer dicing property, in the reference examples 1 to 3, the composition having the same composition as that of the above-mentioned Examples 1 to 3 was measured for peeling in addition to light transmittance and wafer cutting resistance. The results of the strength are shown in Table 2. 200839324 [Table 2]

單位:質爾份 分子《 辨例1 參考例2 辦例3 寊施_ 實施例" 實讎2 實施例13 宵施例Μ 寅施例15 寘施例16 Η施倒17 比酬 Ccllraidc 202ΪΡ 3?.4 39.4 39.4 39.4 39.4 24.4 39.4 59.4 39Λ 39,4 310 一 39.4 KRM 2】99 42.0 97.5 一 Kuraray 多元 _Ρ·5】0 500 116 Kuraray 多元餘Ρ-1010 10QQ 參 11.6 Preminol PPG4000 4100 Kuraray 多 Jt 醇C-590 500 Kuraray 多元醇C-1090 IDD0 Kuraray 多元醇C-2050 麵 Kuraray 多元醇 C-2090 20D0 Kuraray 多元醇C-3090 3DQ0 Kuraray 多元醇C-2065N 2P00 Kuraray 多元醇C-2015N 2000 <〇 cpj-noA 2.5 2.3 15 2.5 2.5 2.5 2.5 3.5 15 25 15 2.5 2.5 其蚊 SR-NPG - 35.4 38.4 38.4 38.4 3ΖΛ 32.4 3S4 5S.4 a‘4 324 秦 - 38.4 m Sunnix CP-400 400 ΖΛ 81 8.1 8.1 8.1 S.1 8.1 S.1 8.1 一 一 19.7 合計(質最份） ioa 100 100 100 100 ιοα 100 100 100 100 100 too 100 I評估1 1光的透過率(％)](波長500mn，膜厚200μιη> 27 1 8? } 86 | 87 | 87 1 87 | 87 1 g7 | ί 87 ) δδ | 87 | 87 卜段:1«晶柄I割性] 屮段:〔保 護膜1舆偏光器間之剝薄強度） 下段:保 護膜2¾僑光器間之剝鑀強度> 偏光板之構造(保護膜丨)/(保護膜2> TAC薄膜2/TAC薄膜1 X X @ X φ © © © €) © 0 © © φ @ @ X Ο X Ο X X X © © © @ © €> φ © Ο ο Ο © ο Φ © ο ο © κ X TAC 薄膜2/Artone^l X X X ❾ ® © Ο Ο X X X ® @ @ Ο ο Ο @ 0 © © © @ ο ο © κ X TAC薄膜2/Zeoiw薄膜 X Κ X ο © © ® Ο ο © X X X X κ ο © Ο Ο ο X Κ 0 @ © ο © © © Ο ο © X X T AC薄膜2/Topas薄膜 X He X ο © €> ® Ο ο X Κ X X κ ο © © © Ο ο @ X X Ο © ο €> ο ο κ X TAC薄膜2/Apd】e薄膜 X Κ X ο @ @ ο ο © X X X X X ο % @ ο ο y X Ο © © ο © % ® @ ο ο © κ X Arlone 薄膜 2/Artone 薄膜 1 κ X X ο @ ® @ 0 ο @ X κ X X X ο © © ο ο @ X X Ο @ ® ο 0 0 X X Zconor薄膜/Zeonor 薄膜 X X X ο © Θ ο 0 © X X X X X ο © ο ο X XUnit: Qualitative Molecule "Recognition 1 Reference Example 2 Case 3 _ 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施 实施?.4 39.4 39.4 39.4 39.4 24.4 39.4 59.4 39Λ 39,4 310 A 39.4 KRM 2]99 42.0 97.5 A Kuraray Multivariate _Ρ·5]0 500 116 Kuraray Multiple Residues-1010 10QQ Reference 11.6 Preminol PPG4000 4100 Kuraray Multi Jt Alcohol C-590 500 Kuraray Polyol C-1090 IDD0 Kuraray Polyol C-2050 Face Kuraray Polyol C-2090 20D0 Kuraray Polyol C-3090 3DQ0 Kuraray Polyol C-2065N 2P00 Kuraray Polyol C-2015N 2000 <〇cpj -noA 2.5 2.3 15 2.5 2.5 2.5 2.5 3.5 15 25 15 2.5 2.5 Its mosquito SR-NPG - 35.4 38.4 38.4 38.4 3ΖΛ 32.4 3S4 5S.4 a'4 324 Qin - 38.4 m Sunnix CP-400 400 ΖΛ 81 8.1 8.1 8.1 S .1 8.1 S.1 8.1 One to one 19.7 total (most important) ioa 100 100 100 100 ιοα 10 0 100 100 100 100 too 100 IEvaluate the transmittance (%) of 1 1 light] (wavelength 500 mn, film thickness 200 μιη > 27 1 8? } 86 | 87 | 87 1 87 | 87 1 g7 | ί 87 ) δδ | 87 | 87 Section: 1 «Clip shank I cut] 屮 Section: [stretching strength between protective film 1 舆 polarizer] Lower section: peeling strength between protective film 23⁄4 occupants> Construction of polarizing plate (protection Membrane 丨) / (Protective film 2 > TAC film 2 / TAC film 1 XX @ X φ © © © €) © 0 © © φ @ @ X Ο X Ο XXX © © © @ © €> φ © Ο ο Ο © ο Φ © ο ο © κ X TAC Film 2/Artone^l XXX ❾ ® © © Ο XXX XXX ® @ @ Ο ο Ο @ 0 © © © ο ο © κ X TAC Film 2/Zeoiw Film X Κ X ο © © Ο ο ο © XXXX κ ο © Ο Ο ο X Κ 0 @ © ο © © Ο ο © XXT AC film 2/Topas film X He X ο © €> ® Ο ο X Κ XX κ ο © © © Ο ο @ XX Ο © ο €> ο ο κ X TAC film 2/Apd] e film X Κ X ο @ @ ο ο © XXXXX ο % @ ο ο y X Ο © © ο © % ® @ ο ο © κ X Arlone Film 2/Artone Film 1 κ XX ο @ ® @ 0 ο @ X κ XXX ο © © ο ο @ XX Ο @ ® ο 0 0 XX Zconor Film /Zeonor film XXX ο © Θ ο 0 © XXXXX ο © ο ο XX

