CN115248472A

CN115248472A - Polarizing plate with adhesive layer and image display device using the same

Info

Publication number: CN115248472A
Application number: CN202210463427.XA
Authority: CN
Inventors: 村上夏纪; 三田聪司
Original assignee: Nitto Denko Corp
Current assignee: Nitto Denko Corp
Priority date: 2021-04-28
Filing date: 2022-04-28
Publication date: 2022-10-28
Also published as: TW202308852A; KR20220148109A

Abstract

Provided are a polarizing plate with an adhesive layer, which has excellent adhesion between a polarizing material and a resin layer and is inhibited from causing defects such as discoloration, and an image display device using the same. The polarizing plate with an adhesive layer according to an embodiment of the present invention includes, in order: a protective layer, a polarizer, a resin layer, and a conductive adhesive layer. The surface resistance value of the conductive adhesive layer is 1.0 x 10 ⁸ Ω/□～1.0×10 ¹² Omega/\9633theresin layer comprises a resin and an isocyanate compound. The resin has a glass transition temperature of 85 ℃ or higher and a weight average molecular weight Mw of 25000 or higher, the isocyanate compound contains 1 or more compounds having 2 or more isocyanate groups in the molecule, and the content ratio of the resin to the isocyanate compound (resin/isocyanate compound) is 90/10 to 5/95.

Description

Polarizing plate with adhesive layer and image display device using the same

Technical Field

The present invention relates to a polarizing plate with an adhesive layer and an image display device using the same.

Background

Typically, polarizers are produced by dyeing a polyvinyl alcohol (PVA) resin film with a dichroic substance such as iodine (for example, patent documents 1 and 2). It is known that a polarizer has a decreased transmittance (undergoes discoloration) under a high-temperature and high-humidity environment due to a decrease in the polarization degree. The polarizer is typically used in the form of a polarizing plate including a polarizer and protective layers disposed on both sides of the polarizer. In recent years, due to the demand for thinner polarizers and protective layers, thinner polarizers and protective layers have been proposed. With such a configuration, moisture is absorbed more rapidly from the end portion, and discoloration of the end portion becomes more noticeable.

The polarizing plate is generally laminated to a desired adherend via an adhesive layer. In response to the demand for thinner thickness, attempts have been made to provide the adhesive layer itself with the function of another layer. For example, attempts are being made to use a conductive adhesive containing a conductive agent in the adhesive layer to impart antistatic properties to the adhesive layer. However, when a binder containing a conductive agent is used, the adhesion between the polarizer and an adjacent layer (e.g., a resin layer) may be reduced.

Documents of the prior art

Patent literature

Patent document 1: japanese patent No. 5048120

Patent document 2: japanese patent laid-open publication No. 2013-156391

Disclosure of Invention

Problems to be solved by the invention

The present invention has been made to solve the above-described conventional problems, and a main object of the present invention is to provide a polarizing plate with an adhesive layer, which has excellent adhesion between a polarizing plate and an adjacent layer and suppresses occurrence of defects such as discoloration in a high-temperature and high-humidity environment.

Means for solving the problems

The polarizing plate with an adhesive layer according to an embodiment of the present invention includes, in order: a protective layer, a polarizer, a resin layer, and a conductive adhesive layer. The surface resistance value of the conductive adhesive layer is 1.0 x 10 ⁸ Ω/□～1.0×10 ¹² Omega/\\ 9633for treating tumor. The resin layer contains a resin and an isocyanate compound, and the resin has a glass transition temperature of 85 ℃ or higher and a weight average molecular weight Mw of 25000 or higher. The isocyanate compound contains 1 or more compounds having 2 or more isocyanate groups in a molecule, and the content ratio of the resin to the isocyanate compound (resin/isocyanate compound) is 90/10 to 5/95.

In 1 embodiment, the isocyanate compound contains 2 or more compounds having 2 or more isocyanate groups in a molecule.

In 1 embodiment, the isocyanate compound comprises: (A) An isocyanate compound having 2 or more isocyanate groups in a molecule and having an isocyanate group directly bonded to an aromatic ring; and (B) an isocyanate compound having 2 or more isocyanate groups in the molecule other than the isocyanate compound (A), wherein the isocyanate compound contains 1 or more of each of the isocyanate compound (A) and the isocyanate compound (B).

In 1 embodiment, the content ratio of the isocyanate compound (a) to the isocyanate compound (B) (isocyanate compound (a)/isocyanate compound (B)) is 50/50 to 95/5.

In 1 embodiment, the resin comprises a copolymer obtained by polymerizing a monomer mixture comprising more than 50 parts by weight of a (meth) acrylic monomer and more than 0 part by weight and less than 50 parts by weight of a monomer represented by formula (1),

(wherein X represents a functional group containing at least 1 reactive group selected from the group consisting of a vinyl group, a (meth) acryloyl group, a styryl group, a (meth) acrylamide group, a vinyl ether group, an epoxy group, an oxetanyl group, a hydroxyl group, an amino group, an aldehyde group, and a carboxyl group, and R ¹ And R ² Each independently represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group or an optionally substituted heterocyclic group, R ¹ And R ² Optionally linked to each other to form a ring).

In 1 embodiment, the resin layer has an elastic recovery evaluation value of 10% or less.

According to another aspect of the present invention, there is provided an image display device. The image display device comprises the polarizing plate with the adhesive layer.

ADVANTAGEOUS EFFECTS OF INVENTION

The polarizing plate with an adhesive layer according to the embodiment of the present invention has excellent adhesion between the polarizing plate and an adjacent layer (for example, a resin layer) even when a conductive adhesive is used, and can suppress occurrence of defects such as discoloration in a high-temperature and high-humidity environment. Furthermore, the polarizing plate with an adhesive layer according to the embodiment of the present invention can exhibit excellent adhesion between the polarizing element and an adjacent layer (for example, a resin layer) even under more severe conditions (for example, a high-temperature and high-humidity environment for a long time).

Drawings

Fig. 1 is a schematic cross-sectional view of a polarizing plate with an adhesive layer according to 1 embodiment of the present invention.

Description of the reference numerals

10. Polarizing piece

20. Protective layer

30. Resin layer

40. Conductive adhesive layer

100. Polarizing plate with adhesive layer

Detailed Description

Embodiments of the present invention will be described below, but the present invention is not limited to these embodiments.

A. Integral constitution of polarizing plate with adhesive layer

Fig. 1 is a schematic cross-sectional view of a polarizing plate with an adhesive layer according to 1 embodiment of the present invention. The polarizing plate 100 with an adhesive layer illustrated in the drawing has, in order: a protective layer 20, a polarizer 10, a resin layer 30, and a conductive adhesive layer 40. The surface resistance value (typically, the surface resistance value of the surface not in contact with the resin layer) of the conductive adhesive layer 40 was 1.0 × 10 ⁸ Ω/□～1.0×10 ¹² Omega/\\ 9633for treating tumor. The resin layer 30 includes a resin and an isocyanate compound. The resin has a glass transition temperature of 85 ℃ or higher and a weight-average molecular weight Mw of 25000 or higher. The isocyanate compound includes 1 or more compounds having 2 or more isocyanate groups in a molecule. In the resin layer 30 (substantially, a composition for forming a resin layer), the content ratio of the resin to the isocyanate compound (resin/isocyanate compound) is 90/10 to 5/95. By disposing such a resin layer 30 between the polarizer 10 and the conductive adhesive layer 40, even when the conductive adhesive layer is used as the adhesive layer, the polarizer has excellent adhesion to the adjacent layer, and the occurrence of defects such as discoloration can be suppressed.

In 1 embodiment, the resin layer 30 is a solidified (cured) product or a cured (cured) product of a coating film of an organic solvent solution. By using the resin layer 30 as a solid or thermosetting coating film of an organic solvent solution, the resin layer 30 can be formed directly (i.e., without an adhesive layer or an adhesive layer interposed therebetween) on the polarizer 10. Therefore, the polarizing plate 100 with an adhesive layer can be made thinner.

The polarizing plate with an adhesive layer 100 may further include any suitable functional layer other than the protective layer 20, the resin layer 30, and the conductive adhesive layer 40 according to the purpose. Examples of the functional layer include a retardation layer, a light diffusion layer, an antireflection layer, and a reflective polarizer. In addition, various functional layers may be included.

In practical use, it is preferable to temporarily adhere a release film to the surface of the conductive adhesive layer 40 before the polarizing plate with the adhesive layer is used. By temporarily adhering the release film, the pressure-sensitive adhesive layer can be protected, and the formation of a roll of the polarizing plate with the pressure-sensitive adhesive layer can be realized.

