KR20190079481A - Adhesive composition and adhesive film - Google Patents

Abstract

Provided by the present invention are: an adhesive composition in which the surface resistivity of an adhesive layer has an excellent antistatic performance of 1.0×10^(+9) Ω/□ or less and the adhesive layer is formed not to degrade durability; and an adhesive film using the same. The acrylic polymer comprises (A) n-butyl acrylate, (B) at least one selected from t-butyl acrylate, isobutyl acrylate, n-butyl methacrylate, and methyl acrylate, (C) a copolymerizable vinyl monomer containing a hydroxyl group and/or a carboxyl group, (D) a copolymerizable vinyl monomer containing an aromatic group, (E) a copolymer obtained by copolymerizing an alkoxy group-containing vinyl monomer or a nitrogen-containing vinyl monomer, (F) an antistatic agent, (G) a crosslinking agent consisting of a trifunctional or higher functional isocyanate compound or a bifunctional or higher epoxy compound, and (H) a silane coupling agent having an epoxy group, a mercapto group, or an acid anhydride group.

Description

[0001] ADHESIVE COMPOSITION AND ADHESIVE FILM [0002]

The present invention relates to a pressure-sensitive adhesive composition and a pressure-sensitive adhesive film which are used for bonding an optical member.

In more detail, with the surface resistivity of the adhesive layer prior art as it may form a pressure-sensitive adhesive layer having an excellent antistatic property that can not be achieved 1.0 × 10 ⁺⁹ Ω / □ or less pressure-sensitive adhesive composition and an adhesive film using the same .

A variety of pressure-sensitive adhesive films for bonding an optical member such as a polarizing plate and a retardation plate to an adherend such as a liquid crystal cell through a pressure-sensitive adhesive layer have been proposed (see, for example, Patent Documents 1 and 2).

Patent Document 1 discloses an acrylic polymer composition comprising (A) an acrylic polymer comprising a (meth) acrylic acid alkyl ester monomer, a hydroxyl group-containing monomer and / or a carboxyl group-containing monomer and an isocyanate crosslinking agent, and (B) Sensitive adhesive composition for a polarizing plate. According to the pressure-sensitive adhesive composition of the invention described in Patent Document 1, not only is it excellent antistatic property, but also when the pressure-sensitive adhesive is pushed out when it is used for bonding a polarizing plate member such as a polarizing film, . However, the surface resistivity of the pressure-sensitive adhesive layer obtained by the pressure-sensitive adhesive composition according to Patent Document 1 was not less than 2.0 × 10 ^{+ 11} Ω / □, and the antistatic property of the pressure-sensitive adhesive layer was insufficient.

Patent Document 2 discloses an acrylic pressure-sensitive adhesive composition which is an aqueous dispersion type acrylic pressure-sensitive adhesive composition comprising (meth) acrylate having an alkyl group having 4 to 8 carbon atoms as a main component monomer and acrylic polymer containing a carboxyl group- Sensitive adhesive composition is disclosed. According to the pressure-sensitive adhesive composition of the invention described in Patent Document 2, it is possible to provide a polarizing film fixing application in an image display apparatus in which excellent environmental responsiveness and high functionality are required, particularly, And can be suitably applied to polarizing film fixing applications in EL display devices and the like. However, Patent Document 2 does not describe the antistatic performance of the pressure-sensitive adhesive layer at all and does not suggest any indication.

Japanese Laid-Open Patent Publication No. 2009-251281 Japanese Laid-Open Patent Publication No. 2012-201734

In the pressure-sensitive adhesive layer to which the polarizing plate and the liquid crystal panel are bonded, when the liquid crystal panel is an in-cell panel having the function of a touch panel, the surface resistivity of the pressure-sensitive adhesive layer is made lower than the conventional surface resistivity .

For this reason, it is desired that the pressure-sensitive adhesive layer for use in bonding the polarizing plate to the liquid crystal panel has a surface resistivity of 1.0 x 10 ^{+ 9} ? /? Or less in the pressure-sensitive adhesive layer. However, It has been a very difficult problem to exhibit the antistatic property.

In addition, even when such an excellent antistatic property can be exhibited, it has been difficult to maintain the antistatic property of the pressure-sensitive adhesive layer and to maintain the durability of the pressure-sensitive adhesive layer at the same time.

The present invention provides a pressure-sensitive adhesive composition capable of forming a pressure-sensitive adhesive layer having a very excellent antistatic performance with a surface resistivity of the pressure-sensitive adhesive layer of 1.0 10 ^{+ 9} ? /? Or less and without impairing durability and an adhesive film using the pressure- .

In order to solve such a difficult problem of achieving both of such excellent antistatic performance and durability at the same time, the present inventors have worked hard to solve this problem. As a result, it has been found that an acryl-based polymer comprising a copolymer in which a specific combination of two or more alkyl (meth) acrylates are copolymerized by limiting the number of carbon atoms in the alkyl group of the alkyl (meth) acrylate constituting the acrylic polymer of the pressure- By weight, and at least one selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer, and an antistatic agent having a melting point of 25 占 폚 or higher are additionally contained in the pressure-sensitive adhesive composition.

The present inventors have found that by containing the above acrylic polymer and an ionic compound having a melting point of 25 ° C. or more and 90 ° C. or less with respect to 100 parts by weight of the acrylic polymer in a proportion of 10 parts by weight or more and 60 parts by weight or less, It is possible to obtain a pressure-sensitive adhesive composition which has excellent antistatic performance and which can form a pressure-sensitive adhesive layer having excellent durability without causing precipitation of an antistatic agent and without deterioration with time.