又，表2中之各成分的化合物名係如以下般。Further, the compound names of the respective components in Table 2 are as follows.

Kuraray 多元醇 C-5 90 :聚[(3-甲基-1,5-戊二醇；1，6-己二 醇）碳酸酯](Kuraray公司製；數目平均分子量500)Kuraray polyol C-5 90 : poly[(3-methyl-1,5-pentanediol; 1,6-hexanediol) carbonate] (manufactured by Kuraray Co., Ltd.; number average molecular weight 500)

Kuraray 多元醇 C- 1 090:聚[(3-甲基-1，5-戊二醇；1，6-己 二醇）碳酸酯KKuraray公司製；數目平均分子量1〇〇〇) Kuraray 多元醇 C-2050:聚[(3-甲基-1，5-戊二醇；1，6-己 二醇）碳酸酯KKuraray公司製；數目平均分子量2000) Kuraray 多元醇 C-3 090:聚[(3-甲基-1，5·戊二醇；1，6-己 二醇）碳酸酯KKuraray公司製；數目平均分子量3 000) Kuraray 多元醇 C-2065N ··聚[(1，9-壬二醇；2-甲基-1，8-辛 二醇）碳酸酯](Kuraray公司製；數目平均分子量2000) Kuraray 多元醇 C-2015N :聚[(1，9-壬二醇；2-甲基-1，8-辛 二醇）碳酸酯](Kuraray公司製；數目平均分子量2000) -52- 200839324 就（A1)成分、（B)成分所使用之Kuraray多元醇P-510 、P-1010，C-2090、Preminol PPG 4000、（C)成分、及其 他之成分係與表1中同樣。 [實施例18〜22、比較例6、7、參考例4] 除以表3記載之比率調配各成分以外，其餘係與實施 例1同樣做法，得到黏著劑用之輻射線硬化性組成物及偏 光板。 將所得到之輻射線硬化性組成物的硬化物之光的透過 率、偏光板的耐晶片切割性、耐濕熱性與實施例1同樣做 法而進行評估，進一步依下述之方法評估偏光板之初期耐 晶片切割性。 [初期耐晶片切割性] 以光照射貼合後，使以23°C、50%RH靜置1小時之偏 光板，使用 Supper Dumbbell Cutter( S S K- 1 2 8 62- 06、 Dumbbell公司製）及、SD型Level式試料裁切機（SDL-2 00 、Dumbbell公司製），沖切成50 mmx80mm之大小。以目 視觀察所沖切之偏光板的周邊’使無剝離爲◎’於端部可 看到條狀模樣，但未被剝離之情形爲〇，於端部可觀察到 被剝離者作爲X。 結果表示於表3中。 又，就比較例6、7而言，對於與上述比較例1、2相同 組成之組成物，除光之透過率、耐晶片切割性、耐濕熱性 -53- 200839324 外，尙測定初期耐晶片切割性之結果，就參考例4而言， 對於與上述實施例2相同組成之組成物，除光之透過率、 耐晶片切割性、耐濕熱性外，尙測定初期晶片切割性之結 果，一倂表不於表3中。 [表3]Kuraray polyol C-1 090: poly[(3-methyl-1,5-pentanediol; 1,6-hexanediol) carbonate manufactured by KKuraray Co., Ltd.; number average molecular weight: 1) Kuraray polyol C -2050: poly[(3-methyl-1,5-pentanediol; 1,6-hexanediol) carbonate manufactured by KKuraray Co., Ltd.; number average molecular weight 2000) Kuraray polyol C-3 090: poly[(3) -Methyl-1,5-pentanediol; 1,6-hexanediol) carbonate manufactured by KKuraray Co., Ltd.; number average molecular weight: 3 000) Kuraray polyol C-2065N ··poly[(1,9-nonanediol) ; 2-methyl-1,8-octanediol) carbonate] (manufactured by Kuraray Co., Ltd.; number average molecular weight 2000) Kuraray polyol C-2015N: poly[(1,9-nonanediol; 2-methyl-) 1,8-octanediol) carbonate] (manufactured by Kuraray Co., Ltd.; number average molecular weight: 2000) -52 - 200839324 Kuraray polyol P-510, P-1010, C used for (A1) component and (B) component -2090, Preminol PPG 4000, (C) component, and other components are the same as in Table 1. [Examples 18 to 22, Comparative Examples 6, 7, and Reference Example 4] The radiation curable composition for the adhesive was obtained in the same manner as in Example 1 except that the components were blended in the ratios shown in Table 3. Polarizer. The transmittance of the light of the cured product of the obtained radiation curable composition, the wafer cut resistance of the polarizing plate, and the heat and humidity resistance of the polarizing plate were evaluated in the same manner as in Example 1, and the polarizing plate was further evaluated by the following method. Initial resistance to wafer cutting. [Initial resistance to wafer cutting property] After bonding with light, the polarizing plate was allowed to stand at 23 ° C and 50% RH for 1 hour, and Supper Dumbbell Cutter (SS K- 1 2 8 62-06, manufactured by Dumbbell Co., Ltd.) was used. And SD type Level sample cutting machine (SDL-2 00, manufactured by Dumbbell), punched into a size of 50 mm x 80 mm. The periphery of the polarizing plate which was punched was visually observed so that no peeling was observed. The strip-like pattern was observed at the end portion, but the peeling was not observed, and the peeled person was observed as X at the end portion. The results are shown in Table 3. Further, in Comparative Examples 6 and 7, the composition having the same composition as that of Comparative Examples 1 and 2 except for light transmittance, wafer cut resistance, and moist heat resistance -53-200839324 As a result of the cutting property, with respect to the composition of the same composition as in the above-mentioned Example 2, in addition to the light transmittance, the wafer cutting resistance, and the moist heat resistance, the result of the initial wafer cutting property was measured. The table is not shown in Table 3. [table 3]