The total thickness of the polarizing plate with an adhesive layer is preferably 80 μm or less, more preferably 75 μm or less, still more preferably 70 μm or less, and particularly preferably 50 μm or less. The total thickness may be 48 μm or more, for example. According to the embodiment of the present invention, even when the polarizing plate is thin as the total thickness and the conductive adhesive layer is used as the adhesive layer, the polarizing plate has excellent adhesion to the adjacent layer, and the occurrence of defects such as discoloration can be suppressed. Furthermore, the polarizing plate with an adhesive layer according to the embodiment of the present invention can exhibit excellent adhesion even under more severe conditions.

Hereinafter, the constituent elements of the polarizing plate with an adhesive layer will be described in more detail.

B. Polarizing piece

The polarizer 10 is typically made of a polyvinyl alcohol (PVA) -based resin film containing a dichroic material (e.g., iodine). The thickness of the polarizer is preferably 1 to 8 μm, more preferably 1 to 7 μm, and still more preferably 2 to 5 μm. When the thickness of the polarizer is in such a range, it greatly contributes to thinning of the polarizer with an adhesive layer. Further, the effect of the present invention is remarkable for a thin polarizing plate with an adhesive layer using such a polarizer.

In 1 embodiment, the polarizer further comprises boric acid. The boric acid content of the polarizing material is preferably 10% by weight or more, more preferably 13% by weight to 25% by weight. When the boric acid content of the polarizer is in such a range, the curling during heating can be favorably suppressed and the appearance durability during heating can be improved while maintaining the easiness of the curling adjustment during the lamination by the synergistic effect with the iodine content described later. The boric acid content is calculated as the amount of boric acid contained in the polarizer per unit weight by the following formula, for example, by a neutralization method.

The iodine content of the polarizer is preferably 2% by weight or more, and more preferably 2% by weight to 10% by weight. When the iodine content of the polarizer is in such a range, the curl adjustment ease during the lamination can be favorably maintained, the curl during the heating can be favorably suppressed, and the appearance durability during the heating can be improved, due to the synergistic effect with the boric acid content. In the present specification, the "iodine content" refers to the amount of all iodine contained in the polarizer (PVA-based resin film). More specifically, in the polarizer, iodine is represented by iodide ion (I) ^- ) Iodine molecule (I) ₂ ) Polyiodide (I) ₃ ^- 、I ₅ ^- ) The iodine content in the present specification means the amount of iodine including all of these forms when they exist. The iodine content can be calculated, for example, by a standard curve method of fluorescent X-ray analysis. Note that, in the polarizer, polyiodide exists in a state of forming a PVA-iodine complex. By forming such a complex, absorption dichroism is exhibited in a wavelength range of visible light. Specifically, a complex of PVA and triiodide ion (PVA. I) ₃ ^- ) A complex of PVA and a pentaiodide ion (PVA. I) having an absorption peak at about 470nm ₅ ^- ) Has an absorption peak around 600 nm. As a result, the polyiodide can absorb light in a wide range of visible light depending on its form. On the other hand, iodide ion (I) ^- ) Has an absorption peak around 230nm and does not substantially interfere with the absorption of visible light. Thus, the presence of polyiodide in the form of a complex with PVA mainly interferes with the absorption properties of the pre-polarizer.

The polarizing element preferably exhibits absorption dichroism at any wavelength of 380nm to 780 nm. The monomer transmittance Ts of the polarizer is preferably 40% to 48%, more preferably 41% to 46%. The degree of polarization P of the polarizer is preferably 97.0% or more, more preferably 99.0% or more, and still more preferably 99.9% or more. The monomer transmittance is typically a Y value measured by an ultraviolet-visible spectrophotometer and corrected for visual sensitivity. The polarization degree is typically determined by the following equation based on the parallel transmittance Tp and the orthogonal transmittance Tc obtained by measuring with an ultraviolet-visible spectrophotometer and performing a visual sensitivity correction.

Polarization degree (%) = { (Tp-Tc)/(Tp + Tc) } ^1/2 ×100

Specific examples of the polarizer obtained by using the laminate of two or more layers include a laminate of a resin substrate and a PVA-based resin layer (PVA-based resin film) laminated on the resin substrate, and a polarizer obtained by coating a laminate of a resin substrate and a PVA-based resin layer formed on the resin substrate. A polarizer obtained by using a laminate of a resin substrate and a PVA-based resin layer formed on the resin substrate by coating can be produced, for example, as follows: applying a PVA-based resin solution to a resin base material, and drying the PVA-based resin solution to form a PVA-based resin layer on the resin base material, thereby obtaining a laminate of the resin base material and the PVA-based resin layer; the laminate is stretched and dyed to form a polarizing material from the PVA-based resin layer. In the present embodiment, it is preferable that a polyvinyl alcohol resin layer containing a halide and a polyvinyl alcohol resin is formed on one side of the resin base. The stretching typically includes immersing the laminate in an aqueous boric acid solution and stretching. Further, the stretching may further include subjecting the laminate to in-air stretching at a high temperature (for example, 95 ℃ or higher) before stretching in the aqueous boric acid solution, if necessary. In the present embodiment, the laminate is preferably subjected to a drying shrinkage treatment of shrinking the laminate by 2% or more in the width direction by heating the laminate while conveying the laminate in the longitudinal direction. Typically, the production method of the present embodiment includes subjecting the laminate to in-air auxiliary stretching treatment, dyeing treatment, underwater stretching treatment, and drying shrinkage treatment in this order. By introducing the auxiliary stretching, even when the PVA is coated on the thermoplastic resin, the crystallinity of the PVA can be improved, and high optical characteristics can be achieved. Further, by improving the orientation of the PVA in advance, it is possible to prevent problems such as a decrease in orientation and dissolution of the PVA when the PVA is immersed in water in a subsequent dyeing step and stretching step, and to achieve high optical characteristics. Further, when the PVA-based resin layer is immersed in a liquid, the alignment disorder and the decrease in alignment of the polyvinyl alcohol molecules can be reduced as compared with the case where the PVA-based resin layer does not contain a halide. This improves the optical properties of the polarizer obtained through a treatment step of immersing the laminate in a liquid, such as dyeing treatment and underwater stretching treatment. Further, the optical characteristics can be improved by shrinking the laminate in the width direction by the drying shrinkage treatment. The obtained resin substrate/polarizer laminate may be used as it is (that is, the resin substrate may be used as a protective layer for the polarizer), or any suitable protective layer may be laminated on a release surface obtained by releasing the resin substrate from the resin substrate/polarizer laminate or on a surface opposite to the release surface. Details of such a method for producing a polarizer are described in, for example, japanese patent laid-open publication No. 2012-73580 and japanese patent No. 6470455. The entire disclosures of these publications are incorporated herein by reference.

C. Protective layer

The protective layer 20 is formed of any suitable thin film that can be used as a protective layer for a polarizer. Specific examples of the material as the main component of the film include cellulose resins such as Triacetylcellulose (TAC), and transparent resins such as polyester resins, polyvinyl alcohol resins, polycarbonate resins, polyamide resins, polyimide resins, polyether sulfone resins, polysulfone resins, polystyrene resins, polynorbornene resins, polyolefin resins, (meth) acrylic resins, and acetate resins. Further, thermosetting resins such as (meth) acrylic, urethane, (meth) acrylic urethane, epoxy, and silicone resins, ultraviolet-curable resins, and the like can be mentioned. Further, for example, a glassy polymer such as a siloxane polymer may be mentioned. Further, the polymer film described in Japanese patent application laid-open No. 2001-343529 (WO 01/37007) may be used. As a material of the film, for example, a resin composition containing a thermoplastic resin having a substituted or unsubstituted imide group in a side chain and a thermoplastic resin having a substituted or unsubstituted phenyl group and a nitrile group in a side chain can be used, and for example, a resin composition containing an alternating copolymer of isobutylene and N-methylmaleimide and an acrylonitrile-styrene copolymer can be mentioned. The polymer film may be, for example, an extrusion molded product of the resin composition.

The polarizing plate with an adhesive layer is typically disposed on the visual recognition side of the image display device, and the protective layer 20 is typically disposed on the visual recognition side. Therefore, the protective layer 20 may be subjected to surface treatment such as hard coating treatment, antireflection treatment, adhesion prevention treatment, and antiglare treatment as needed.

The thickness of the protective layer 20 is preferably 10 μm to 50 μm, and more preferably 10 μm to 30 μm. When the surface treatment is performed, the thickness of the protective layer 20 is a thickness including the thickness of the surface treatment layer.

D. Resin layer

The resin layer 30 includes a resin and an isocyanate compound. The resin has a glass transition temperature of 85 ℃ or higher and a weight average molecular weight Mw of 25000 or higher. The isocyanate compound contains 1 or more compounds having 2 or more isocyanate groups in a molecule. The content ratio of the resin to the isocyanate compound (resin/isocyanate compound) in the resin layer 30 is 90/10 to 5/95. By disposing such a resin layer between the conductive adhesive layer and the polarizer, the polarizer has excellent adhesion to an adjacent layer (for example, a resin layer), and occurrence of defects such as discoloration can be suppressed. Furthermore, the polarizing plate with an adhesive layer according to the embodiment of the present invention exhibits excellent adhesion even under more severe conditions.

