TW202308852A - Polarizing plate having pressure sensitive adhesive layer and image display device using same - Google Patents

Abstract

Provided are: a polarizing plate with an adhesive layer, which has excellent adhesion between a polarizer and a resin layer and in which the occurrence of defects such as discoloration is suppressed; and an image display device using the polarizing plate. A polarizing plate with an adhesive layer according to an embodiment of the present invention is provided with a protective layer, a polarizer, a resin layer, and a conductive adhesive layer in this order. The conductive adhesive layer has a surface resistance value of 1.0*10<SP>8</SP>-1.0*10<SP>12</SP> [Omega]/□, and the resin layer contains a resin and an isocyanate compound. The resin has a glass transition temperature of 85 DEG C or more and a weight average molecular weight Mw of 25000 or more, the isocyanate compound contains one or more compounds having two or more isocyanate groups in each 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 same

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

Polarizers are typically manufactured by dyeing a polyvinyl alcohol (PVA)-based resin film with a dichroic substance such as iodine (for example, Patent Documents 1 and 2). It is known that the polarization degree of the polarizer decreases and the transmittance increases (discoloration occurs) in a high-temperature and high-humidity environment. The polarizer is typically used in the form of a polarizer including a polarizer and protective layers on both sides of the polarizer. In recent years, due to the requirement of thinning, thinning of polarizers and protective layers has been proposed. In such a configuration, moisture absorption from the edge becomes faster, and discoloration of the edge becomes more conspicuous.

A polarizing plate is usually laminated on a desired adherend through an adhesive layer. Due to the requirement of thinning, an attempt was made to make the adhesive layer itself have the functions of other layers. For example, attempts have been made to use a conductive adhesive containing a conductive agent in the adhesive layer to impart antistatic properties to the adhesive layer. However, when an adhesive containing a conductive agent is used, the adhesion between the polarizer and an adjacent layer (for example, a resin layer) may decrease. Current Technical Literature patent documents

Patent Document 1: Japanese Patent No. 5048120 Patent Document 2: Japanese Patent Laid-Open No. 2013-156391

The problem to be solved by the invention The present invention is made to solve the above-mentioned conventional problems, and its main purpose is to provide a polarizing plate with an adhesive layer, which has excellent adhesion between the polarizer and the adjacent layer, and has suppressed fading under high-temperature and high-humidity environments and other bad situations.

(式中，X表示包含選自於由乙烯基、(甲基)丙烯醯基、苯乙烯基、(甲基)丙烯醯胺基、乙烯基醚基、環氧基、氧雜環丁烷基、羥基、胺基、醛基及羧基所構成群組中之至少1種反應性基的官能基；R ¹及R ²分別獨立表示氫原子、可具有取代基之脂肪族烴基、可具有取代基之芳基或可具有取代基之雜環基；R ¹及R ²可互相連結而形成環)。 在一實施形態中，上述樹脂層之彈性回復評估值為10%以下。 根據本發明另一面向，提供一種影像顯示裝置。該影像顯示裝置包含上述附黏著劑層之偏光板。 MEANS TO SOLVE THE PROBLEM An adhesive layer-attached polarizing plate according to an embodiment of the present invention includes a protective layer, a polarizer, a resin layer, and a conductive adhesive layer in this order. The surface resistance of the conductive adhesive layer is 1.0×10 ⁸ Ω/□ to 1.0×10 ¹² Ω/□. The above-mentioned resin layer includes a resin and an isocyanate compound, the glass transition temperature of the resin is above 85° C., and the weight average molecular weight Mw is above 25000. The above-mentioned isocyanate compound contains one or more compounds having two 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. In one embodiment, the isocyanate compound includes two or more compounds having two or more isocyanate groups in the molecule. In one embodiment, the isocyanate compound includes: (A) an isocyanate compound having two or more isocyanate groups in the molecule, and the isocyanate group is directly bonded to an aromatic ring; and (B) an isocyanate compound other than the isocyanate compound (A). An isocyanate compound having two or more isocyanate groups in the molecule; the aforementioned isocyanate compound includes one or more of each of the isocyanate compound (A) and the isocyanate compound (B). In one 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 one embodiment, the above-mentioned 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 parts by weight and less than 50 parts by weight. The monomer shown in the formula (1) of parts by weight: [chemical formula 1]

(In the formula, X represents a group selected from vinyl, (meth)acryl, styryl, (meth)acrylamide, vinyl ether, epoxy, oxetanyl , hydroxyl group, amino group, aldehyde group and carboxyl group constitute the functional group of at least one reactive group; R ¹ and R ² independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, and a substituent that may have a substituent The aryl group or the heterocyclic group which may have a substituent; R ¹ and R ² may be connected to each other to form a ring). In one embodiment, the elastic recovery evaluation value of the resin layer is 10% or less. According to another aspect of the present invention, an image display device is provided. The image display device includes the above-mentioned polarizer attached with an adhesive layer.

Invention effect Even when a conductive adhesive is used in the polarizing plate with an adhesive layer according to the embodiment of the present invention, the adhesion between the polarizer and the adjacent layer (for example, a resin layer) is excellent, and the generation of the polarizer in a high-temperature and high-humidity environment can be suppressed. Discoloration and other adverse conditions. Furthermore, the polarizing plate with the adhesive layer according to the embodiment of the present invention can still exert the excellent properties of the polarizer and the adjacent layer (for example, the resin layer) even under more severe conditions (for example, a long-term high-temperature and high-humidity environment). Adhesion.

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

A. Overall configuration of polarizing plate with adhesive layer FIG. 1 is a schematic cross-sectional view of a polarizing plate with an adhesive layer according to one embodiment of the present invention. The polarizing plate 100 with an adhesive layer shown in the figure has a protective layer 20 , a polarizer 10 , a resin layer 30 and a conductive adhesive layer 40 in sequence. The surface resistance value of the conductive adhesive layer 40 (typically, the surface resistance value of the surface not in contact with the resin layer) is 1.0×10 ⁸ Ω/□~1.0×10 ¹² Ω/□. The resin layer 30 includes resin and isocyanate compound. The glass transition temperature of the resin is above 85° C., and the weight average molecular weight Mw is above 25000. As the isocyanate compound, one or more compounds having two or more isocyanate groups in the molecule are included. In the resin layer 30 (essentially, the composition forming the resin layer), the content ratio of the resin to the isocyanate compound (resin/isocyanate compound) is 90/10 to 5/95. By arranging the 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 adhesion between the polarizer and the adjacent layer is excellent. , can suppress occurrence of defects such as discoloration.

In one embodiment, the resin layer 30 is a cured or thermally cured product of an organic solvent solution coating film. The resin layer 30 can be directly formed on the polarizer 10 (that is, without an adhesive layer or an adhesive layer) because the resin layer 30 is a cured product or a thermosetting product of a coating film of an organic solvent solution. Therefore, it can contribute to the thinning of the polarizing plate 100 with the adhesive layer attached.

The polarizing plate 100 with an adhesive layer may also include any appropriate functional layers other than the protective layer 20 , the resin layer 30 and the conductive adhesive layer 40 according to the purpose. As the functional layer, a retardation layer, a light diffusion layer, an antireflection layer, a reflective polarizer, and the like are exemplified. In addition, multiple functional layers may be included.

In practice, it is preferable to temporarily adhere a peeling film to the surface of the conductive adhesive layer 40 before using the polarizing plate with the adhesive layer attached. By temporarily adhering the release film, it is possible to form a roll of a polarizing plate with an adhesive layer while protecting the adhesive layer.

The total thickness of the polarizing plate with the adhesive layer is preferably not more than 80 μm, more preferably not more than 75 μm, more preferably not more than 70 μm, and especially preferably not more than 50 μm. The total thickness may be, for example, 48 μm or more. According to the embodiment of the present invention, even when the total thickness is as thin as described above and the conductive adhesive layer is used as the adhesive layer, the adhesion between the polarizer and the adjacent layer is excellent, and occurrence of defects such as discoloration can be suppressed. . Furthermore, the polarizing plate with the adhesive layer according to the embodiment of the present invention can exhibit excellent adhesiveness even under severer conditions.

