KR101609435B1 - Adhesive composition for polarizing plate, adhesive film for polarizing plate comprising the same, polarizing plate comprising the same and display apparatus comprising the same - Google Patents

Abstract

An object of the present invention is to provide an adhesive composition for a polarizing plate which is excellent in initial curability and adhesiveness. In order to solve the above object, the adhesive composition for a polarizing plate of the present invention comprises (A) 20 to 70 parts by mass of a (meth) acrylate monomer containing an allyl group and a hydroxyl group; (B) 20 to 80 parts by mass of an epoxy group-containing compound; (C) 0 to 30 parts by mass of other monomers; (D) a photoacid generator; And (E) at least one of a photopolymerization initiator and a photosensitizer.

Description

TECHNICAL FIELD [0001] The present invention relates to an adhesive composition for a polarizing plate, an adhesive film for a polarizing plate containing the same, a polarizing plate including the same, and a display device including the same. BACKGROUND ART THE SAME}

The present invention relates to an adhesive composition for a polarizing plate for use in producing a polarizing plate and for bonding a polarizing plate and a protective film, an adhesive film for a polarizing plate using the same, and a polarizing plate and a display device including the same. More specifically, the present invention relates to an adhesive composition for a polarizing plate that is excellent in initial curability and adhesiveness, an adhesive film for a polarizing plate using the same, a polarizing plate using the same, and a display device containing the same.

2. Description of the Related Art In recent years, flat displays such as liquid crystal displays and plasma displays have been widely used as display devices because they are space-saving and highly precise. Of these, liquid crystal monitors are attracting attention because they are more power-saving and more stable, and their development is progressing.

In a liquid crystal display panel, a polarizing plate serving as an optical shutter is used in combination with a liquid crystal to exert its function. The polarizing plate is an integral part of a liquid crystal display panel having a polarizer. Usually, the polarizer is produced by uniaxially stretching a polyvinyl alcohol (PVA) resin at a stretching ratio of 5 to 6 times in a water bath, so that it tends to be torn in the stretching direction and has drawbacks. Therefore, the polarizer is used by forming a polarizing plate by adhering a protective film to its surface and / or its back surface. At this time, it is required that the adhesive for bonding the protective film to the polarizer is also required to meet a specific requirement when the polarizer is used.

As such an adhesive for a polarizing plate, there is disclosed an adhesive composition for a polarizing plate comprising an acrylic monomer having a hydroxy group, a radical polymerization initiator, an epoxy resin and a cationic photopolymerization initiator (see Patent Document 1). This document provides an adhesive for a low-viscosity polarizing plate having excellent adhesion and water resistance while maintaining the low viscosity of the adhesive.

(A) 50 to 99.5% by weight of a hydroxyl group-containing alkyl (meth) acrylate, (B) 0.49 to 10% by weight of a photopolymerization initiator, (C) 0.01 to 1% by weight of an epoxy compound to be used for a polarizing plate (see Patent Document 2).

According to the above-mentioned document, it is intended to make it possible to improve the productivity, the equipment cost, the adhesive property, and the freedom of the combination of the protective film and the like.

Further, it is also possible to use a main agent comprising a cationically polymerizable compound containing a radical polymerizing compound mainly containing a monofunctional radically polymerizable compound and a compound having an alicyclic epoxy group and containing no (meth) acryloyl group and , A photo radical polymerization initiator, and a photo cationic polymerization initiator (see Patent Document 3). This document describes that the above adhesive is excellent not only in adhesion between the protective film and the polarizer but also excellent punching workability and water resistance.

<Prior Art Literature>

(Patent Document 1) JP2012-62471 A

(Patent Document 2) JP2010-18722 A

(Patent Document 3) JP2011-76058 A

However, the adhesive compositions for polarizing plates used in Patent Documents 1 to 3 did not satisfy both of these requirements at the same time.

An object of the present invention is to provide an adhesive composition for a polarizing plate which is excellent in initial curability and adhesive property in view of the above circumstances. Another object of the present invention is to provide a polarizer excellent in durability by using such an adhesive composition.

The inventors of the present invention have conducted intensive studies to solve the above problems and found that by using an adhesive composition for a polarizing plate containing an allyl group and a (meth) acrylate monomer containing a hydroxy group in a specific ratio, initial curability and adhesiveness An adhesive composition for an excellent polarizing plate can be obtained. Based on the above findings, the present invention has been completed.

That is, the above object is attained by a resin composition comprising (A) 20 to 70 parts by mass of a (meth) acrylate monomer containing an allyl group and a hydroxyl group; (B) 20 to 80 parts by mass of an epoxy group-containing compound; (C) 0 to 30 parts by mass of other monomers; (D) a photoacid generator; And (E) at least one of a photopolymerization initiator and a photosensitizer.

According to the adhesive composition for a polarizing plate of the present invention, when used in a polarizing plate using various protective films, excellent initial curability and adhesiveness can be exhibited. Therefore, the polarizing plate using the adhesive composition for a polarizing plate of the present invention can be a polarizing plate having good adhesion to a protective film and high durability.

1 is a schematic view for explaining a production process of a polarizing plate in the examples;
2 is a schematic view for explaining a method of an initial curability test in Examples;
3 is a schematic view for explaining a method of a hot water immersion test in the embodiment;
4 is a schematic view for explaining a method of peel strength in the embodiment.
5 is a cross-sectional view of a polarizer of an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described. The present invention is not limited to the following embodiments. In addition, the dimensional ratios in the drawings are exaggerated for the sake of explanation, and may differ from the actual ratios. In the present specification, &quot; X to Y &quot; representing the range means &quot; X or more and Y or less &quot;, and &quot; weight &quot;, &quot; Mass part "are treated as synonyms. Unless otherwise stated, the measurement of the operation and physical properties is carried out under the conditions of room temperature (20 to 25 ° C) / relative humidity of 40 to 60%. As used herein, the term &quot; protective film &quot; includes not only a non-phase difference protection film without phase difference but also a phase difference protection film having a phase difference. In the present specification, Quot; is based on the drawing, and &quot; upper &quot; may be changed to &quot; lower &quot; and &quot; lower &quot; may be changed to &quot; upper &quot; In the present specification, the (meth) acrylate base material means acrylate or methacrylate.

(1) Adhesive composition for polarizer

According to a first aspect of the present invention, there is provided a resin composition comprising (A) 20 to 70 parts by mass of a (meth) acrylate monomer containing an allyl group and a hydroxyl group; (B) 20 to 80 parts by mass of an epoxy group-containing compound; (C) 0 to 30 parts by mass of other monomers; (D) a photoacid generator; And (E) at least one of a photopolymerization initiator and a photosensitizer. The "adhesive composition for a polarizing plate" is hereinafter also simply referred to as a "composition".

As described above, the conventional adhesive for a polarizing plate is not yet sufficient in terms of achieving both initial curability and adhesive properties. In the present invention, (meth) acrylate monomers containing an allyl group and a hydroxy group; By using an adhesive composition for a polarizing plate containing an epoxy group-containing compound in a specific ratio, excellent both of initial curability and adhesive property are realized.