The content ratio of the resin to the isocyanate compound (resin/isocyanate compound) is, as described above, 90/10 to 5/95, preferably 85/15 to 10/90, more preferably 80/20 to 15/85, and further preferably 75/25 to 20/80. With such a configuration, even when a conductive adhesive layer is used as the adhesive layer, the polarizing plate with an adhesive layer is excellent in adhesion between the polarizing plate and the adjacent layer, and occurrence of defects such as discoloration can be suppressed.

The resin layer 30 preferably has an elastic recovery evaluation value of 10% or less, more preferably 9% or less, and still more preferably 8% or less. When the elastic recovery evaluation value is in the above range, the adhesiveness between the polarizer and the adjacent layer is excellent even under more severe conditions. In the present specification, the elastic recovery evaluation value is a value measured and calculated by the following method.

The samples were put into an environment of 60 ℃ 90% RH for 3 days (aging), and then left at room temperature (25 ℃ 55% RH) for 1 day. Subsequently, nanoindentation measurement was performed to measure the elastic recovery rate. The sample that was not aged was subjected to nanoindentation measurement at room temperature (25 ℃, 55% RH) in the same manner to determine the elastic recovery rate. The values of the elastic recovery rates are calculated by the following equation.

Elastic recovery evaluation value = | (elastic recovery rate (%) of matured specimen) (elastic recovery rate (%) of non-matured specimen)

In embodiment 1, the resin layer 30 is preferably a solid or a thermoset of a coating film of an organic solvent solution of the resin. With such a configuration, the thickness of the resin layer 30 can be made very thin (e.g., 10 μm or less). The thickness of the resin layer is preferably 0.05 to 10 μm, more preferably 0.08 to 5 μm, still more preferably 0.1 to 1 μm, and particularly preferably 0.2 to 0.7. Mu.m.

When the resin layer 30 is a solid or thermosetting coating film of an organic solvent solution of a resin, the resin layer can be formed directly (i.e., without an adhesive layer or an adhesive layer interposed therebetween) on the polarizer. According to the embodiment of the present invention, since the polarizer and the resin layer are extremely thin as described above, and the adhesive layer or the adhesive layer for laminating the resin layer can be omitted, the total thickness of the polarizing plate with the adhesive layer can be extremely thin. Further, such a resin layer has an advantage of excellent moisture absorption and moisture permeability compared to a solid product of an aqueous coating film such as an aqueous solution or an aqueous dispersion, and thus has excellent moisture resistance. As a result, a polarizing plate with an adhesive layer having excellent durability can be realized, which maintains optical characteristics even in a high-temperature and high-humidity environment. In addition, such a resin layer can suppress adverse effects of ultraviolet irradiation on the polarizer, compared to, for example, a cured product of an ultraviolet curable resin. The resin layer is preferably a solid product of a coating film of an organic solvent solution. The solid material has less shrinkage during film formation than a cured material, and contains no residual monomer or the like, so that deterioration of the film itself can be suppressed, and adverse effects on a polarizing plate (polarizer) due to the residual monomer or the like can be suppressed. The resin layer as a solid or cured product of the coating film of the organic solvent solution will be described in detail below.

D-1 resin

The resin constituting the resin layer has a glass transition temperature (Tg) of 85 ℃ or higher and a weight-average molecular weight Mw of 25000 or higher. When the Tg and Mw of the resin are in such ranges, the polarizer has excellent adhesion to an adjacent layer (e.g., a resin layer) even though it is very thin, and occurrence of defects such as discoloration can be suppressed. Further, excellent adhesion is exhibited even under more severe conditions.

The Tg of the resin is 85 ℃ or higher, preferably 90 ℃ or higher, more preferably 100 ℃ or higher, still more preferably 110 ℃ or higher, and particularly preferably 120 ℃ or higher. The Tg may be, for example, 200 ℃ or lower. The Mw of the resin is 25000 or more, preferably 30000 or more, more preferably 35000 or more, and further preferably 40000 or more. The Mw may be, for example, 150000 or less.

As the resin constituting the resin layer, any suitable thermoplastic resin or thermosetting resin can be used as long as it can form a solid or a thermally cured product of a coating film of an organic solvent solution and has Tg and Mw as described above. Preferably a thermoplastic resin. Examples of the thermoplastic resin include epoxy resins and acrylic resins. The epoxy resin and the acrylic resin may be used in combination. Hereinafter, representative examples of epoxy resins and acrylic resins that can be used in the resin layer will be described.

< epoxy resin >

As the epoxy resin, an epoxy resin having an aromatic ring is preferably used. When an epoxy resin having an aromatic ring is used as the epoxy resin and the resin layer is disposed adjacent to the polarizer, the adhesiveness to the polarizer is improved. Further, when the adhesive layer (conductive adhesive layer) is disposed adjacent to the resin layer, the anchoring force of the adhesive layer is increased. Examples of the epoxy resin having an aromatic ring include bisphenol type epoxy resins such as bisphenol a type epoxy resin, bisphenol F type epoxy resin, and bisphenol S type epoxy resin; novolac type epoxy resins such as phenol novolac epoxy resin, cresol novolac epoxy resin, hydroxybenzaldehyde phenol novolac epoxy resin, and the like; polyfunctional epoxy resins such as glycidyl ethers of tetrahydroxyphenylmethane, glycidyl ethers of tetrahydroxybenzophenone, and epoxidized polyvinylphenol, naphthol-type epoxy resins, naphthalene-type epoxy resins, and biphenyl-type epoxy resins. Bisphenol a type epoxy resin, biphenyl type epoxy resin, bisphenol F type epoxy resin are preferably used. The epoxy resin may be used in 1 kind alone, or 2 or more kinds may be used in combination.

< acrylic resin >

The acrylic resin typically contains, as a main component, a repeating unit derived from a (meth) acrylate monomer having a linear or branched structure. In the present specification, (meth) acrylic acid means acrylic acid and/or methacrylic acid. The acrylic resin may contain a repeating unit derived from any suitable comonomer used according to the purpose. Examples of the comonomer (comonomer) include a carboxyl group-containing monomer, a hydroxyl group-containing monomer, an amide group-containing monomer, an aromatic ring-containing (meth) acrylate, and a heterocyclic ring-containing vinyl monomer. By appropriately setting the kind, number, combination, copolymerization ratio, and the like of the monomer units, an acrylic resin having the above-mentioned predetermined Tg and Mw can be obtained.

< boric acrylic resin >

The acrylic resin includes, in 1 embodiment, a copolymer (hereinafter, sometimes referred to as a boron-containing acrylic resin) obtained by polymerizing a monomer mixture including more than 50 parts by weight of a (meth) acrylic monomer and more than 0 part by weight and less than 50 parts by weight of a monomer represented by formula (1) (hereinafter, sometimes referred to as a comonomer).

(wherein X represents a functional group containing at least 1 reactive group selected from the group consisting of a vinyl group, (meth) acryloyl group, styryl group, (meth) acrylamide group, vinyl ether group, epoxy group, oxetanyl group, hydroxyl group, amino group, aldehyde group, and carboxyl group, and R ¹ And R ² Each independently represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group or an optionally substituted heterocyclic group, R ¹ And R ² Optionally linked to each other to form a ring).

The boron-containing acrylic resin typically has a repeating unit represented by the following formula. The boron-containing acrylic resin has a substituent containing boron (for example, a repeating unit of k in the following formula) in a side chain by polymerizing a monomer mixture containing a comonomer represented by formula (1) and a (meth) acrylic monomer. Thus, when the resin layer is disposed adjacent to the polarizer, the adhesion to the polarizer is improved. The substituent containing boron may be contained continuously (i.e., in a block form) in the boron-containing acrylic resin or may be contained randomly in the boron-containing acrylic resin.

(in the formula, R ⁶ Represents an arbitrary functional group, and j and k represent an integer of 1 or more).

[ meth (acrylic) monomer ]

As the (meth) acrylic monomer, any appropriate (meth) acrylic monomer can be used. Examples thereof include a (meth) acrylate monomer having a linear or branched structure and a (meth) acrylate monomer having a cyclic structure.

Examples of the (meth) acrylate monomer having a linear or branched structure include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, and 2-hydroxyethyl (meth) acrylate. Methyl (meth) acrylate is preferably used. The (meth) acrylate monomer may be used in a single amount of 1 kind, or may be used in combination of 2 or more kinds.