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

B. Polarizer The polarizer 10 is typically composed of a polyvinyl alcohol (PVA) resin film containing a dichroic substance (such as iodine). The thickness of the polarizer is preferably 1 μm to 8 μm, more preferably 1 μm to 7 μm, more preferably 2 μm to 5 μm. If the thickness of the polarizer is in the above-mentioned range, it can greatly contribute to the thinning of the polarizing plate with the adhesive layer attached. Furthermore, the effect of the present invention is remarkable in a polarizing plate using the thin adhesive layer of the above-mentioned polarizer.

In one embodiment, the polarizer further contains boric acid. The boric acid content of the polarizer is preferably more than 10% by weight, more preferably 13% to 25% by weight. If the boric acid content of the polarizer is within the above range, the ease of curl adjustment during lamination can be maintained well, and curl during heating can be well suppressed and curl during heating can be improved by synergistic effect with the iodine content described later. Appearance durability. The content of boric acid can be calculated as the amount of boric acid contained in the polarizer per unit weight by the neutralization method using the following formula, for example. [mathematical formula 1]

The iodine content of the polarizer is preferably more than 2% by weight, more preferably 2% to 10% by weight. If the iodine content of the polarizer is within the above range, the synergistic effect with the above-mentioned boric acid content can well maintain the ease of curl adjustment during lamination, suppress curl during heating well, and improve the curl during heating. Appearance durability. In this specification, "iodine content" means the amount of all iodine contained in a polarizer (PVA-type resin film). More specifically, in polarizers, iodine exists in the form of iodide ions (I ^- ), iodine molecules (I ₂ ), polyiodide ions (I ₃ ^- , I ₅ ^- ), and the iodine content in this specification Refers to the amount of iodine that includes all of these forms. The iodine content can be calculated by the calibration curve method of X-ray fluorescence analysis, for example. In addition, polyiodide ions exist in the state of forming PVA-iodine complex in the polarizer. By forming the complex, absorption dichroism is exhibited in the wavelength range of visible light. Specifically, the complex of PVA and triiodide ions (PVA・I ₃ ^- ) has an absorption peak around 470nm, and the complex of PVA and pentaiodide ions (PVA・I ₅ ^- ) has an absorption peak around 600nm Has an absorption peak. As a result, polyiodide ions can absorb light in a wide range of visible light depending on their form. On the other hand, iodide ion (I ^- ) has an absorption peak around 230 nm and does not substantially interfere with the absorption of visible light. Therefore, polyiodide ions existing in the state of complex with PVA mainly interfere with the absorption performance of the polarizer.

The polarizer should exhibit absorption dichroism at any wavelength between 380nm and 780nm. The single transmittance Ts of the polarizer is preferably 40%~48%, more preferably 41%~46%. The degree of polarization P of the polarizer is preferably 97.0% or more, more preferably 99.0% or more, more preferably 99.9% or more. The above-mentioned monomer transmittance is representatively the Y value measured with a UV-visible spectrophotometer and corrected for visual sensitivity. The above-mentioned degree of polarization is representatively obtained by the following formula based on the parallel transmittance Tp and the cross transmittance Tc measured with an ultraviolet-visible spectrophotometer and corrected for visual sensitivity. Degree of polarization (%)={(Tp-Tc)/(Tp+Tc)} ^{1 /2} ×100

Specific examples of polarizers obtained by using the above-mentioned laminate of two or more layers include polarizers obtained by using a laminate of a resin substrate and a PVA-based resin layer (PVA-based resin film) laminated on the resin substrate. or a polarizer obtained by using a laminate of a resin substrate and a PVA-based resin layer coated and formed on the resin substrate. A polarizer obtained by using a laminate of a resin base material and a PVA-based resin layer coated and formed on the resin base material can be produced, for example, by applying a PVA-based resin solution to the resin base material and drying it. A PVA-based resin layer is formed on the resin substrate to obtain a laminate of the resin substrate and the PVA-based resin layer; the laminate is stretched and dyed to make the PVA-based resin layer into a polarizer. In this embodiment, it is preferable to form a polyvinyl alcohol-based resin layer containing a halide and a polyvinyl alcohol-based resin on one side of the resin substrate. Extending typically includes immersing the laminate in an aqueous solution of boric acid and extending it. Furthermore, stretching may include stretching the laminate in air at a high temperature (for example, 95° C. or higher) before stretching in a boric acid aqueous solution as needed. In addition, in this embodiment, it is preferable to subject the laminated body to drying shrinkage treatment in which the laminated body is heated while being transported in the longitudinal direction, thereby shrinking the laminated body by 2% or more in the width direction. Typically, the manufacturing method of this embodiment includes sequentially performing aerial assisted stretching treatment, dyeing treatment, underwater stretching treatment, and drying shrinkage treatment on the laminated body. By introducing auxiliary stretching, even when PVA is coated on thermoplastic resin, the crystallinity of PVA can be improved, and high optical characteristics can be achieved. Also, by improving the orientation of PVA in advance at the same time, it is possible to prevent problems such as decrease in orientation or dissolution of PVA when immersed in water in the subsequent dyeing step or stretching step, and achieve high optical characteristics. Furthermore, when the PVA-based resin layer is immersed in a liquid, compared with the case where the PVA-based resin layer does not contain a halide, it is possible to reduce disorientation and decrease in orientation of polyvinyl alcohol molecules. Thereby, the optical characteristics of the polarizer obtained through the processing step of immersing the laminate in liquid, such as dyeing treatment and underwater stretching treatment, can be improved. Furthermore, optical characteristics can be improved by shrinking the laminate in the width direction by drying shrinkage treatment. The obtained resin substrate/polarizer laminate can be used directly (i.e., the resin substrate can be used as a protective layer of the polarizer), or after the resin substrate is peeled off from the resin substrate/polarizer laminate. Any suitable protective layer suitable for the purpose of the peeling surface or the surface layer on the opposite side to the peeling surface is used. The details of the manufacturing method of the polarizer are described in, for example, Japanese Patent Laid-Open No. 2012-73580 and Japanese Patent No. 6470455. In this specification, the entire description of these publications is used as a reference.

C. Protective layer The protective layer 20 is formed of any suitable film that can be used as a protective layer of a polarizer. Specific examples of the material used as the main component of the film include cellulose-based resins such as cellulose triacetate (TAC), polyester-based, polyvinyl alcohol-based, polycarbonate-based, polyamide-based, polyamide-based resins, etc. Transparent resins such as amine-based, polyether-based, polystyrene-based, polystyrene-based, polynorolefin-based, polyolefin-based, (meth)acrylic-based, and acetate-based, etc. Further, thermosetting resins such as (meth)acrylic, urethane, (meth)acrylate urethane, epoxy, and silicone, or ultraviolet curable resins are also mentioned. In addition, for example, glassy polymers such as siloxane-based polymers are also mentioned. Moreover, the polymer film described in Unexamined-Japanese-Patent No. 2001-343529 (WO01/37007) can also be used. As the material of the film, for example, a resin composition containing a thermoplastic resin having a substituted or unsubstituted imide group in the side chain and a thermoplastic resin having a substituted or unsubstituted phenyl group and a nitrile group in the side chain can be used, such as , A resin composition having an alternating copolymer of isobutylene and N-methylmaleimide and an acrylonitrile-styrene copolymer can be cited. The polymer film can be, for example, an extruded product of the above-mentioned resin composition.

The polarizing plate with the adhesive layer is typically disposed on the viewing side of the image display device, and the protective layer 20 is typically disposed on the viewing side. Therefore, surface treatments such as hard coating treatment, anti-reflection treatment, anti-adhesion treatment, and anti-glare treatment may also be performed on the protective layer 20 as required.

The thickness of the protective layer 20 is preferably 10 μm-50 μm, more preferably 10 μm-30 μm. In addition, when 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 contains a resin and an isocyanate compound. The resin is a resin having a glass transition temperature of 85° C. or higher and a weight average molecular weight Mw of 25,000 or higher. The isocyanate compound includes one or more compounds having two or more isocyanate groups in the molecule. The content ratio of the resin and the isocyanate compound in the resin layer 30 (resin/isocyanate compound) is 90/10˜5/95. By arranging the resin layer between the conductive adhesive layer and the polarizer, the adhesion between the polarizer and the adjacent layer (for example, resin layer) is excellent, and occurrence of defects such as discoloration can be suppressed. Furthermore, the polarizing plate with the adhesive layer according to the embodiment of the present invention can exhibit excellent adhesiveness even under severer conditions.

