JP2022000508A - Photocurable resin composition - Google Patents

Photocurable resin composition Download PDF

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JP2022000508A
JP2022000508A JP2021142177A JP2021142177A JP2022000508A JP 2022000508 A JP2022000508 A JP 2022000508A JP 2021142177 A JP2021142177 A JP 2021142177A JP 2021142177 A JP2021142177 A JP 2021142177A JP 2022000508 A JP2022000508 A JP 2022000508A
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resin composition
heating
acrylate
photocurable resin
photocurable
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司 中村
Tsukasa Nakamura
大輔 原
Daisuke Hara
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Dexerials Corp
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Dexerials Corp
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Priority to JP2021142177A priority Critical patent/JP2022000508A/en
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Priority to JP2023075432A priority patent/JP2023086991A/en
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    • 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
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • 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
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C27/00—Joining pieces of glass to pieces of other inorganic material; Joining glass to glass other than by fusing
    • C03C27/06—Joining glass to glass by processes other than fusing
    • C03C27/10—Joining glass to glass by processes other than fusing with the aid of adhesive specially adapted for that purpose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/067—Polyurethanes; Polyureas
    • 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
    • C09J11/08—Macromolecular additives
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/06—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving heating of the applied adhesive
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
    • B05D3/065—After-treatment
    • B05D3/067—Curing or cross-linking the coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/12—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by mechanical means
    • 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
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B2037/1253—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
    • 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
    • B32B2310/00—Treatment by energy or chemical effects
    • B32B2310/08—Treatment by energy or chemical effects by wave energy or particle radiation
    • B32B2310/0806—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation
    • B32B2310/0831—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation using UV radiation
    • 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
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
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    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • C—CHEMISTRY; METALLURGY
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    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/416—Additional features of adhesives in the form of films or foils characterized by the presence of essential components use of irradiation
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09J2433/00—Presence of (meth)acrylic polymer
    • 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
    • G02F1/133308—Support structures for LCD panels, e.g. frames or bezels
    • G02F1/133331—Cover glasses
    • 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
    • G02F2202/00—Materials and properties
    • G02F2202/28—Adhesive materials or arrangements

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Abstract

To achieve both high viscosity of dam material and low viscosity of fill material and ensure good adhesion between members even when the dam material and the fill material are made of a resin composition of the same components.SOLUTION: This production method includes the step (A) of using a first resin composition to form, on a first member, an area 7 to be coated with a second resin composition 8; the step (B) of coating the area 7 with the second resin composition 8; the step (C) of bonding the first member and the second member together through the second resin composition 8 and charging the second resin composition 8 into the coated area 7; and the step (D) of irradiating the second resin composition 8 with light to form a cured resin layer 1. The step (C) includes heating the second resin composition 8. The second resin composition 8 contains monofunctional monomers that demonstrate a residual rate of 95.0% or more after heating for 30 minutes at 60°C. The second resin composition 8 demonstrates a residual rate of 95.0% or more after heating for 3 hours at 80°C.SELECTED DRAWING: Figure 1

Description

本技術は、光硬化性樹脂組成物に関する。 The present technology relates to a photocurable resin composition.

従来、部材同士を光硬化性樹脂組成物で貼り合わせ、光透過性樹脂層で固定する技術が知られている。例えば、例えば特許文献１には、画像表示部材と、光透過性部材との間に、光硬化性樹脂組成物を配して樹脂組成物層を形成し、樹脂組成物層に光を照射して硬化樹脂層を形成する方法が記載されている。ここで、画像表示装置における光透過性部材と画像表示部材とは、密着性が良好であることが望ましい。 Conventionally, there is known a technique in which members are bonded to each other with a photocurable resin composition and fixed with a light-transmitting resin layer. For example, in Patent Document 1, for example, in Patent Document 1, a photocurable resin composition is arranged between an image display member and a light-transmitting member to form a resin composition layer, and the resin composition layer is irradiated with light. A method for forming a cured resin layer is described. Here, it is desirable that the light transmissive member and the image display member in the image display device have good adhesion.

また、被塗布体（光透過性部材や画像表示部材）からの光硬化性樹脂組成物のはみ出しを抑制する観点から、いわゆるダムフィルプロセスが採用されることがある。ダムフィルプロセスでは、例えば、第１の樹脂組成物（ダム材）を用いて、画像表示部材の表面に、第２の樹脂組成物（フィル材）の塗布領域を形成する。次に、形成した塗布領域に第２の樹脂組成物を塗布し、画像表示部材と光透過性部材とを第２の樹脂組成物を介して貼合せる。そして、第２の樹脂組成物に光を照射して硬化樹脂層を形成する。 Further, a so-called dumb-fill process may be adopted from the viewpoint of suppressing the protrusion of the photocurable resin composition from the object to be coated (light transmissive member or image display member). In the dam fill process, for example, the first resin composition (dam material) is used to form a coating region of the second resin composition (fill material) on the surface of the image display member. Next, the second resin composition is applied to the formed coating region, and the image display member and the light transmissive member are bonded to each other via the second resin composition. Then, the second resin composition is irradiated with light to form a cured resin layer.

ダムフィルプロセスにおいて、ダム材は、液ダレ防止の観点から、高粘度であることが好ましい。一方、フィル材は、気泡を防止し短いタクトタイムで貼合せする観点から、低粘度であることが好ましい。ここで、ダム材とフィル材の境界部の視認性を良好にする、すなわちダム材とフィル材の境界線が目立たないようにするために、ダム材とフィル材として、同一成分の樹脂組成物を用いる場合がある。しかし、ダム材とフィル材として、同一成分の樹脂組成物を用いると、ダム材の高粘度性、又はフィル材の低粘度性が犠牲になってしまうことが懸念される。 In the dam fill process, the dam material preferably has a high viscosity from the viewpoint of preventing liquid dripping. On the other hand, the fill material preferably has a low viscosity from the viewpoint of preventing air bubbles and laminating in a short tact time. Here, in order to improve the visibility of the boundary portion between the dam material and the fill material, that is, to make the boundary line between the dam material and the fill material inconspicuous, a resin composition having the same composition as the dam material and the fill material. May be used. However, if a resin composition having the same composition is used as the dam material and the fill material, there is a concern that the high viscosity of the dam material or the low viscosity of the fill material will be sacrificed.

特開２０１４−２２２３５０号公報Japanese Unexamined Patent Publication No. 2014-222350

本技術は、このような従来の実情に鑑みて提案されたものであり、ダム材とフィル材として同一成分の樹脂組成物を用いた場合でも、ダム材の高粘度性とフィル材の低粘度性を両立し、部材同士の密着性を良好にできる光硬化性樹脂組成物を提供する。 This technique has been proposed in view of such conventional circumstances, and even when a resin composition having the same composition as the dam material and the fill material is used, the high viscosity of the dam material and the low viscosity of the fill material are used. Provided is a photocurable resin composition capable of achieving both properties and good adhesion between members.

本技術に係る光硬化性樹脂組成物は、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーと、（メタ）アクリレート樹脂と、光重合開始剤と、可塑剤とを含有し、８０℃で３時間加熱後の加熱残分が９５．０％以上であり、単官能モノマーは、ノニルフェノールＰＯ変性（メタ）アクリレート及び２−エチルヘキシルＥＯ変性（メタ）アクリレートの少なくとも１種である。 The photocurable resin composition according to the present technology comprises a monofunctional monomer having a heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes, a (meth) acrylate resin, a photopolymerization initiator, and a plasticizer. The monofunctional monomer contains at least 95.0% or more of the heating residue after heating at 80 ° C. for 3 hours, and the monofunctional monomer is at least one of nonylphenol PO-modified (meth) acrylate and 2-ethylhexyl EO-modified (meth) acrylate. It is one kind.

本技術によれば、第１の樹脂組成物（ダム材）と、第２の樹脂組成物（フィル材）として同一成分の樹脂組成物を用いた場合でも、ダム材の高粘度性とフィル材の低粘度性を両立し、部材同士の密着性を良好にできる。 According to this technology, even when a resin composition having the same composition as the first resin composition (dam material) and the second resin composition (fill material) are used, the high viscosity of the dam material and the fill material are used. It is possible to achieve both low viscosity and good adhesion between members.