Hereinafter, the constituent components of the composition of the present invention will be described in detail.

[Polymerizable component]

(A) 20 to 70 parts by mass of a (meth) acrylate monomer containing an allyl group and a hydroxyl group; (B) 20 to 80 parts by mass of an epoxy group-containing compound; (C) 0 to 30 parts by mass of other monomers; (D) a photoacid generator; And (E) a photopolymerization initiator and a photosensitizer. (A) to (C) of the adhesive composition for a polarizing plate are polymerizable components.

(A) a (meth) acrylate monomer containing an allyl group and a hydroxy group

The (meth) acrylate monomer containing an allyl group and a hydroxy group is not particularly limited as long as it has an allyl group and a hydroxy group in the molecule. For example, a (meth) acrylic acid and a "compound having one allyl group and one epoxy group" . &Lt; / RTI &gt;

As described above, when (A) the (meth) acrylate monomer containing an allyl group and a hydroxy group is used, unlike the (meth) acrylate moiety (acryloyl group), the allyl group also undergoes a reaction, It becomes a delusion. As a result, not only the initial curability but also the adhesiveness can be improved.

Specific examples of the (meth) acrylate monomer containing an allyl group and a hydroxyl group include a (meth) acrylic acid ester having an alkyl group having 1 to 10 carbon atoms and having an allyl group and a hydroxyl group, wherein the " and the carbon number excluding a group of the allyl ester, wherein "allyl group" is an allyl group _{(CH 2 = CH-CH 2} - *), allyloxy groups _{(CH 2 = CH-CH 2} -O- *), allyl thio ( CH ₂ = CH-CH ₂ -S- *). For example, 3-allyloxy-2-hydroxypropyl (meth) acrylate, 3-allyloxy-1-hydroxypropyl (meth) acrylate and the like can be given. Of course, other than these specific examples, (meth) acrylate containing an allyl group and a hydroxy group may be used. It may be in the form of a mixture at all.

(A) A (meth) acrylate monomer containing an allyl group and a hydroxy group may be prepared by purchasing a commercial product. As a commercial product, ALHA (product of Osaka Organic Chemical Industry Co., Ltd.) is preferably used.

The blending amount of the (A) allyl group and the (meth) acrylate monomer containing a hydroxyl group is 20 to 70 parts by mass based on 100 parts by mass of the total amount of the components (A) to (C). When the amount exceeds 70 parts by mass, the "penetration" of the component (A), which can contribute to the anchor effect described later, becomes excessive, and the adhesiveness deteriorates, and the amount of the component (B) There is a problem that the heat resistance is deteriorated. On the other hand, if it is lower than 20 parts by mass, it is not possible to obtain a sufficient anchor effect since the wetting property is not developed, that is, the "penetration" is small and the adhesiveness is lowered, none. For example, it is 23 to 70 parts by mass or 30 to 50 parts by mass with the total amount of the components (A) to (C) being 100 parts by mass.

Assuming that an acrylic resin is used as the protective film, the content of the component (A) is preferably 25 to 65 parts by mass, more preferably 40 to 60 parts by mass, and the content of the component (A) 60 parts by mass.

Assuming that TAC (triacetyl cellulose) is used as the protective film, the content of the component (A) is preferably 21 to 65 parts by mass, particularly preferably 100 to 200 parts by mass, Is preferably from 24 to 55 parts by mass, particularly preferably from 40 to 60 parts by mass.

(B) an epoxy group-containing compound

The epoxy group-containing compound used in the present invention is not particularly limited as long as it is an epoxy group-containing compound, but preferably contains two or more epoxy groups. When a compound containing two or more epoxy groups is used, since two or more ring-opened epoxy groups are reacted in one molecule, the polymer does not have a linear structure and has a network structure. In addition to initial curability, Can be improved. Here, the number of epoxy groups is preferably 1 to 3, particularly preferably 2, from the viewpoint of obtaining the effects of the present invention and from the viewpoint of availability.

Specific examples thereof include, for example, bisphenol A, bisphenol F, bisphenol S, brominated bisphenol A, hydrogenated bisphenol A, bisphenol AF, biphenyl, naphthalene, fluorene, Bifunctional epoxy resins such as hydroxyphenylmethane type and tetraphenylol ethane type; Novolak type epoxy resins such as phenol novolak type epoxy resin and cresol novolak type epoxy resin; Polyfunctional epoxy resins; Glycidylamine type epoxy resin; A heterocyclic ring containing epoxy resin; And alicyclic epoxy resins. In addition, aliphatic epoxy resins and hydrogenated aromatic epoxy resins can also be used. These epoxy resins may be used alone or in combination of two or more. The epoxy resin may be a synthetic resin or a commercially available product. For example, bisphenol F type aromatic epoxy resins and alicyclic epoxy resins can be used.

The preferred epoxy group-containing compounds to be used in the present invention may be prepared by synthesizing with reference to conventional knowledge, or a commercially available product may be obtained. As a commercial product, Epicote (registered trademark) series (Epikote (registered trademark) 807, Epikote (registered trademark) 815, Epikote (registered trademark) 825, Epikote (registered trademark) 827, Epikote (registered trademark) , Epicote (registered trademark) 834, Epicote (registered trademark) 1001, Epicote (registered trademark) 1004, Epicote (registered trademark) DER-361 (manufactured by Dow Chemical Co.), YD8125 and YDF8170 (manufactured by Tohto Kasei Co., Ltd.); Epiclon (registered trademark) EXA-1514 (manufactured by DIC Corporation); Epocote (registered trademark) 152, EPICOT (registered trademark) 154 (manufactured by Japan Epoxy Resin Co., Ltd.), EPPN-501 (manufactured by NIPPON KAYAKU CO., LTD. EOCN-1025, and EOCN-1027 (all manufactured by Nippon Kayaku Co., Ltd.); DEN-438 (manufactured by Dow Chemical); EOCN-102S, EOCN-103S, EOCN- Epal 1031S (manufactured by Japan Epoxy Resin Co., Ltd.), ARALITE (registered trademark) 0163 (manufactured by TOKYO KABUSHIKI KOGYO CO., LTD.), YDCN700-10 (manufactured by Toto Kasei Co., EX-421, EX-421, EX-621, EX-621, EX-521, EX-421, EX-411 and EX-321 (products of SPECIALTY CHEMICALS CORPORATION) TETRAD (registered trademark) -X, TETRAD (registered trademark) -C (manufactured by Nippon Steel Chemical Co., Ltd.), etc.); Epikote (registered trademark) 604 (manufactured by Japan Epoxy Resin Co., ERL4234, ERL4299, ERL4221, and ERL4206 (manufactured by UCC Co., Ltd.)), ELM-120 (manufactured by Sumitomo Chemical Co., Ltd.), Aralite (registered trademark) PT810 (manufactured by Ciba Specialty Chemicals) ; Epolide (registered trademark) series, Cellokide (registered trademark) series 2021P (manufactured by Daicel Chemical Industries, Ltd.); EXA-4820 series, Epiclon (registered trademark) HPC-8000-65T (registered trademark) EXA-830CRP, Epiclon (registered trademark) (Manufactured by DIC Co., Ltd.).