To the pressure-sensitive adhesive composition is the surface resistivity of the pressure-sensitive adhesive layer according to the invention prevents a very good charging performance of 1.0 × 10 ^{+ 9} Ω / □ or less, based on 100 parts by weight of an acrylic polymer, a melting point of 25 ℃ or more ionic compound to 10 parts by weight By weight or more. As described above, in the present invention, the content of the antistatic agent is significantly increased in comparison with the content of the conventional pressure sensitive adhesive composition so as to obtain a very excellent antistatic performance that can not be achieved by the prior art.

Therefore, for the purpose of avoiding the precipitation of an antistatic agent contained in a large amount in the pressure-sensitive adhesive layer on the surface of the pressure-sensitive adhesive layer and the decrease in durability after the endurance test of the pressure-sensitive adhesive layer in a high temperature and high humidity environment, A technical idea is to make a copolymer based on n-butyl acrylate (BA), copolymerizing a monomer having good copolymerization with BA and copolymerizing with a specific silane coupling agent for the acrylic polymer.

In order to solve the above problems, the present invention provides a pressure-sensitive adhesive composition comprising an acrylic polymer, (F) an antistatic agent, and (G) a crosslinking agent, wherein the acrylic polymer comprises (A) n-butyl acrylate, ) at least one of (C) at least one selected from the group consisting of t-butyl acrylate, isobutyl acrylate, n-butyl methacrylate and methyl acrylate, and (C) a copolymerizable vinyl monomer containing a hydroxyl group and / And (D) at least one copolymerizable vinyl monomer containing an aromatic group, and (E) a copolymer obtained by copolymerizing at least one selected from an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer, wherein the copolymer has a weight average molecular weight of 1,000,000 And 10 parts by weight of an ionic compound having a melting point of 25 占 폚 or more and 90 占 폚 or less as the antistatic agent (F), based on 100 parts by weight of the acrylic polymer, Wherein the crosslinking agent (G) comprises at least one crosslinking agent selected from the group consisting of an isocyanate compound having three or more functional groups and an epoxy compound having two or more functional groups, wherein the crosslinking agent (G) (H) a pressure-sensitive adhesive layer which further comprises a monomer type or oligomer type silane coupling agent containing at least one functional group selected from an epoxy group, a mercapto group and an acid anhydride group, Is 1.0 × 10 ^{+ 9} Ω / □ or less and the pressure-sensitive adhesive layer is provided in a durability test under a test environment of 85 ° C. × 750 hr or a durability test under a test environment of 60 ° C. × 90% RH × 750 hr And the antistatic agent is not precipitated on the surface of the pressure-sensitive adhesive layer. It provides.

(A) n-butyl acrylate in an amount of 40 to 89 parts by weight based on 100 parts by weight of the acryl-based polymer, and (B) t-butyl acrylate, isobutyl acrylate, n- (A) / (B) is in the range of 1.0 to 17.8 parts by weight, the ratio of (A) to (B) .

When the polarizing plate having a total thickness of 80 占 퐉 was bonded to a non-alkali glass via a pressure-sensitive adhesive layer having a thickness of 20 占 퐉 in which the pressure-sensitive adhesive composition was crosslinked, the pressure-sensitive adhesive layer had an adhesive force of 1.0 to 6.0 N / 25 mm , A test piece comprising a pressure-sensitive adhesive layer having a thickness of 20 占 퐉 bridged with the above pressure-sensitive adhesive composition and having a thickness of 80 占 퐉 and a thickness of 80 占 퐉 laminated on a non-alkali glass was durability It is preferable that there is no foaming or peeling after being provided for the test or provided in the durability test under the test environment of 60 캜 x 90% RH x 750 hr.

(C) a copolymerizable vinyl monomer containing a hydroxyl group and / or a carboxyl group, with respect to 100 parts by weight of the total of (A), (B) and (D) (Meth) acrylate, 6-hydroxyoctyl (meth) acrylate, and 2-hydroxyethyl (meth) acrylate. Hydroxyethyl (meth) acrylate, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, , And N-hydroxyethyl (meth) acrylamide, wherein the copolymerizable monomer containing a carboxyl group is at least one selected from the group consisting of (meth) acrylic acid, (Meth) acrylate, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (meth) acryloyloxypropylhexahydrophthalic acid, 2- (Meth) acryloyloxyethyl maleate, carboxypolycaprolactone mono (meth) acrylate, 2- (meth) acryloyloxyethyl methacrylate, And at least one member selected from the group consisting of compounds of oxyethyltetrahydrophthalic acid.

At least one selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer is at least one selected from the group consisting of an alkoxyalkyl (meth) acrylate, an alkoxypolyalkylene glycol mono (meth) acrylate, an N-vinyl substituted lactam, (Meth) acrylamide, dialkyl-substituted aminoalkyl (meth) acrylate, dialkyl-substituted (meth) acrylamide, (E) at least one member selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer is contained in an amount of 1 to 20 parts by weight based on 100 parts by weight of the component (A).

The antistatic agent (F) is preferably an ionic compound other than an alkali metal salt having a melting point of 25 占 폚 or more and 90 占 폚 or less.

It is preferable that both the initial surface resistivity of the pressure-sensitive adhesive layer and the surface resistivity after being provided in the durability test under the test environment of 85 占 폚 占 750 hr are both 1.0 占 10 ^{+ 9} ? /? Or less.

Further, the present invention provides an adhesive film comprising a resin film laminated on one side thereof with a pressure-sensitive adhesive layer formed by crosslinking the pressure-sensitive adhesive composition.

The present invention also provides an adhesive film for a polarizing plate using the adhesive film.

The present invention also provides a pressure-sensitive adhesive film for a polarizing plate, which is used for bonding a polarizing plate and a phosphor cell panel.

Further, the present invention provides an adhesive film comprising a release film / pressure-sensitive adhesive layer / release film having a pressure-sensitive adhesive layer formed by crosslinking the pressure-sensitive adhesive composition on one side of a release film in a thickness of 1 to 25 m do.