The content ratio of resin and isocyanate compound (resin/isocyanate compound) is 90/10~5/95 as mentioned above, preferably 85/15~10/90, more preferably 80/20~15/85, more preferably 75/ 25~20/80. According to the above structure, it is possible to provide a polarizing plate with an adhesive layer, which is excellent in the adhesion between the polarizer and the adjacent layer even when a conductive adhesive layer is used as the adhesive layer, and suppresses the In case of adverse conditions such as discoloration.

The resin layer 30 preferably has an elastic recovery evaluation value of less than 10%, more preferably less than 9%, more preferably less than 8%. With the elastic recovery evaluation value within the above range, the adhesiveness between the polarizer and the adjacent layer is excellent even under severer conditions. In this specification, the elastic recovery evaluation value refers to the value measured and calculated by the following method. Put the sample into an environment of 60°C and 90%RH for 3 days (curing), and then leave it at room temperature (25°C, 55%RH) for 1 day. Next, nanoindentation measurement was performed to obtain the elastic recovery rate. Similarly, nanoindentation measurement was performed on samples that were not aged at room temperature (25°C, 55%RH) to obtain elastic recovery. It refers to the value calculated from the value of the elastic recovery rate by the following formula. Evaluation value of elastic recovery =｜(elastic recovery rate of cured sample (%))-(elastic recovery rate of uncured sample (%))｜

In one embodiment, the resin layer 30 is preferably a cured product or a thermally cured product of a coating film of an organic solvent solution of a resin. By having such a structure, the thickness of the resin layer 30 can be made very thin (for example, 10 micrometers or less). The thickness of the resin layer is preferably 0.05 μm-10 μm, more preferably 0.08 μm-5 μm, more preferably 0.1 μm-1 μm, especially 0.2 μm-0.7 μm.

When the resin layer 30 is a cured product or a thermally cured product of a coated film of an organic solvent solution of resin, the resin layer can be formed directly on the polarizer (that is, without an adhesive layer or an adhesive layer). According to the embodiment of the present invention, the above-mentioned polarizer and resin layer are very thin, and the adhesive layer or adhesive layer for laminating the resin layer can be omitted, so the total thickness of the polarizer with the adhesive layer can be made extremely thin. Furthermore, the resin layer has an advantage of being excellent in humidity durability because it has lower hygroscopicity and moisture permeability than cured products of water-based coating films such as aqueous solutions or aqueous dispersions. As a result, it is possible to realize a polarizing plate with an adhesive layer that maintains optical properties and is excellent in durability even in a high-temperature, high-humidity environment. In addition, the resin layer can suppress the adverse effect of ultraviolet radiation on the polarizer compared with, for example, cured products of ultraviolet curable resins. The resin layer is preferably a cured product of a coating film of an organic solvent solution. Compared with the hardened product, the cured product has less shrinkage during film forming and does not contain residual monomers, etc., so the deterioration of the film itself can be suppressed, and the failure of the polarizer (polarizer) caused by residual monomers, etc. can be suppressed Influence. Hereinafter, the resin layer which is a cured product of a coating film of an organic solvent solution or a cured product will be described in detail.

D-1. Resin The glass transition temperature (Tg) of the resin which comprises a resin layer is 85 degreeC or more, and the weight average molecular weight Mw is 25000 or more. If the Tg and Mw of the resin are in the above-mentioned ranges, the adhesiveness between the polarizer and the adjacent layer (for example, resin layer) is excellent even though it is very thin, and occurrence of defects such as discoloration can be suppressed. Furthermore, excellent adhesiveness can be exhibited even under severer conditions.

The Tg of the resin is above 85°C, preferably above 90°C, more preferably above 100°C, more preferably above 110°C, especially above 120°C. Tg may be 200 degrees C or less, for example. The Mw of the resin is above 25000, preferably above 30000, more preferably above 35000, more preferably above 40000. Mw may be 150000 or less, for example.

As the resin constituting the resin layer, any appropriate thermoplastic resin or thermosetting resin can be used as long as it can form a cured product or a thermosetting product of a coating film of an organic solvent solution, and has the above-mentioned Tg and Mw. It is preferably a thermoplastic resin. Examples of thermoplastic resins include epoxy resins and acrylic resins. An epoxy resin and an acrylic resin can also be used in combination. Hereinafter, representative examples of epoxy resins and acrylic resins that can be used for the resin layer will be described.

＜Epoxy resin＞ As the epoxy resin, an epoxy resin having an aromatic ring is preferably used. By using the epoxy resin which has an aromatic ring as an epoxy resin, when a resin layer is arrange|positioned adjacent to a polarizer, the adhesiveness with a polarizer improves. Furthermore, when an adhesive layer (conductive adhesive layer) is arrange|positioned adjacent to a resin layer, the anchor force of an adhesive layer will improve. Examples of epoxy resins having an aromatic ring include: bisphenol-type epoxy resins such as bisphenol A-type epoxy resins, bisphenol-F-type epoxy resins, and bisphenol-S-type epoxy resins; phenol novolak epoxy resins; Resin, cresol novolak epoxy resin, hydroxybenzaldehyde phenol novolak epoxy resin and other novolac epoxy resins; glycidyl ether of tetrahydroxyphenylmethane, glycidyl ether of tetrahydroxybenzophenone, epoxy poly Polyfunctional epoxy resins such as vinylphenol, naphthol-type epoxy resins, naphthalene-type epoxy resins, biphenyl-type epoxy resins, etc. It is advisable to use bisphenol A type epoxy resin, biphenyl type epoxy resin, bisphenol F type epoxy resin. Epoxy resins may be used alone or in combination of two or more.

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

(式中，X表示包含選自於由乙烯基、(甲基)丙烯醯基、苯乙烯基、(甲基)丙烯醯胺基、乙烯基醚基、環氧基、氧雜環丁烷基、羥基、胺基、醛基及羧基所構成群組中之至少1種反應性基的官能基；R ¹及R ²分別獨立表示氫原子、可具有取代基之脂肪族烴基、可具有取代基之芳基或可具有取代基之雜環基；R ¹及R ²可互相連結而形成環)。 <Boron-containing acrylic resin> In one embodiment, the acrylic resin includes a copolymer obtained by polymerizing a monomer mixture (hereinafter, may be referred to as a boron-containing acrylic resin), and the monomer mixture includes More than 50 parts by weight of (meth)acrylic monomers and more than 0 parts by weight and less than 50 parts by weight of monomers represented by formula (1) (hereinafter sometimes referred to as comonomers): [Chemical formula 2]

(In the formula, X represents a group selected from vinyl, (meth)acryl, styryl, (meth)acrylamide, vinyl ether, epoxy, oxetanyl , hydroxyl group, amino group, aldehyde group and carboxyl group constitute the functional group of at least one reactive group; R ¹ and R ² independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, and a substituent that may have a substituent The aryl group or the heterocyclic group which may have a substituent; R ¹ and R ² may be connected to each other to form a ring).

(式中，R ⁶表示任意之官能基，j及k表示1以上之整數)。 Boron-containing acrylic resins typically have repeating units represented by the following formula. By polymerizing a monomer mixture comprising a comonomer represented by formula (1) and a (meth)acrylic monomer, the boron-containing acrylic resin will have a boron-containing substituent in the side chain (for example, the following The repeating unit of k in the formula). Thereby, when a resin layer is arrange|positioned adjacent to a polarizer, the adhesiveness with a polarizer improves. The boron-containing substituents may be contained in the boron-containing acrylic resin continuously (that is, in a block form), or may be randomly contained in the boron-containing acrylic resin. [chemical formula 3]

(In the formula, R ⁶ represents an arbitrary functional group, and j and k represent integers of 1 or more).

＜(Meth)acrylic monomer＞ Any appropriate (meth)acrylic monomer can be used as the (meth)acrylic monomer. Examples thereof include (meth)acrylate monomers having a linear or branched structure and (meth)acrylate monomers having a cyclic structure.

Examples of (meth)acrylate-based monomers having a linear or branched chain structure include methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, (meth)acrylate, base) isopropyl acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, (meth) ) 2-hydroxyethyl acrylate, etc. Methyl (meth)acrylate is preferably used. The (meth)acrylate-based monomer may be used alone or in combination of two or more.