單位:質贵份 分子童 參考W W施例18 實施卵9 實麵20 寅施例21 實施例22 比較例6 mmi …ΙτΔΙ、 Celloxidc 202IP 39.4 32.5 32.5 32.5 32.5 32.0 - 39.4 KRM2199 - 一 - - - 32.0 97.5 一 Kuraray 多元醇P-510 500 - 10.0 一 一 一 — 一 一 KurdTuy多元醇Ρ·丨0】0 1000 11.6 一 10.0 一 一 - 一 一 W Kuraray 多兄醇C-2090 2000 一 一 一 10.0 10.0 15.4 一 一 Kuraray 多元醇 C-590 500 一 一 一 - — 6.1 一 一 CO CPM10A 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Aronix M-3J5 — 12.0 12.0 12.0 一 iO.O 一 一 (β) Aronix M-215 一 - 一 一 12.0 一 一 一 SR-NPG 38.4 33.0 33.0 33.0 33.0 一 一 38.4 其他之 成分 Sunnix GP-400 8.1 8.0 8.0 SO 8.0 一 一 19.7 IRGACURE 184 一 2.0 · 2.0 2.0 2.0 2.0 一 一 HITALOID486I KAYARAD DPHA — 合計【質a份) 100 100 ΪΟΟ 100 100 100 100 100 ί_ [光的透過率(％)丨(波長5001^^200 # m) 87 | S7 1 87 | 87 1 87 1 87 | 87 1 87 卜.段··丨初期酎晶片切剂性(光照射後P丨僻之晶片切割性)] 中段:间晶片切割性洸照射後24小時之耐晶片切剖性)1 下段:嘛濕熱性(濕热後之耐晶片切割性)] 偏光板之描造(保護膜υ/(保護膜2) X 〇 〇 <S> Ο X X TAC 薄膜 © © © <§> © © © X X X X X Ο Ο <§> X X TACj® 膜 2/Artone薄膜 1 © Ο © <S> X X © Ο <§> © ® X X X ο 〇 (s> X X 丁八0^膜2/2〇〇11〇1·薄膜 ® ο ο <§> © <S> © % X X X X X ο ο (§> X X TAC薄膜2/Topas薄膜 ο X X ο @ X X X ο ο X X TAGS腰 2/Apdle 薄膜 ο ο <§> © © X X X X Artone 薄膜 2Mrtone 薄膜 1 X (§> ® ο ο ο ο <s> <§> © <s> ® X X X X X X X ο ο © X X Zeono满膜/Zeonor薄膜 ο © © <§> X X ο X X 又，表3中之各成分的化合物名係如以下般。 [(D)成分]Unit: Qualified Molecular Reference WW Example 18 Implementing Egg 9 Solid 20 寅 Example 21 Example 22 Comparative Example 6 mmi ... ΙτΔΙ, Celloxidc 202IP 39.4 32.5 32.5 32.5 32.5 32.0 - 39.4 KRM2199 - One - - - 32.0 97.5 A Kuraray polyol P-510 500 - 10.0 One to one - one one KurdTuy polyol Ρ · 丨 0] 0 1000 11.6 a 10.0 one one - one W Wuraura C-290 2000 one one one 10.0 10.0 15.4 one A Kuraray polyol C-590 500 One-one - 6.1 One CO CPM10A 2.5 2.5 2.5 2.5 2.5 2.5 2.5 2.5 Aronix M-3J5 — 12.0 12.0 12.0 One iO.O One (β) Aronix M-215 One - one 12.011_11 SR-NPG 38.4 33.0 33.0 33.0 33.0 One 38.4 Other components Sunnix GP-400 8.1 8.0 8.0 SO 8.0 One 19.7 IRGACURE 184 A 2.0 · 2.0 2.0 2.0 2.0 One HITALOID486I KAYARAD DPHA — Total [Quality a 100 100 ΪΟΟ 100 100 100 100 100 ί_ [Light transmittance (%) 丨 (wavelength 5001^^200 # m) 87 | S7 1 87 | 87 1 87 1 87 | 87 1 87 卜.段··丨Initial 酎Slice cut-off property (P-cut wafer cutting property after light irradiation)] Middle section: Wafer cut-off resistance 24 hours after wafer cutting 洸 irradiation) 1 Lower section: Wet heat (wafer cutting resistance after wet heat) )] Description of polarizing plate (protective film υ / (protective film 2) X 〇〇 < S > Ο XX TAC film © © © <§> © © XXXXX Ο Ο <§> XX TACj® Membrane 2/Artone Film 1 © Ο © <S> XX © Ο <§> © ® XXX ο 〇(s> XX Ding 8 0^ Film 2/2〇〇11〇1·Film® ο ο <§> © <S> © % XXXXX ο ο (§> XX TAC Film 2/Topas Film ο XX ο @ XXX ο ο XX TAGS Waist 2/Apdle Film ο ο <§> © © XXXX Artone Film 2Mrtone film 1 X (§> ® ο ο ο ο <s><§> © <s> ® XXXXXXX ο ο © XX Zeono Full Film / Zeonor film ο © © <§> XX ο XX Moreover, the compound name of each component in Table 3 is as follows. [(D) ingredient]