Further, the present invention provides an optical film provided with a pressure-sensitive adhesive layer formed by laminating a pressure-sensitive adhesive layer formed by crosslinking the pressure-sensitive adhesive composition on at least one surface of an optical film and comprising a release film / pressure-sensitive adhesive layer / optical film do.

The present invention also provides a polarizing plate having a pressure-sensitive adhesive layer formed by laminating a pressure-sensitive adhesive layer formed by crosslinking the pressure-sensitive adhesive composition on one side of a polarizing plate and comprising a releasing film / pressure-sensitive adhesive layer / polarizing plate.

Further, the present invention provides a liquid crystal panel characterized in that a polarizing plate on which the pressure-sensitive adhesive layer is formed is used.

Further, the present invention provides an in-cell liquid crystal panel characterized in that a polarizing plate on which the pressure-sensitive adhesive layer is formed is used.

According to the present invention, it is possible to provide a pressure-sensitive adhesive which can form a pressure-sensitive adhesive layer which has an excellent antistatic performance with a surface resistivity of the pressure-sensitive adhesive layer of not higher than 1.0 x 10 ^{+ 9} ? /? And a pressure-sensitive adhesive film using the composition.

On the other hand, in the present invention, the content of the antistatic agent is significantly increased in comparison with the content of the conventional pressure sensitive adhesive composition so as to obtain a very excellent antistatic property which can not be achieved by the prior art. Therefore, in the present invention, for the purpose of preventing the antistatic agent contained in a large amount in the pressure-sensitive adhesive layer from being deposited on the surface of the pressure-sensitive adhesive layer and lowering the durability after the durability test in a high temperature and high humidity environment of the pressure- (BA) as a main component and a monomer having a good copolymerization with BA are selected and copolymerized with a specific silane coupling agent.

Hereinafter, the present invention will be described with reference to preferred embodiments.

The pressure-sensitive adhesive composition of the present embodiment is a pressure-sensitive adhesive composition comprising an acrylic polymer, (F) an antistatic agent, and (G) a crosslinking agent, wherein the acrylic polymer comprises (A) n-butyl acrylate, (B) (C) at least one selected from the group consisting of isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, n-butyl methacrylate and methyl acrylate, and (C) at least one copolymerizable vinyl monomer containing a hydroxyl group and / ) At least one copolymerizable vinyl monomer containing an aromatic group and (E) a copolymer obtained by copolymerizing at least one selected from an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer, and an acrylic polymer having a weight average molecular weight of 1,000,000 to 3,000,000 , And as the antistatic agent (F), an ionic compound having a melting point of 25 占 폚 or more is added in an amount of 10 parts by weight or more and 60 parts by weight or less based on 100 parts by weight of the acrylic polymer (G) at least one crosslinking agent selected from the group consisting of an isocyanate compound having three or more functional groups and an epoxy compound having two or more functional groups, wherein the pressure-sensitive adhesive composition comprises (H) an epoxy group, the surface resistivity of the pressure-sensitive adhesive layer crosslinked with the pressure-sensitive adhesive composition 1.0 × 10 ^{+ 9} is made to contain a Cobb clay, adding a silane coupling agent of the monomer-type or oligomer-type containing the selected at least one functional group from the acid anhydride group, Ω / □ or less, and the pressure-sensitive adhesive layer is provided in a durability test under a test environment of 85 ° C. × 750 hr, or in a durability test under a test environment of 60 ° C. × 90% RH × 750 hr, And the antistatic agent is not precipitated on the surface of the pressure-sensitive adhesive layer.

At least one selected from the group consisting of (A) n-butyl acrylate and (B) t-butyl acrylate, isobutyl acrylate, n-butyl methacrylate and methyl acrylate, It corresponds to the monomer. The pressure-sensitive adhesive composition of the present embodiment is preferably a combination of (A) and (B) which are two or more specific monomers of alkyl (meth) acrylate constituting the acrylic polymer.

The acrylic polymer of the present embodiment is preferably composed of (A) n-butyl acrylate as a main component and (A) n-butyl acrylate in an amount of 40 to 89 parts by weight based on 100 parts by weight of the acrylic polymer . (A) an alkyl (meth) acrylate monomer other than n-butyl acrylate, (B) at least one selected from the group consisting of t-butyl acrylate, isobutyl acrylate, n-butyl methacrylate, And the total amount of at least one member selected from the group consisting of the above-mentioned components is in the range of 5 to 40 parts by weight. Further, the ratio (A) / (B) of (A) and (B) is preferably 1.0 to 17.8 as a weight ratio.

(C) a copolymerizable vinyl monomer containing a hydroxyl group and / or a carboxyl group is preferably selected from the group consisting of a copolymerizable monomer containing a hydroxyl group (a hydroxyl group-containing monomer) and a copolymerizable monomer containing a carboxyl group (a carboxyl group-containing monomer) At least one of them may be mentioned. That is, either one of the hydroxyl group-containing monomer and the carboxyl group-containing monomer may be selected and copolymerized, or both the hydroxyl group-containing monomer and the carboxyl group-containing monomer may be copolymerized. (C) is contained in an amount of 0.1 to 5 parts by weight per 100 parts by weight of the total of (A), (B) and (D).

Examples of the hydroxyl group-containing monomer include, for example, 8-hydroxyoctyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxyethyl Hydroxyalkyl (meth) acrylates such as hydroxyalkyl (meth) acrylates, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-hydroxyethyl (Meth) acrylamides having a carboxyl group and a carboxyl group-containing (meth) acryl amide.