図１は、画像表示装置の一例を示す断面図である。FIG. 1 is a cross-sectional view showing an example of an image display device. 図２（Ａ）は、画像表示部材の一例を示す正面図であり、図２（Ｂ）は図２（Ａ）に示すＡ−Ａ’断面図である。2A is a front view showing an example of an image display member, and FIG. 2B is a cross-sectional view taken along the line AA'shown in FIG. 2A. 図３（Ａ）は、画像表示部材の表面に、第１の樹脂組成物を用いて第２の樹脂組成物の塗布領域を形成する方法の一例を説明するための正面図であり、図３（Ｂ）は図３（Ａ）に示すＡ−Ａ’断面図である。FIG. 3A is a front view for explaining an example of a method of forming a coating region of the second resin composition on the surface of the image display member by using the first resin composition. FIG. 3A is a front view. (B) is a cross-sectional view taken along the line AA'shown in FIG. 3 (A). 図４は、画像表示部材の表面に、第１の樹脂組成物を用いて第２の樹脂組成物の塗布領域を形成する方法の一例を説明するための断面図である。FIG. 4 is a cross-sectional view for explaining an example of a method of forming a coating region of the second resin composition on the surface of the image display member by using the first resin composition. 図５（Ａ）は、第２の樹脂組成物を塗布する方法の一例を説明するための正面図であり、図５（Ｂ）は図５（Ａ）に示すＡ−Ａ’断面図である。5 (A) is a front view for explaining an example of a method of applying the second resin composition, and FIG. 5 (B) is a cross-sectional view taken along the line AA'shown in FIG. 5 (A). .. 図６（Ａ）は、画像表示部材と光透過性部材とを第２の樹脂組成物を介して貼合せる方法の一例を説明するための正面図であり、図６（Ｂ）は図６（Ａ）に示すＡ−Ａ’断面図である。FIG. 6A is a front view for explaining an example of a method of bonding an image display member and a light transmissive member via a second resin composition, and FIG. 6B is a front view showing FIG. 6 (B). It is a cross-sectional view of AA'shown in A). 図７は、第２の樹脂組成物に光を照射して硬化樹脂層を形成する方法の一例を説明するための断面図である。FIG. 7 is a cross-sectional view for explaining an example of a method of irradiating the second resin composition with light to form a cured resin layer. 図８は、単官能モノマーの加熱残分の測定方法を説明するための図である。FIG. 8 is a diagram for explaining a method for measuring the heating residue of the monofunctional monomer. 図９は、光硬化性樹脂組成物の加熱残分の測定方法を説明するための図である。FIG. 9 is a diagram for explaining a method for measuring a heating residue of a photocurable resin composition. 図１０は、接着強度試験の測定方法を説明するための斜視図である。FIG. 10 is a perspective view for explaining a measuring method of an adhesive strength test. 図１１は、図１０中のＡ−Ａ’断面図である。FIG. 11 is a cross-sectional view taken along the line AA'in FIG. 図１２は、接着強度試験の測定方法を説明するための斜視図である。FIG. 12 is a perspective view for explaining a measuring method of the adhesive strength test. 図１３は、図１２中のＡ−Ａ’断面図である。FIG. 13 is a cross-sectional view taken along the line AA'in FIG. 図１４は、接着強度試験の測定方法を説明するための斜視図である。FIG. 14 is a perspective view for explaining a measuring method of the adhesive strength test.

［積層体の製造方法］
本実施の形態に係る積層体の製造方法は、下記工程（Ａ）〜（Ｄ）を有し、工程（Ｃ）が第２の樹脂組成物を加熱することを含む。また、本製造方法で用いられる第２の樹脂組成物は、後に詳述するように、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーを含有し、かつ８０℃で３時間加熱後の加熱残分が９５．０％以上である。 [Manufacturing method of laminated body]
The method for producing a laminate according to the present embodiment includes the following steps (A) to (D), in which the step (C) heats the second resin composition. Further, as will be described in detail later, the second resin composition used in the present production method contains a monofunctional monomer having a residual heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes. The heating residue after heating at 80 ° C. for 3 hours is 95.0% or more.

工程（Ａ）：第１の部材の表面に、第１の樹脂組成物を用いて光硬化性の第２の樹脂組成物の塗布領域を形成する。
工程（Ｂ）：塗布領域に第２の樹脂組成物を塗布する。
工程（Ｃ）：第１の部材と、第２の部材とを、第２の樹脂組成物を介して貼合せ、第２の樹脂組成物を塗布領域に充填させる。
工程（Ｄ）：第２の樹脂組成物に光を照射して硬化樹脂層を形成する。 Step (A): A coating region of the photocurable second resin composition is formed on the surface of the first member by using the first resin composition.
Step (B): The second resin composition is applied to the application area.
Step (C): The first member and the second member are bonded to each other via the second resin composition, and the second resin composition is filled in the coated region.
Step (D): The second resin composition is irradiated with light to form a cured resin layer.

本製造方法によれば、工程（Ｃ）で第２の樹脂組成物を加熱することにより、第２の樹脂組成物の粘度を低くできる。そのため、第１の樹脂組成物と第２の樹脂組成物として同一成分の樹脂組成物を用いた場合でも、第１の樹脂組成物の高粘度性と第２の樹脂組成物の低粘度性とを両立することができる。また、本製造方法では、８０℃で３時間加熱後の加熱残分が９５．０％以上である第２の樹脂組成物を用いることにより、第２の樹脂組成物を加熱する際に第２の樹脂組成物中の成分が揮発するのを抑制できるため、第１の部材と第２の部材との密着性を良好にできる。 According to this production method, the viscosity of the second resin composition can be lowered by heating the second resin composition in the step (C). Therefore, even when a resin composition having the same composition as the first resin composition and the second resin composition is used, the high viscosity of the first resin composition and the low viscosity of the second resin composition can be obtained. Can be compatible with each other. Further, in the present production method, by using the second resin composition in which the heating residue after heating at 80 ° C. for 3 hours is 95.0% or more, the second resin composition is heated when the second resin composition is heated. Since it is possible to suppress the volatilization of the components in the resin composition of the above, it is possible to improve the adhesion between the first member and the second member.

本製造方法で用いられる第２の樹脂組成物は、８０℃で３時間加熱後の加熱残分が９５．０％以上であり、９７．０％以上が好ましく、９８．０％以上がより好ましく、９９．０％以上がさらに好ましい。加熱残分がより多いことにより、第２の樹脂組成物を加熱する際に第２の樹脂組成物中の成分の揮発をより効果的に抑制できる。また、第２の樹脂組成物の加熱残分の上限値は、特に制限されない。ここで、第２の樹脂組成物の加熱残分は、熱量計測定装置（装置名：Ｑ５０、ＴＡ Ｉｎｓｔｒｕｍｅｎｔｓ社製）を用いて、樹脂組成物１０ｍｇを８０℃で３時間加熱する前後の質量を測定して求めた値をいう。第２の樹脂組成物の詳細については、後述する。 The second resin composition used in the present production method has a heating residue of 95.0% or more, preferably 97.0% or more, more preferably 98.0% or more after heating at 80 ° C. for 3 hours. , 99.0% or more is more preferable. Since the heating residue is larger, the volatilization of the components in the second resin composition can be more effectively suppressed when the second resin composition is heated. Further, the upper limit of the heating residue of the second resin composition is not particularly limited. Here, the heating residue of the second resin composition is the mass before and after heating 10 mg of the resin composition at 80 ° C. for 3 hours using a calorimeter measuring device (device name: Q50, manufactured by TA Instruments). The value obtained by measurement. Details of the second resin composition will be described later.

以下、図面を参照しながら各工程の詳細について説明する。本製造方法では、例えば図１に示すように、画像表示部材２（第１の部材）と、周縁部に遮光層４が形成された光透過性部材３（第２の部材）とが、硬化樹脂層１を介して積層した画像表示装置５（積層体）を得る。 Hereinafter, details of each process will be described with reference to the drawings. In this manufacturing method, for example, as shown in FIG. 1, the image display member 2 (first member) and the light transmissive member 3 (second member) having a light-shielding layer 4 formed on the peripheral edge thereof are cured. An image display device 5 (laminated body) laminated via the resin layer 1 is obtained.

硬化樹脂層１は、後述する第１の樹脂組成物６と第２の樹脂組成物８とから形成されている。硬化樹脂層１の屈折率は、画像表示部材２や光透過性部材３の屈折率とほぼ同等とすることが好ましく、例えば１．４５以上１．５５以下であることが好ましい。これにより、画像表示部材２からの映像光の輝度やコントラストを高め、視認性を良好にすることができる。また、硬化樹脂層１の透過率は、９０％を超えることが好ましい。これにより、画像表示部材２に形成された画像の視認性をより良好にすることができる。硬化樹脂層１の厚みは、例えば、５０〜２００μｍであることが好ましい。 The cured resin layer 1 is formed of a first resin composition 6 and a second resin composition 8, which will be described later. The refractive index of the cured resin layer 1 is preferably substantially the same as the refractive index of the image display member 2 and the light transmissive member 3, and is preferably 1.45 or more and 1.55 or less, for example. As a result, the brightness and contrast of the image light from the image display member 2 can be increased, and the visibility can be improved. Further, the transmittance of the cured resin layer 1 preferably exceeds 90%. This makes it possible to improve the visibility of the image formed on the image display member 2. The thickness of the cured resin layer 1 is preferably, for example, 50 to 200 μm.