The compounding amount of the epoxy group-containing compound (B) according to the present invention is 20 to 80 parts by mass, with the total amount of the components (A) to (C) being 100 parts by mass. When the blending amount of the component (B) is less than 20 parts by mass, the amount of the component (A) becomes excessively large, causing the above-described problems and deteriorating the heat resistance. On the other hand, when the amount exceeds 80 parts by mass, the amount of the component (A) is relatively reduced, and the adhesion and permeability to the protective film are lowered, and the adhesive strength is lowered. Furthermore, viscosity of the adhesive solution becomes higher, It becomes. For example, it is 30 to 80 parts by mass or 30 to 50 parts by mass with the total amount of the components (A) to (C) being 100 parts by mass.

When the acrylic resin is used as the protective film, the content of the component (B) is preferably 35 to 75 parts by mass, and more preferably 40 to 60 parts by mass. When the content of the component (B) is less than 35 parts by mass, it is also preferable to supplement the component (C) described later.

The content of the component (B) is preferably from 35 to 79 parts by mass, particularly preferably from 45 to 76 parts by mass, and particularly preferably from 40 to 60 parts by mass, assuming that TAC is used as the protective film.

As described above, in the epoxy-group-containing compound (B), since two or more ring-opened epoxy groups react with each other, the polymer does not have a linear structure but has a network structure. On the other hand, in the case of (A) a (meth) acrylate monomer containing an allyl group and a hydroxyl group, unlike the (meth) acrylate moiety, the allyl moiety also undergoes a reaction, . Since these are simultaneously undergoing polymerization, they are considered to be a crosslinked structure having the same structure as that of each other. Thus, it is considered that not only the initial curability but also the adhesiveness are improved by entangling the components (A) and (B) in a complex manner. However, such a mechanism is merely an inference, and does not adversely affect the technical scope of the present invention.

As described above, in the present invention, by using the adhesive composition for a polarizing plate, which contains a (meth) acrylate monomer containing an allyl group and a hydroxy group and an epoxy group-containing compound at a specific ratio, excellent both of initial curability and Specifically, the component (A): the component (B) in the adhesive composition may be in a mass ratio of 1: 0.25 to 1: 3.5, and both of excellent initial curability and adhesive property in the above range can be realized.

(C) Other monomers

The adhesive composition for a polarizing plate of the present invention contains the component (A) and the component (B) as essential components, but may contain other monomers (other monomers).

The upper limit is up to 30 parts by mass with the total amount of the components (A) to (C) being 100 parts by mass. When the amount is more than 30 parts by mass, the content of the essential components such as the component (A) and the component (B) is excessively reduced, and the desired effect of the present invention can not be obtained. The content of the component (C) is preferably up to 25 parts by mass, and more preferably up to 23 parts by mass. For example, 0.1 to 30 parts by mass, or 10 to 20 parts by mass.

(Meth) acrylate monomer, an aromatic ring-containing (meth) acrylate monomer, an alicyclic (meth) acrylate monomer, an alicyclic (meth) acrylate monomer, Acrylate monomer or a heterocyclic ring-containing (meth) acrylate monomer.

The (meth) acrylic monomer having a hydroxyl group is not particularly limited as long as it is a (meth) acrylic monomer having a hydroxy group in the molecule. There are no particular restrictions on the number of hydroxyl groups in the molecule, and there can be one, two, three, or more. Use of the monomer having a hydroxy group in the molecule as the other monomer has an advantage of improving the hydrogen bonding force and improving the adhesion to PVA (polyvinyl alcohol) used in the polarizer.

The hydroxy group-containing (meth) acrylic monomer may be a non-allyl-based (meth) acrylic monomer containing no allyl group.

Specific examples of the hydroxyl group-containing (meth) acrylic monomer include, but are not limited to, a (meth) acrylic acid ester having at least one hydroxyl group-containing alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 5 carbon atoms having at least one hydroxy group Substituted (meth) acrylamides such as 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 1,6-hexanediol mono (Meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, neopentyl glycol mono (meth) acrylate, trimethylolpropane di Acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxy- 2-hydroxyethyl (meth) acrylamide, cyclohexanedimethanol mono (meth) acrylate, 2- (meth) acryloyloxyethyl- -Hydroxyethyl-phthalic acid, and lactone-modified hydroxyethyl (meth) acrylate (trade name &quot; Plaqueel &quot; manufactured by Daicel Chemical Industries, Ltd.). These may be used alone or in combination of two or more.

Among them, as the adhesive composition for a polarizing plate, from the viewpoints of excellent initial curability and an improvement in adhesion with a film, it is preferable to use a polymerizable monomer having at least one of 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, Ethyl (meth) acrylate is more preferable.

The (meth) acrylate monomer containing an aromatic ring according to the present invention is not particularly limited as long as it is a (meth) acrylic monomer having an aromatic ring in the molecule. The aromatic ring (for example, a mono- or fused aromatic ring having 6 to 20 carbon atoms) is not particularly limited and includes, for example, a benzene ring. As described above, when a monomer having a bulky portion (such as a benzene ring) having a large volume in the molecule is used as the other monomer, an ANCHOR effect as in the case where the bulky one enters the protective film is also described later. Specific examples thereof include, for example, phenoxyethyl (meth) acrylate, phenoxy triethylene glycol di (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, phenoxyethylene glycol di (Meth) acrylate, phenyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) acrylate, phenylethyl Methyl (meth) acrylate, phenoxyethyl (meth) acrylate, 4-methylphenoxyethyl (meth) acrylate, 3 (Meth) acrylate, p-chlorophenylethyl (meth) acrylate, m-chlorophenylethyl (meth) acrylate, , O-chlorophenylethyl (meth) acrylate (Meth) acrylate, p-bromophenylethyl (meth) acrylate, m-bromophenylethyl (meth) acrylate, o- (Meth) acrylate, pentachlorophenylethyl (meth) acrylate, naphthyl (meth) acrylate, and naphthylethyl (meth) acrylate.

Among these, as the adhesive composition for a polarizing plate, from the viewpoints of excellent initial curability and improvement of adhesion with a film, (meth) acrylic acid having a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms (Meth) acrylate, methylphenoxyethyl (meth) acrylate, methylphenoxyethyl (meth) acrylate and the like. The term "substituted" may mean that a hydrogen atom is substituted with an alkyl group having 1 to 5 carbon atoms, The rate is more preferred.

The alicyclic (meth) acrylate monomer is not particularly limited as long as it is a (meth) acrylic monomer having an alicyclic ring in the molecule. The alicyclic ring (for example, an alicyclic ring having 3 to 20 carbon atoms) is not particularly limited and includes, for example, cyclohexane ring and adamantane ring. As described above, if a monomer having a bulky portion (such as a cyclohexane ring or an adamantyl group) having a large volume in the molecule is used as the other monomer, an anchor effect such as a bulky one introduced into the protective film do. Specific examples thereof include cyclohexyl (meth) acrylate, dicyclopentadienyl di (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, 3,5-dimethyladamantyl (Meth) acrylate, and 4-t-butylcyclohexyl (meth) acrylate. Among them, cyclohexyl acrylate and dicyclopentadienyl diacrylate are more preferable as the adhesive composition for a polarizing plate from the viewpoints of excellent initial curability and improvement of adhesion with a film.