Further, the hydroxyl group-containing monomer to be contained in the pressure-sensitive adhesive composition according to the present embodiment is preferably such that the pressure-sensitive adhesive layer to be obtained has a content of the carboxyl group-containing monomer which is considered to have an influence on the corrosiveness to an adherable substance such as the ITO surface of the transparent conductive film As a copolymerizable monomer for reducing the amount of the monomer. For this reason, the monomer containing a hydroxyl group can help to improve the adhesion of the pressure-sensitive adhesive layer and also to reduce the corrosiveness. The proportion of the hydroxyl group-containing monomer to be contained in the pressure-sensitive adhesive composition of the present embodiment is preferably in a ratio of 0.1 to 5.0 parts by weight, more preferably 0.1 to 4.4 parts by weight, relative to 100 parts by weight of the acrylic polymer, more preferably 0.1 To 3.8 parts by weight.

Examples of the carboxyl group-containing monomer include (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (Meth) acryloyloxyethylmaleic acid, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, carboxypolycaprolactone mono (Meth) acrylate, 2- (meth) acryloyloxyethyltetrahydrophthalic acid, and the like.

Further, the carboxyl group-containing monomer contained in the pressure-sensitive adhesive composition according to the present embodiment can impart necessary cohesive force to the pressure-sensitive adhesive layer to be obtained. The proportion of the carboxyl group-containing monomer in the pressure-sensitive adhesive composition according to the present embodiment is preferably 0 to 5.0 parts by weight (even when the carboxyl group-containing monomer is not copolymerized) relative to 100 parts by weight of the acrylic polymer, , It is more preferably 0.01 to 2.3 parts by weight, particularly preferably 0.01 to 1.2 parts by weight, most preferably 0.01 to 0.8 parts by weight.

Examples of the copolymerizable vinyl monomer containing (D) an aromatic group include benzyl (meth) acrylate, naphthyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxybutyl Acrylate, 6- (1-naphthyloxy) ethyl (meth) acrylate, 2- (2-naphthyloxy) ethyl (Meth) acrylate, 8- (2-naphthyloxy) hexyl (meth) acrylate, 8- Or more. (Meth) acrylate monomer containing an aromatic group as the copolymerizable vinyl monomer containing (D) an aromatic group, the copolymerization with the alkyl (meth) acrylate monomer comprising the combination of (A) and (B) Is preferable.

(D) is preferably free of a hydroxyl group, a carboxyl group, an alkoxy group and nitrogen in order to distinguish (D) from (C) and (E).

In order to obtain a pressure-sensitive adhesive layer having a high refractive index, it is preferable to blend at least one or more (meth) acrylate monomers containing an aromatic group in the pressure-sensitive adhesive composition according to the present embodiment. By copolymerizing these (meth) acrylate monomers containing an aromatic group with an acryl-based polymer, the refractive index of the obtained pressure-sensitive adhesive layer can be raised and adjusted, the refractive index difference between the optical members can be reduced, and the total light transmittance can be improved by reducing total reflection. In the pressure-sensitive adhesive composition according to the present embodiment, the (meth) acrylate monomer containing an aromatic group is preferably contained in a proportion of 5 to 30 parts by weight, more preferably 6 to 28 parts by weight, based on 100 parts by weight of the acrylic polymer. More preferably from 6 to 24 parts by weight.

At least one selected from (E) an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer may be at least one selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer. That is, either one of the alkoxy group-containing vinyl monomer and the nitrogen-containing vinyl monomer may be selected and copolymerized, or both the alkoxy group-containing vinyl monomer and the nitrogen-containing vinyl monomer may be copolymerized. (E) is preferably contained in a proportion of 1 to 20 parts by weight, more preferably 1 to 18 parts by weight, relative to 100 parts by weight of the total of (A), (B) and (D) Particularly preferably 2 to 16 parts by weight.

(E) is preferably different from (C), it is preferable that (E) does not contain a hydroxyl group and a carboxyl group. Further, in order for (E) to be distinguished from (D), it is preferable that (E) does not contain an aromatic group. The alkoxy group-containing vinyl monomer may not contain nitrogen, and the nitrogen-containing vinyl monomer may not contain an alkoxy group. (E) may be a vinyl monomer containing an alkoxy group and nitrogen, such as, for example, alkoxyalkyl (meth) acrylamide.

Examples of the alkoxy group-containing vinyl monomer include at least one selected from alkoxyalkyl (meth) acrylate and alkoxypolyalkylene glycol mono (meth) acrylate.

Specific examples of the alkoxyalkyl acrylate include 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2-propoxyethyl (meth) acrylate, 2-isopropoxyethyl 2-ethoxypropyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-methoxypropyl (meth) (Meth) acrylate, 3-methoxypropyl (meth) acrylate, 3-ethoxypropyl (meth) acrylate, 3-propoxypropyl (Meth) acrylate, 4-methoxybutyl (meth) acrylate, 4-ethoxybutyl (meth) acrylate, Propoxybutyl (meth) acrylate, 4-isopropoxybutyl (meth) acrylate, 4-butoxy Butyl (meth) acrylate.

Specific examples of the alkoxypolyalkylene glycol mono (meth) acrylate include methoxypolyethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, ethoxy (Meth) acrylate, methoxypolybutylene glycol (meth) acrylate, ethoxypolybutylene glycol (meth) acrylate, and the like. On the other hand, the alkoxypolyalkylene glycol mono (meth) acrylate is a monomer in which the hydroxyl group at one end of the polyalkylene glycol is an alkyl ether and the hydroxyl group at the other end is a (meth) acrylate.

Examples of the nitrogen-containing vinyl monomer include at least one selected from N-vinyl substituted lactams, dialkyl-substituted aminoalkyl (meth) acrylamides, dialkyl-substituted aminoalkyl (meth) acrylates, .

Examples of the N-vinyl substituted lactams include N-vinyl-2-pyrrolidone, N-vinylcaprolactam and N-vinyl-2-piperidone.

Examples of dialkyl substituted aminoalkyl (meth) acrylamides include dimethylaminoethyl (meth) acrylamide, diethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) (Meth) acrylamides such as dipropylaminopropyl (meth) acrylamide, diisopropylaminopropyl (meth) acrylamide, ethylmethylaminopropyl (meth) acrylamide, methylpropylaminopropyl Amides and the like.