Examples of the (meth) acrylate-based monomer having a cyclic structure include biphenyl-containing monomers such as cyclohexyl (meth) acrylate, benzyl (meth) acrylate, isobornyl (meth) acrylate, 1-adamantyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, dicyclopentanyl (meth) acrylate, biphenyl (meth) acrylate, o-biphenyloxyethyl (meth) acrylate, m-biphenyloxyethyl acrylate, p-biphenyloxyethyl (meth) acrylate, o-biphenyloxy-2-hydroxypropyl (meth) acrylate, p-biphenyloxy-2-hydroxypropyl (meth) acrylate, m-biphenyloxy-2-hydroxypropyl (meth) acrylate, N- (meth) acryloyloxyethyl-o-biphenyl = urethane, N- (meth) acryloyloxyethyl-p-biphenyl = urethane, N- (meth) acryloyloxyethyl-m-biphenyl = urethane, and o-phenylphenol glycidyl ether acrylate, terphenyl (meth) acrylate, and o-terphenyl oxyethyl (meth) acrylate. 1-adamantyl (meth) acrylate and dicyclopentyl (meth) acrylate are preferably used. By using these monomers, a polymer having a high glass transition temperature can be obtained. These monomers may be used alone in 1 kind, or in combination of 2 or more kinds.

A silsesquioxane compound having a (meth) acryloyl group may be used instead of the (meth) acrylate monomer. By using the silsesquioxane compound, an acrylic polymer having a high glass transition temperature is obtained. Silsesquioxane compounds having various skeleton structures, for example, a cage structure, a ladder structure, a random structure, and the like are known. The silsesquioxane compound may have only 1 of these structures, or may have 2 or more of these structures. The silsesquioxane compound may be used alone in 1 kind, or in combination with 2 or more kinds.

Examples of the (meth) acryloyl group-containing silsesquioxane compound include MAC grades and AC grades of SQ series of east asia synthesis company. The MAC-grade is a silsesquioxane compound containing a methacryloyl group, and specific examples thereof include MAC-SQTM-100, MAC-SQSI-20, and MAC-SQHDM. The AC-grade is a silsesquioxane compound containing an acryloyl group, and specific examples thereof include AC-SQTA-100 and AC-SQSI-20.

The (meth) acrylic monomer is used in an amount exceeding 50 parts by weight relative to 100 parts by weight of the monomer mixture.

< comonomers >

As the comonomer, a monomer represented by the above formula (1) is used. By using such a comonomer, a substituent containing boron is introduced into the side chain of the resulting polymer. Only 1 kind of the comonomer may be used, or 2 or more kinds may be used in combination.

Examples of the aliphatic hydrocarbon group in the formula (1) include a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent, a cyclic alkyl group having 3 to 20 carbon atoms which may have a substituent, and an alkenyl group having 2 to 20 carbon atoms. Examples of the aryl group include a phenyl group having 6 to 20 carbon atoms which may have a substituent, a naphthyl group having 10 to 20 carbon atoms which may have a substituent, and the like. Examples of the heterocyclic group include a 5-membered cyclic group or a 6-membered cyclic group containing at least 1 kind of hetero atom, which may be substituted. In addition, R is ¹ And R ² Optionally linked to each other to form a ring. R is ¹ And R ² Preferably a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom.

The reactive group included in the functional group represented by X is at least 1 selected from the group consisting of a vinyl group, a (meth) acryloyl group, a styryl group, a (meth) acrylamide group, a vinyl ether group, an epoxy group, an oxetanyl group, a hydroxyl group, an amino group, an aldehyde group, and a carboxyl group. Preferably, the reactive group is a (meth) acryloyl group and/or a (meth) acrylamide group. By having these reactive groups, adhesion to the polarizer is further improved when the resin layer is disposed adjacent to the polarizer.

In 1 embodiment, the functional group represented by X is preferably a functional group represented by Z-Y-. Here, Z represents a functional group containing at least 1 reactive group selected from the group consisting of a vinyl group, a (meth) acryloyl group, a styryl group, a (meth) acrylamide group, a vinyl ether group, an epoxy group, an oxetanyl group, a hydroxyl group, an amino group, an aldehyde group, and a carboxyl group, and Y represents a phenylene group or an alkylene group.

As the comonomer, specifically, the following compounds can be used.

The comonomer is used in a content of more than 0 parts by weight and less than 50 parts by weight relative to 100 parts by weight of the monomer mixture. Preferably 0.01 part by weight or more and less than 50 parts by weight, more preferably 0.05 part by weight to 20 parts by weight, still more preferably 0.1 part by weight to 10 parts by weight, and particularly preferably 0.5 part by weight to 5 parts by weight.

< acrylic resin containing lactone Ring, etc. >

In another embodiment, the acrylic resin has a repeating unit comprising a ring structure selected from the group consisting of a lactone ring unit, a glutaric anhydride unit, a glutarimide unit, a maleic anhydride unit, and a maleimide (N-substituted maleimide) unit. The repeating unit including a ring structure may be included in only 1 kind of repeating unit of the acrylic resin, or may be included in 2 or more kinds.

The lactone ring unit is preferably represented by the following general formula (2):

in the general formula (2), R ³ 、R ⁴ And R ⁵ Each independently represents a hydrogen atom or an organic residue having 1 to 20 carbon atoms. The organic residue may contain an oxygen atom. The acrylic resin may contain only a single lactone ring unit, or may contain R in the above general formula (2) ³ 、R ⁴ And R ⁵ Different multiple lactone ring units. An acrylic resin having a lactone ring unit is described in, for example, japanese patent application laid-open No. 2008-181078, and the description of this publication is incorporated herein by reference.

The glutarimide unit is preferably represented by the following general formula (3):

in the general formula (3), R ¹¹ And R ¹² Each independently represents hydrogen or an alkyl group having 1 to 8 carbon atoms, R ¹³ Represents an alkyl group having 1 to 18 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms. In the general formula (3), R is preferably ¹¹ And R ¹² Each independently is hydrogen or methyl, R ¹³ Is hydrogen, methyl, butyl or cyclohexyl. More preferably, R ¹¹ Is methyl, R ¹² Is hydrogen, R ¹³ Is a methyl group. The acrylic resin may contain only a single glutarimide unit, or may contain R in the above general formula (3) ¹¹ 、R ¹² And R ¹³ Different glutarimide units. Acrylic resins having a glutarimide unit are described in, for example, japanese patent laid-open Nos. 2006-309033, 2006-317560, 2006-328334, 2006-337491, 2006-337492, 2006-337493 and 2006-337569, the disclosures of which are incorporated herein by reference. With respect to the glutaric anhydride unit, in addition to the units represented by R in the above general formula (3) ¹³ The above description of the glutarimide units applies except that the substituted nitrogen atom is an oxygen atom.

Since the structure of the maleic anhydride unit and the maleimide (N-substituted maleimide) unit is determined by name, detailed description thereof will be omitted.

The content ratio of the repeating unit including a ring structure in the acrylic resin is preferably 1 to 50 mol%, more preferably 10 to 40 mol%, and still more preferably 20 to 30 mol%. The acrylic resin contains, as a main repeating unit, a repeating unit derived from the above-mentioned (meth) acrylic monomer.

D-2 isocyanate Compound

As the isocyanate compound, a compound having 2 or more isocyanate groups in a molecule is used. By including 1 or more kinds of compounds having 2 or more isocyanate groups in a molecule in the resin layer, a more stable crosslinked structure can be formed between the polarizer and the adjacent layer (for example, the resin layer). Therefore, even in the case of a polarizing plate with an adhesive layer using a conductive adhesive layer, it is possible to provide a polarizing plate with an adhesive layer having excellent adhesion between a polarizer and an adjacent layer.

As the isocyanate compound, any suitable isocyanate compound having 2 or more isocyanate groups in the molecule can be used. Examples thereof include aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and polymers of these diisocyanates (e.g., 2-mer, 3-mer, and 5-mer). Also, trimethylolpropane adducts of the above polyisocyanate compounds and the like can be used.

Examples of the aliphatic polyisocyanate include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1, 2-propylene diisocyanate, 1, 3-butylene diisocyanate, dodecamethylene diisocyanate, and 2, 4-trimethylhexamethylene diisocyanate.

Examples of the alicyclic polyisocyanate include 1, 3-cyclopentene diisocyanate, 1, 3-cyclohexane diisocyanate, 1, 4-cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated toluene diisocyanate, hydrogenated tetramethylxylylene diisocyanate, dicyclohexylmethane-4, 4' -diisocyanate, norbornene diisocyanate, trimethylhexamethylene diisocyanate, and 1, 5-pentamethylene diisocyanate.

Examples of the aromatic polyisocyanate include phenylene diisocyanate, 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, 2 '-diphenylmethane diisocyanate, 4' -toluidine diisocyanate, 4 '-diphenyl ether diisocyanate, 4' -diphenyl diisocyanate, 1, 5-naphthalene diisocyanate, and xylylene diisocyanate.

As the isocyanate compound, commercially available products can be used. Examples of commercially available isocyanate compounds include those available under the trade names "Millonate MT", "Millonate MTL", "Millonate MR-200", "Millonate MR-400", "CORONATE L", "CORONATE HL", "CORONATE HX", those available under the trade names "TAKENATE D-110N", "TAKENATE D-120N", "TAKENATE D-140N", "TAKENATE D-160N", "TAKENATE D-165N", "TAKENATE D-170HN", "TAKENATE D-178N", "TAKENATE 500" and "TAKENATE 600" available from Tosoh corporation.