Examples of (meth)acrylate-based monomers having a ring structure include cyclohexyl (meth)acrylate, benzyl (meth)acrylate, isobornyl (meth)acrylate, (meth) 1-adamantyl acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, biphenyl (meth) Acrylate, o-biphenoxyethyl (meth)acrylate, o-biphenoxyethoxyethyl (meth)acrylate, m-biphenoxyethyl acrylate, p-biphenoxyethyl (Meth)acrylate, o-biphenoxy-2-hydroxypropyl (meth)acrylate, p-biphenoxy-2-hydroxypropyl (meth)acrylate, m-biphenoxy-2- Hydroxypropyl (meth)acrylate, N-(meth)acryloxyethyl-o-biphenyl=carbamate, N-(meth)acryloxyethyl-p-biphenyl=carbamate Ester, N-(meth)acryloxyethyl-m-diphenyl=carbamate, o-phenylphenol glycidyl ether acrylate and other biphenyl-containing monomers, terphenyl (meth)acrylic acid ester, ortho-terphenyloxyethyl (meth)acrylate, etc. Preferably, 1-adamantyl (meth)acrylate and dicyclopentyl (meth)acrylate are used. By using these monomers, a polymer having a high glass transition temperature can be obtained. These monomers may be used alone or in combination of two or more.

A silsesquioxane compound having a (meth)acryl group can also be used instead of the above-mentioned (meth)acrylate-based monomer. By using a silsesquioxane compound, an acrylic polymer having a high glass transition temperature can be obtained. Silsesquioxane compounds are known to have various skeleton structures, such as skeletons such as cage structures, ladder structures, and random structures. A silsesquioxane compound may have only 1 type of these structures, and may have 2 or more types. Silsesquioxane compounds may be used alone or in combination of two or more.

As the (meth)acryl group-containing silsesquioxane compound, for example, MAC grade and AC grade of Toagosei Co., Ltd. SQ series can be used. MAC grades are silsesquioxane compounds containing methacryl groups, specifically, MAC-SQ TM-100, MAC-SQ SI-20, MAC-SQ HDM, etc. AC grades are silsesquioxane compounds containing acryl groups, specifically AC-SQ TA-100, AC-SQ SI-20, etc.

The (meth)acrylic monomer is used in an amount of more than 50 parts by weight with respect to 100 parts by weight of the monomer mixture.

＜Co-monomer＞ As the comonomer, a monomer represented by the above formula (1) is used. By using the comonomer, a substituent including boron is introduced into the side chain of the obtained polymer. Comonomers may be used alone or in combination of two or more.

Examples of the aliphatic hydrocarbon group in the above formula (1) include straight chain or branched chain alkyl groups having 1 to 20 carbon atoms which may have substituents, cyclic alkyl groups having 3 to 20 carbon atoms which may have substituents, carbon Number 2~20 alkenyl. 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. The heterocyclic group includes a 5-membered or 6-membered ring group which may have a substituent and contains at least one heteroatom. In addition, R ¹ and R ² may be connected to each other to form a ring. R ¹ and R ² are preferably hydrogen atoms, or straight-chain or branched-chain alkyl groups with 1 to 3 carbons, more preferably hydrogen atoms.

The reactive group contained in the functional group represented by X is selected from vinyl, (meth)acryl, styryl, (meth)acrylamide, vinyl ether, epoxy, At least one selected from the group consisting of oxetanyl group, hydroxyl group, amino group, aldehyde group and carboxyl group. Preferably, the reactive group is a (meth)acrylyl group and/or a (meth)acrylamide group. By having these reactive groups, when the resin layer is arranged adjacent to the polarizer, the adhesiveness with the polarizer can be further improved.

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

[化學式5]

As comonomers, specifically, the following compounds can be used. [chemical formula 4]

[chemical formula 5]

The comonomer system is used at a content of more than 0 parts by weight and less than 50 parts by weight with respect to 100 parts by weight of the monomer mixture. Preferably it is more than 0.01 parts by weight and less than 50 parts by weight, more preferably 0.05 parts by weight to 20 parts by weight, more preferably 0.1 parts by weight to 10 parts by weight, especially preferably 0.5 parts by weight to 5 parts by weight.

<Acrylic resins containing lactone rings, etc.> In another embodiment, the acrylic resin has a unit selected from a lactone ring unit, a glutaric anhydride unit, a glutarimide unit, a maleic anhydride unit, and a maleimide (N-substituted maleimide) unit. It contains repeating units of ring structure. The repeating unit containing a ring structure may contain only 1 type in the repeating unit of an acrylic resin, and may contain 2 or more types.

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

通式(2)中，R ³、R ⁴及R ⁵分別獨立表示氫原子或碳數1~20之有機殘基。此外，有機殘基亦可包含有氧原子。丙烯酸系樹脂中可僅包含有單一內酯環單元，亦可包含有上述通式(2)中之R ³、R ⁴及R ⁵不同之複數內酯環單元。具有內酯環單元之丙烯酸系樹脂例如記載於日本專利特開2008-181078號公報中，本說明書中係援用該公報之記載作為參考。 [chemical formula 6]

In the general formula (2), R ³ , R ⁴ and R ⁵ independently represent a hydrogen atom or an organic residue with 1 to 20 carbons. In addition, the organic residues may also contain oxygen atoms. The acrylic resin may contain only a single lactone ring unit, or may contain multiple lactone ring units with different R ³ , R ⁴ and R ⁵ in the above general formula (2). An acrylic resin having a lactone ring unit is described in, for example, JP 2008-181078 A, and the description in this publication is incorporated herein by reference.

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

[chemical formula 7]

In the general formula (3), R ¹¹ and R ¹² independently represent hydrogen or an alkyl group with 1 to 8 carbons, and R ¹³ represents an alkyl group with 1 to 18 carbons, a cycloalkyl group with 3 to 12 carbons, or an alkyl group with 6 to 8 carbons. 10 aryl. In the general formula (3), preferably: R ¹¹ and R ¹² are independently hydrogen or methyl, and R ¹³ is hydrogen, methyl, butyl or cyclohexyl. Preferably: R ¹¹ is methyl, R ¹² is hydrogen, R ¹³ is methyl. The acrylic resin may contain only a single glutarimide unit, or may contain multiple glutarimide units with different R ¹¹ , R ¹² and R ¹³ in the above general formula (3). Acrylic resins having glutarimide units are described in, for example, Japanese Patent Laid-Open No. 2006-309033, Japanese Patent Laid-Open No. 2006-317560, Japanese Patent Laid-Open No. 2006-328334, Japanese Patent Laid-Open No. 2006- In JP-A-337491, JP-A-2006-337492, JP-A-2006-337493, and JP-A-2006-337569, the descriptions of these publications are incorporated herein by reference. In addition, regarding the glutaric anhydride unit, except that the nitrogen atom substituted at R ¹³ in the above general formula (3) is an oxygen atom, the above-mentioned explanations about the glutarimide unit are applied.

Regarding the maleic anhydride unit and the maleimide (N-substituted maleimide) unit, since the structure is specified by the name, a detailed description is omitted.

The proportion of repeating units containing ring structures in the acrylic resin is preferably 1 mol % to 50 mol %, more preferably 10 mol % to 40 mol %, more preferably 20 mol % to 30 mol % . In addition, the acrylic resin contains repeating units derived from the above-mentioned (meth)acrylic monomers as main repeating units.

D-2. Isocyanate compound As the isocyanate compound, a compound having two or more isocyanate groups in the molecule is used. When the resin layer contains one or more compounds having two or more isocyanate groups in the molecule, a more stable crosslinked structure can be formed between the polarizer and the adjacent layer (for example, the resin layer). Therefore, even if it is a polarizing plate with an adhesive layer using a conductive adhesive layer, it is possible to provide a polarizing plate with an adhesive layer that is excellent in the adhesion between the polarizer and the adjacent layer.

Any appropriate isocyanate compound having two or more isocyanate groups in the molecule can be used as the isocyanate compound. Examples thereof include aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and multimers (dimers, trimers, pentamers, etc.) of these diisocyanates. Moreover, the trimethylolpropane adduct etc. of the said polyisocyanate compound may be sufficient.