Examples of the dialkyl-substituted aminoalkyl (meth) acrylate include dimethylaminomethyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, dimethylaminoisopropyl (Meth) acrylate, diethylaminomethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, ethylmethylaminoethyl (meth) acrylate, methylpropylaminoethyl Propylaminoethyl (meth) acrylate, dibutylaminoethyl (meth) acrylate, and t-butylaminoethyl (meth) acrylate.

Examples of dialkyl substituted (meth) acrylamides include dimethyl (meth) acrylamide, diethyl (meth) acrylamide, dipropyl acrylamide, diisopropyl (meth) acrylamide, dibutyl (Meth) acrylamide, methylpropyl (meth) acrylamide, and methyl isopropyl (meth) acrylamide.

The method of producing the acrylic polymer to be contained in the pressure-sensitive adhesive composition according to the present embodiment is not particularly limited, and a well-known polymerization method such as a solution polymerization method or an emulsion polymerization method can be appropriately used. The weight average molecular weight of the copolymer of the acrylic polymer is preferably from 1 million to 3 million.

The pressure-sensitive adhesive composition according to the present embodiment contains (F) an antistatic agent to obtain an antistatic property. (F) an antistatic agent in an amount of 10 parts by weight or more and 60 parts by weight or less based on 100 parts by weight of the acrylic polymer, and more preferably from 16 to 40 parts by weight of an ionic compound having a melting point of from 25 캜 to 90 캜 , More preferably from 16 to 38 parts by weight. This antistatic agent is an ionic compound composed of an anion and a cation. The ionic compound is an ionic compound having a melting point of 25 캜 or higher, and is preferably a solid at ordinary temperature (for example, 25 캜). The ionic compound is more preferably an ionic compound having a melting point of 25 to 90 캜 which is a solid at a temperature of 25 캜, and particularly preferably an ionic compound having a melting point of 25 캜 to 50 캜.

Examples of the anions contained in the antistatic agent (F) include inorganic or organic anions. Examples of inorganic anions include PF ₆ ^- , AsF ₆ ^- , SbF ₆ ^- , BF ₄ ^- , AlF ₄ ^- , (FSO ₂ ) ₂ N ^- , FSO ₃ ^- , SCN ^- and ClO ₄ ^- . The organic anion is a sulfonate anion (RSO ₃ ^-), carboxylate anion (RCOO ^-), an alkoxide or phenoxide anion (RO ^-), organic imide anion (R ₂ N ^-), methide (R ₃ C ^- An anion, an organic borate (R ₄ B ^- ) anion, and the like, and at least one of R is an anion having an organic group. Examples of the organic group include an alkyl group, an alkoxy group, an aromatic group (aryl group, aralkyl group, etc.), an alkylcarbonyl group, an aromatic carbonyl group, an alkylsulfonyl group and an aromatic sulfonyl group. When the anion has 2 or more R, it may be cyclic having a bond between 2 or more R's. It is preferable that the organic group R contains a fluorine atom (fluoro group). Among them, it is preferable to use at least one member selected from the group consisting of pentafluorobenzenesulfonate, hexafluorophosphate, bis (trifluoromethanesulfonyl) imide, bis (fluorosulfonyl) imide, triflate, nonafluorobutanesulfonate, Fluorophenylborate, tris (pentafluorobenzenesulfonyl) methide, and the like.

Examples of the cations contained in the antistatic agent (E) include pyridinium cations, imidazolium cations, pyrimidinium cations, pyrazolium cations, pyrrolidinium cations, ammonium cations, phosphonium cations and sulfonium cations. (R ₄ N ⁺ ) having an organic group R at least at the nitrogen atom, an N-substituted pyridinium cation, an N-substituted imidazolium cation and the like are preferable Do. R may be a hydrocarbon group such as a noncyclic or cyclic alkyl group or an aromatic group (aryl group, aralkyl group, etc.). When the cation has two or more R's, it may be cyclic having a bond between two or more R's.

The pressure-sensitive adhesive composition according to the present embodiment further contains (G) at least one crosslinking agent selected from the group consisting of an isocyanate compound having three or more functional groups and an epoxy compound having two or more functional groups as a crosslinking agent. The ratio of the crosslinking agent (G) contained in the pressure-sensitive adhesive composition according to the present embodiment is preferably 0.01 to 5 parts by weight, more preferably 0.01 to 3 parts by weight, relative to 100 parts by weight of the acrylic polymer, To 0.8 parts by weight is particularly preferable.

Examples of the trifunctional or higher isocyanate compound include biuret-modified products of diisocyanates such as hexamethylene diisocyanate, isophorone diisocyanate, diphenylmethane diisocyanate, tolylene diisocyanate and xylylene diisocyanate, and biuret modified products of isocyanurate modified products , Trimethylol propane, and adducts with tri- or higher-valent polyols such as glycerin.

Examples of the epoxy compound having two or more functional groups include diglycidyl ether of glycols, diglycidyl ether of bisphenol, triglycidyl ether of triol, diglycidyl ester of dicarboxylic acid, Amines, diamines of tetraglycidyl substitution, and the like.

The pressure-sensitive adhesive composition according to the present embodiment further contains (H) a silane coupling agent. (H) The silane coupling agent includes a compound having at least one organic functional group and at least one hydrolysable group in one molecule, and the hydrolyzable group is an alkoxy group bonded to a silicon atom. (H) The silane coupling agent contains at least one or more functional groups selected from an epoxy group, a mercapto group and an acid anhydride group. (H) The silane coupling agent may use one or both of a monomer type and an oligomer type. The proportion of the silane coupling agent contained in the pressure-sensitive adhesive composition according to the present embodiment is preferably 0.01 to 0.5 parts by weight based on 100 parts by weight of the acrylic polymer.