Aronix M-315:三[2-(甲基）丙烯醯氧乙基]三聚異氰酸酯（ 東亞合成公司製）Aronix M-315: Tris[2-(methyl)acryloyloxyethyl]trimeric isocyanate (manufactured by Toagosei Co., Ltd.)

Aronix M-215:雙[2-(甲基）丙烯醯氧乙基](2-羥乙基）三聚 -54- 200839324 異氰酸酯（東亞合成公司製） [其他之成分]Aronix M-215: bis[2-(methyl)acryloyloxyethyl](2-hydroxyethyl) trimer -54- 200839324 Isocyanate (manufactured by Toagosei Co., Ltd.) [Other Ingredients]

Irgacure 184 :1-經環己基苯基酮（Ciba SpecialtyIrgacure 184 : 1-cyclohexyl phenyl ketone (Ciba Specialty

Chemicals 公司製）Chemicals company)

Hitaloid 48 61 ··胺基甲酸酯丙烯酸酯（日立化成工業公司製） Kayarad DPHA:二季戊四醇六丙烯酸酯（日本化藥公司製） 使用來作用（A1)成分、（B)成分之Kuraray多元醇？-510、P-1010、C-20 90、C-590、使用來作爲（C)成分、及 其他成分之 SR-NPG、Sunnix、GP-400係與表1中或表2中 同樣。 [實施例23〜26、比較例8、參考例5、6] 除以表4記載之比率調配各成分以外，其餘係與實施 例1同樣做法，得到偏光板。 將所得到之偏光板的剝離強度與實施例1 0同樣做法而 進行評估，進一步依下述之方法評估偏光板之翹曲。 [翹曲] 將所製作之偏光板裁切成縱l〇cm、橫l〇cm之尺寸， 呈平坦玻璃板狀以偏光板的4角浮起的狀態靜置。測定偏 光板之4角離玻璃板的距離，以4點之平均値做爲平均翹曲 量。Hitaloid 48 61 · urethane acrylate (manufactured by Hitachi Chemical Co., Ltd.) Kayarad DPHA: dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) Kuraray polyol which is used as component (A1) and component (B) ? -510, P-1010, C-20 90, C-590, SR-NPG, Sunnix, and GP-400 which are used as the component (C) and other components are the same as those in Table 1 or Table 2. [Examples 23 to 26, Comparative Example 8, and Reference Examples 5 and 6] A polarizing plate was obtained in the same manner as in Example 1 except that the components were blended in the ratios shown in Table 4. The peel strength of the obtained polarizing plate was evaluated in the same manner as in Example 10, and the warpage of the polarizing plate was further evaluated by the following method. [warpage] The polarizing plate to be produced is cut into a size of a length of l〇cm and a width of l〇cm, and is placed in a flat glass plate shape and suspended in a state where four corners of the polarizing plate are floated. The distance between the four corners of the polarizing plate and the glass plate was measured, and the average enthalpy of four points was used as the average warpage amount.