Examples of aliphatic polyisocyanates include trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-propylidene diisocyanate, 1,3 - butyl diisocyanate, dodecamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate.

Examples of alicyclic polyisocyanates include 1,3-cyclopentene diisocyanate, 1,3-cyclohexane diisocyanate, 1,4-cyclohexane diisocyanate, isophorone diisocyanate, hydrogenated diphenyl Methane diisocyanate, hydrogenated stubble diisocyanate, hydrogenated toluene diisocyanate, hydrogenated tetramethyl stubble diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, northylene diisocyanate, trimethylhexamethylene Methyl diisocyanate, 1,5-pentamethylene diisocyanate.

Examples of the aromatic polyisocyanate include: phenylene diisocyanate, 2,4-cresyl diisocyanate, 2,6-cresyl diisocyanate, 2,2'-diphenylmethane diisocyanate, 4 ,4'-Diphenylmethane diisocyanate, 4,4'-toluidine diisocyanate, 4,4'-diphenyl ether diisocyanate, 4,4'-diphenyl diisocyanate, 1,5-naphthalene diisocyanate , Extended stubble diisocyanate.

As an isocyanate compound, a commercial item can be used. Commercially available isocyanate compounds include, for example, trade names "Millionate MT", "Millionate MTL", "Millionate MR-200", "Millionate MR-400", "CORONATE L", "Millionate MTL" manufactured by Tosoh Co., Ltd. CORONATE HL", "CORONATE HX", Mitsui Chemicals' 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", "TAKENATE 600".

In the embodiment of the present invention, the resin layer preferably contains two or more compounds having two or more isocyanate groups in the molecule. When two or more isocyanate compounds are used in combination, two or more cross-linked structures are formed between the polarizer and the adjacent layer, resulting in a more stable cross-linked structure. Therefore, even under severe conditions (for example, a long-term high-temperature and high-humidity environment), the polarizer and the adjacent layer can still have excellent adhesion.

In one embodiment, the isocyanate compound includes: (A) an isocyanate compound having two or more isocyanate groups in the molecule, and the isocyanate group is directly bonded to an aromatic ring (hereinafter also referred to as isocyanate compound (A)) and ( B) One or more types of isocyanate compounds (isocyanate compounds (B)) other than the isocyanate compound (A) having two or more isocyanate groups in the molecule. It is known that the reaction rate of the isocyanate compound (A) is fast, and that of the isocyanate compound (B) is slow. By using the isocyanate compound (A) and the isocyanate compound (B) in combination, the reaction speed will be faster than the case of using the isocyanate compound (A) alone, and a crosslinked structure will be formed between the adjacent layer more quickly, so that Quickly ensure the adhesion between the polarizer and the adjacent layer. Furthermore, by using in combination the isocyanate compound (A) and the isocyanate compound (B), it becomes possible to form the polymer structure of the isocyanate which is hard to hydrolyze in a larger amount. Therefore, the adhesion between the polarizer and the adjacent layer can be further improved under harsher conditions (for example, a long-term high-temperature and high-humidity environment).

The isocyanate compound (A) should just be an isocyanate compound which has 2 or more isocyanate groups in a molecule|numerator, and the isocyanate group is directly bonded to an aromatic ring, and arbitrary appropriate isocyanate compounds can be used. In the isocyanate compound (A), at least one of the isocyanate groups that the isocyanate compound has may be directly bonded to the aromatic ring, and may contain an isocyanate group not directly bonded to the aromatic ring. As the isocyanate compound (A), trimethylolpropane adducts of toluene diisocyanate and trimethylolpropane adducts 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 the adhesion between the resin layer and the adjacent layer can be ensured.

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

The content ratio of the above-mentioned isocyanate compound (A) to isocyanate compound (B) (isocyanate compound (A)/isocyanate compound (B)) is preferably 50/50~95/5, more preferably 600/40~90/10, more preferably It should be 65/35~85/15. By using the isocyanate compound (A) and the isocyanate compound (B) in the above content ratio, the density between the polarizer and the adjacent layer (for example, resin layer) under severe conditions (for example, a long-term high-temperature and high-humidity environment) can be further improved. Attachment.

In one embodiment, the resin layer can be formed by applying an organic solvent solution containing the resin and an isocyanate compound to form a coating film, and curing or thermosetting the coating film. As the organic solvent, any appropriate organic solvent that can dissolve or uniformly disperse the above-mentioned 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 in the solution is preferably 3 to 20 parts by weight relative to 100 parts by weight of the solvent. If the resin concentration is the above, a uniform coating film can be formed.

The solution can be applied to any suitable substrate, and can also be applied to a polarizer. When the solution is applied to the substrate, the cured product (resin layer) of the coating film formed on the substrate is transferred to the polarizer. When the solution is applied to the polarizer, the protective layer is directly formed on the polarizer by drying (curing) the coating film. Preferably, the solution is applied to the polarizer, and the protective layer is directly formed on the polarizer. According to the above structure, the adhesive layer or the adhesive layer required for transfer can be omitted, so the polarizing plate with the adhesive layer can be further thinned. Any appropriate method can be adopted as the method of applying the solution. Specific examples include roll coating, spin coating, wire bar coating, dip coating, die coating, curtain coating, spray coating, and knife coating (cutting wheel coating, etc.).

The resin layer can be formed by curing or thermosetting the coating film of the solution. The heating temperature for curing or thermosetting should be below 100°C, more preferably 50°C~70°C. If the heating temperature is within the above range, adverse effects on the polarizer can be prevented. The heating time may vary according to 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 above-mentioned resin) may also contain any appropriate additives according to the purpose. Specific examples of additives include: ultraviolet absorbers; leveling agents; hindered phenol-based, phosphorus-based, sulfur-based, and other antioxidants; stabilizers such as light-resistant stabilizers, weather-resistant stabilizers, and heat stabilizers; glass fibers, carbon fibers, etc. Reinforcing materials, etc.; near-infrared absorbers; flame retardants such as tris(dibromopropyl) phosphate, triallyl phosphate, antimony oxide, etc.; antistatic agents such as anionic, cationic, and nonionic surfactants ; Inorganic pigments, organic pigments, dyes and other colorants; Organic fillers or inorganic fillers; Resin modifiers; Organic fillers, inorganic fillers; Plasticizers; Lubricants; Flame retardants; etc. The type, amount, combination, addition amount, etc. 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 ⁸ Ω/□~1.0×10 ¹² Ω/□ as mentioned above, preferably 1.0×10 ⁸ Ω/□~1.0× 10 ¹¹ Ω/□, more preferably 1.0×10 ⁸ Ω/□~1.0×10 ¹⁰ Ω/□, more preferably 1.0×10 ⁸ Ω/□~1.0×10 ⁹ Ω/□. If the surface resistance value of the conductive adhesive layer is within the above range, the desired antistatic performance can be achieved when the polarizing plate is applied to an image display device. As a result, the polarizing plate can also be suitably applied to image display devices with narrow bezels (preferably without bezels), so-called in-cell image display devices in which a conductive layer for a touch panel is assembled in a display panel, and the like.

The adhesive force of the conductive adhesive layer to glass should be above 1.5N/25mm and below 5.5N/25mm, more preferably above 2.5N/25mm and below 4.5N/25mm, more preferably above 3.0N/25mm and below 4.0N /25mm or less. When the adhesive force is within the above-mentioned range, the adhesiveness to the image display panel is excellent, and the reworkability is excellent.

The storage elastic modulus of the conductive adhesive layer at 25°C is preferably 1.0×10 ⁴ Pa to 1.0×10 ⁶ Pa, more preferably 1.0×10 ⁴ Pa to 1.0×10 ⁵ Pa. When the storage elastic modulus of the conductive adhesive layer is within the above-mentioned range, it is possible to suppress the poor appearance of the polarizing plate under a high-temperature and high-humidity environment. In addition, the storage elastic modulus can be obtained by dynamic viscoelasticity measurement.