In the embodiment of the present invention, the resin layer preferably contains 2 or more kinds of compounds having 2 or more isocyanate groups in the molecule. By using 2 or more kinds of isocyanate compounds in combination, 2 or more kinds of crosslinked structures are formed between the polarizing element and the adjacent layer, and a more stable crosslinked structure can be obtained. Therefore, the polarizer and the adjacent layer have excellent adhesion even under severe conditions (e.g., a high-temperature and high-humidity environment for a long time).

In 1 embodiment, the isocyanate compound includes 1 or more of (a) an isocyanate compound having 2 or more isocyanate groups in a molecule and having an isocyanate group directly bonded to an aromatic ring (hereinafter, also referred to as an isocyanate compound (a)) and (B) an isocyanate compound other than the isocyanate compound (a) (an isocyanate compound (B)) having 2 or more isocyanate groups in a molecule. It is known that the reaction rate of the isocyanate compound (A) is high and the reaction rate of the isocyanate compound (B) is low. By using the isocyanate compound (a) and the isocyanate compound (B) in combination, the reaction rate becomes faster than that in the case of using the isocyanate compound (a) alone, a crosslinked structure is formed between the adjacent layer and the polarizing plate, and the adhesion between the polarizing plate and the adjacent layer can be rapidly secured. Further, by using the isocyanate compound (A) and the isocyanate compound (B) in combination, a polymer structure of isocyanate which is not easily hydrolyzed can be formed more. Therefore, the adhesion between the polarizer and the adjacent layer under more severe conditions (for example, a high-temperature and high-humidity environment for a long time) can be further improved.

The isocyanate compound (a) may be any suitable isocyanate compound as long as it has 2 or more isocyanate groups in the molecule and the isocyanate group is directly bonded to the aromatic ring. In the isocyanate compound (a), at least 1 of the isocyanate groups of the isocyanate compound may be directly bonded to the aromatic ring, and an isocyanate group not directly bonded to the aromatic ring may be contained. As the isocyanate compound (a), trimethylolpropane adduct of toluene diisocyanate and trimethylolpropane adduct of diphenylmethane diisocyanate are preferably used. By using these as the isocyanate compound (a), a crosslinked structure is rapidly formed in a resin layer forming step (for example, a drying step), and adhesion between the resin layer and the adjacent layer can be ensured.

As the isocyanate compound (B), an isocyanate compound other than the isocyanate compound (a) having 2 or more isocyanate groups in the molecule is used. Specifically, the aliphatic polyisocyanate, the alicyclic polyisocyanate, and the aromatic polyisocyanate in which an isocyanate group is bonded to an aromatic ring via an alkylene group such as ethylene or methylene are mentioned. As the isocyanate compound (B), trimethylolpropane adduct of xylylene diisocyanate, trimethylolpropane adduct of hexamethylene diisocyanate, and trimethylolpropane adduct of isophorone diisocyanate are preferably used. By using these as the isocyanate compound (B), a crosslinked structure having excellent high-temperature durability and moisture and water resistance can be formed.

The content ratio of the isocyanate compound (a) to the isocyanate compound (B) (isocyanate compound (a)/isocyanate compound (B)) is preferably 50/50 to 95/5, more preferably 60/40 to 90/10, and still more preferably 65/35 to 85/15. By using the isocyanate compound (a) and the isocyanate compound (B) in the above-mentioned content ratio, adhesion between the polarizing plate and an adjacent layer (for example, a resin layer) under severe conditions (for example, a high-temperature and high-humidity environment for a long time) is further provided.

In 1 embodiment, the resin layer may be formed by forming a coating film by applying an organic solvent solution containing the resin and the isocyanate compound, and solidifying or thermally curing the coating film. As the organic solvent, any suitable organic solvent that can dissolve or uniformly disperse the resin can be used. Specific examples of the organic solvent include ethyl acetate, toluene, methyl Ethyl Ketone (MEK), methyl isobutyl ketone (MIBK), cyclopentanone, and cyclohexanone. The resin concentration of the solution is preferably 3 to 20 parts by weight with respect to 100 parts by weight of the solvent. At such a resin concentration, a uniform coating film can be formed.

The solution can be applied to any suitable substrate and can also be applied to the polarizer. When the solution is applied to a substrate, a solid material (resin layer) of a coating film formed on the substrate is transferred to a polarizer. When the solution is applied to the polarizer, the protective layer is directly formed on the polarizer by drying (solidifying) the coating film. Preferably, the solution is applied to the polarizing plate and the protective layer is formed directly on the polarizing plate. In such a configuration, the adhesive layer or the pressure-sensitive adhesive layer required for transfer can be omitted, and thus the polarizing plate with the pressure-sensitive adhesive layer can be further thinned. As the method of applying the solution, any suitable method may be adopted. Specific examples thereof include a roll coating method, a spin coating method, a wire bar coating method, a dip coating method, a die coating method, a curtain coating method, a spray coating method, and a knife coating method (comma coating method and the like).

The resin layer can be formed by solidifying or thermally curing the coating film of the solution. The heating temperature for solidification or thermosetting is preferably 100 ℃ or lower, more preferably 50 to 70 ℃. When the heating temperature is within such a range, adverse effects on the polarizer can be prevented. The heating time may vary depending on the heating temperature. The heating time may be, for example, 1 minute to 10 minutes.

The resin layer (substantially, an organic solvent solution of the resin) may contain any appropriate additive according to the purpose. Specific examples of the additive include an ultraviolet absorber; a leveling agent; antioxidants such as hindered phenol type, phosphorus type, and sulfur type; stabilizers such as light-resistant stabilizers, weather-resistant stabilizers, and heat stabilizers; reinforcing materials such as glass fibers and carbon fibers; a near infrared ray absorber; flame retardants such as tris (dibromopropyl) phosphate, triallyl phosphate, and antimony oxide; antistatic agents such as anionic, cationic and nonionic surfactants; colorants such as inorganic pigments, organic pigments, and dyes; an organic filler or an inorganic filler; a resin modifier; organic fillers and inorganic fillers; a plasticizer; a lubricant; a flame retardant; and the like. The kind, amount, combination, addition amount, and the like of the additives can be appropriately set according to the purpose.

E. Conductive adhesive layer

The surface resistance value of the conductive adhesive layer 40 is typically 1.0 × 10 as described above ⁸ Ω/□～1.0×10 ¹² Omega/\ 9633, preferably 1.0X 10 ⁸ Ω/□～1.0×10 ¹¹ Omega/\\ 9633, more preferably 1.0X 10 ⁸ Ω/□～1.0×10 ¹⁰ Omega/\ 9633and more preferably 1.0X 10 ⁸ Ω/□～1.0×10 ⁹ Omega/\\ 9633for treating tumor. When the surface resistance value of the conductive adhesive layer is in such a range, a desired antistatic performance can be achieved when the polarizing plate is applied to an image display device. As a result, the polarizing plate can be suitably used for an image display device having a narrow frame (preferably, no frame), a so-called in-cell image display device in which a conductive layer for a touch panel is incorporated in a display panel, or the like.

The adhesion of the conductive adhesive layer to glass is preferably 1.5N/25mm or more and less than 5.5N/25mm, more preferably 2.5N/25mm or more and 4.5N/25mm or less, and still more preferably 3.0N/25mm or more and 4.0N/25mm or less. When the adhesive strength is in such a range, the adhesion to the image display panel is excellent and the reworkability is excellent.

The storage modulus of the conductive adhesive layer at 25 ℃ is preferably 1.0X 10 ⁴ Pa～1.0×10 ⁶ Pa, more preferably 1.0X 10 ⁴ Pa～1.0×10 ⁵ Pa. When the storage modulus of the conductive adhesive layer is in such a range, appearance defects of the polarizing plate in a high-temperature and high-humidity environment can be suppressed. The storage modulus can be obtained by dynamic viscoelasticity measurement.

The amount of creep Δ Cr of the conductive pressure-sensitive adhesive layer at 70 ℃ is, for example, 65 μm or less, and may be 50 μm or less, 45 μm or less, 40 μm or less, 35 μm or less, 30 μm or less, 25 μm or less, 20 μm or less, and further 15 μm or less. The lower limit of the creep amount Δ Cr is, for example, 0.5 μm. When the amount of creep is within such a range, as in the case of the storage modulus, appearance defects of the polarizing plate in a high-temperature and high-humidity environment can be suppressed. The creep value can be measured, for example, by the following procedure: a pressure-sensitive adhesive layer of a stainless test plate was bonded to a bonding surface of 20mm in the vertical direction and 20mm in the horizontal direction, and a load of 500gf was applied vertically downward while the test plate was fixed. The creep amounts (offset amounts) of the adhesive layer with respect to the test plate at respective times after 100 seconds and 3600 seconds from the start of the application of the load were measured and are respectively represented as Cr100 and Cr3600. The creep amount Δ Cr can be obtained from the measured Cr100 and Cr3600 and the formula Δ Cr = Cr3600 — Cr 100.