Examples of the silane coupling agent having an epoxy group include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ) Ethylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 5,6-epoxyhexyltrimethoxysilane, 5,6-epoxyhexylmethyldimethoxysilane, 5,6- Epoxy hexylmethyldiethoxysilane, 5,6-epoxyhexyltriethoxysilane, and the like. Examples of the silane coupling agent having a mercapto group include 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropylmethyldiethoxysilane, 3-mercaptopropyltri Ethoxy silane, and the like. Examples of the silane coupling agent having an acid anhydride group include 3-trimethoxysilylpropylsuccinic anhydride and 3-triethoxysilylpropylsuccinic anhydride. An oligomerized alkoxy oligomer (silicon alkoxy oligomer) or the like can also be used as the silane coupling agent.

The pressure-sensitive adhesive composition of the present embodiment can be appropriately compounded with known additives such as antioxidants, surfactants, curing accelerators, plasticizers, fillers, crosslinking catalysts, crosslinking retarders, curing retarders, processing aids and antioxidants have. These may be used alone or in combination of two or more.

The surface resistivity of the pressure-sensitive adhesive layer crosslinked pressure-sensitive adhesive composition of the present embodiment, 1.0 × 10 ⁺⁹ Ω / □ or less it is preferred, more preferably 9.0 × 10 ^{+ 8} Ω / □ or ^{less, 6.0 × 10 + 8 Ω /} □ Or less. The pressure-sensitive adhesive layer is the surface resistivity after the initial surface resistivity and durability test, all of 1.0 × 10 ^{+ 9} Ω / □ or less it is preferred, more preferably 9.0 × 10 ^{+ 8} Ω / □ or less, 6.0 × 10 ^{+ 8} Ω / □ or less. Here, the initial surface resistivity is the surface resistivity before the pressure-sensitive adhesive layer is provided in the durability test. The surface resistivity after the durability test is a surface resistivity after providing the pressure-sensitive adhesive layer in a durability test under a test environment of 85 캜 x 750 hr. Here, the test environment of 85 占 폚 占 750 hr may be a dry condition.

The pressure-sensitive adhesive layer obtained by crosslinking the pressure-sensitive adhesive composition of the present embodiment was subjected to a durability test under a test environment of 85 ° C. × 750 hr and a durability test under a test environment of 60 ° C. × 90% RH × 750 hr. (F) the antistatic agent does not precipitate. Here, the test environment of 85 占 폚 占 750 hr may be a dry condition.

The antistatic property of the antistatic agent (F) in the pressure-sensitive adhesive composition of this embodiment can be obtained by preparing two or more samples of the pressure-sensitive adhesive layer in which the same pressure-sensitive adhesive composition is crosslinked and measuring one sample under a test environment of 85 ° C. × 750 hr (F) an antistatic agent is not precipitated, and another sample is subjected to a durability test under a test environment of 60 캜 x 90% RH x 750 hr. (F) .

The pressure-sensitive adhesive layer to which the pressure-sensitive adhesive composition of the present embodiment is crosslinked is a pressure-sensitive adhesive layer having a pressure-sensitive adhesive force of 1.0 to 6.0 N / 25 mm.

Further, a test piece comprising a pressure-sensitive adhesive layer having a thickness of 20 占 퐉 interposed between a polarizing plate having a total thickness of 80 占 퐉 and a width of 10 cm and an alkali-free glass was subjected to a durability test under a test environment of 85 占 폚 for 750 hours, It is preferable that there is no foaming and peeling after being provided in the durability test under the test environment of 90% RH x 750 hr.

The performance without foaming and peeling in the pressure-sensitive adhesive composition of this embodiment can be evaluated by preparing two or more test pieces produced using the same pressure-sensitive adhesive composition and measuring one test piece in a durability test under a test environment of 85 ° C. × 750 hr The test piece may be free from foaming and peeling after providing the other test piece to the durability test under the test environment of 60 占 폚 占 90% RH 占 占 750 hr.

The pressure-sensitive adhesive layer according to the present embodiment can be obtained by applying the pressure-sensitive adhesive composition of the present embodiment to a substrate such as a resin film or a release film, and then crosslinking the pressure-sensitive adhesive composition.

When the pressure-sensitive adhesive layer according to the present embodiment is used for bonding the layers of the optical member or the like, it is preferable that the refractive index difference is as small as possible in order to reduce reflection of light rays at the interface between the pressure-sensitive adhesive layer and the optical member. Therefore, the refractive index of the pressure-sensitive adhesive layer is preferably 1.47 to 1.50.

The pressure-sensitive adhesive film according to the present embodiment can be produced by forming the pressure-sensitive adhesive layer according to the present embodiment on one side of a substrate such as a resin film or a release film. As a resin film or a release film (separator) to be a substrate, a resin film such as a polyester film and the like can be used. The releasing film may be subjected to releasing treatment by a silicone-based or fluorine-releasing agent or the like on the side surface to be brought into contact with the pressure-sensitive adhesive surface of the pressure-sensitive adhesive layer. Antistatic treatment with an antifouling treatment with a silicon-based or fluorine-based releasing agent, a coating agent, fine silica particles or the like, coating with an antistatic agent, or the like is applied to the resin film as a base material on the side opposite to the side where the pressure- . The thickness of the pressure-sensitive adhesive layer is, for example, 1 占 퐉 to 25 占 퐉.

Release film / pressure-sensitive adhesive layer / release film "may be formed by abutting on the both surfaces of one pressure-sensitive adhesive layer the surface subjected to the releasing treatment of the releasing film. In this case, the releasing films on both sides are sequentially or simultaneously peeled off to expose the adhesive surface, so that the releasing film can be bonded to an optical member such as an optical film. Examples of the optical film include a polarizing film, a retardation film, an antireflection film, an antiglare film, an ultraviolet absorbing film, an infrared absorbing film, an optical compensating film, and a brightness improving film. Examples of the device to which the optical member is applied include a liquid crystal panel, an organic EL panel, a touch panel, and an in-cell type liquid crystal panel.