The heterocyclic ring containing (meth) acrylate monomer according to the present invention is a (meth) acrylic monomer having a heterocyclic ring in a molecule. The heterocyclic ring is not particularly limited, and examples thereof include morpholine ring, piperidine ring, pyrrolidine ring and piperazine ring. As described above, when a monomer having a bulky portion (such as a heterocycle) having a large volume in a molecule is used as the other monomer, an anchor effect such as a bulky one enters the protective film is also described later. Specific examples thereof include, for example, N- (meth) acryloyl morpholine, N- (meth) acryloylpiperidine, N- (meth) acryloylpiperidine, tetrahydrofurfuryl And N- (meth) acryloylpyrrolidone.

Of these, tetrahydrofurfuryl (meth) acrylate is more preferred because of its low viscosity and high film solubility as an adhesive composition for a polarizing plate, in view of excellent initial curability and improvement of adhesion with a film.

[Photo acid generators]

The photoacid generator generates strong acid upon irradiation with light, and the strong acid attacks the epoxy group-containing compound to initiate polymerization of the epoxy group-containing compound. As the photoacid generator, conventionally known photoacid generators may be used without particular limitation. Specifically, there may be mentioned, for example, aromatic diazonium salts, onium salts such as aromatic iodonium salts and aromatic sulfonium salts, and iron-arene complexes. These may be used alone or in combination of two or more.

Examples of the aromatic diazonium salt include benzene diazonium hexafluoroantimonate, benzene diazonium hexafluorophosphate, benzene diazonium hexafluoroborate, and the like.

Examples of the aromatic iodonium salt include diphenyl iodonium tetrakis (pentafluorophenyl) borate, diphenyl iodonium hexafluorophosphate, diphenyl iodonium hexafluoroantimonate, diester 4 -Nonylphenyl) iodonium hexafluorophosphate, and the like.

Examples of the aromatic sulfonium salts include triphenylsulfonium hexafluorophosphate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenyl Thio) phenyl] sulfonium hexafluoroantimonate, 4,4'-bis [diphenylsulfonio] diphenylsulfide bishexafluorophosphate, 4,4'-bis [di ((β-hydroxyethoxy ) Phenylsulfonio] diphenyl sulfide bishexafluoroantimonate, 4,4'-bis [di (? - hydroxyethoxy) phenylsulfonio] diphenylsulfide bishexafluorophosphate, 7- [ Di (p-toluyl) sulfonio] -2-isopropylthioxanthone hexafluoroantimonate, 7- [di (p- (Pentafluorophenyl) borate, 4-phenylcarbonyl-4'-diphenylsulfonio-diphenyl (P-tert-butylphenylcarbonyl) -4'-diphenylsulfonio-diphenylsulfide hexafluoroantimonate, 4- (p-tert- butylphenylcarbonyl) (P-toluyl) sulfonio-diphenylsulfide tetrakis (pentafluorophenyl) borate, diphenyl [4- (phenylthio) phenyl] sulfonium phosphate, and the like.

Examples of the iron-arene complexes include xylene-cyclopentadienyl iron (II) hexafluoroantimonate, cumene-cyclopentadienyl iron (II) hexafluorophosphate, xylene-cyclopentadiene (II) -tris (trifluoromethylsulfonyl) methanide, and the like.

The photoacid generator may be a commercially available product, for example, CPI-100P, 101A, 200K, 210S (manufactured by San A Pro Co.), KAYARAd (registered trademark) PCI-220, (Manufactured by Nippon Kayaku Co., Ltd.), UVI-6990 (manufactured by Union Carbide Corp.), Adeka Optomer (registered trademark) SP-150 and SP- , DPI-101, 102, 103, 105, MPI-103, 105, BBI-101, 102, 103 (manufactured by Nippon Soda Co., Ltd.), CIT-1370, 1682, CIP-1866S, 2048S, , 105, TPS-101, 102, 103, 105, MDS-103, 105, DTS-102, 103 (manufactured by Midori Kagaku Co., Ltd.) and PI-2074 (Rodia Japan KK).

The amount of the photoacid generator to be used is 1 to 7 parts by mass, preferably 1.5 to 4 parts by mass, based on 100 parts by mass of the polymerizable component. If the amount of the photoacid generator used is less than 1 part by mass, the curing property of the adhesive composition after ultraviolet irradiation may deteriorate. If the amount is more than 7 parts by mass, the adhesive property and durability may be insufficient due to the bleed-out component.

[Photopolymerization initiator, photosensitizer]

The adhesive composition of the present invention further includes at least one of a photopolymerization initiator and a photosensitizer. The photopolymerization initiator is not particularly limited, and conventionally known photopolymerization initiators can be preferably used. The photopolymerization initiator may be used alone or in combination of two or more.

Specific examples of the photopolymerization initiator include inorganic peroxides such as hydrogen peroxide, potassium persulfate and ammonium persulfate, t-butyl hydroperoxide, t-dibutyl peroxide, cumene hydroperoxide, acetyl peroxide, benzoyl peroxide and lauroyl peroxide , Azobisisobutyronitrile, azobis-2,4-dimethylvaleronitrile, azobiscyclohexanecarbonitrile, methyl azobisisobarylate, azobisisobutylamidine hydrochloride, and azo compounds such as azo Azobisisobutyronitrile, azobisisobutyronitrile and biscyanobalic acid, azo compounds such as acetophenone, benzoin, benzophenone, phosphine oxides, ketaldehyde, anthraquinones, thioxanthones, 2,3-dialkyldiones, disulfide Fluoroamine compounds, aromatic sulfonic acids, ropin dicarboxylic acids, onium salts, borate salts, active esters, active halogens, inorganic complexes, coumarins It can be given.

More specifically, there may be mentioned acetophenone, 3-methylacetophenone, benzyl dimethyl ketal, 1- (4-isopropylphenyl) -2-hydroxy- 4- (methylthio) phenyl] -2-morpholinopropane-1-one, and 2-hydroxy-2-methyl-1-phenylpropan-1-one; Benzophenones including benzophenone, 4-chlorobenzophenone, and 4,4'-diaminobenzophenone; Benzoin ethers such as benzoin propyl ether and benzoin ethyl ether; Thioxanthones such as 4-isopropylthioxanthone; Xanthene, fluorenone, camphorquinone, benzaldehyde, anthraquinone, and the like.

184, 651, 1700, 1800, 819, 369, 261, DAROCUR-TPO (hereinafter referred to as &quot; BASF Japan &quot;), IRGACURE (registered trademark) (Manufactured by Nippon Kayaku Co., Ltd.), DARACURE (registered trademark) -1173 (manufactured by Merck Co., Ltd.), EZACURE KIP150 and TZT (manufactured by DKSH Japan KK), Kayacure (registered trademark) And the like.