The thickness of the conductive adhesive layer is preferably 2 to 55 μm, more preferably 2 to 30 μm, further preferably 5 to 25 μm, and particularly preferably 10 to 20 μm.

The adhesive composition constituting the conductive adhesive layer typically contains a base polymer and a conductive component (e.g., a conductive agent).

Examples of the base polymer include a (meth) acrylic polymer, a urethane polymer, a silicone polymer, and a rubber polymer. The (meth) acrylic polymer is preferred. In the present specification, a (meth) acrylic polymer as a base polymer is sometimes referred to as a (meth) acrylic base polymer.

The (meth) acrylic base polymer typically contains, as a monomer component, an alkyl (meth) acrylate as a main component. Examples of the alkyl group of the alkyl (meth) acrylate include a linear or branched alkyl group having 1 to 18 carbon atoms. The average carbon number of the alkyl group is preferably 3 to 9, more preferably 3 to 6. The preferred alkyl (meth) acrylate is butyl acrylate. The content of the alkoxy group-containing monomer in the base polymer is preferably 50 parts by weight or more, more preferably 60 parts by weight or more, further preferably 70 parts by weight or more, and particularly preferably 80 parts by weight or more, based on 100 parts by weight of the total monomer components. The alkyl (meth) acrylates may be used alone or in combination of 2 or more.

The (meth) acrylic base polymer typically contains a monomer component (comonomer component) copolymerizable with the alkyl (meth) acrylate. Examples of the comonomer component include a carboxyl group-containing monomer, a hydroxyl group-containing monomer, an alkoxy group-containing monomer, an amide group-containing monomer, an aromatic ring-containing (meth) acrylate, and a heterocycle-containing vinyl monomer. By appropriately adjusting the kind, amount, combination, blending amount (content), and the like of the comonomer, a base polymer (as a result, an adhesive layer) having desired characteristics can be obtained.

The weight average molecular weight Mw of the (meth) acrylic base polymer is preferably 100 to 300 ten thousand, more preferably 200 to 300 ten thousand, and further preferably 200 to 280 ten thousand. When the weight average molecular weight Mw is less than 100 ten thousand, the suppression of cracks may be insufficient. When the weight average molecular weight Mw exceeds 300 ten thousand, the viscosity may increase and/or gelation may occur during the polymerization of the polymer.

Typical examples of the conductive component include inorganic cation salts and organic cation salts.

The inorganic cation salt is specifically an inorganic cation-anion salt. Representative examples of the cation constituting the cation portion of the inorganic cation salt include alkali metal ions. Specific examples thereof include lithium ion, sodium ion, and potassium ion. Lithium ions are preferred. Thus, the preferred inorganic cation salt is a lithium salt.

Examples of the anion constituting the anion portion of the inorganic cation salt include Cl ^- 、Br ^- 、I ^- 、AlCl ₄ ^- 、Al ₂ Cl ₇ ^- 、BF ₄ ^- 、PF ₆ ^- 、ClO ₄ ^- 、NO ₃ ^- 、CH ₃ COO ^- 、CF ₃ COO ^- 、CH ₃ SO ₃ ^- 、CF ₃ SO ₃ ^- 、(CF ₃ SO ₂ ) ₃ C ^- 、AsF ₆ ^- 、SbF ₆ ^- 、NbF ₆ ^- 、TaF ₆ ^- 、(CN) ₂ N ^- 、C ₄ F ₉ SO ₃ ^- 、C ₃ F ₇ COO ^- 、(CF ₃ SO ₂ )(CF ₃ CO)N ^- 、-O ₃ S(CF ₂ ) ₃ SO ₃ ^- And anions represented by the following general formulae (1) to (4), preferably fluorine-containing anions, and more preferably fluorine-containing imide anions.

(1)：(C _n F _2n+1 SO ₂ ) ₂ N ^- (n is an integer of 1 to 10),

(2)：CF ₂ (C _m F _2m SO ₂ ) ₂ N ^- (m is an integer of 1 to 10),

(3)：-O ₃ S(CF ₂ ) _l SO ₃ ^- (l is an integer of 1 to 10),

(4)：(C _p F _2p+1 SO ₂ )N ^- (C _q F _2q+1 SO ₂ ) (p and q are integers of 1 to 10).

Examples of the fluorine-containing imide anion include imide anions having a perfluoroalkyl group. Specific examples thereof include the above-mentioned (CF) ₃ SO ₂ )(CF ₃ CO)N ^- And general formulae (1), (2) and (4)The anions shown.

(1)：(C _n F _2n+1 SO ₂ ) ₂ N ^- (n is an integer of 1 to 10),

(2)：CF ₂ (C _m F _2m SO ₂ ) ₂ N ^- (m is an integer of 1 to 10),

(4)：(C _p F _2p+1 SO ₂ )N ^- (C _q F _2q+1 SO ₂ ) (p and q are integers of 1 to 10),

Preferably (CF) ₃ SO ₂ ) ₂ N ^- 、(C ₂ F ₅ SO ₂ ) ₂ N ^- The (perfluoroalkylsulfonyl) imide represented by the general formula (1) is more preferably (CF) ₃ SO ₂ ) ₂ N ^- Bis (trifluoromethanesulfonyl) imide shown. Thus, a preferred inorganic cation salt that may be used in embodiments of the present invention is lithium bis (trifluoromethanesulfonyl) imide.

The organic cation salt is specifically an organic cation-anion salt. As the cation constituting the cation portion of the organic cation salt, there is representatively exemplified an organic onium which forms an onium ion by substitution with an organic group. Examples of the onium in the organic onium include nitrogen-containing onium, sulfur-containing onium, and phosphorus-containing onium. Preferably a nitrogen-containing onium or a sulfur-containing onium. Examples of the nitrogen-containing onium include an ammonium cation, a piperidinium cation, a pyrrolidinium cation, a pyridinium cation, a cation having a pyrroline skeleton, a cation having a pyrrole skeleton, an imidazolium cation, a tetrahydropyrimidium cation, a dihydropyrimidinium cation, a pyrazolium cation, and a pyrazolinium cation. Examples of the sulfonium-containing onium include a sulfonium cation. Examples of the phosphonium-containing onium include phosphonium cation. Examples of the organic group in the organic onium include an alkyl group, an alkoxy group, and an alkenyl group. Specific examples of preferable organic onium include tetraalkylammonium cation (e.g., trimethylbutylammonium cation), alkylpiperidinium cation, and alkylpyrrolidinium cation. The anions constituting the anion portion of the organic cation salt are as described with respect to the anions constituting the anion portion of the inorganic cation. Preferred organic cation salts that may be used in embodiments of the present invention are methylpropylpyrrolidinium bis (trifluoromethanesulfonyl) imide, 1-ethyl-3-methylimidazolium bis (fluorosulfonyl) imide, trimethylbutylammonium bis (trifluoromethanesulfonyl) imide.

Inorganic cation salts and organic cation salts may be used in combination.

The conductive component may be a solid or a liquid (i.e., an ionic liquid).

The content of the conductive component in the adhesive composition is preferably 5 to 15 parts by weight, and more preferably 8 to 12 parts by weight, based on 100 parts by weight of the base polymer. When the content of the conductive component is within such a range, desired antistatic properties can be obtained without adversely affecting other properties.

The adhesive composition typically contains a silane coupling agent and/or a crosslinking agent. Typical examples of the silane coupling agent include a silane coupling agent having a functional group. Examples of the functional group include an epoxy group, a mercapto group, an amino group, an isocyanate group, an isocyanurate group, a vinyl group, a styryl group, an acetoacetyl group, a ureido group, a thioureido group, a (meth) acryloyl group, a heterocyclic group, an acid anhydride group, and a combination thereof. The functional group-containing silane coupling agents may be used alone or in combination. Examples of the crosslinking agent include isocyanate-based crosslinking agents and peroxide-based crosslinking agents. In addition, the crosslinking agents may be used alone or in combination.

The adhesive composition may contain additives. Specific examples of the additives include powders such as colorants and pigments, dyes, surfactants, plasticizers, tackifiers, surface lubricants, leveling agents, softeners, antioxidants, light stabilizers, ultraviolet absorbers, polymerization inhibitors, inorganic or organic fillers, metal powders, particulates, and foils. Further, a redox system in which a reducing agent is added may be used within a controllable range. The kind, amount, combination, content and the like of the additives may be appropriately set according to the purpose.