画像表示部材２は、例えば液晶表示パネル、タッチパネル等を挙げることができる。ここで、タッチパネルとは、液晶表示パネルのような表示素子とタッチパッドのような位置入力装置を組み合わせた画像表示・入力パネルを意味する。 Examples of the image display member 2 include a liquid crystal display panel and a touch panel. Here, the touch panel means an image display / input panel in which a display element such as a liquid crystal display panel and a position input device such as a touch pad are combined.

光透過性部材３は、画像表示部材２に形成された画像が視認可能となるような光透過性を有するものであればよい。例えば、ガラス、アクリル樹脂、ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリカーボネート等の板状材料やシート状材料が挙げられる。これらの材料には、少なくとも一方の面にハードコート処理、反射防止処理等が施されていてもよい。光透過性部材３の厚さや弾性率などの物性は、使用目的に応じて適宜決定することができる。 The light transmissive member 3 may be any as long as it has a light transmissive property so that the image formed on the image display member 2 can be visually recognized. Examples thereof include plate-like materials such as glass, acrylic resin, polyethylene terephthalate, polyethylene naphthalate, and polycarbonate, and sheet-like materials. These materials may be hard-coated, anti-reflective, or the like on at least one surface. Physical properties such as the thickness and elastic modulus of the light transmissive member 3 can be appropriately determined according to the purpose of use.

遮光層４は、画像のコントラスト向上のために設けられるものであり、例えば、黒色等に着色された塗料をスクリーン印刷法などで塗布し、乾燥・硬化させて形成することができる。遮光層４の厚みは、通常５〜１００μｍである。 The light-shielding layer 4 is provided for improving the contrast of an image, and can be formed by, for example, applying a paint colored in black or the like by a screen printing method or the like, drying and curing the paint. The thickness of the light-shielding layer 4 is usually 5 to 100 μm.

［工程（Ａ）］
工程（Ａ）では、例えば図２、３に示すように、画像表示部材２の表面に、第１の樹脂組成物６を用いて第２の樹脂組成物８の塗布領域７を形成する。塗布領域７は、例えば図３、４に示すように、画像表示部材２の表示領域中、第１の樹脂組成物６から形成された枠状の液止め部（ダム）１１で囲まれた領域である。 [Step (A)]
In the step (A), for example, as shown in FIGS. 2 and 3, a coating region 7 of the second resin composition 8 is formed on the surface of the image display member 2 by using the first resin composition 6. As shown in FIGS. 3 and 4, the coating region 7 is a region surrounded by a frame-shaped liquid stop portion (dam) 11 formed from the first resin composition 6 in the display region of the image display member 2, for example. Is.

第１の樹脂組成物６は、工程（Ｂ）で塗布領域７に塗布する第２の樹脂組成物８の液ダレ防止のための材料である。第１の樹脂組成物６は、例えば、熱硬化性の樹脂組成物、光硬化性（例えば紫外線硬化性）の樹脂組成物等を用いることができる。第１の樹脂組成物６が光硬化性の樹脂組成物である場合、工程（Ａ）では、例えば図４に示すように、第１の樹脂組成物６に紫外線照射器９から紫外線１０を照射して第１の樹脂組成物６を硬化させ、液止め部１１を形成することにより、塗布領域７を画定できる。 The first resin composition 6 is a material for preventing liquid dripping of the second resin composition 8 to be applied to the coating region 7 in the step (B). As the first resin composition 6, for example, a thermosetting resin composition, a photocurable (for example, ultraviolet curable) resin composition, or the like can be used. When the first resin composition 6 is a photocurable resin composition, in the step (A), for example, as shown in FIG. 4, the first resin composition 6 is irradiated with ultraviolet rays 10 from the ultraviolet irradiator 9. The coating region 7 can be defined by curing the first resin composition 6 to form the liquid stop portion 11.

第１の樹脂組成物６は、液ダレ防止の観点から高粘度であることが好ましい。例えば、第１の樹脂組成物６は、２５℃における粘度が１００００〜５００００ｍＰａ・ｓであることが好ましい。 The first resin composition 6 preferably has a high viscosity from the viewpoint of preventing liquid dripping. For example, the first resin composition 6 preferably has a viscosity at 25 ° C. of 1000 to 50000 mPa · s.

第１の樹脂組成物６の塗布方法は、各種の塗布方法を採用でき、例えば、ディスペンサを用いる方法、コーターを用いる方法、スプレーを用いる方法等が挙げられる。特に、液ダレ抑制の観点からディスペンサを用いる方法が好ましい。第１の樹脂組成物６の塗布厚さは、例えば、本製造方法の工程（Ｂ）で塗布領域７に塗布する第２の樹脂組成物８の厚さ以下とすることができる。 As the coating method of the first resin composition 6, various coating methods can be adopted, and examples thereof include a method using a dispenser, a method using a coater, and a method using a spray. In particular, a method using a dispenser is preferable from the viewpoint of suppressing liquid dripping. The coating thickness of the first resin composition 6 can be, for example, equal to or less than the thickness of the second resin composition 8 coated on the coating region 7 in the step (B) of the present production method.

［工程（Ｂ）］
工程（Ｂ）では、例えば図５に示すように、塗布領域７に第２の樹脂組成物８を塗布する。第２の樹脂組成物８の塗布方法としては、各種の塗布方法を採用でき、例えば上述した第１の樹脂組成物６の塗布方法が挙げられる。また、第２の樹脂組成物８の塗布量は、例えば、工程（Ｃ）における貼合せの際に、塗布領域７に充填させることができる量とすることが好ましい。 [Step (B)]
In the step (B), for example, as shown in FIG. 5, the second resin composition 8 is applied to the coating area 7. As the coating method of the second resin composition 8, various coating methods can be adopted, and examples thereof include the above-mentioned coating method of the first resin composition 6. Further, the coating amount of the second resin composition 8 is preferably an amount that can be filled in the coating region 7 at the time of bonding in the step (C), for example.

第２の樹脂組成物８は、工程（Ｄ）で硬化させたときに、第１の樹脂組成物６から形成された液止め部１１との境界線が目視で目立たないようにすることが好ましい。そのため、第２の樹脂組成物８は、第１の樹脂組成物６と実質的に同一成分であることが好ましい。同一成分とは、少なくとも第１の樹脂組成物６と第２の樹脂組成物８とが光学特性が同じこと、例えば光透過率と屈折率とが実質的に等しいことを意味する。第１の樹脂組成６と第２の樹脂組成物８の光学特性が実質的に等しい場合、例えば第１の樹脂組成物６と第２の樹脂組成物８の粘度が異なっていても、同一成分に含まれるものとする。 When the second resin composition 8 is cured in the step (D), it is preferable that the boundary line with the liquid stop portion 11 formed from the first resin composition 6 is not visually conspicuous. .. Therefore, it is preferable that the second resin composition 8 has substantially the same components as the first resin composition 6. The same component means that at least the first resin composition 6 and the second resin composition 8 have the same optical properties, for example, the light transmittance and the refractive index are substantially the same. When the optical properties of the first resin composition 6 and the second resin composition 8 are substantially the same, for example, even if the viscosities of the first resin composition 6 and the second resin composition 8 are different, the same components are used. It shall be included in.

また、第２の樹脂組成物８は、気泡を防止し、短いタクトタイムで貼合せする観点から、工程（Ｃ）における貼合せの際に低粘度であることが好ましい。例えば、第２の樹脂組成物８は、貼合せ時の温度における粘度が３０００ｍＰａ・ｓ以下であることが好ましく、１０００〜３０００ｍＰａ・ｓであることがより好ましい。 Further, the second resin composition 8 preferably has a low viscosity at the time of bonding in the step (C) from the viewpoint of preventing air bubbles and bonding in a short tact time. For example, the viscosity of the second resin composition 8 at the temperature at the time of bonding is preferably 3000 mPa · s or less, and more preferably 1000 to 3000 mPa · s.

本製造方法では、以下の工程（Ｃ）において第２の樹脂組成物８を加熱（加温）することにより、第２の樹脂組成物８の粘度を低粘度（例えば３０００ｍＰａ・ｓ以下）に調整ができる。そのため、第１の樹脂組成物６と第２の樹脂組成物８として同一成分の樹脂組成物を用いた場合でも、第１の樹脂組成物６の高粘度性と、第２の樹脂組成物８の低粘度性とを両立できる。 In this production method, the viscosity of the second resin composition 8 is adjusted to a low viscosity (for example, 3000 mPa · s or less) by heating (heating) the second resin composition 8 in the following step (C). Can be done. Therefore, even when the resin composition having the same component is used as the first resin composition 6 and the second resin composition 8, the high viscosity of the first resin composition 6 and the second resin composition 8 are obtained. It is possible to achieve both low viscosity and low viscosity.