The latent variable ΔCr of the conductive adhesive layer at 70°C is, for example, 65 μm or less, or 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, or 15 μm or less. The lower limit of the latent variable ΔCr is, for example, 0.5 μm. If the latent variable is within the above range, similar to the case of the storage elastic modulus, the poor appearance of the polarizing plate in a high-temperature and high-humidity environment can be suppressed. In addition, the creep value can be measured, for example, according to the following procedure: Apply a load of 500gf vertically downward with the test panel fixed to the adhesive layer attached to the stainless steel test panel with a joint surface of 20mm in length x 20mm in width . Measure the latent variable (deviation) of the adhesive layer relative to the test plate at each time point after 100 seconds and 3600 seconds from the start of the load, and record them as Cr100 and Cr3600 respectively. From the measured Cr100 and Cr3600, the latent variable ΔCr can be obtained by using the formula ΔCr=Cr3600-Cr100.

The thickness of the conductive adhesive layer is preferably 2 μm-55 μm, more preferably 2 μm-30 μm, more preferably 5 μm-25 μm, especially 10 μm-20 μm.

The adhesive composition constituting the conductive adhesive layer typically includes a base polymer and a conductive component (eg, a conductive agent).

Examples of the base polymer include (meth)acrylic polymers, urethane-based polymers, silicone-based polymers, and rubber-based polymers. It is preferably a (meth)acrylic polymer. In this specification, the (meth)acrylic-type polymer which is a base polymer may be called a (meth)acryl-type base polymer.

The (meth)acrylic base polymer typically contains an alkyl (meth)acrylate as a main component as a monomer component. Examples of the alkyl group of the alkyl (meth)acrylate include linear or branched alkyl groups having 1 to 18 carbon atoms. The average carbon number of the alkyl group is preferably 3 to 9, more preferably 3 to 6. A desirable alkyl (meth)acrylate is butyl acrylate. The content of the alkoxy-containing monomer in the base polymer is preferably at least 50 parts by weight, more preferably at least 60 parts by weight, more preferably at least 70 parts by weight, and especially preferably at least 80 parts by weight, relative to 100 parts by weight of all monomer components in the base polymer. servings or more. Alkyl (meth)acrylate may be used individually or in combination of 2 or more types.

The (meth)acrylic base polymer typically contains a monomer component (comonomer component) copolymerizable with an alkyl (meth)acrylate. Examples of comonomer components include carboxyl-containing monomers, hydroxyl-containing monomers, alkoxy-containing monomers, amide-containing monomers, aromatic ring-containing (meth)acrylates, and heterocyclic-containing vinyl groups. System monomer. By appropriately adjusting the type, amount, combination, blending amount (content), etc. of the comonomer, a base polymer (resulting in an adhesive layer) having desired characteristics can be obtained.

The weight average molecular weight Mw of the (meth)acrylic base polymer is preferably 1 million to 3 million, more preferably 2 million to 3 million, more preferably 2 million to 2.8 million. When the weight average molecular weight Mw is less than 1 million, suppression of cracks may be insufficient. When the weight-average molecular weight Mw exceeds 3 million, a viscosity increase and/or gelation during polymer polymerization may occur.

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

Inorganic cation salts are specifically inorganic cation-anion salts. Typical examples of the cation constituting the cationic portion of the inorganic cationic salt include alkali metal ions. Specific examples include lithium ions, sodium ions, and potassium ions. Lithium ions are preferred. Therefore, the ideal inorganic cation salt is a lithium salt.

Examples of the anion constituting the anion part of the ^inorganic cationic 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 the following general formula Anions shown in (1)~(4): (1): (C _n F _{2n +1} SO ₂ ) ₂ N ^- (n is an integer from 1 to 10), (2): CF ₂ (C _m F _2m SO ₂ ) ₂ N ^- (m is an integer from 1 to 10), (3): -O ₃ S(CF ₂ ) _l SO ₃ ^- (l is an integer from 1 to 10), (4): (C _p F _{2p +1} SO ₂ )N ^- (C _q F _{2q +1} SO ₂ ) (p, q are integers from 1 to 10). It is preferably a fluorine-containing anion, more preferably a fluorine-containing imide anion.

Examples of the fluorine-containing imide anion include imide anions having a perfluoroalkyl group. As specific examples, the above-mentioned (CF ₃ SO ₂ )(CF ₃ CO)N ^- , and the anions represented by the general formulas (1), (2) and (4): (1): (C _n F _{2n +1} SO ₂ ) ₂ N ^- (n is an integer from 1 to 10), (2): CF ₂ (C _m F _2m SO ₂ ) ₂ N ^- (m is an integer from 1 to 10), (4): (C _p F _{2p +1} SO ₂ )N ^- (C _q F _{2q +1} SO ₂ ) (p, q are integers from 1 to 10). It is preferably (CF ₃ SO ₂ ) ₂ N ^- , (C ₂ F ₅ SO ₂ ) ₂ N ^- and other (perfluoroalkylsulfonyl)imides represented by general formula (1), more preferably (CF ₃ SO ₂ ) ₂ N ^- Bis(trifluoromethanesulfonyl)imide shown. Therefore, the ideal inorganic cation salt that can be used in the embodiment of the present invention is lithium bis(trifluoroformyl)imide.

Organic cation salts are specifically organic cation-anion salts. Typical examples of the cation constituting the cation portion of the organic cation salt include an organic onium that forms an onium ion by substitution with an organic group. Examples of the onium in the organic onium include nitrogen onium, sulfur-containing onium, and phosphonium-containing onium. Nitrogen-containing onium and sulfur-containing onium are preferred. Examples of the nitrogen-containing onium include ammonium cations, piperidinium cations, pyrrolidinium cations, pyridinium cations, cations having a pyrroline skeleton, cations having a pyrrole skeleton, imidazolium cations, tetrahydropyrimidinium cations, dihydropyrimidinium cations, and dihydropyrimidinium cations. Pyrimidinium cation, pyrazolium cation, pyrazolinium cation. As the sulfur-containing onium, for example, a caldium cation is mentioned. Phosphonium-containing oniums include, for example, phosphonium cations. Examples of the organic group in the organic onium include an alkyl group, an alkoxy group, and an alkenyl group. Specific examples of ideal organic onium include tetraalkylammonium cations (for example, trimethylbutylammonium cations), alkylpiperidinium cations, and alkylpyrrolidinium cations. The anion constituting the anion portion of the organic cation salt is as described for the anion constituting the anion portion of the inorganic cation salt. The ideal organic cation salts that can be used in the embodiment of the present invention are methylpropylpyrrolidinium bis(trifluoromethylsulfonyl)imide, 1-ethyl-3-methylimidazolium bis(fluorosulfonyl) base) imide, trimethylbutylammonium bis(trifluoromethanesulfonyl)imide.

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

The conductive component can be solid or liquid (ie, ionic liquid).

The content of the conductive component in the adhesive composition is preferably 5 to 15 parts by weight, more preferably 8 to 12 parts by weight relative to 100 parts by weight of the base polymer. If the content of the conductive component is within the above range, desired antistatic performance can be obtained without adversely affecting other properties.

The adhesive composition typically contains a silane coupling agent and/or a crosslinking agent. As a silane coupling agent, a silane coupling agent containing a functional group is representatively mentioned. Examples of functional groups include epoxy groups, mercapto groups, amine groups, isocyanate groups, isocyanurate groups, vinyl groups, styryl groups, acetylacetoyl groups, ureido groups, thiourea groups, and (meth)acryl groups. Acyl group, heterocyclic group, acid anhydride group and combinations thereof. Silane coupling agents containing functional groups can be used alone or in combination. As a crosslinking agent, an isocyanate type crosslinking agent and a peroxide type crosslinking agent are mentioned. And the crosslinking agent can also be used individually or in combination.

The adhesive composition may also contain additives. Specific examples of additives include powders such as colorants and pigments, dyes, surfactants, plasticizers, thickeners, surface lubricants, leveling agents, softeners, antioxidants, antiaging agents, optical Stabilizers, UV absorbers, polymerization inhibitors, inorganic or organic fillers, metal powders, granules, and foils. Also, a redox system in which a reducing agent is added can also be used within a controllable range. The type, quantity, combination, content, etc. of the additives can be appropriately set according to the purpose.

F. Image display device The above-mentioned polarizing plate with an adhesive layer can be used for any appropriate purpose. In the embodiment of the present invention, the polarizing plate with the adhesive layer can be applied to an image display device. Therefore, the embodiment of the present invention includes an image display device using the polarizing plate with the adhesive layer attached. Representative examples of image display devices include liquid crystal display devices and electroluminescence (EL) display devices (for example, organic EL display devices and inorganic EL display devices).