Examples of the inorganic peroxide and the organic peroxide include organic amine compounds such as amines such as ethylamine, triethanolamine and dimethyl aniline, polyamines, divalent iron salt compounds, organic metal compounds such as ammonia, triethyl aluminum, triethyl boron, diethyl zinc, , Sodium hydrogen sulfite, cobalt naphthenate, sulfinic acid, and mercaptan may be used in combination.

In the adhesive composition for a polarizing plate of the present invention, a photosensitizer may be used instead of or in combination with a photopolymerization initiator. The photosensitizer is not particularly limited, and conventionally known photosensitizer can be preferably used. The photosensitizer may be used alone or in combination of two or more.

Specific examples of the photosensitizer include anthracene compounds, pyrene compounds, carbonyl compounds, sulfur compounds, persulfates, redox compounds, azo and diazo compounds, halogen compounds, These may be used in combination of two or more.

As a more specific photosensitizer, for example, an anthracene compound represented by the following general formula I; Pyrene; Benzoin derivatives such as benzoin methyl ether, benzoin isopropyl ether, and?,? -Dimethoxy-? -Phenylacetophenone; Benzophenone derivatives such as benzophenone, 2,4-dichlorobenzophenone, methyl o-benzoylbenzoate, 4,4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) ; Thioxanthone derivatives such as 2-chlorothioxanthone and 2-isopropylthioxanthone; Anthraquinone derivatives such as 2-chloro anthraquinone and 2-methyl anthraquinone; Acridone derivatives such as N-methyl acridone and N-bithylacridone; Other α, α-diethoxyacetophenones, fluorenones, xanthones, uranyl compounds, halogen compounds and the like can be mentioned.

[Formula I]

In the formulas, R and R 'each independently represent a straight chain, a branched chain having 1 to 18 carbon atoms, a cyclic alkyl group having 3 to 18 carbon atoms, or an ether group having 2 to 18 carbon atoms, R "represents a hydrogen atom or a linear chain having 1 to 18 carbon atoms, a branched chain having 1 to 18 carbon atoms, or a cyclic alkyl group having 3 to 18 carbon atoms.

Examples of the linear, branched or cyclic alkyl group having 1 to 18 carbon atoms represented by R, R 'and R "in the above general formula (I) include a methyl group, an ethyl group, a propyl group, , a tert-butyl group, a tert-butyl group, an isobutyl group, an amyl group, an isoamyl group, a tert-amyl group, an n-hexyl group, a 2-hexyl group, a 3-hexyl group, a cyclohexyl group, A heptyl group, a heptyl group, a heptyl group, a heptyl group, a n-heptyl group, a 2-heptyl group, a 3-heptyl group, an isoheptyl group, A decyl group, a decyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, or an octadecyl group.

Examples of the ether group having 2 to 18 carbon atoms represented by R and R 'include 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl, 2-phenoxyethyl, 2- Methoxypropyl group, 3-phenoxypropyl group, 2-methoxy-1-methylethyl group, 2-methoxy-2-methylethyl group, 2- Ethoxyethyl group, 2-ethoxyethyl group, 2-butoxyethyl group, 2-phenoxyethyl group and the like. The ether group mentioned here is a hydrocarbon group having at least one ether bond and includes an alkoxyalkyl group, an alkoxyalkoxyalkyl group, an aryloxyalkyl group and the like, as understood from the above examples.

The photosensitizer may be a synthetic or commercial product. BMBI, DETX-S, EPA (manufactured by Nippon Kayaku Co., Ltd.), Anthracure (registered trademark) UVS-1331, UVS-1221 (manufactured by Kawasaki Kasei Kogyo Co., Ltd.), Yubecryl P102, 103, 104 and 105 (manufactured by UCB Co., Ltd.) and the like.

The amount of use of at least one of the photopolymerization initiator and the photosensitizer (when the photopolymerization initiator and the photosensitizer are used together, the total amount thereof is used) is from 0.1 to 7 parts by mass relative to 100 parts by mass of the polymerizable component, Is 0.5 to 2.5 parts by mass. If the amount is less than 0.1 part by mass, it is difficult to be cured by ultraviolet irradiation. If the amount is more than 7 parts by mass, the adhesion and durability may be insufficient due to the bleed-out component.

The adhesive composition for a polarizing plate of the present invention comprises 20 to 70 mass% of a solid component (A), 25 to 75 mass% of a component (B), 1 to 5 mass% of a component (D) %, And both the initial hardenability, adhesion, and durability can be realized in the above range.

The adhesive composition for a polarizing plate according to another embodiment of the present invention comprises 25 to 50 mass% of a solid component (A), 25 to 50 mass% of a component (B), 15 to 20 mass% of a component (C) %, And 0.1 to 1% by mass of the component (E), and both of the initial curability, adhesion and durability can be achieved within the above range.

The adhesive composition for a polarizing plate of the present invention may contain additives such as ultraviolet absorbers, antioxidants, heat stabilizers, silane coupling agents, inorganic fillers, softeners, antioxidants, antioxidants, stabilizers, (Coloring pigments, extender pigments, etc.), a treating agent, a sunscreen agent, a fluorescent whitening agent, a dispersing agent, a light stabilizer, an antistatic agent, and an antistatic agent Other components such as a lubricant may be added.

[Method of producing adhesive composition]

In order to produce the adhesive composition of the present invention, there is no particular limitation, and usually, the adhesive composition can be obtained by mixing the above components. An organic solvent may be appropriately used for adjusting the viscosity. The mixing method is not particularly limited, and it may be sufficiently stirred and mixed at room temperature (25 캜) until the liquid becomes homogeneous.

(2) Adhesive film for polarizer

According to a second aspect of the present invention, there is provided an adhesive film for a polarizing plate formed using the adhesive composition for a polarizing plate of the present invention. The polarizing plate adhesive film of the present invention can realize a polarizer having excellent initial curability and excellent durability by bonding a polarizer and a protective film. The adhesive film for a polarizing plate of the present invention can be produced by drying or curing an adhesive composition for a polarizing plate.

      The thickness of the polarizing plate adhesive film is more preferably 500 nm to 3 占 퐉 in order to obtain a uniform in-plane thickness and to obtain a sufficient adhesive force.

(3) Polarizer

According to a third aspect of the present invention, there is provided a polarizing plate comprising a protective film and a polarizer adhered using the adhesive composition for a polarizing plate of the present invention. The polarizing plate of the present invention has excellent processability at the time of production and exhibits sufficient adhesiveness. 5 is a cross-sectional view of a polarizing plate of one embodiment of the present invention.

5, a polarizing plate 100 according to an embodiment of the present invention includes a polarizer 13, a first polarizing plate adhesive film 40 formed on the polarizer 13, and a first polarizing plate adhesive film 40 The second protective film 30 formed on the lower portion of the second polarizing plate adhesive film 50 and the second polarizing plate adhesive film 50 formed on the lower portion of the polarizer 13, And one or more of the first polarizing plate adhesive film 40 and the second polarizing plate adhesive film 50 may be composed of the adhesive composition for a polarizing plate of the present invention. Hereinafter, the structure of the polarizing plate of the present invention will be described.