平均翹曲量爲5mm以下時作爲〇，超過5mm時作爲X -55- 200839324 結果表示於表4中。 又，就比較例8而言，對於與上述比較例2(比較例5) 相同組成之組成物，除剝離強度外，尙測定翹曲之結果， 就參考例5、6而言，對於與上述實施例4、20相同組成之 組成物，除剝離強度外，尙測定翹曲之結果，——倂表示於 表4中。 1^表4] TAC薄肢2/TAC薄膜1 ®®ι X <§>©1 〇〇〇 0©<§>| 0©<§> TAC薄膜2/Artone薄膜1 X®® X®® Ο Ο 〇 ο®® ο®® 0<§><§> X 00 TAC薄膜2/Zeonor薄膜 X©® 00 0 ο©® X0 0 TAC薄膜2/Topas薄膜 X®® ο ο ο 0(§)€> 0®® 0®® X oo TAC薄膜2/Ape】le薄膜 ©<§> X©® 0 00 οΘ(§>ι 0©<§>| ο®® xooWhen the average warpage amount is 5 mm or less, it is 〇, and when it exceeds 5 mm, it is shown in Table 4 as X-55-200839324. Further, in Comparative Example 8, the composition of the same composition as that of Comparative Example 2 (Comparative Example 5) was measured for warpage in addition to the peel strength, and in the case of Reference Examples 5 and 6, In the compositions of the same composition of Examples 4 and 20, in addition to the peel strength, the results of the warpage were measured by 尙, and 倂 is shown in Table 4. 1^Table 4] TAC Thin 2/TAC Film 1 ®® ι X <§>©1 〇〇〇0©<§>| 0©<§> TAC Film 2/Artone Film 1 X ®® X®® Ο Ο 〇ο®® ο®® 0<§><§> X 00 TAC film 2/Zeonor film X©® 00 0 ο©® X0 0 TAC film 2/Topas film X® ® ο ο ο 0(§)€> 0®® 0®® X oo TAC film 2/Ape]le film©<§> X©® 0 00 οΘ(§>ι 0©<§&gt ;| ο®® xoo