[Example] Hereinafter, the present invention will be specifically described by way of examples, but the present invention is not limited by these examples. The measurement method of each characteristic is as follows. In addition, unless otherwise specified, "part" and "%" in an Example and a comparative example are based on weight.

(1) Thickness The thickness of 10 μm or less was measured using an interference film thickness meter (manufactured by Otsuka Electronics Co., Ltd., product name "MCPD-3000"). The thickness of more than 10 μm was measured using a digital micrometer (manufactured by ANRITSU CORPORATION, product name "KC-351C").

(2) Surface resistance value According to JIS K 6911, the surface resistance value of the adhesive layer was measured. Specifically, the probe was pressed against the adhesive layer of the polarizing plate with the adhesive layer attached, and the stable value after 30 seconds passed was read. The measurement was carried out under the following measurement conditions. ＜Measurement conditions＞ Resistance Meter: Hiresta Probe: URS Temperature: 23±2℃ Humidity: 50±5%RH

(3) Evaluation value of elastic recovery The polarizing plates with the adhesive layer obtained in Examples and Comparative Examples were cut into 3 cm×3 cm and used as samples. Put the sample into an environment of 60°C and 90%RH for 3 days (curing), and then leave it at room temperature (25°C, 55%RH) for 1 day. Thereafter, the sample was embedded with epoxy resin, and a cross-section was prepared with an ultramicrotome. The prepared cross-section was fixed on a support, and the nanoindentation measurement was performed under the following conditions, and the elastic recovery rate was obtained from the following formula. Similarly, nanoindentation measurement was performed on samples that were not aged at room temperature (25°C, 55%RH) to obtain elastic recovery. ＜Analytical equipment and conditions＞ Device: Hysitron Inc., product name: Triboindenter Indenter used: Berkovich (triangular cone type) Measurement method: single indentation measurement Indentation depth: 50nm Measuring position: 500nm away from the polarizer interface ＜Calculation method of elastic recovery rate＞ Elastic recovery rate (%)={maximum displacement (displacement at the deepest indentation) (hmax)-plastic deformation (hf)}/maximum displacement (hmax)

Using the elastic recovery rate of the cured sample and the elastic recovery rate of the uncured sample, calculate the elastic recovery evaluation value from the following formula. Evaluation value of elastic recovery =｜(Elastic recovery rate of cured sample (%))-(Elastic recovery rate of uncured sample (%))｜

(4) Peel test The polarizing plates with the adhesive layer obtained in the examples and comparative examples were cut into 50 mm×50 mm, and attached to a glass plate with a larger size than the cut out, as test samples. This test sample was immersed in warm water at 60°C. The immersion time at the point where the peeling distance of the resin layer is the largest becomes 3mm or more is evaluated according to the following criteria. A: No peeling for 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

[Manufacturing example 1: Production of boron-containing acrylic resin] 99.0 parts by weight of methyl methacrylate (MMA, manufactured by FUJIFILM Wako Pure Chemical Corporation, trade name: Methyl Methacrylate Monomer), 1.0 parts by weight of a monomer of general formula (1e), a polymerization initiator (manufactured by FUJIFILM Wako Pure Chemical Corporation, Trade name: 0.2 parts by weight of 2,2'-azobis(isobutyronitrile)) was dissolved in 100 parts by weight of toluene. Next, it heated to 70 degreeC in nitrogen atmosphere, and performed polymerization reaction for 5 hours, and obtained the copolymer 1 (solid content concentration: 50 weight%). Copolymer 1 had a Tg of 110°C and a weight average molecular weight of 80,000.

[Manufacturing Example 2: Production of Polarizing Plate] 1. Production of polarizer As the thermoplastic resin substrate, a long amorphous isophthalic acid-copolymerized polyethylene terephthalate film (thickness: 100 μm) with a water absorption rate of 0.75% and a Tg of about 75° C. was used. Corona treatment is performed on one side of the resin substrate. A PVA-based resin that mixes polyvinyl alcohol (polymerization degree 4200, saponification degree 99.2 mol%) and acetoacetyl-modified PVA (manufactured by Nippon Synthetic Chemical Industry Co., Ltd., trade name "GOHSEFIMER Z410") at a ratio of 9:1 13 parts by weight of potassium iodide was added to 100 parts by weight, and the resultant was dissolved in water to prepare an aqueous PVA solution (coating solution). The above-mentioned PVA aqueous solution was applied to the corona-treated surface of the resin substrate and dried at 60° C. to form a PVA-based resin layer with a thickness of 13 μm to produce a laminate. The obtained laminate was uniaxially stretched at the free end to 2.4 times in the longitudinal direction (longitudinal direction) between rollers with different peripheral speeds in an oven at 130°C (in-air assisted stretching treatment). Next, the laminated body was immersed for 30 seconds in an insoluble bath (an aqueous solution of boric acid obtained by mixing 4 parts by weight of boric acid with respect to 100 parts by weight of water) at a liquid temperature of 40° C. (insoluble treatment). Next, in a dyeing bath with a liquid temperature of 30°C (an iodine aqueous solution obtained by mixing iodine and potassium iodide at a weight ratio of 1:7 with respect to 100 parts by weight of water), the single transmittance (Ts) of the final polarizer was measured. Adjust the concentration so that it becomes 43.0% or more and dip for 60 seconds (dyeing treatment). Next, it was immersed for 30 seconds in a crosslinking bath (a boric acid aqueous solution obtained by mixing 3 parts by weight of potassium iodide and 5 parts by weight of boric acid with respect to 100 parts by weight of water) at a liquid temperature of 40° C. (crosslinking treatment). Thereafter, while the laminate was immersed in a boric acid aqueous solution (boric acid concentration: 4.0% by weight, potassium iodide concentration: 5% by weight) at a liquid temperature of 70°C, it was stretched in the longitudinal direction (longitudinal direction) between rolls with different circumferential speeds. Uniaxial stretching was performed so that the magnification was 5.5 times (underwater stretching treatment). Thereafter, the laminate was immersed in a cleaning bath (an aqueous solution obtained by mixing 4 parts by weight of potassium iodide with respect to 100 parts by weight of water) at a liquid temperature of 20° C. (washing treatment). Thereafter, while drying in an oven maintained at 90° C., it was brought into contact with a SUS heated roll maintained at a surface temperature of 75° C. for about 2 seconds (drying shrinkage treatment). The shrinkage rate in the width direction of the laminate obtained by drying shrinkage treatment was 5.2%. In the manner described above, a polarizer having a thickness of 5 μm was formed on the resin substrate.

2. Fabrication of polarizing plate A hard coat (HC) layer (thickness 7 μm) was formed on one side of a triacetyl cellulose (TAC) film (thickness 25 μm). details as follows. Prepare 40 parts by weight of ultraviolet curable acrylate resin (manufactured by Toagosei Co., Ltd., trade name "M-920", solid content 100%), ultraviolet curable acrylate resin (manufactured by Mitsubishi Chemical Co., Ltd., trade name "UV -1700TL", solid content 80%) 60 parts by weight. For every 100 parts by weight of the resin solid content of the resin, 3 parts by weight of a photopolymerization initiator (manufactured by BASF Corporation, trade name "OMNIRAD907"), a leveling agent (manufactured by Kyyoei Chemical Co., Ltd., trade name "LE- 303", solid content 40%) 0.12 parts by weight. This mixture was diluted with MIBK/cyclopentanone mixed solvent (weight ratio 70/30) so that the solid content concentration might become 30%, and the coating liquid for hard-coat layer formation was prepared. This coating solution for forming a hard coat layer was applied to the TAC film with a bar coater to form a coating layer. The TAC film on which the coating layer was formed was heated at 80° C. for 1 minute to dry the coating layer to form a coating film. The obtained coating film was irradiated with ultraviolet rays with a cumulative light intensity of 240 mJ/cm ² from a high-pressure mercury lamp to harden the coating film to form an HC layer with a thickness of 7 μm. Attach the laminate of HC layer/TAC film to the surface of the polarizer obtained in 1. above (the surface opposite to the resin substrate) through a UV-curable adhesive. Specifically, it applied so that the total thickness of the hardening adhesive might become 1.0 micrometers, and bonded using the roll mill. Thereafter, the adhesive was cured by irradiating UV rays from the protective layer side to obtain a laminate (polarizing plate) of resin substrate/polarizer/TAC film/HC layer.