[Polarizer]

The polarizer is not particularly limited and conventionally known polarizers can be used. For example, a dichroic material such as iodine or a dichroic dye is adsorbed onto a hydrophilic polymer film such as a polyvinyl alcohol film, a partially formalized polyvinyl alcohol film, or an ethylene / vinyl acetate copolymer system partially saponified film Polyvinyl alcohol, polyvinyl alcohol, polyvinyl alcohol, polyvinyl alcohol, polyvinyl alcohol, polyvinyl alcohol, and the like.

Among them, a polarizer prepared by dyeing a polyvinyl alcohol film having an average polymerization degree of 2000 to 2800 and a degree of saponification of 90 to 100 mol% with iodine and monoaxially stretching 5 to 6 times is particularly preferable. More specifically, such a polarizer can be obtained by, for example, dipping a polyvinyl alcohol film in an aqueous solution of iodine, and stretching it. As the aqueous solution of iodine, for example, it is preferable to immerse in an aqueous solution of 0.1 to 1.0% by weight of iodine / potassium iodide. If necessary, it may be immersed in an aqueous solution of boric acid or potassium iodide at 50 to 70 DEG C, or may be immersed in water at 25 to 35 DEG C in order to prevent washing or staining unevenness. The stretching may be performed after dyeing with iodine, or may be stretched while being dyed, followed by stretching, followed by dyeing with iodine. After dyeing and stretching, it may be washed with water and dried at 35 to 55 ° C for about 1 to 10 minutes.

[Protection film]

As the protective film, a material excellent in transparency, mechanical strength, thermal stability, moisture barrier property, isotropy and the like is preferable. For example, cellulose-based resins such as cellulose diacetate and cellulose triacetate; polyester-based resins such as polyethylene terephthalate and polyethylene naphthalate; acrylic resins such as polymethyl methacrylate; and acrylic resins such as polystyrene, acrylonitrile and styrene Polyolefin resins such as polyethylene, polypropylene, cycloolefin having a cyclic or norbornene structure, polyolefin resins such as an ethylene / propylene copolymer, vinyl chloride resins, nylon resins or the like Based resin, an amide-based resin such as an aromatic polyamide, an imide resin, a sulfon resin, a polyether sulfone resin, a polyether ether ketone resin, a polyphenylene sulfide resin, a vinyl alcohol resin, a vinylidene chloride resin, Based resin, an aryl-based resin, a polyoxy Butyl-series resin may include an epoxy-based resin, or the like of the resin blend.

Of the above contents, the polarizing plate protective film is preferably a cellulose-based resin, which is an ester of cellulose and fatty acid, or a cycloolefin polymer (COP film), polyethylene terephthalate (PET film), or acrylic resin. Examples of the cellulose-based resin include cellulose triacetate (TAC film), cellulose diacetate, cellulose triopropionate, and cellulose dipropionate. Of these, cellulose triacetate (TAC film) and cycloolefin polymer (COP film) are particularly preferred from the viewpoints of availability and cost, and acrylic resins are preferable in view of availability and water permeability. If the moisture permeability of the protective film is high, moisture permeates through the protective film and easily enters the polarizer side, thereby deteriorating the quality of the polarizer. However, when an acrylic resin is used, it can be significantly suppressed. Further, the adhesive composition for a polarizing plate of the present invention contains (A) an allyl group and a (meth) acrylate monomer containing a hydroxy group in a predetermined range. The (meth) acrylate monomer (A) containing an allyl group and a hydroxyl group has an action of dissolving the acrylic resin. Therefore, when an acrylic resin is used as the protective film, when a polarizing plate is formed by adhering a protective film (acrylic resin) through the adhesive composition for a polarizing plate of the present invention on the surface and / or the back surface of the polarizer, , It permeates the protective film and then is cured by UV irradiation, so that the so-called anchor effect by the permeated acrylic resin is generated, and the adhesion strength is considered to be improved. It is particularly preferable to use an acrylic resin as the protective film. However, this mechanism is by speculation, and the technical scope is not limited by the mechanism.

The cellulose triacetate may be saponified, but it is more preferably unabsorbed. Examples of the cycloolefin polymer include polymers obtained by hydrogenating a ring-opening polymer of tetracyclododecene disclosed in Japanese Patent Publication No. Hei 2-9619.

Commercially available acrylic resin films include acrylic films RT, SO, HI series manufactured by Kuraray Co., Ltd., and the like.

Examples of the commercially available TAC film include UV-50, UV-80, SH-80, TD-80U, TD-TAC, UZ-TAC and KC series manufactured by Konica Minolta Opto Co.,

Examples of commercially available COP films include Aton (registered trademark) of JSR Corporation, Zeonex (registered trademark) series and Zeonoa (registered trademark) series of Nippon Zeon Corporation.

As a commercially available product of PET film, Cosmo Shine (registered trademark) series manufactured by Toyoboseki Co., Ltd. can be mentioned.

The surface of the protective film is preferably modified by a corona discharge treatment. The method of the corona discharge treatment is not particularly limited and can be carried out using a general corona discharge treatment apparatus (for example, a product of Kasuga Denki Co., Ltd.). By the corona discharge treatment, active groups such as a hydroxyl group are formed on the surface of the protective film, which is considered to contribute to further improvement in the adhesiveness. When the saponified cellulose triacetate is used as the protective film, the corona discharge treatment is not necessarily required since the same effect as the corona discharge treatment can be expected. However, since the saponification treatment is complicated and expensive, it is preferable in view of the manufacturing process to use the unevaporated cellulose triacetate by corona discharge treatment.

The discharge amount at the time of corona treatment is not particularly limited, but is preferably 30 to 300 W / min / m ² , and more preferably 50 to 250 W / min / m ² . Within this range, it is preferable to improve the adhesion between the protective film and the adhesive without deteriorating the protective film itself. Here, the discharge amount is the amount of the object to the object by the corona discharge determined by the next calculation, and the corona discharge power is determined based on this.

(C) Production method of polarizing plate

The method of producing the polarizing plate is not particularly limited, and can be produced by joining the protective film and the polarizer using the adhesive composition of the present invention by a conventionally known method. The applied adhesive composition exhibits adhesiveness by ultraviolet irradiation to constitute an adhesive layer.

When the adhesive composition is applied, it may be applied to either a protective film or a polarizer, or may be applied to both. The adhesive composition is preferably applied so that the thickness of the adhesive layer after drying is 10 nm to 5 m. The thickness of the adhesive layer is more preferably 500 nm to 3 占 퐉 in terms of obtaining a uniform in-plane thickness and obtaining a sufficient adhesive force. The thickness of the adhesive layer can be adjusted by the solid content concentration in the solution of the adhesive composition or by the application device of the adhesive composition. The thickness of the adhesive layer can be confirmed by observing a cross section with a scanning electron microscope (SEM). The method of applying the adhesive composition is not particularly limited, and various means such as a method of dropping the adhesive composition directly, a roll coating method, a spraying method, and a dipping method may be employed.