Arion 满膜 2/Artone 薄膜 1 X®© X®® ο ο ο 〇 <§>® 〇<2><2> 0<§>© X 00 X®® οοο ΟΘΦ 0©<§> 0<2>@ X ο Ο 單位:質量份 分了坌 詩例5 參考例6 寅施例23 實施例24 寅施例25 寶施例26 比餃例8 cA)[(An Celloxidc2021P 39.4 32.5 39.4 39.4 32.5 32.5 39.4 (Β) Kuraray 多元醇 C-2090 2000 11.6 10.0 - 11.6 10.0 10.0 一 (ο 二本基M-(苯基硫成基丨硫箱六氣辑酸酷 一 - 2.5 2,5 2.5 - 一 lrgacure250 - 一 - 一 - 2.5 — 一.苯基[4-(苯基硫)苯基]砖錤六氟銻酸酋 2.5 2.5 - 一 — - 2.S (β) Aronix M-315 一 12.0 - - 12.0 12.0 一 SR-NPG 38.4 33.0 38.4 38.4 33.0 33.0 Sunnix GP-400 8.1 8.0 19.7 8.1 8.0 8.0 38.4 IRGACURE 】84 一 2.0 — - 2.0 2.0 19.7 合計(質堡份） 100 100 100 100 100 100 100 上段:(翹曲} 中段:(保護晈I與偏光器間之剝睡強度) 下段.·(保護膜2與偏光器間之剝離強度) 偏光板之構造(保護膜IV(保護膜2> 又，表4中之各成分的化合物名係如以下般。 [(C)成分] 二苯基[4-(苯基硫）苯基]硫鑰六氟磷酸酯：（Sun-apro公司製） IRGACURE 25 0 : (4_甲基苯基）[4-(2-甲基丙基）苯基]碘鑰 六氟磷酸酯（Ciba Specialty Chemicals公司製） -56- 200839324 二苯基[4-(苯基硫）苯基]硫鎗六氟銻酸酯：（Sun-apro公司製）。 (A1)成分、（B)成分及其他之成分係與表1中或表3中 相同。 從表1，可知本發明之偏光板（實施例1〜9)係耐晶片切 割性（光照射後，經過24小時之時點）、耐濕熱性優。進一 步，從表2可知若使用以式（2)所示之化合物作爲（B)成分 ，除耐晶片切割性，尙可得到剝離強度（保護膜與偏光器 之間的接着性）優之偏光板（實施例1〇〜17)。 從表3，進一步若調配（D)成分，除耐晶片切割性（光 照射後，經過24小時之時點）、耐濕熱性外，尙可得到初 期耐晶片切割性（光照射後，經過1小時之時點）亦優之偏 光板（實施例18〜22)。 從表4可知若使用式（4)之鎰鹽（陰離子種爲PFr之鑰 鹽）作爲（C)成分，相較於使用其他之陰離子種的鍚鹽之情 形，可得到翹曲變形小之偏光板（實施例23〜26)。 從表1〜4可知，在比較例1、2(對應於表2中之比較例4 、5、表3中之比較例6、7、表4中之比較例8)中，係耐晶 片切割性（光照射後，經過24小時之時點）、初期耐晶片切 割性（光照射後，經過1小時之時點）、耐濕熱性、剝離強 度及翹曲之任一者均差。從表1中可知，比較例3之偏光板 係耐晶片切割性、耐濕熱性差。 【圖式簡單說明】 圖1係模式地表示本發明之偏光板的一例之截面圖’ -57- 200839324 圖2係表示本發明之偏光板的製造方法一例之流程圖 【主要元件符號說明】 1 :偏光板 2 :聚乙烯醇系偏光膜 3 :黏著劑層 3 ’ ：輻射線硬化性組成物層 4 :黏著劑層 4 ’ ：輻射線硬化性組成物層 5 :保護膜 6 :保護膜 7 :輻射線Arion Full Film 2/Artone Film 1 X®© X®® ο ο ο 〇<§>® 〇<2><2>0<§>© X 00 X®® οοο ΟΘΦ 0©<§>0<2>@ X ο Ο Unit: mass fraction of 坌 5 5 5 5 参考 参考 参考 参考 参考 参考 参考 参考 参考 参考 参考 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 23 32.5 39.4 39.4 32.5 32.5 39.4 (Β) Kuraray polyol C-2090 2000 11.6 10.0 - 11.6 10.0 10.0 one (o two base M-(phenyl thiosulfanyl sulfide) six gas series acid one - 2.5 2,5 2.5 - a lrgacure250 - one - one - 2.5 - a. phenyl [4-(phenylthio)phenyl] brick hexafluoroantimonate emirate 2.5 2.5 - one - - 2.S (β) Aronix M-315 12.0 - - 12.0 12.0 A SR-NPG 38.4 33.0 38.4 38.4 33.0 33.0 Sunnix GP-400 8.1 8.0 19.7 8.1 8.0 8.0 38.4 IRGACURE 】84 A 2.0 — - 2.0 2.0 19.7 Total (Qingbao) 100 100 100 100 100 100 100 Upper section : (warpage) Middle section: (protection of the peeling strength between 晈I and the polarizer) Lower section. (The peeling strength between the protective film 2 and the polarizer) Structure of the polarizing plate (protective film IV) (protective film 2 > In Table 4 The compound name of each component is as follows. [(C) component] Diphenyl [4-(phenylthio)phenyl] sulphur hexafluorophosphate: (manufactured by Sun-apro) IRGACURE 25 0 : (4 _Methylphenyl)[4-(2-methylpropyl)phenyl]iodyl hexafluorophosphate (manufactured by Ciba Specialty Chemicals) -56- 200839324 Diphenyl[4-(phenylthio)phenyl Sulfur hexafluoroantimonate: (manufactured by Sun-apro Co., Ltd.) The components (A1), (B) and other components are the same as those in Table 1 or Table 3. From Table 1, the polarized light of the present invention is known. The plates (Examples 1 to 9) were excellent in wafer cut resistance (at a time of 24 hours after light irradiation) and excellent in moist heat resistance. Further, as shown in Table 2, the compound represented by the formula (2) was used as (B). In addition to the wafer cutting resistance, the composition has a peeling strength (adhesion between the protective film and the polarizer) which is excellent in polarizing plates (Examples 1 to 17). From Table 3, further, if the component (D) is blended, in addition to the wafer cutting resistance (at the time of 24 hours after light irradiation) and the moist heat resistance, the initial chip resistance can be obtained (after one hour of light irradiation). At the time of the point), the polarizing plate is also excellent (Examples 18 to 22). As is clear from Table 4, when the sulfonium salt of the formula (4) (the anion species is the key salt of PFr) is used as the component (C), the warpage with small warpage can be obtained as compared with the case of using the cerium salt of other anionic species. Plates (Examples 23 to 26). As can be seen from Tables 1 to 4, in Comparative Examples 1 and 2 (corresponding to Comparative Examples 4 and 5 in Table 2, Comparative Examples 6 and 7 in Table 3, and Comparative Example 8 in Table 4), the wafer resistance was cut. The properties (after 24 hours of light irradiation), initial chip resistance (after 1 hour of light irradiation), moisture heat resistance, peel strength, and warpage were all poor. As is clear from Table 1, the polarizing plate of Comparative Example 3 was inferior in wafer cut resistance and moist heat resistance. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a cross-sectional view showing an example of a polarizing plate of the present invention. -57-200839324 FIG. 2 is a flow chart showing an example of a method for producing a polarizing plate of the present invention. Polarizing plate 2: polyvinyl alcohol-based polarizing film 3: adhesive layer 3': radiation curable composition layer 4: adhesive layer 4': radiation curable composition layer 5: protective film 6: protective film 7 : radiation