また、本製造方法では、８０℃で３時間加熱後の加熱残分が９５．０％以上である第２の樹脂組成物８を用いることにより、以下の工程（Ｃ）において第２の樹脂組成物８を加熱する際に、第２の樹脂組成物８中の成分（例えば後述する単官能モノマー）の揮発を抑制できる。そのため、光透過性部材３と画像表示部材２との密着性を良好にできる。 Further, in the present production method, by using the second resin composition 8 in which the heating residue after heating at 80 ° C. for 3 hours is 95.0% or more, the second resin composition is obtained in the following step (C). When the object 8 is heated, the volatilization of the components (for example, the monofunctional monomer described later) in the second resin composition 8 can be suppressed. Therefore, the adhesion between the light transmissive member 3 and the image display member 2 can be improved.

［工程（Ｃ）］
工程（Ｃ）では、例えば図６に示すように画像表示部材２と光透過性部材３とを第２の樹脂組成物８を介して貼合せ、第２の樹脂組成物８を塗布領域７に充填させる。画像表示部材２と光透過性部材３との貼合せは、例えば、公知の圧着装置を用いて行うことができる。 [Step (C)]
In the step (C), for example, as shown in FIG. 6, the image display member 2 and the light transmissive member 3 are bonded to each other via the second resin composition 8, and the second resin composition 8 is applied to the coating region 7. Fill. The image display member 2 and the light transmissive member 3 can be bonded to each other by using, for example, a known crimping device.

また、工程（Ｃ）は、上述したように第２の樹脂組成物８を加熱することを含む。第２の樹脂組成物８を加熱することにより、第２の樹脂組成物８が減粘された状態で塗布領域７に充填される。これにより、第２の樹脂組成物８中の気泡を防止し、短いタクトタイムでの貼合せが可能となる。加熱条件は、第２の樹脂組成物８の粘度が低粘度（例えば例えば３０００ｍＰａ・ｓ以下）に調整されるように設定することが好ましい。例えば、加熱温度は、画像表示部材２や光透過性部材３への熱による影響を考慮して、８０℃以下が好ましく、６０〜８０℃がより好ましい。加熱時間は、例えば、３０分〜３時間程度とすることができる。加熱のタイミングは、画像表示部材２と光透過性部材３との貼合せ前に行ってもよいし、貼合せる際に行ってもよいし、貼合せ後に行ってもよい。加熱方法としては、例えば、加熱ヒータ等を用いる方法等が挙げられる。 Further, the step (C) includes heating the second resin composition 8 as described above. By heating the second resin composition 8, the second resin composition 8 is filled in the coating region 7 in a reduced viscosity state. This prevents air bubbles in the second resin composition 8 and enables bonding in a short tact time. The heating conditions are preferably set so that the viscosity of the second resin composition 8 is adjusted to a low viscosity (for example, 3000 mPa · s or less). For example, the heating temperature is preferably 80 ° C. or lower, more preferably 60 to 80 ° C., in consideration of the influence of heat on the image display member 2 and the light transmissive member 3. The heating time can be, for example, about 30 minutes to 3 hours. The heating timing may be performed before the image display member 2 and the light transmissive member 3 are bonded, may be performed at the time of bonding, or may be performed after the bonding. Examples of the heating method include a method using a heater and the like.

［工程（Ｄ）］
工程（Ｄ）では、例えば図７に示すように、第２の樹脂組成物８に紫外線照射器９から紫外線１０を照射し、硬化樹脂層１（図１を参照）を形成する。工程（Ｄ）における光照射は、工程（Ｃ）において加熱した第２の樹脂組成物８を放熱させてから行うことが好ましい。 [Step (D)]
In the step (D), for example, as shown in FIG. 7, the second resin composition 8 is irradiated with ultraviolet rays 10 from the ultraviolet irradiator 9 to form the cured resin layer 1 (see FIG. 1). It is preferable that the light irradiation in the step (D) is performed after the second resin composition 8 heated in the step (C) is dissipated.

ここで、第２の樹脂組成物８が第１の樹脂組成物６と実質的に同一成分である場合、光照射後の第２の樹脂組成物８は、液止め部１１と一体化し、光学的に同じ性質を有する単一の硬化樹脂層１となる。これにより、液止め部１１と、硬化後の第２の樹脂組成物８との境界部の視認性をより良好にできる。 Here, when the second resin composition 8 has substantially the same components as the first resin composition 6, the second resin composition 8 after light irradiation is integrated with the liquid stop portion 11 and is optically used. It becomes a single cured resin layer 1 having the same properties. As a result, the visibility of the boundary portion between the liquid stop portion 11 and the second resin composition 8 after curing can be improved.

以上のように、本製造方法によれば、工程（Ｃ）で第２の樹脂組成物８を加熱することにより、第２の樹脂組成物８の粘度が低くなる。そのため、第１の樹脂組成物６と第２の樹脂組成物８として同一成分の樹脂組成物を用いた場合でも、第１の樹脂組成物６の高粘度性と、第２の樹脂組成物８の低粘度性とを両立できる。また、本製造方法では、第２の樹脂組成物８として、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーを含有し、かつ８０℃で３時間加熱後の加熱残分が９５．０％以上である光硬化性樹脂組成物を用いる。これにより、第２の樹脂組成物８を加熱する際に第２の樹脂組成物８中の成分の揮発を抑制し、光透過性部材３と画像表示部材２との密着性を良好にできる。 As described above, according to the present production method, the viscosity of the second resin composition 8 is lowered by heating the second resin composition 8 in the step (C). Therefore, even when the resin composition having the same component is used as the first resin composition 6 and the second resin composition 8, the high viscosity of the first resin composition 6 and the second resin composition 8 are obtained. It is possible to achieve both low viscosity and low viscosity. Further, in the present production method, the second resin composition 8 contains a monofunctional monomer having a heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes, and after heating at 80 ° C. for 3 hours. A photocurable resin composition having a heating residue of 95.0% or more is used. As a result, when the second resin composition 8 is heated, the volatilization of the components in the second resin composition 8 can be suppressed, and the adhesion between the light transmissive member 3 and the image display member 2 can be improved.

なお、上述した製造方法は、画像表示部材２の表面に、第１の樹脂組成物６と、第２の樹脂組成物８とを塗布するようにしたが、この方法に限定されるものではない。例えば、光透過性部材３の表面に第１の樹脂組成物６と第２の樹脂組成物８を塗布してもよい。また、上述した製造方法では、遮光層４が形成された光透過性部材３を用いたが、この例に限定されるものではない。例えば、遮光層が形成されていない光透過性部材を用いてもよい。 In the above-mentioned manufacturing method, the first resin composition 6 and the second resin composition 8 are applied to the surface of the image display member 2, but the method is not limited to this method. .. For example, the first resin composition 6 and the second resin composition 8 may be applied to the surface of the light transmissive member 3. Further, in the above-mentioned manufacturing method, the light transmissive member 3 on which the light-shielding layer 4 is formed is used, but the present invention is not limited to this example. For example, a light-transmitting member having no light-shielding layer may be used.

また、上述した工程（Ａ）では、光硬化性の樹脂組成物６を光照射により硬化させて液止め部１１を形成するようにしたが、この方法に限定されるものではない。例えば、工程（Ａ）では、熱硬化性の第１の樹脂組成物６を用いて、第１の樹脂組成物６を加熱し硬化させ、液止め部１１を形成してもよい。また、第１の樹脂組成物６の粘度が、第２の樹脂組成物８の液ダレを防止できる程度に十分高い場合、第１の樹脂組成物６を熱や光により硬化させなくてもよい。 Further, in the above-mentioned step (A), the photocurable resin composition 6 is cured by light irradiation to form the liquid stop portion 11, but the method is not limited to this method. For example, in the step (A), the thermosetting first resin composition 6 may be used to heat and cure the first resin composition 6 to form the liquid stop portion 11. Further, when the viscosity of the first resin composition 6 is sufficiently high enough to prevent the liquid dripping of the second resin composition 8, the first resin composition 6 does not have to be cured by heat or light. ..