The pressure-sensitive adhesive film of the present embodiment is preferable as a pressure-sensitive adhesive film for a polarizing plate. In particular, it may be used for bonding the polarizing plate and the phosphor panel. Further, the optical film may be formed with a pressure-sensitive adhesive layer formed by laminating the pressure-sensitive adhesive layer on at least one surface of the optical film. By using the above-mentioned pressure-sensitive adhesive film on one side of the polarizing plate, a polarizing plate having a pressure-sensitive adhesive layer can be provided. A liquid crystal panel such as a phosphor cell type liquid crystal panel can be provided using the polarizer plate having the pressure-sensitive adhesive layer formed thereon.

Sensitive adhesive layer / optical film / pressure-sensitive adhesive layer / release film ", " optical film / pressure-sensitive adhesive layer / optical film " Film "," optical film / pressure-sensitive adhesive layer "and" pressure-sensitive adhesive layer / optical film / pressure-sensitive adhesive layer ". Sensitive adhesive layer / polarizer / pressure-sensitive adhesive layer / release film ", " polarizer / pressure-sensitive adhesive layer ", " pressure-sensitive adhesive layer / pressure- Polarizer / pressure-sensitive adhesive layer " These laminated structures may be included as partial structures such as liquid crystal panels.

Example

Hereinafter, the present invention will be described in detail by way of examples.

≪ Preparation of acrylic polymer &

[Example 1]

Nitrogen gas was introduced into a reactor equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen inlet tube to replace the air in the reactor with nitrogen gas. Thereafter, 70 parts by weight of n-butyl acrylate, 15 parts by weight of n-butyl methacrylate, 2.0 parts by weight of 8-hydroxyoctyl acrylate, 15 parts by weight of benzyl acrylate, 15 parts by weight of methoxyethyl acrylate And a solvent (ethyl acetate) was added thereto. Thereafter, 0.1 part by weight of azobisisobutyronitrile as a polymerization initiator was added dropwise over 2 hours, and the mixture was reacted at 65 DEG C for 6 hours to obtain an acrylic polymer solution used in Example 1. [

[Examples 2 to 6 and Comparative Examples 1 to 3]

The acrylic polymer solution used in Examples 2 to 6 and Comparative Examples 1 to 3 was obtained in the same manner as in Example 1 except that the monomers were changed as described in (A) to (E) of Table 1, respectively.

On the other hand, although the measurement results are not particularly shown, the weight average molecular weights of the copolymers contained in the acrylic polymer solutions of Examples 1 to 6 and Comparative Examples 1 to 3 are in the range of 1 million to 3 million.

≪ Preparation of pressure-sensitive adhesive film &

[Example 1]

20 parts by weight of tetrabutylammonium triflate salt, 0.1 part by weight of a crosslinking agent (D-110N) and 0.05 part by weight of a silane coupling agent (KBM-403) were added to the acrylic polymer solution of Example 1, And the mixture was stirred and mixed to obtain the pressure-sensitive adhesive composition of Example 1.

This pressure-sensitive adhesive composition was coated on a releasing film made of a polyethylene terephthalate (PET) film coated with silicone resin so that the thickness of the pressure-sensitive adhesive layer after drying was 20 占 퐉 and dried at 90 占 폚 to remove the solvent. Thereafter, the pressure-sensitive adhesive layer obtained by crosslinking the pressure-sensitive adhesive composition on one side of the release film was aged under an atmosphere of 23 DEG C and 50% RH for 7 days to obtain a pressure-sensitive adhesive layer of Example 1 which is a constitution of a release film / pressure- A film was obtained.

[Examples 2 to 6 and Comparative Examples 1 to 3]

The pressure-sensitive adhesive films of Examples 2 to 6 and Comparative Examples 1 to 3 were obtained in the same manner as in the pressure-sensitive adhesive film of Example 1 except that the additives were changed as described in (F) to (H) of Table 1, respectively.

In Table 1, the numerical values described after the abbreviation of each component represent parts by weight. This weight portion was obtained by setting the total of (A), (B) and (D) to 100 parts by weight. Table 2 shows the abbreviated names of the respective components used in Table 1. The IOA was included in (B) for convenience. (C), a monomer containing a hydroxyl group is classified as "(C) OH", and a monomer containing a carboxyl group is classified as "(C) COOH".

In Table 2, Coronate (registered trademark) L is a trade name of Tosoh Corporation, D-110N is a trade name of Mitsui Chemicals, Inc., and TETRAD (trade name) -X is a trade name of Mitsubishi Gas Chemical Co., Also, TDI means tolylene diisocyanate, TMP means trimethylol propane, and XDI means xylylene diisocyanate. KBM-403, X-12-967C, X-41-1805 and KBM-503 are trade names of Shin-Etsu Chemical Co.,

<Test Method and Evaluation>

A releasing film (PET film coated with a silicone resin) was peeled from the pressure-sensitive adhesive films of Examples 1 to 6 and Comparative Examples 1 to 3 to expose one side of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive film. Thereafter, the pressure-sensitive adhesive film was laminated on one side of a polarizing plate (resin film) having a thickness of 80 占 퐉 with the pressure-sensitive adhesive layer interposed therebetween to obtain a polarizing plate having a pressure-sensitive adhesive layer constituting the releasing film / pressure-sensitive adhesive layer / polarizing plate.