-58--58-

Claims (1)

200839324 十、申請專利範圍 1 · 一種偏光板，其係於聚乙烯醇系偏光膜的至少單面 ’介由黏著劑層而層合保護膜所構成，其特徵在於：上述 黏者劑層由含有如下之輻射線硬化性組成物的硬化物所構 成，即（A)脂環式環氧化合物、（B)具有至少一個羥基且數 目平均分子量爲5 0 0以上之化合物、及（C)光酸產生劑。 2 .如申請專利範圍第1項之偏光板，其中上述成分（A) 爲具有（A1)於1分子中具有2個以上脂環式環氧基之化合物 、及/或（A2)以下述式（1)所示之具有1個脂環式環氧基之化 合物， R3200839324 X. Patent Application No. 1 A polarizing plate comprising at least one side of a polyvinyl alcohol-based polarizing film formed by laminating a protective film via an adhesive layer, characterized in that the adhesive layer is contained a cured product of a radiation curable composition, that is, (A) an alicyclic epoxy compound, (B) a compound having at least one hydroxyl group and having a number average molecular weight of 500 or more, and (C) a photoacid Producing agent. 2. The polarizing plate of claim 1, wherein the component (A) is a compound having (A1) having two or more alicyclic epoxy groups in one molecule, and/or (A2) is represented by the following formula: (1) A compound having one alicyclic epoxy group, R3 R2 (式中，R1、R2及R3係分別獨立地爲氫原子或甲基）。 3 .如申請專利範圍第1或2項之偏光板，其中上述成分 (B)之數目平均分子量爲以上。 4.如申請專利範圍第1〜3項中任一項的偏光板，其中 上述成分（B)爲以下述式（2)所示之化合物， H0-(R4-0-C0-0)m-(R5-0-C0-0)n-R6-0H (2) -59- 200839324 (式中，R4及R1係分別獨立地表示碳數2-12的2價烴基， R2係表示與R4與R1之任一者相同的構造；m爲2〜150，η 爲0〜1 5 0，且m + η爲2〜2 0 0)。 5 .如申請專利範圍第1〜4項中任一項的偏光板，其中 上述（C)成分爲以下述式（4)所示之鑰鹽， [R3aR4bR9cR10dZ] + PF6- (4)R2 (wherein R1, R2 and R3 are each independently a hydrogen atom or a methyl group). 3. The polarizing plate of claim 1 or 2, wherein the component (B) has a number average molecular weight of at least the above. 4. The polarizing plate according to any one of claims 1 to 3, wherein the component (B) is a compound represented by the following formula (2), H0-(R4-0-C0-0)m- (R5-0-C0-0)n-R6-0H (2) -59- 200839324 (wherein R4 and R1 each independently represent a divalent hydrocarbon group having 2 to 12 carbon atoms, and R2 represents R4 and R1 Either the same configuration; m is 2 to 150, η is 0 to 1 50, and m + η is 2 to 2 0 0). 5. The polarizing plate according to any one of claims 1 to 4, wherein the component (C) is a key salt represented by the following formula (4), [R3aR4bR9cR10dZ] + PF6- (4) (式中’陽離子爲f翁離子，Z表示S、Se、Te、P、As、Sb 、：Bi、Ο、I、Βι:、Cl 或 Ne N，H3、r8、R9 及 Rl〇係表示 互爲相同或相異之有機基；a、b、c及d分別爲0〜3之整 數，（a +b + c + d-1)係相等於z之價數）。 6 .如申請專利範圍第1〜5項中任一項的偏光板，其中 上述_射線硬化性組成物進一步含有（D )以下述式（5)所示 之化合物，(wherein the 'cation is a gonio ion, Z means S, Se, Te, P, As, Sb, :Bi, Ο, I, Βι:, Cl or Ne N, H3, r8, R9 and Rl 表示 represent each other The same or different organic groups; a, b, c and d are each an integer of 0 to 3, and (a + b + c + d-1) is equivalent to the valence of z). The polarizing plate according to any one of claims 1 to 5, wherein the _ ray hardening composition further contains (D) a compound represented by the following formula (5), -60 - 1 2 (式中，R11、R及R13係分別獨立地爲一價之有機基，而 3 R11〜R13之中至少2個爲_R"0C0CRl5 = CH2，R“係碳數2〜8 4 之2價有機基’R爲氫原子或甲基）。 200839324 7 . —種偏光板，其係於聚乙烯醇系偏光膜的至少單面 ，介由黏著劑層而層合保護膜所形成，其特徵在於：上述 黏著劑層由含有如下之輻射線硬化性組成物的硬化物所構 成，即（A)脂環式環氧化合物、及（C)以下述式（4)所示之光 酸產生劑， [R7aR8bR9cR10dZ] + PF6· (4) (式中，陽離子爲銷離子，Z表示S、Se、Te、P、As、Sb 、Bi、Ο、I、Br、Cl 或 N 三 N，R7、R8、R9及 R10係表示 互爲相同或相異之有機基；a、b、c及d分別爲0〜3之整 數，（a + b + c + d-1)係相等於Z之價數）。 8 .