［光硬化性樹脂組成物］
本実施の形態に係る光硬化性樹脂組成物は、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーと、（メタ）アクリレート樹脂と、光重合開始剤と、可塑剤とを含有し、８０℃で３時間加熱後の加熱残分が９５．０％以上である。ここで、（メタ）アクリレートは、メタクリレートとアクリレートとの両方を包含する。光硬化性樹脂組成物は、上述した第１の樹脂組成物６、及び第２の樹脂組成物８として好ましく用いられる。 [Photocurable resin composition]
The photocurable resin composition according to the present embodiment contains a monofunctional monomer having a heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes, a (meth) acrylate resin, and a photopolymerization initiator. , And a plasticizer is contained, and the heating residue after heating at 80 ° C. for 3 hours is 95.0% or more. Here, (meth) acrylate includes both methacrylate and acrylate. The photocurable resin composition is preferably used as the first resin composition 6 and the second resin composition 8 described above.

［単官能モノマー］
単官能モノマーは、６０℃で３０分間加熱後の加熱残分が９５．０％以上であることが好ましく、９７．０％以上であることがより好ましく、９８．０％以上であることがさらに好ましく、９９．５０％以上であることが特に好ましい。 [Monofunctional monomer]
The monofunctional monomer preferably has a heating residue of 95.0% or more, more preferably 97.0% or more, and further preferably 98.0% or more after heating at 60 ° C. for 30 minutes. It is preferably 99.50% or more, and particularly preferably 99.50% or more.

ここで、単官能モノマーの加熱残分は、熱量計測定装置（装置名：Ｑ５０、ＴＡ Ｉｎｓｔｒｕｍｅｎｔｓ社製）を用いて、単官能モノマー１０ｍｇを６０℃で３０分間加熱する前後の質量を測定して求めた値をいう。 Here, the heating residue of the monofunctional monomer is measured by measuring the mass before and after heating 10 mg of the monofunctional monomer at 60 ° C. for 30 minutes using a calorimeter measuring device (device name: Q50, manufactured by TA Instruments). The calculated value.

光硬化性樹脂組成物が上述の単官能モノマーを含有することにより、上述した工程（Ｃ）において第２の樹脂組成物を加熱する際に、この単官能モノマーの揮発をより効果的に抑制できる。そのため、光透過性部材３と画像表示部材２との密着性をより良好にすることができる。 When the photocurable resin composition contains the above-mentioned monofunctional monomer, the volatilization of the monofunctional monomer can be more effectively suppressed when the second resin composition is heated in the above-mentioned step (C). .. Therefore, the adhesion between the light transmissive member 3 and the image display member 2 can be further improved.

具体的に、単官能モノマーは、単官能（メタ）アクリレートであることが好ましく、例えば、式（Ａ）で表される化合物、及び式（Ｂ）で表される化合物の少なくとも１種であることが好ましい。

Figure 2022000508
Specifically, the monofunctional monomer is preferably a monofunctional (meth) acrylate, and is, for example, at least one of a compound represented by the formula (A) and a compound represented by the formula (B). Is preferable.
Figure 2022000508

式（Ａ）中、Ｒ１は水素原子又はメチル基を表す。Ｒ２は炭素数２又は３のアルキレン基を表す。Ｒ３は炭化水素基を表し、脂肪族炭化水素基であってもよいし、芳香族炭化水素基であってもよい。Ｒ３が脂肪族炭化水素基である場合、炭素数５〜１０の脂肪族炭化水素基であることが好ましい。また、Ｒ３が芳香族炭化水素基である場合、炭素数６〜１２の芳香族炭化水素基であることが好ましく、炭素数６〜８の芳香族炭化水素基であることがより好ましい。また、Ｒ３が芳香族炭化水素基である場合、Ｒ３は置換基を有していてもよい。置換基としては、炭素数１〜１０の直鎖状のアルキル基、炭素数３〜１０の分岐状のアルキル基、炭素数６〜１２の芳香族炭化水素基等が挙げられる。ｎは１〜１５の整数を表し、１〜１０の整数を表すことが好ましい。 In formula (A), R 1 represents a hydrogen atom or a methyl group. R 2 represents an alkylene group having 2 or 3 carbon atoms. R 3 represents a hydrocarbon group, which may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group. When R 3 is an aliphatic hydrocarbon group, it is preferably an aliphatic hydrocarbon group having 5 to 10 carbon atoms. When R 3 is an aromatic hydrocarbon group, it is preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably an aromatic hydrocarbon group having 6 to 8 carbon atoms. Further, when R 3 is an aromatic hydrocarbon group, R 3 may have a substituent. Examples of the substituent include a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, and the like. n represents an integer of 1 to 15, and preferably represents an integer of 1 to 10.

式（Ｂ）中、Ｒ４は水素原子又はメチル基を表す。Ｒ５の炭素数は、１１〜２０であり、１５〜２０であることが好ましい。Ｒ５は直鎖状、分岐状、又は環状のアルキル基のいずれであってもよく、直鎖状又は分岐状のアルキル基であることが好ましく、分岐状のアルキル基であることがより好ましい。 Wherein (B), R 4 represents a hydrogen atom or a methyl group. The number of carbon atoms of R 5 is 11 to 20, is preferably 15 to 20. R 5 may be any of a linear, branched, or cyclic alkyl group, preferably a linear or branched alkyl group, and more preferably a branched alkyl group.

単官能モノマーの具体例としては、イソステアリル（メタ）アクリレート、ノニルフェノールＥＯ変性（メタ）アクリレート、ノニルフェノールＰＯ変性（メタ）アクリレート、２−エチルヘキシルＥＯ変性（メタ）アクリレート、フェノールＥＯ変性（メタ）アクリレート、о−フェニルフェノールＥＯ変性アクリレート、パラクミルフェノールＥＯ変性アクリレート、Ｎ−アクリロイルオキシエチルヘキサヒドロフタルイミド、及び２−ヒドロキシ−３−フェノキシプロピルアクリレート等が挙げられる。 Specific examples of the monofunctional monomer include isostearyl (meth) acrylate, nonylphenol EO-modified (meth) acrylate, nonylphenol PO-modified (meth) acrylate, 2-ethylhexyl EO-modified (meth) acrylate, and phenol EO-modified (meth) acrylate. о-Phenylphenol EO modified acrylate, paracumylphenol EO modified acrylate, N-acryloyloxyethyl hexahydrophthalimide, 2-hydroxy-3-phenoxypropyl acrylate and the like can be mentioned.

光硬化性樹脂組成物中、単官能モノマーの含有量は、５〜６０質量％が好ましく、５〜４０質量％がより好ましく、１０〜３０質量％がさらに好ましい。単官能モノマーは、１種単独で用いてもよいし、２種以上を併用してもよい。２種以上の単官能モノマーを併用する場合、その含有量が上記含有量の範囲を満たすことが好ましい。 The content of the monofunctional monomer in the photocurable resin composition is preferably 5 to 60% by mass, more preferably 5 to 40% by mass, still more preferably 10 to 30% by mass. The monofunctional monomer may be used alone or in combination of two or more. When two or more kinds of monofunctional monomers are used in combination, it is preferable that the content thereof satisfies the above range of contents.

［（メタ）アクリレート樹脂］
（メタ）アクリレート樹脂は、例えば、光硬化性の（メタ）アクリレート樹脂であり、ポリマーであっても、オリゴマーであってもよい。（メタ）アクリレート樹脂は、例えば、ポリウレタン（メタ）アクリレートオリゴマー、ポリイソプレン（メタ）アクリレートオリゴマー、ポリブタジエン（メタ）アクリレートオリゴマー、及びポリエーテル（メタ）アクリレートオリゴマーの少なくとも１種であることが好ましい。（メタ）アクリレート樹脂の具体例としては、ＵＣ−２０３（クラレ社製）、ＵＶ３７００Ｂ（日本合成化学社製）等が挙げられる。 [(Meta) acrylate resin]
The (meth) acrylate resin is, for example, a photocurable (meth) acrylate resin, and may be a polymer or an oligomer. The (meth) acrylate resin is preferably, for example, at least one of a polyurethane (meth) acrylate oligomer, a polyisoprene (meth) acrylate oligomer, a polybutadiene (meth) acrylate oligomer, and a polyether (meth) acrylate oligomer. Specific examples of the (meth) acrylate resin include UC-203 (manufactured by Kuraray Co., Ltd.) and UV3700B (manufactured by Nippon Synthetic Chemistry Co., Ltd.).

光硬化性樹脂組成物中、（メタ）アクリレート樹脂の含有量は、５〜８０質量％が好ましく、１０〜７０質量％がより好ましく、１０〜６０質量％がさらに好ましく、３０〜５０質量％が特に好ましい。（メタ）アクリレート樹脂は、１種単独で用いてもよいし、２種以上を併用してもよい。２種以上の（メタ）アクリレート樹脂を併用する場合、その含有量が上記含有量の範囲を満たすことが好ましい。 The content of the (meth) acrylate resin in the photocurable resin composition is preferably 5 to 80% by mass, more preferably 10 to 70% by mass, further preferably 10 to 60% by mass, and 30 to 50% by mass. Especially preferable. The (meth) acrylate resin may be used alone or in combination of two or more. When two or more kinds of (meth) acrylate resins are used in combination, it is preferable that the content thereof satisfies the above range of contents.