After the adhesive composition is applied, the polarizer and the protective film are bonded together by a roll laminator or the like.

After bonding, the polarizer is irradiated with ultraviolet rays for curing the adhesive composition. The ultraviolet light source is not particularly limited, but low pressure mercury lamps, medium pressure mercury lamps, high pressure mercury lamps, ultra high pressure mercury lamps, chemical lamps, blank lamp lamps, microwave excited mercury lamps, metal halide lamps and the like having a light emission distribution with a wavelength of 400 nm or less can be used . The ultraviolet irradiation dose is not particularly limited, but it is preferable that the ultraviolet irradiation dose in the wavelength range effective for activating the polymerization initiator is 100 to 2,000 mJ / cm ² . With this range, the reaction time is appropriate, and there is no risk of deterioration of the adhesive itself or the polarizing film due to heat radiated from the lamp and heat generated during polymerization.

After irradiation with ultraviolet rays, the dark reaction proceeds with respect to the epoxy resin. Therefore, the polarizing plate is stored at room temperature (23 ° C) for about 16 to 30 hours immediately after ultraviolet irradiation. Upon completion of curing, the polarizing plate is completed.

(4) Display device

       Next, the display device will be described. The display device according to an embodiment of the present invention may include the polarizer of one embodiment of the present invention. The display device may be a liquid crystal display device, an organic light emitting diode display device, or the like.

[Example]

Hereinafter, the present invention will be described with reference to examples and comparative examples. However, the technical scope of the present invention is not limited to the following embodiments.

&Lt; Example 1 >

&Lt; Preparation of adhesive composition >

The components shown in Table 1 were stirred and mixed in a constant temperature chamber at 23 DEG C and a relative humidity of 50% RH until they became visually uniform according to the compounding amounts shown in Table 1 to obtain Examples 1 to 11 and Comparative Examples 1 to 4 Of the adhesive composition. The units in Tables 1 to 3 are &quot; g &quot;.

&Lt; Production of polarizing plate &

Polarizers were prepared in the following manner. A polyvinyl alcohol film having an average degree of polymerization of 2400 and a degree of saponification of 99.9% and a thickness of 75 占 퐉 was immersed in hot water at 28 占 폚 for 90 seconds to swell and then an aqueous solution of 0.6% by weight of iodine / potassium iodide (weight ratio 2/3) , And the polyvinyl alcohol film was dyed while being stretched 2.1 times. Thereafter, stretching was carried out in an aqueous solution of boric acid ester at 60 캜 so that the total draw ratio was 5.8 times. After washing with water, drying was conducted at 45 캜 for 3 minutes to prepare a polarizer (thickness 25 탆).

Fig. 1 is a schematic view showing a manufacturing method of a polarizing plate in the present embodiment. 1, the polarizer 1 is sandwiched between the protective film 3 and the protective film 4 and the adhesive composition 2 obtained as described above is applied to the protective film 3 and the polarizer 1, , The protective film 4 and the polarizer 1 by a dropper, and they are bonded together by a roll press equipped with the rolls 6 and 7.

In Examples 1 to 8 and Comparative Examples 1 to 4, a COP film (thickness 30 μm, manufactured by Nippon Zeon Co., Ltd.) was used as the protective film 3 and an acrylic film (thickness 75 μm, manufactured by Kuraray Co., Ltd.) Respectively.

In Examples 9 to 11, a COP film (thickness 30 μm, manufactured by Nippon Zeon Co., Ltd.) was used as the protective film 3, and a cellulose triacetate film (TAC film, thickness 80 μm, manufactured by Fuji Film Co., Ltd.) .

The ultraviolet ray pre-polarizer 5 bonded in this manner was irradiated with ultraviolet rays at an irradiation dose of 1000 mJ / cm ² (wavelength 365 nm metal halide lamp) from the protective film 3 side. The steps from the bonding step of the polarizer and the protective film using the adhesive composition to the ultraviolet irradiation were performed at 23 DEG C and a relative humidity of 50% RH.

After irradiation with ultraviolet rays, the polarizing plate was stored in a constant temperature chamber (23 캜, relative humidity of 50% RH) for 24 hours, and the adhesive composition was cured to complete the polarizing plate. The thickness of the adhesive layer in the completed polarizing plate was 2.0 占 퐉.

The polarizing plate obtained in each of the Examples and Comparative Examples was subjected to an initial curing test immediately after ultraviolet irradiation and further irradiated with ultraviolet rays and then stored at room temperature (23 ° C) for 24 hours, and then subjected to a cutting test and a hot water immersion test And evaluated.

<Initial Curability Test>

The polarizing plate immediately after the ultraviolet irradiation prepared in Examples 1 to 11 and Comparative Examples 1 to 4 was bent so that the interval between the polarizing plates 8 bent to 10 mm (R 10 mm) as shown in Fig. 2, Was judged by the naked eye. When no peeling was observed, it was rated as O, and when it was observed, it was evaluated as x. The evaluation results are shown in Tables 1 to 3 below.

<Test of Foundation>

The polarizing plates produced in Examples 1 to 11 and Comparative Examples 1 to 4 were cut with a Thomson knife to a size of 50 mm x 50 mm (width x length), and the peeling state of the ends at the time of cutting was visually observed. As an evaluation standard, 0.5 mm or less was accepted. The evaluation results are shown in Tables 1 and 2. The preferable result is 0.3 mm or less, more preferably 0.2 mm or less, and particularly preferably 0 mm.

<Hot water immersion test>

The polarizing plates prepared in Examples 1 to 11 and Comparative Examples 1 to 4 were cut with a Thomson knife to a size of 50 mm x 50 mm (width x length), immersed in a water bath at 60 deg. C, and held for 2 hours. Then, each sample was taken out from the water bath and the size of the shrinkage of the polarizer was measured. As shown in Fig. 3 (A), from the end of the polarizing plate 8 before the test to the end of the polarizing plate 8 contracted in the stretching direction as shown in Fig. 3 (B) ). If the adhesiveness of the adhesive is high, the shrinkage is small, and if the adhesive property is not sufficient, the shrinkage of the polarizing plate becomes a larger value. As a criterion for evaluation, a size of shrinkage of less than 1.0 mm was considered acceptable. The evaluation results are shown in Tables 1 to 3. The preferable result is 0.5 mm or less, more preferably 0.2 mm or less, particularly preferably 0 mm.

<Peel strength>

4 is a schematic view showing a method for producing a sample for peeling strength measurement in this embodiment. The adhesive composition 2 obtained as described above was dropped between the PET film 10 and the acrylic film 11 in an appropriate amount by a dropper as shown in Fig. 4, and the rolls 6, 7, And they were joined by a press. The PET film and the acrylic film were subjected to corona treatment on their respective adhesive surfaces.

The ultraviolet ray of 1000 mJ / cm ² (wavelength 365 nm metal halide lamp) was irradiated from the PET film 10 as a sample for peeling strength measurement before ultraviolet irradiation. The steps from the bonding step of the PET film and the acrylic film using the adhesive composition to the ultraviolet irradiation were performed at 23 ° C and a relative humidity of 50% RH.