如申請專利範圍第1〜7項中任一項的偏光板，其中 上述輻射線硬化性組成物當形成厚度200 μπι之硬化物時， 波長5 50nm之光的透過率爲70%以上。 9. 如申請專利範圍第1〜8項中任一項的偏光板，其中 上述保護膜由環狀烯烴系樹脂所構成。 10. —種偏光板之製造方法，係如申請專利範圍第1〜9 項中任一項的偏光板之製造方法，包含如下步驟：於偏光 膜之至少單面，介由上述輻射線硬化性組成物而層合保護 膜之步驟；與光照射該輻射線硬化性組成物而硬化，得到 偏光板之硬化步驟。 -61 --60 - 1 2 (wherein R11, R and R13 are each independently a monovalent organic group, and at least two of 3 R11 to R13 are _R" 0C0CRl5 = CH2, R "carbon number 2~ 8 4 of the divalent organic group 'R is a hydrogen atom or a methyl group.) 200839324 7 . A polarizing plate which is bonded to at least one side of a polyvinyl alcohol-based polarizing film and laminated with a protective film via an adhesive layer The adhesive layer is formed of a cured product containing a radiation curable composition, that is, (A) an alicyclic epoxy compound, and (C) is represented by the following formula (4). Photoacid generator, [R7aR8bR9cR10dZ] + PF6· (4) (wherein, the cation is a pin ion, and Z represents S, Se, Te, P, As, Sb, Bi, Ο, I, Br, Cl or N , R7, R8, R9 and R10 represent an organic group which are the same or different from each other; a, b, c and d are each an integer of 0 to 3, and (a + b + c + d-1) is equivalent to Z The polarizing plate according to any one of claims 1 to 7, wherein the radiation curable composition is light having a wavelength of 50 nm when formed into a cured product having a thickness of 200 μm. The polarizing plate according to any one of claims 1 to 8, wherein the protective film is composed of a cyclic olefin resin. 10. A method for producing a polarizing plate. The method for producing a polarizing plate according to any one of claims 1 to 9, further comprising the step of laminating a protective film on at least one side of the polarizing film via the radiation curable composition; The radiation hardening composition is irradiated with light to be hardened, and a hardening step of the polarizing plate is obtained.
TW097101655A 2007-02-02 2008-01-16 Polarizing plate and method of manufacturing the same TW200839324A (en)

Applications Claiming Priority (6)

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JP2007024789 2007-02-02
JP2007044687 2007-02-23
JP2007062694A JP4816515B2 (en) 2007-03-12 2007-03-12 Polarizing plate and manufacturing method thereof
JP2007069667A JP2008233279A (en) 2007-03-16 2007-03-16 Polarizing plate and its manufacturing method
JP2007080423A JP2008241946A (en) 2007-03-27 2007-03-27 Polarizing plate and method for manufacturing the same
JP2007080422A JP4816533B2 (en) 2007-03-27 2007-03-27 Polarizing plate and manufacturing method thereof

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TWI493005B (en) * 2009-07-28 2015-07-21 Toagosei Co Ltd An active energy ray hardening agent composition for a plastic film or sheet

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US20110300387A1 (en) * 2009-02-20 2011-12-08 Seong-Jun Park Modified polyvinyl alcohol resins and adhesive, polarizer, and display device containing the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI493005B (en) * 2009-07-28 2015-07-21 Toagosei Co Ltd An active energy ray hardening agent composition for a plastic film or sheet

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