［光重合開始剤］
光重合開始剤は、光ラジカル重合開始剤が好ましく、アルキルフェノン系光重合開始剤、及びアシルフォスフィンオキサイド系光重合開始剤の少なくとも１種を含有することがより好ましい。アルキルフェノン系光重合開始剤としては、１−ヒドロキシシクロへキシルフェニルケトン（イルガキュア１８４、ＢＡＳＦ社製）、２−ヒドロキシ−１−｛４−[４−（２一ヒドロキシ−２−メチル−プロピロニル）ベンジル]フェニル｝−２−メチル−１−プロパン−１−オン（イルガキュア１２７、ＢＡＳＦ社製）等を用いることができる。アシルフォスフィンオキサイド系光重合開始剤としては、２，４，６−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド（ＴＰＯ、ＢＡＳＦ社製）等を用いることができる。その他、光重合開始剤としては、ベンゾフェノン、アセトフェノン等を用いることもできる。 [Photopolymerization initiator]
The photopolymerization initiator is preferably a photoradical polymerization initiator, and more preferably contains at least one of an alkylphenone-based photopolymerization initiator and an acylphosphine oxide-based photopolymerization initiator. Examples of the alkylphenone-based photopolymerization initiator include 1-hydroxycyclohexylphenyl ketone (Irgacure 184, manufactured by BASF), 2-hydroxy-1- {4- [4- (2-1 hydroxy-2-methyl-propyronyl). Benzyl] phenyl} -2-methyl-1-propane-1-one (Irgacure 127, manufactured by BASF) and the like can be used. As the acylphosphine oxide-based photopolymerization initiator, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (TPO, manufactured by BASF) or the like can be used. In addition, benzophenone, acetophenone and the like can also be used as the photopolymerization initiator.

光硬化性樹脂組成物中、光重合開始剤の含有量は、上述した単官能モノマー、及び（メタ）アクリレート樹脂の合計１００質量部に対し、０．１〜５質量部が好ましく、０．２〜３質量部がより好ましい。このような範囲にすることにより、光照射時に硬化不足となるのをより効果的に防ぐとともに、開裂によるアウトガスの増加をより効果的に防ぐことができる。光重合開始剤は、１種単独で用いてもよいし、２種以上を併用してもよい。２種以上の光重合開始剤を併用する場合、その合計量が上記範囲を満たすことが好ましい。 The content of the photopolymerization initiator in the photocurable resin composition is preferably 0.1 to 5 parts by mass, preferably 0.2 parts by mass, based on 100 parts by mass of the total of the monofunctional monomer and the (meth) acrylate resin described above. ~ 3 parts by mass is more preferable. By setting it in such a range, it is possible to more effectively prevent insufficient curing during light irradiation and more effectively prevent an increase in outgas due to cleavage. The photopolymerization initiator may be used alone or in combination of two or more. When two or more kinds of photopolymerization initiators are used in combination, it is preferable that the total amount satisfies the above range.

［可塑剤］
可塑剤は、光照射によりそれ自身が光硬化をせず、光硬化後の硬化樹脂層に柔軟性を与えるものである。例えば、ポリイソプレン系可塑剤、ポリエーテル系可塑剤、ポリブタジエン系可塑剤、フタル酸エステル系可塑剤、アジピン酸エステル系可塑剤等を用いることができる。ポリイソプレン系可塑剤の具体例としては、ＬＩＲ−３０、ＬＩＲ−５０（以上、クラレ社製）、ＥＰＯＬ（出光興産社製）等が挙げられる。ポリエーテル系可塑剤の具体例としては、Ｐ−３０００（ＡＤＥＫＡ社製）等が挙げられる。ポリブタジエン系可塑剤の具体例としては、ＨＬＢＨ−Ｐ２０００、ＨＬＢＨ−Ｐ３０００、ＬＢＨ−Ｐ２０００、ＬＢＨＰ３０００、ＬＢＨ−Ｐ５０００（以上、クレイバレー社製）等が挙げられる。 [Plasticizer]
The plasticizer itself does not photo-cure by light irradiation, and gives flexibility to the cured resin layer after photo-curing. For example, a polyisoprene-based plasticizer, a polyether-based plasticizer, a polybutadiene-based plasticizer, a phthalate ester-based plasticizer, an adipate-based plasticizer, and the like can be used. Specific examples of the polyisoprene-based plasticizer include LIR-30, LIR-50 (all manufactured by Kuraray Co., Ltd.), EPOL (manufactured by Idemitsu Kosan Co., Ltd.) and the like. Specific examples of the polyether plasticizer include P-3000 (manufactured by ADEKA Corporation) and the like. Specific examples of the polybutadiene plasticizer include HLBH-P2000, HLBH-P3000, LBH-P2000, LBHP3000, LBH-P5000 (all manufactured by Clay Valley Co., Ltd.) and the like.

光硬化性樹脂組成物中、可塑剤の含有量は、５〜７０質量％が好ましく、１０〜７０質量％がより好ましく、１５〜５０質量％がさらに好ましい。可塑剤は、１種のみを単独で用いてもよいし、２種以上を併用してもよい。２種以上の可塑剤を併用する場合、その合計量が上記範囲を満たすことが好ましい。 The content of the plasticizer in the photocurable resin composition is preferably 5 to 70% by mass, more preferably 10 to 70% by mass, still more preferably 15 to 50% by mass. As the plasticizer, only one kind may be used alone, or two or more kinds may be used in combination. When two or more kinds of plasticizers are used in combination, it is preferable that the total amount satisfies the above range.

［その他の成分］
光硬化性樹脂組成物は、本技術の効果を損なわない範囲で、上述した成分以外の他の成分をさらに含有していてもよい。例えば、無機微粒子、粘着付与剤等が挙げられる。 [Other ingredients]
The photocurable resin composition may further contain components other than the above-mentioned components as long as the effects of the present technology are not impaired. For example, inorganic fine particles, adhesives and the like can be mentioned.

光硬化性樹脂組成物は、上述した第１の樹脂組成物６、及び第２の樹脂組成物８の少なくとも一方の屈折率を調整する目的で、無機微粒子を含有してもよい。無機微粒子は、例えば、表面がアルキルシリル基で修飾されたシリカ粒子を用いることができる。アルキルシリル基としては、モノアルキルシリル基、ジアルキルシリル基、トリアルキルシリル基を用いることができる。無機微粒子の形状は、例えば、球状、楕円形状、扁平状、ロッド状、繊維状などが挙げられる。無機微粒子の平均粒子径は、光硬化性樹脂組成物中での分散性などを考慮して、例えば、１〜１０００ｎｍとすることが好ましい。無機微粒子の比表面積（ＢＥＴ吸着法）は、例えば、５０〜４００ｍ２／ｇ程度である。 The photocurable resin composition may contain inorganic fine particles for the purpose of adjusting the refractive index of at least one of the first resin composition 6 and the second resin composition 8 described above. As the inorganic fine particles, for example, silica particles whose surface is modified with an alkylsilyl group can be used. As the alkylsilyl group, a monoalkylsilyl group, a dialkylsilyl group and a trialkylsilyl group can be used. Examples of the shape of the inorganic fine particles include a spherical shape, an elliptical shape, a flat shape, a rod shape, and a fibrous shape. The average particle size of the inorganic fine particles is preferably, for example, 1 to 1000 nm in consideration of dispersibility in the photocurable resin composition and the like. The specific surface area (BET adsorption method) of the inorganic fine particles is, for example, about 50 to 400 m 2 / g.

粘着付与剤は、光硬化性樹脂組成物から形成された硬化樹脂層に柔軟性を与え、硬化樹脂層の初期接着強度（いわゆるタック性）をより向上させる。粘着付与剤としては、例えば、テルペン樹脂、テルペンフェノール樹脂、水素添加テルペン樹脂等のテルペン系樹脂、天然ロジン、重合ロジン、ロジンエステル、水素添加ロジン等のロジン樹脂、ポリブタジエン、ポリイソプレン等の石油樹脂などを使用することができる。 The tackifier imparts flexibility to the cured resin layer formed from the photocurable resin composition, and further improves the initial adhesive strength (so-called tackiness) of the cured resin layer. Examples of the tackifier include terpene resins such as terpene resin, terpene phenol resin and hydrogenated terpene resin, rosin resins such as natural rosin, polymerized rosin, rosin ester and hydrogenated rosin, and petroleum resins such as polybutadiene and polyisoprene. Etc. can be used.