F. Image display device

The polarizing plate with an adhesive layer may be used for any suitable purpose. In the embodiment of the present invention, the polarizing plate with an adhesive layer may be applied to an image display device. Accordingly, embodiments of the present invention include an image display device using such a polarizing plate with an adhesive layer. Typical examples of the image display device include a liquid crystal display device and an Electroluminescence (EL) display device (for example, an organic EL display device and an inorganic EL display device).

[ examples ]

The present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples. The measurement method of each property is as follows. Unless otherwise specified, "parts" and "%" in examples and comparative examples are based on weight.

(1) Thickness of

The thickness of 10 μm or less was measured by using an interference film thickness meter (available from Otsuka electronics Co., ltd., product name "MCPD-3000"). The thickness exceeding 10 μm was measured by using a digital micrometer (manufactured by ANRITSU CORPORATION, product name "KC-351C").

(2) Surface resistance value

The surface resistance of the pressure-sensitive adhesive layer was measured in accordance with JIS K6911. Specifically, the probe was pressed against the pressure-sensitive adhesive layer of the polarizing plate with the pressure-sensitive adhesive layer, and the stable value after 30 seconds had elapsed was read. The measurement was performed under the following measurement conditions.

< measurement conditions >

Resistance meter: hiresta

And (3) probe: URS

Temperature: 23 + -2 deg.C

Humidity: 50. + -.5% RH

(3) Evaluation value of elastic recovery

The polarizing plates with adhesive layers obtained in examples and comparative examples were cut into pieces of 3cm × 3cm to obtain samples. The samples were charged into an environment of 60 ℃ 90% RH for 3 days (aging), and then left at room temperature (25 ℃, 55% RH) for 1 day. Thereafter, the sample was embedded in epoxy resin, and a cross section was made with a microtome. The prepared cross section was fixed to a support, and nanoindentation measurement was performed under the following conditions, and the elastic recovery rate was obtained from the following equation. The sample that was not aged was subjected to nanoindentation measurement at room temperature (25 ℃, 55% RH) in the same manner to determine the elastic recovery rate.

< analytical apparatus and conditions >

The device comprises the following steps: product name made by Hysitron inc: triboindenter

Using a pressure head: berkovich (triangular pyramid type)

The determination method comprises the following steps: single indentation assay

Pressing depth: 50nm

And (3) measuring the position: at a distance of 500nm from the interface of the polarizer

< method for calculating elastic recovery >

Elastic recovery rate (%) = { maximum displacement (displacement amount at the deepest press-in) (hmax) -plastic deformation amount (hf) }/maximum displacement (hmax)

The elastic recovery evaluation value was calculated from the elastic recovery rate of the aged sample and the elastic recovery rate of the sample that was not aged by the following equation.

(4) Peeling test

The polarizing plates with adhesive layers obtained in examples and comparative examples were cut into pieces of 50mm × 50mm, and attached to a glass plate having a size larger than the cut size to prepare test samples. The test specimen was immersed in warm water at 60 ℃. The impregnation time at the time when the peeling distance of the portion of the resin layer having the largest peeling distance was 3mm or more was evaluated according to the following criteria.

A: no peeling in 3 hours

B: more than 2 hours and less than 3 hours

C: more than 1 hour and less than 2 hours

D: more than 30 minutes and less than 1 hour

E: less than 30 minutes

Production example 1: production of boron-containing acrylic resin

Methyl Methacrylate (MMA, product name: methyl Methacrylate Monomer, manufactured by FUJIFILM Wako Pure Chemical Corporation) 99.0 parts by weight, a Monomer of the general formula (1 e) 1.0 part by weight, and a polymerization initiator (product name: 2,2' -azobis (isobutyronitrile), manufactured by FUJIFILM Wako Pure Chemical Corporation) 0.2 part by weight were dissolved in toluene 100 parts by weight. Subsequently, the mixture was heated to 70 ℃ under a nitrogen atmosphere and subjected to polymerization reaction for 5 hours to obtain copolymer 1 (solid content concentration: 50% by weight). The copolymer 1 had a Tg of 110 ℃ and a weight average molecular weight of 80,000.

Production example 2: production of polarizing plate

1. Fabrication of polarizing elements

As the thermoplastic resin substrate, a long-sized amorphous isophthalic acid copolymerized polyethylene terephthalate film (thickness: 100 μm) having a water absorption of 0.75% and a Tg of about 75 ℃ was used. One surface of the resin substrate is subjected to corona treatment.

In a state where 9: 1A PVA resin (coating solution) was prepared by mixing 100 parts by weight of a PVA resin containing polyvinyl alcohol (degree of polymerization 4200, degree of saponification 99.2 mol%) and acetoacetyl-modified PVA (product name "GOHSEFIMER Z410" manufactured by Nippon Kagaku Kogyo Co., ltd.) and adding 13 parts by weight of potassium iodide to the mixture, and dissolving the resulting mixture in water.

The aqueous PVA solution was applied to the corona-treated surface of the resin substrate and dried at 60 ℃ to form a PVA-based resin layer having a thickness of 13 μm, thereby producing a laminate.

The obtained laminate was subjected to uniaxial stretching of the free end in the longitudinal direction (longitudinal direction) between rolls having different peripheral speeds in an oven at 130 ℃.

Next, the laminate was immersed in an insolubilization bath (aqueous boric acid solution prepared by adding 4 parts by weight of boric acid to 100 parts by weight of water) at a liquid temperature of 40 ℃ for 30 seconds (insolubilization treatment).

Next, the resultant polarizer was immersed for 60 seconds (dyeing treatment) in a dyeing bath (aqueous iodine solution prepared by mixing iodine and potassium iodide at a weight ratio of 1:7 relative to 100 parts by weight of water) at a liquid temperature of 30 ℃.

Next, the substrate was immersed for 30 seconds in a crosslinking bath (an aqueous boric acid solution prepared by adding 3 parts by weight of potassium iodide and 5 parts by weight of boric acid to 100 parts by weight of water) at a liquid temperature of 40 ℃ (crosslinking treatment).

Thereafter, while the laminate was immersed in an aqueous boric acid solution (boric acid concentration of 4.0 wt% and potassium iodide concentration of 5 wt%) at a liquid temperature of 70 ℃, uniaxial stretching was performed between rolls having different peripheral speeds in the longitudinal direction (longitudinal direction) so that the total stretching ratio became 5.5 times (underwater stretching treatment).

Thereafter, the laminate was immersed in a cleaning bath (aqueous solution prepared by adding 4 parts by weight of potassium iodide to 100 parts by weight of water) at a liquid temperature of 20 ℃ (cleaning treatment).

Thereafter, the sheet was dried in an oven maintained at 90 ℃ and contacted with a heated roll made of SUS maintained at a surface temperature of 75 ℃ for about 2 seconds (drying shrinkage treatment). The shrinkage in the width direction of the laminate due to the drying shrinkage treatment was 5.2%.

Thus, a polarizing plate having a thickness of 5 μm was formed on the resin substrate.

2. Manufacture of polarizing plate

A Hard Coat (HC) layer (thickness 7 μm) was formed on one side of a cellulose Triacetate (TAC) film (thickness 25 μm). The details are as follows. 40 parts by weight of an ultraviolet-curable acrylate resin (trade name "M-920" and a solid content of 100%) and 60 parts by weight of an ultraviolet-curable acrylate resin (trade name "UV-1700TL" and a solid content of 80%) were prepared, the trade name being "M-920" and the solid content being manufactured by Tokyo chemical Co., ltd. A photopolymerization initiator (product name: OMNIRAD907, manufactured by BASF) 3 parts by weight and a leveling agent (product name: LE-303, manufactured by Kyoeisha chemical Co., ltd., solid content: 40%) 0.12 part by weight were mixed to 100 parts by weight of the resin solid content of the resin. The mixture was diluted with a MIBK/cyclopentanone mixed solvent (weight ratio 70/30) so that the solid content concentration became 30%, to prepare a coating liquid for forming a hard coat layer. The coating liquid for forming a hard coat layer was applied to a TAC film by a bar coater to form a coating layer. The TAC film with the coating layer formed thereon was heated at 80 ℃ for 1 minute, thereby drying the coating layerDrying to form a coating film. The obtained coating film was irradiated with a cumulative light amount of 240mJ/cm by a high-pressure mercury lamp ² The coating film was cured by the ultraviolet ray of (2) to form an HC layer having a thickness of 7 μm.

The laminate of the HC layer/TAC film was bonded to the surface (the surface opposite to the resin substrate) of the polarizer obtained in the above 1. Specifically, the curable adhesive was applied so that the total thickness thereof became 1.0 μm, and was bonded using a roll mill. Then, the adhesive was cured by irradiation with UV light from the protective layer side, and a laminate (polarizing plate) of a resin base material, a polarizing material, a TAC film, and an HC layer was obtained.