[Manufacturing Example 3: Preparation of Conductive Adhesive 1] A monomer mixture containing 99 parts of butyl acrylate and 1 part of 4-hydroxybutyl acrylate was charged into a four-necked flask equipped with a stirring blade, a thermometer, a nitrogen gas introduction tube, and a cooler. Furthermore, with respect to 100 parts of this monomer mixture (solid content), 0.1 part of 2,2'-azobisisobutyronitrile as a polymerization initiator was added together with ethyl acetate, and nitrogen gas was introduced while stirring slowly to carry out nitrogen replacement. Thereafter, the liquid temperature in the flask was maintained at around 60° C., and the polymerization reaction was carried out for 7 hours. Thereafter, ethyl acetate was added to the obtained reaction solution to adjust the solid content concentration to 30%, and a solution of an acrylic polymer having a weight average molecular weight of 1.4 million was prepared. 1-Ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide (manufactured by Tokyo Kasei Kogyo) 0.2 0.1 part of trimethylolpropane diisocyanate (manufactured by Mitsui Chemicals: TAKENATE D110N), 0.3 part of dibenzoyl peroxide and γ-glycidoxypropyl methoxysilane (Shin-Etsu Chemical Co., Ltd.: KBM-403) 0.075 parts to prepare a conductive adhesive 1.

[Manufacturing Example 4: Preparation of Conductive Adhesive 2] A conductive adhesive 2 was prepared in the same manner as in Production Example 3 except that 10 parts of 1-ethyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide was used.

[Example 1] To 90 parts of copolymer 1 (boron-containing acrylic resin), 10 parts of an isocyanate compound (manufactured by Tosoh Corporation, "CORONATE L": trimethylolpropane adduct of cresyl diisocyanate) was added. This mixture was dissolved in 80 parts of mixed solvents of ethyl acetate/cyclopentanone (70/30) to obtain a resin solution (20%). The resin substrate is peeled off from the polarizing plate, and the resin solution is coated on the peeled surface of the polarizing plate obtained above using a wire bar, and the coated film is dried at 60° C. for 5 minutes to form a resin-based organic solvent solution. A resin layer (thickness: 0.5 μm) formed in the form of a cured product of the coating film. Next, use the conductive adhesive obtained in Production Example 3 to place an adhesive layer (15 μm in thickness) on the surface of the resin layer to obtain a protective layer (HC layer/TAC film)/adhesive layer/polarizer/resin layer/ A polarizing plate with an adhesive layer composed of a conductive adhesive layer. The total thickness of the obtained polarizing plate with adhesive layer was 53.5 μm. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 2] Except for using 80 parts of boron-containing acrylic resin and 20 parts of isocyanate compound, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 1. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 3] Except for using 5 parts of boron-containing acrylic resin and 95 parts of isocyanate compound, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 1. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 4] As the isocyanate compound, TAKENATE D110N (manufactured by Mitsui Chemicals Co., Ltd., trimethylolpropane adduct of intermolecular diisocyanate) was used instead of CORONATE L, and adhesion was obtained in the same manner as in Example 2. The polarizing plate of the agent layer. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 5] As the isocyanate compound, TAKENATE D160N (manufactured by Mitsui Chemicals Co., Ltd., a trimethylolpropane adduct of hexamethylene diisocyanate) was used instead of CORONATE L, and an adhesive was obtained in the same manner as in Example 2. layer of polarizers. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 6] As the isocyanate compound, except for using 10 parts of CORONATE L and 10 parts of TAKENATE D160N, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 2. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 7] As the isocyanate compound, except that 15 parts of CORONATE L and 5 parts of Takenate D160N were used, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 2. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 8] Instead of boron-containing acrylic resin, 15 parts (in terms of solid content) of copolymer 1 (boron-containing acrylic resin) obtained in Production Example 1 and thermoplastic epoxy resin (manufactured by Mitsubishi Chemical Co., Ltd., trade name " A polarizing plate with an adhesive layer was obtained in the same manner as in Example 7 except that 80 parts of a mixture of 85 parts of jER (registered trademark) (YX6954BH30") (calculated as solid content) was used. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 9] As the isocyanate compound, except for using 19 parts of CORONATE L and 1 part of TAKENATE D160N, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 2. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) 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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) 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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Example 13] Except for using 70 parts of boron-containing acrylic resin, 22.5 parts of CORONATE L, and 7.5 parts of TAKENATE D160N, a polarizing plate with an adhesive layer was obtained in the same manner as in Example 6. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) 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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(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 boron-containing acrylic resin was used (that is, no isocyanate compound was used). The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) 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 polysiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: KBM-603) was used instead of the isocyanate compound. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) 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 (manufactured by Matsumoto Fine Chemical Co. Ltd., trade name: TA-21) was used instead of the isocyanate compound. The obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(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 obtained polarizing plate with the adhesive layer attached was used for the evaluation of (3)-(4) above. The results are shown in Table 1.

[Table 1]

In addition, in Table 1, "epoxy/acrylic" in the column of constituent resin means a mixture of epoxy resin and acrylic resin.

[Evaluate] It is evident from Table 1 that the polarizing plate with the adhesive layer of the embodiment of the present invention maintains the state of adhesion between the polarizer and the resin layer even when it is immersed in warm water. On the other hand, in the polarizing plates with the adhesive layer of Comparative Examples 1 to 3, the resin layer was peeled off from the polarizing member within 30 minutes after dipping in warm water.

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

10: Polarizer 20: protective layer 30: resin layer 40: Adhesive layer 100: Polarizing plate with adhesive layer

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

10: Polarizer

20: protective layer

30: resin layer

40: Adhesive layer

100: Polarizing plate with adhesive layer

Claims (7)

A polarizing plate with an adhesive layer, which sequentially comprises a protective layer, a polarizer, a resin layer, and a conductive adhesive layer; the surface resistance of the conductive adhesive layer is 1.0×10 ⁸ Ω/□~1.0×10 ¹² Ω/□; The resin layer contains resin and isocyanate compound; The glass transition temperature of the resin is above 85°C, and the weight average molecular weight Mw is above 25000; The isocyanate compound contains one or more isocyanate groups in the molecule. compound; the ratio of the resin to the isocyanate compound (resin/isocyanate compound) is 90/10~5/95. The polarizing plate with an adhesive layer according to claim 1, wherein the isocyanate compound includes two or more compounds having two or more isocyanate groups in the molecule. A polarizing plate with an adhesive layer according to Claim 2, wherein the aforementioned isocyanate compound includes: (A) an isocyanate compound having two or more isocyanate groups in the molecule, and the isocyanate groups are directly bonded to an aromatic ring; and (B) an isocyanate compound having two or more isocyanate groups in the molecule other than the isocyanate compound (A); and The said isocyanate compound contains 1 or more types of each of this isocyanate compound (A) and this isocyanate compound (B). A polarizing plate with an adhesive layer according to claim 3, wherein the content ratio of the isocyanate compound (A) to the isocyanate compound (B) (isocyanate compound (A)/isocyanate compound (B)) is 50/50~95/5 . A polarizing plate with an adhesive layer according to any one of claims 1 to 4, wherein the aforementioned resin comprises a copolymer obtained by polymerizing a monomer mixture containing more than 50 parts by weight of (methyl) Acrylic monomers and monomers represented by formula (1) greater than 0 parts by weight and less than 50 parts by weight: [Chemical formula 1]

(In the formula, X represents a group selected from vinyl, (meth)acryl, styryl, (meth)acrylamide, vinyl ether, epoxy, oxetanyl , hydroxyl group, amino group, aldehyde group and carboxyl group constitute the functional group of at least one reactive group; R ¹ and R ² independently represent a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, and a substituent that may have a substituent The aryl group or the heterocyclic group which may have a substituent; R ¹ and R ² may be connected to each other to form a ring). The polarizing plate with an adhesive layer according to claim 1, wherein the elastic recovery evaluation value of the aforementioned resin layer is 10% or less. An image display device, comprising a polarizing plate with an adhesive layer according to Claim 1.

Images