光硬化性樹脂組成物は、透過率が９０％を超えることが好ましい。これにより、硬化樹脂層１を形成したときに、画像表示部材２に形成された画像の視認性をより良好にすることができる。 The photocurable resin composition preferably has a transmittance of more than 90%. Thereby, when the cured resin layer 1 is formed, the visibility of the image formed on the image display member 2 can be further improved.

光硬化性樹脂組成物の屈折率は、画像表示部材２や光透過性部材３の屈折率とほぼ同等であることが好ましく、例えば１．４５以上１．５５以下であることが好ましい。これにより、画像表示部材２からの映像光の輝度やコントラストを高め、視認性を向上させることができる。 The refractive index of the photocurable resin composition is preferably substantially the same as the refractive index of the image display member 2 and the light transmissive member 3, and is preferably 1.45 or more and 1.55 or less, for example. This makes it possible to increase the brightness and contrast of the image light from the image display member 2 and improve the visibility.

光硬化性樹脂組成物は、上述した各成分を、公知の混合手法に従って均一に混合することにより調製することができる。 The photocurable resin composition can be prepared by uniformly mixing each of the above-mentioned components according to a known mixing method.

以下、本技術の実施例について説明する。 Hereinafter, examples of the present technology will be described.

［（メタ）アクリレート樹脂］
ＵＣ−２０３：イソプレンオリゴマー、クラレ社製
ＵＶ３７００Ｂ：ウレタンアクリレートオリゴマー、日本合成化学社製 [(Meta) acrylate resin]
UC-203: isoprene oligomer, manufactured by Kuraray UV3700B: urethane acrylate oligomer, manufactured by Nippon Synthetic Chemistry Co., Ltd.

［単官能モノマー］
ＩＳＴＡ：イソステアリルアクリレート、大阪有機化学工業社製
Ｍ−１１１：ノニルフェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１１３：ノニルフェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１１７：ノニルフェノールＰＯ変性アクリレート、東亞合成社製
Ｍ−１２０：２−エチルヘキシルＥＯ変性アクリレート、東亞合成社製
Ｍ−１０１Ａ：フェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１０２：フェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１０６：о−フェニルフェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１１０：パラクミルフェノールＥＯ変性アクリレート、東亞合成社製
Ｍ−１４０：Ｎ−アクリロイルオキシエチルヘキサヒドロフタルイミド、東亞合成社製
Ｍ−５７００：２−ヒドロキシ−３−フェノキシプロピルアクリレート、東亞合成社製
ＩＢＸＡ：イソボルニルアクリレート、大阪有機化学工業社製
ＨＰＡ：ヒドロキシプロピルアクリレート、大阪有機化学工業社製 [Monofunctional monomer]
ISTA: Isostearyl acrylate, Osaka Organic Chemical Industry Co., Ltd. M-111: Nonylphenol EO modified acrylate, Toa Synthetic Co., Ltd. M-113: Nonylphenol EO modified acrylate, Toa Synthetic Co., Ltd. M-117: Nonylphenol PO modified acrylate, Toa Synthetic Co., Ltd. M-120: 2-ethylhexyl EO modified acrylate, Toa Synthetic M-101A: Phenol EO modified acrylate, Toa Synthetic M-102: Phenol EO modified acrylate, Toa Synthetic M-106: о-phenylphenol EO-modified acrylate, manufactured by Toa Synthetic Co., Ltd. M-110: Paracumylphenol EO-modified acrylate, manufactured by Toa Synthetic Co., Ltd. M-140: N-acryloyloxyethyl hexahydrophthalimide, manufactured by Toa Synthetic Co., Ltd. M-5700: 2-hydroxy-3- Phenoxypropyl acrylate, IBXA: Isobornyl acrylate, HPA: Hydroxypropyl acrylate, Osaka Organic Chemical Industry Co., Ltd.

［可塑剤］
ＬＩＲ−３０：イソプレンポリマー、クラレ社製
Ｐ−３０００：ポリエーテルポリオール、ＡＤＥＫＡ社製 [Plasticizer]
LIR-30: isoprene polymer, manufactured by Kuraray P-3000: polyether polyol, manufactured by ADEKA

［重合開始剤］
Ｉｒｇ１８４：１−ヒドロキシシクロヘキシルフェニルケトン、ＢＡＳＦ社製 [Polymerization initiator]
Irg184: 1-Hydroxycyclohexylphenyl ketone, manufactured by BASF

［単官能モノマーの加熱残分］
各単官能モノマーの加熱残分（％）は、熱量計測定装置（装置名：Ｑ５０、ＴＡ Ｉｎｓｔｒｕｍｅｎｔｓ社製）を用いて求めた。具体的には、図８に示すように、容器１２に、１０ｍｇの単官能モノマー１３を入れ、単官能モノマー１３を６０℃で３０分間加熱する前後の質量を測定することにより求めた。 [Heating residue of monofunctional monomer]
The heating residue (%) of each monofunctional monomer was determined using a calorimeter measuring device (device name: Q50, manufactured by TA Instruments). Specifically, as shown in FIG. 8, 10 mg of the monofunctional monomer 13 was placed in the container 12, and the mass of the monofunctional monomer 13 before and after heating at 60 ° C. for 30 minutes was measured.

［光硬化性樹脂組成物の調製］
表１に示す配合量（質量部）で各成分を均一に混合して光硬化性樹脂組成物を調製した。 [Preparation of photocurable resin composition]
Each component was uniformly mixed in the blending amount (part by mass) shown in Table 1 to prepare a photocurable resin composition.

［光硬化性樹脂組成物の粘度］
光硬化性樹脂組成物の２５℃、又は８０℃における粘度を、レオメータ（ＲＳ６００、ＨＡＡＫＥ社製、コーン角度Ｃ３５／２°）で測定した。 [Viscosity of photocurable resin composition]
The viscosity of the photocurable resin composition at 25 ° C. or 80 ° C. was measured with a rheometer (RS600, manufactured by HAAKE, cone angle C35 / 2 °).

［光硬化性樹脂組成物の屈折率］
各光硬化性樹脂組成物を８０℃で３時間加熱した後の屈折率と、加熱する前の屈折率をアッベ屈折率計（ナトリウムＤ線（５８５ｎｍ)、２５℃)を用いて測定した。 [Refractive index of photocurable resin composition]
The refractive index after heating each photocurable resin composition at 80 ° C. for 3 hours and the refractive index before heating were measured using an Abbe refractive index meter (sodium D line (585 nm), 25 ° C.).

［光硬化性樹脂組成物の加熱残分］
各光硬化性樹脂組成物の加熱残分（％）は、熱量計測定装置（装置名：Ｑ５０、ＴＡ Ｉｎｓｔｒｕｍｅｎｔｓ社製）を用いて求めた。具体的には、図９に示すように、容器１４に、１０ｍｇの光硬化性樹脂組成物１５を入れ、光硬化性樹脂組成物１５を８０℃で３時間加熱する前後の質量を測定することにより求めた。 [The heating residue of the photocurable resin composition]
The heating residue (%) of each photocurable resin composition was determined using a calorimeter measuring device (device name: Q50, manufactured by TA Instruments). Specifically, as shown in FIG. 9, 10 mg of the photocurable resin composition 15 is placed in a container 14, and the mass before and after heating the photocurable resin composition 15 at 80 ° C. for 3 hours is measured. Asked by.

［光硬化性樹脂組成物を加熱しない場合の接着強度］
図１０、図１１に示すように、厚さ１．１ｍｍのガラス板１６の中央部に光硬化性樹脂組成物を滴下し、０．１５ｍｍのスペーサ１９を介して、厚さ１．１ｍｍのガラス板１７を直交するように載置した。これにより、ガラス板１６、１７の間に、直径６ｍｍ、厚さ０．１５ｍｍの樹脂組成物層１８が形成されたガラス接合体２０を得た。 [Adhesive strength when the photocurable resin composition is not heated]
As shown in FIGS. 10 and 11, a photocurable resin composition is dropped onto the central portion of a glass plate 16 having a thickness of 1.1 mm, and glass having a thickness of 1.1 mm is interposed through a spacer 19 having a thickness of 0.15 mm. The plates 17 were placed so as to be orthogonal to each other. As a result, a glass bonded body 20 having a resin composition layer 18 having a diameter of 6 mm and a thickness of 0.15 mm formed between the glass plates 16 and 17 was obtained.