Production example 3: preparation of conductive adhesive 1

A4-neck flask equipped with a stirring blade, a thermometer, a nitrogen inlet tube, and a condenser was charged with a monomer mixture containing 99 parts of butyl acrylate and 1 part of 4-hydroxybutyl acrylate. Further, 0.1 part of 2,2' -azobisisobutyronitrile as a polymerization initiator was charged together with ethyl acetate per 100 parts of the monomer mixture (solid content), nitrogen gas was introduced while slowly stirring for nitrogen substitution, and then the polymerization reaction was carried out for 7 hours while maintaining the liquid temperature in the flask at about 60 ℃. Subsequently, ethyl acetate was added to the obtained reaction solution to adjust the solid content concentration to 30%, thereby preparing a solution of an acrylic polymer having a weight average molecular weight of 140 ten thousand. Conductive adhesive 1 was prepared by adding 0.2 part of 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide (manufactured by Tokyo Kasei Co., ltd.) as a conductive component to 100 parts of the solid content of the obtained acrylic polymer solution, and further adding 0.1 part of trimethylolpropane xylylene diisocyanate (manufactured by Mitsui chemical Co., ltd.: TAKENATE D110N), 0.3 part of dibenzoyl peroxide, and 0.075 part of γ -glycidoxypropylmethoxysilane (manufactured by shin-Etsu chemical Co., ltd.: KBM-403).

Production example 4: preparation of conductive adhesive 2

Conductive adhesive 2 was prepared in the same manner as in preparation example 3, except that 10 parts of 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide was used.

[ example 1]

10 parts of an isocyanate compound (made by Tosoh corporation, "CORONATE L": a trimethylolpropane adduct of tolylene diisocyanate) was added to 90 parts of the copolymer 1 (boron-containing acrylic resin). This mixture was dissolved in 80 parts of a mixed solvent of ethyl acetate/cyclopentanone (70/30) to obtain a resin solution (20%). The resin substrate was peeled from the polarizing plate, the resin solution was applied to the peeled surface of the polarizing plate obtained above using a wire bar, and the coated film was dried at 60 ℃ for 5 minutes to form a resin layer (thickness: 0.5 μm) in the form of a solid of the coated film of the organic solvent solution of the resin. Next, an adhesive layer (thickness 15 μm) was formed on the surface of the resin layer using the conductive adhesive obtained in production example 3, to obtain a polarizing plate with an adhesive layer having a structure of a protective layer (HC layer/TAC film)/adhesive layer/polarizing material/resin layer/conductive adhesive layer. The total thickness of the polarizing plate with an adhesive layer was 53.5 μm. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 2]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 1, except that 80 parts of a boron-containing acrylic resin and 20 parts of an isocyanate compound were used. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 3]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 1, except that 5 parts of a boron-containing acrylic resin and 95 parts of an isocyanate compound were used. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 4]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 2 except that TACKENATE D110N (a trimethylolpropane adduct of m-xylylene diisocyanate, manufactured by Mitsui chemical Co., ltd.) was used instead of CORONATE L as the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 5]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 2, except that TAKENATE D160N (trimethylolpropane adduct of hexamethylene diisocyanate, manufactured by mitsui chemical) was used instead of CORONATE L as the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 6]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 2, except that 10 parts of CORONATE L and 10 parts of TAKENATE D160N were used as the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 7]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 2, except that 15 parts of CORONATE L and 5 parts of TAKENATE D160N were used as the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 8]

A polarizing plate with a pressure-sensitive adhesive layer was obtained in the same manner as in example 7 except that 80 parts (in terms of solid content) of a mixture of 15 parts (in terms of solid content) of the copolymer 1 (boron-containing acrylic resin) obtained in production example 1 and 85 parts (in terms of solid content) of a thermoplastic epoxy resin (product name "jER (registered trademark) YX6954BH30" manufactured by mitsubishi chemical corporation) was used instead of the boron-containing acrylic resin. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 9]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 2, except that 19 parts of CORONATE L and 1 part of TAKENATE D160N were used as the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 10]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 6, except that TAKENATE D110N was used instead of TAKENATE D160N. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 11]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 7, except that TAKENATE D110N was used instead of TAKENATE D160N. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 12]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 9, except that TAKENATE D110N was used instead of TAKENATE D160N. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 13]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 6 except for using 70 parts of a boron-containing acrylic resin, 22.5 parts of CORONATE L, and 7.5 parts of TAKENATE D160N. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

[ example 14]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 7, except that the conductive adhesive 2 was used instead of the conductive adhesive 1. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ example 15]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 13, except that the conductive adhesive 2 was used instead of the conductive adhesive 1. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

Comparative example 1

A polarizing plate with an adhesive layer was produced in the same manner as in example 1, except that only 100 parts of the boron-containing acrylic resin (i.e., no isocyanate compound was used). The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

Comparative example 2

A polarizing plate with an adhesive layer was produced in the same manner as in example 2, except that organosilane (product name: KBM-603, manufactured by shin-Etsu chemical Co., ltd.) was used instead of the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) described above. The results are shown in Table 1.

Comparative example 3

A polarizing plate with an adhesive layer was produced in the same manner as in example 2, except that organic titanium (product name: TA-21, manufactured by Matsumoto Fine Chemical co.ltd.) was used instead of the isocyanate compound. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ reference example 1]

An adhesive composition was obtained in the same manner as in production example 3, except that 1-ethyl-3-methylimidazolium bis (trifluoromethanesulfonyl) imide was not added as a conductive component. A polarizing plate with an adhesive layer was obtained in the same manner as in comparative example 1, except that the obtained adhesive composition was used instead of the conductive adhesive. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ reference example 2]

A polarizing plate with an adhesive layer was obtained in the same manner as in example 1, except that no resin layer was formed. The polarizing plate with the pressure-sensitive adhesive layer obtained was subjected to the evaluations (3) to (4) above. The results are shown in Table 1.

[ Table 1]

In table 1, "epoxy/acrylic" in the column of the resin means a mixture of an epoxy resin and an acrylic resin.

[ evaluation ]

As is clear from table 1, the polarizing plate with an adhesive layer according to the example of the present invention maintained the state in which the polarizer and the resin layer were in close contact with each other even when the polarizing plate was immersed in warm water. On the other hand, in the polarizing plates with adhesive layers of comparative examples 1 to 3, the resin layer was peeled from the polarizer within 30 minutes after the immersion in warm water.

Industrial applicability

The polarizing plate with an adhesive layer of the present invention is suitably used for image display devices such as liquid crystal display devices, organic EL display devices, and inorganic EL display devices.

Claims

1. A polarizing plate with an adhesive layer, comprising in order: a protective layer, a polarizer, a resin layer, and a conductive adhesive layer,

the surface resistance value of the conductive adhesive layer is 1.0 x 10 ⁸ Ω/□～1.0×10 ¹² Ω/□，

The resin layer comprises a resin and an isocyanate compound,

the resin has a glass transition temperature of 85 ℃ or higher and a weight-average molecular weight Mw of 25000 or higher,

the isocyanate compound contains 1 or more compounds having 2 or more isocyanate groups in a molecule,

the content ratio of the resin to the isocyanate compound, i.e., resin/isocyanate compound, is 90/10 to 5/95.

2. The polarizing plate with an adhesive layer according to claim 1, wherein the isocyanate compound comprises 2 or more compounds having 2 or more isocyanate groups in a molecule.

3. The polarizing plate with an adhesive layer according to claim 2, wherein the isocyanate compound comprises: (A) An isocyanate compound having 2 or more isocyanate groups in a molecule and having an isocyanate group directly bonded to an aromatic ring; and (B) an isocyanate compound having 2 or more isocyanate groups in the molecule other than the isocyanate compound (A),

the isocyanate compound includes 1 or more of the isocyanate compound (A) and the isocyanate compound (B), respectively.

4. The polarizing plate with an adhesive layer according to claim 3, wherein the isocyanate compound (A)/isocyanate compound (B) ratio of the isocyanate compound (A) to the isocyanate compound (B) is 50/50 to 95/5.

5. The polarizing plate with an adhesive layer according to any one of claims 1 to 4, wherein the resin comprises a copolymer obtained by polymerizing a monomer mixture comprising more than 50 parts by weight of a (meth) acrylic monomer and more than 0 part by weight and less than 50 parts by weight of a monomer represented by formula (1),

wherein X represents a functional group containing at least 1 reactive group selected from the group consisting of a vinyl group, a (meth) acryloyl group, a styryl group, a (meth) acrylamide group, a vinyl ether group, an epoxy group, an oxetanyl group, a hydroxyl group, an amino group, an aldehyde group and a carboxyl group, and R ¹ And R ² Each independently represents a hydrogen atom, an optionally substituted aliphatic hydrocarbon group, an optionally substituted aryl group or an optionally substituted heterocyclic group, R ¹ And R ² Optionally linked to each other to form a ring.

6. The polarizing plate with an adhesive layer according to any one of claims 1 to 5, wherein the resin layer has an elasticity recovery evaluation value of 10% or less.

7. An image display device comprising the polarizing plate with an adhesive layer according to any one of claims 1 to 6.