After irradiating ultraviolet rays, samples for peeling strength measurement were stored in a constant temperature room (23 캜, relative humidity 50% RH) for 24 hours, and the adhesive composition was cured to complete a polarizing plate. The thickness of the adhesive layer in the completed polarizing plate was 2.0 占 퐉.

The PET film 10 was peeled at an angle of peeling 90 ° and peeled off at a peeling speed of 10 mm by using a tensile tester. Mm / min, and the peel strength was measured.

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 The acrylate (A) containing an allyl group and a hydroxyl group ALHA 70 50 23 30 30 50 The epoxy resin (B) 830CRP 30 50 77 70 - 50 2021P - - - - 70 - Acrylate (C) POA - - - - - - 4HBA - - - - - - The photoacid generator (D) CPI210S 3 3 3 3 3 3 Photopolymerization initiator (E) Ig 907 One One One One One - Photosensitizer
(E) DETX-S - - - - - One Film composition
acryl/
COP acryl/
COP acryl/
COP acryl/
COP acryl/
COP acryl/
COP Initial hardenability test
○ ○ ○ ○ ○ ○ Cut test mm 0.2 0.0 0.2 0.2 0.2 0.0 Hot water immersion test mm 0.2 0.0 0.2 0.2 0.2 0.0 Peel strength N / 25mm 5.0 12 7.0 9.0 10 13

Example 7 Example 8 Example 9 Example 10 Example 11
The acrylate (A) containing an allyl group and a hydroxyl group ALHA 30 50 70 50 23 The epoxy resin (B) 830CRP 50 30 30 50 77 2021P - - - - - Acrylate (C) POA 20 20 - - - 4HBA - - - - - The photoacid generator (D) CPI210S 3 3 3 3 3 Photopolymerization initiator (E) Ig 907 - One One One One Photosensitizer
(E) DETX-S One - - - - Film composition
acryl/
COP acryl/
COP TAC /
COP TAC /
COP TAC /
COP Initial hardenability test
○ ○ ○ ○ ○ Cut test mm 0.0 0.0 0.0 0.0 0.0 Hot water immersion test mm 0.0 0.0 0.0 0.0 0.0 Peel strength N / 25mm 9.0 10 8.0 18 10

Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 The acrylate (A) containing an allyl group and a hydroxyl group ALHA 100 75 19 - The epoxy resin (B) 830CRP - 15 81 - 2021P - - - 30 Acrylate (C) POA - - - - 4HBA - 10 - 70 The photoacid generator (D) CPI210S 3 3 3 3 Photopolymerization initiator (E) Ig 907 One One One One Photosensitizer
(E) DETX-S - - - - Film composition
acryl/
COP acryl/
COP acryl/
COP acryl/
COP Initial hardenability test
○ ○ ○ ○ Cut test mm 1.5 1.0 1.0 1.0 Hot water immersion test mm 3.0 2.5 1.0 2.0 Peel strength N / 25mm 2.0 1.5 4.0 0.8

ALHA: Osaka Organic Chemical Industry Co., Ltd. ALHA

2021P: Die-cell Co., Ltd. Celllock 2021P

830CRP: DIC Corporation Epiclon EXA-830CRP

POA: Koeishakagaku Co., Ltd. POA Phenoxyethyl acrylate

4HBA: 4-hydroxybutyl acrylate

CPI 210: San A Pro Co., Ltd. CPI-210

Ig907: Irgacure 907 from BASF

DETX-S: Nippon Kayaku Co., Ltd. DETX

Acrylic: Kurare Co., Ltd. Products

TAC: Fuji Film Co., Ltd. Products

COP: manufactured by Nippon Zeon Co., Ltd.,

As shown in Tables 1 and 2, in Examples 1 to 11, good results were obtained in both the peel strength test, the cutting test, the hot water immersion test and the initial curability test. On the other hand, as shown in Table 3, in Comparative Examples 1 to 4, the results of the peeling strength test and the cutting test did not satisfy the evaluation criteria, and the results of the hot water immersion test were inferior to those in Examples, This resulted in a lag. In particular, it is considered that the adhesive composition used in Comparative Example 4 can not achieve the desired adhesiveness of the present invention because it does not have a complicated entangled network structure like the adhesive composition of the present invention. That is, it can not be a linear structure, and it is considered that the desired adhesiveness of the present invention can not be obtained. Further, since the TAC film contains an OH group, the polarity of the TAC film is higher than that of the acrylic film. For this reason, it is also suggested that the TAC film has a characteristic of being easy to adhere to the acrylic film.

As described above, from the comparison between the examples and the comparative examples, it was shown that the adhesive composition of the present invention can achieve both excellent initial curability and adhesive property when used in a polarizing plate.

1, 13: Polarizer, 2: Adhesive composition solution
3, 4, 20, 30: protective film, 5: ultraviolet ray pre-polarizer
6, 7: roll, 8: polarizer
9: size of shrinkage, 10: PET film
11: acrylic film, 12: sample for peeling strength measurement
40, 50: Adhesive film for polarizer

Claims (9)

(A) 20 to 70 parts by mass of a (meth) acrylate monomer containing an allyl group and a hydroxyl group;
(B) 20 to 80 parts by mass of an epoxy group-containing compound;
(C) 0 to 30 parts by mass of other monomers;
(D) a photoacid generator; And
(E) at least one of a photopolymerization initiator and a photosensitizer
/ RTI &gt;
(C) is a monomer having a hydroxyl group-containing (meth) acrylic monomer, an aromatic ring-containing (meth) acrylate monomer, an alicyclic containing (meth) acrylate monomer or a heterocyclic ring- Adhesive composition. The positive resist composition as claimed in claim 1, wherein 20 to 70 parts by mass of the component (A), 30 to 80 parts by mass of the component (B), 100 to 200 parts by mass of the component (C) are contained in 100 parts by mass of the total amount of the components (A) Component is contained in 0 part by mass of the adhesive composition for a polarizing plate. (A) is 30 to 50 parts by mass, the component (B) is 30 to 50 parts by mass, the component (C) is 100 parts by mass, Is contained in an amount of 0.1 to 30 parts by mass. The adhesive composition for a polarizing plate according to claim 1, wherein the component (A) is a (meth) acrylic acid ester having at least one of an allyl group, an allyloxy group and an allylthio group and an alkyl group having 1 to 10 carbon atoms and a hydroxyl group . The adhesive composition for a polarizing plate according to claim 1, wherein the component (C) is a (meth) acrylic acid ester having a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms and an aryloxy group having 6 to 10 carbon atoms. An adhesive film for a polarizing plate formed from the adhesive composition for a polarizing plate according to any one of claims 1 to 5. A polarizing plate comprising a protective film and a polarizer adhered using the adhesive composition for a polarizing plate according to any one of claims 1 to 5. The polarizing plate according to claim 7, wherein the protective film is an acrylic film, a cellulose-based film, or a cycloolefin polymer film. A display device comprising the polarizer of claim 7.

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