図１２、図１３に示すように、紫外線照射器９を用いて、積算光量が５０００ｍＪ／ｃｍ２となるように、ガラス板１７側から紫外線１０を照射して樹脂組成物層１８を硬化させ、硬化樹脂層２１を形成した。 As shown in FIGS. 12 and 13, the resin composition layer 18 is cured by irradiating the resin composition layer 18 with ultraviolet rays 10 from the glass plate 17 side so that the integrated light amount becomes 5000 mJ / cm 2 using the ultraviolet irradiator 9. The cured resin layer 21 was formed.

図１４に示すように、ガラス接合体２０のガラス板１６、１７を治具２２Ａ、２２Ｂで固定するとともに、治具２２Ｂ側から垂直方向に５ｍｍ／分の速度で押し込み、以下の基準で接着状態を評価した。接着強度の測定には、荷重試験機（ＪＳＶ−１０００、日本計測システム社製）を用いた。接着強度は、２５℃においてガラス板１６とガラス板１７とが分離するまでに要した応力を測定し、その応力を硬化樹脂層２１の単位面積で除することにより算出した。 As shown in FIG. 14, the glass plates 16 and 17 of the glass joint 20 are fixed by the jigs 22A and 22B, and are pushed vertically from the jig 22B side at a speed of 5 mm / min, and adhered according to the following criteria. Was evaluated. A load tester (JSV-1000, manufactured by Nippon Measuring Systems Co., Ltd.) was used to measure the adhesive strength. The adhesive strength was calculated by measuring the stress required for the glass plate 16 and the glass plate 17 to separate at 25 ° C. and dividing the stress by the unit area of the cured resin layer 21.

［光硬化性樹脂組成物を加熱する場合の接着強度］
ガラス板１６に滴下する光硬化性樹脂組成物として、８０℃で３時間加熱したものを用いたこと以外は、上述した光硬化性樹脂組成物を加熱しない場合の接着強度の測定と同様に行った。 [Adhesive strength when heating a photocurable resin composition]
The same as the above-mentioned measurement of the adhesive strength when the photocurable resin composition was not heated was performed except that the photocurable resin composition dropped on the glass plate 16 was heated at 80 ° C. for 3 hours. rice field.

［透過率］
紫外可視分光光度計（島津製作所製、ＵＶ−２４５０）を用いて、ガラス接合体２０における硬化樹脂層２１の可視光領域の透過率を測定した。実用上、硬化樹脂層２１の透過率が９０％以上であることが好ましい。 [Transmittance]
Using an ultraviolet-visible spectrophotometer (UV-2450, manufactured by Shimadzu Corporation), the transmittance of the cured resin layer 21 in the glass junction 20 in the visible light region was measured. Practically, the transmittance of the cured resin layer 21 is preferably 90% or more.

Figure 2022000508
Figure 2022000508

実施例の光硬化性樹脂組成物は、加熱することにより粘度が低くなる。そのため、ダムフィルプロセスにおいて、ダム材（第１の樹脂組成物）とフィル材（第２の樹脂組成物）として同一成分の樹脂組成物を用いた場合でも、ダム材の高粘度性と、フィル材の低粘度性とを両立できる。 The photocurable resin composition of the example becomes low in viscosity by heating. Therefore, even when a resin composition having the same composition as the dam material (first resin composition) and the fill material (second resin composition) is used in the dam fill process, the high viscosity of the dam material and the fill It is possible to achieve both low viscosity of the material.

また、実施例の光硬化性樹脂組成物は、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーを含有し、かつ８０℃で３時間加熱後の加熱残分が９５．０％以上である。そのため、予め硬化性樹脂組成物を加熱した場合でも、接着強度が良好であることが分かった。これにより、例えばダムフィルプロセスにおいて、フィル材を加熱する際に、フィル材中の成分の揮発を抑制でき、部材同士の密着性を良好にできる。 Further, the photocurable resin composition of the example contains a monofunctional monomer having a heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes, and the heating residue after heating at 80 ° C. for 3 hours. Minutes are 95.0% or more. Therefore, it was found that the adhesive strength was good even when the curable resin composition was heated in advance. Thereby, for example, in the dam fill process, when the fill material is heated, the volatilization of the components in the fill material can be suppressed, and the adhesion between the members can be improved.

一方、８０℃で３時間加熱後の加熱残分が９５．０％未満の樹脂組成物を用いた比較例１、２では、予め樹脂組成物を加熱した場合、接着強度が良好ではないことが分かった。そのため、例えばダムフィルプロセスにおいて、フィル材を加熱する際に、フィル材中の成分の揮発を抑制できず、部材同士の密着性を良好にすることが困難である。また、比較例３、４では、樹脂組成物として、６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーを含有しない樹脂組成物を用いたため、接着強度が良好ではないことが分かった。 On the other hand, in Comparative Examples 1 and 2 in which the resin composition having a residual heating residue of less than 95.0% after heating at 80 ° C. for 3 hours was used, the adhesive strength was not good when the resin composition was heated in advance. Do you get it. Therefore, for example, in the dam fill process, when the fill material is heated, it is not possible to suppress the volatilization of the components in the fill material, and it is difficult to improve the adhesion between the members. Further, in Comparative Examples 3 and 4, as the resin composition, a resin composition containing no monofunctional monomer having a heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes was used, so that the adhesive strength was good. It turned out not.

１ 硬化樹脂層、２ 画像表示部材、３ 光透過性部材、４ 遮光層、５ 画像表示装置、６ 第１の樹脂組成物、７ 第２の樹脂組成物の塗布領域、８ 第２の樹脂組成物、９ 紫外線照射器、１０ 紫外線、１１ 液止め部（ダム）、１２ 容器、１３ 単官能モノマー、１４ 容器、１５ 光硬化性樹脂組成物、１６ ガラス板、１７ ガラス板、１８ 樹脂組成物層、１９ スペーサ、２０ ガラス接合体、２１ 硬化樹脂層、２２Ａ，２２Ｂ 治具 1 Cured resin layer, 2 Image display member, 3 Light transmissive member, 4 Light-shielding layer, 5 Image display device, 6 1st resin composition, 7 2nd resin composition coating area, 8 2nd resin composition Object, 9 UV irradiator, 10 UV, 11 liquid stop (dam), 12 container, 13 monofunctional monomer, 14 container, 15 photocurable resin composition, 16 glass plate, 17 glass plate, 18 resin composition layer , 19 spacers, 20 glass joints, 21 hardened resin layers, 22A, 22B jigs

Claims (6)

６０℃で３０分間加熱後の加熱残分が９５．０％以上である単官能モノマーと、
（メタ）アクリレート樹脂と、
光重合開始剤と、
可塑剤とを含有し、
８０℃で３時間加熱後の加熱残分が９５．０％以上であり、
上記単官能モノマーは、ノニルフェノールＰＯ変性（メタ）アクリレート及び２−エチルヘキシルＥＯ変性（メタ）アクリレートの少なくとも１種である、光硬化性樹脂組成物。 A monofunctional monomer having a residual heating residue of 95.0% or more after heating at 60 ° C. for 30 minutes,
(Meta) acrylate resin and
Photopolymerization initiator and
Contains a plasticizer and
The heating residue after heating at 80 ° C. for 3 hours is 95.0% or more.
The monofunctional monomer is a photocurable resin composition which is at least one of nonylphenol PO-modified (meth) acrylate and 2-ethylhexyl EO-modified (meth) acrylate. ２５℃における粘度が１００００〜５００００ｍＰａ・ｓである、請求項１に記載の光硬化性樹脂組成物。 The photocurable resin composition according to claim 1, which has a viscosity at 25 ° C. of 1000 to 50000 mPa · s. 上記単官能モノマーの含有量は５〜６０質量％である、請求項１又は２に記載の光硬化性樹脂組成物。 The photocurable resin composition according to claim 1 or 2, wherein the content of the monofunctional monomer is 5 to 60% by mass. 上記（メタ）アクリレート樹脂の含有量は１０〜６０質量％であり、
上記可塑剤の含有量は１０〜７０質量％である、請求項１〜３のいずれか１項に記載の光硬化性樹脂組成物。 The content of the above (meth) acrylate resin is 10 to 60% by mass.
The photocurable resin composition according to any one of claims 1 to 3, wherein the content of the plasticizer is 10 to 70% by mass. 上記８０℃で３時間加熱後の加熱残分が９７．０％以上である、請求項１〜４のいずれか１項に記載の光硬化性樹脂組成物。 The photocurable resin composition according to any one of claims 1 to 4, wherein the heating residue after heating at 80 ° C. for 3 hours is 97.0% or more. 無機微粒子をさらに含有する、請求項１〜５のいずれか１項に記載の光硬化性樹脂組成物。 The photocurable resin composition according to any one of claims 1 to 5, further containing inorganic fine particles.
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