&Lt; Measurement method of adhesive force &gt;

The release film of the polarizing plate on which the pressure-sensitive adhesive layer obtained above was formed was peeled off, and a polarizing plate on which the pressure-sensitive adhesive layer was formed was pressed on the surface of the glass plate cleaned with acetone of alkali-free glass (Eagle XG (registered trademark) Roll, and a test piece was prepared. Thereafter, the test piece was autoclaved under the conditions of 50 占 폚 and 0.5 MPa 占 20 minutes. The peeling strength of the polarizing plate on which the pressure-sensitive adhesive layer after one hour had passed was then measured by a tensile tester in accordance with JIS Z0237 &quot; Pressure-sensitive adhesive tape / pressure-sensitive adhesive sheet test method &quot; Deg.] At a rate of 0.3 m / min as the adhesive strength of the pressure-sensitive adhesive layer to the alkali-free glass.

&Lt; Method of measuring surface resistivity &

The surface resistivity (Ω) of the pressure-sensitive adhesive layer in the atmosphere of 23 ° C. × 50% RH was measured using a resistivity meter HILESTAR (registered trademark) UP-HT450 (manufactured by Mitsubishi Chemical Engineering Co., Ltd.) / &Amp; squ &amp;) was measured to obtain an initial surface resistivity. The polarizer having the same pressure-sensitive adhesive layer was subjected to a durability test under a test environment of 85 DEG C x 750 hours, and then the surface resistivity was similarly measured to determine the surface resistivity after the durability test.

<Test method of durability>

The release film of the polarizing plate on which the pressure-sensitive adhesive layer having a side length of 10 cm was formed was peeled off in the same manner as in the measurement of the adhesive force, and was bonded to a surface cleaned with acetone of an alkali-free glass to prepare a test piece. Thereafter, the test piece was subjected to a durability test under a test environment of 85 占 폚 占 750 hours and a durability test under a test environment of 60 占 폚 占 90% RH 占 占 750 hours and then taken out under an atmosphere of 23 占 폚 占 50% RH After 1 hour, the state of the pressure-sensitive adhesive layer was visually observed to determine durability.

The criteria for durability were as follows.

No blowing or peeling of the pressure-sensitive adhesive layer.

DELTA ... Foaming and peeling occur in a part of the pressure-sensitive adhesive layer.

X · · The entirety of the pressure-sensitive adhesive layer is subjected to foaming and peeling.

&Lt; Evaluation method of precipitation state of antistatic agent &gt;

The release film of the polarizing plate on which the pressure-sensitive adhesive layer having a side length of 10 cm was formed was peeled off in the same manner as in the measurement of the adhesive force, and was bonded to a surface cleaned with acetone of an alkali-free glass to prepare a test piece. Thereafter, the test piece was subjected to a durability test under a test environment of 85 占 폚 占 750 hours and a durability test under a test environment of 60 占 폚 占 90% RH 占 占 750 hours and then taken out under an atmosphere of 23 占 폚 占 50% RH After 1 hour, the state of the pressure-sensitive adhesive layer was visually observed to determine the state of precipitation of the antistatic agent on the surface of the pressure-sensitive adhesive layer.

On the other hand, criteria for judging the deposition state of the antistatic agent were as follows.

No antistatic agent precipitates on the surface of the pressure-sensitive adhesive layer.

DELTA ... precipitation of an antistatic agent occurs on a part of the surface of the pressure-sensitive adhesive layer.

X 占 占 precipitation of an antistatic agent is generated on the entire surface of the pressure-sensitive adhesive layer.

Table 3 shows the evaluation results.

The adhesive films of Examples 1 to 6 had an adhesive force of 1.0 to 6.0 N / 25 mm to a non-alkali glass. The initial surface resistivity of the pressure-sensitive adhesive layer and the surface resistivity after the durability test under the test environment of 85 占 폚 占 750 hr were both 1.0 占 10 ^{+ 9} ? /? Or less. In addition, after the durability test under the test environment of 85 占 폚 占 750 hr and the durability test under the test environment of 60 占 폚 占 90% RH 占 占 폚 for 750 hours, there was no foaming and peeling and durability and the antistatic agent There was no precipitation. That is, it has been demonstrated that the problems of the present invention can be solved by the evaluation results of the adhesive films of Examples 1 to 6.

The pressure-sensitive adhesive film of Comparative Example 1 was obtained in the same manner as in Example 1, except that the alkyl (meth) acrylate monomer copolymerized with the acrylic polymer was not any of TBA, IBA, BMA and MA and also had (D) a copolymerizable vinyl monomer containing an aromatic group and Containing vinyl monomer and the nitrogen-containing vinyl monomer were not copolymerized. Therefore, the pressure-sensitive adhesive layer of Comparative Example 1 had an excessively high adhesive strength before the durability test, but had poor durability. In addition, since the pressure-sensitive adhesive film of Comparative Example 1 had a higher content ratio of (F) the antistatic agent than that of Comparative Example 3, the surface resistivity of the pressure-sensitive adhesive layer became low, but after the durability test, Precipitation.

In the pressure-sensitive adhesive film of Comparative Example 2, at least one selected from the (E) alkoxy group-containing vinyl monomer and the nitrogen-containing vinyl monomer was not copolymerized with the acrylic polymer. It contains (H) a silane coupling agent, but does not contain at least one functional group selected from an epoxy group, a mercapto group and an acid anhydride group. Therefore, the pressure-sensitive adhesive film of Comparative Example 2 had poor durability of the pressure-sensitive adhesive layer, and after the durability test, the antistatic agent partially precipitated on the pressure-sensitive adhesive layer surface.

In the pressure-sensitive adhesive film of Comparative Example 3, the alkyl (meth) acrylate monomer copolymerized with the acrylic polymer was not any of TBA, IBA, BMA, and MA, and the copolymerizable vinyl monomer containing the aromatic group (D) was not copolymerized. For this reason, the pressure-sensitive adhesive film of Comparative Example 3 did not contain (H) the silane coupling agent, but the adhesive strength of the pressure-sensitive adhesive layer before the durability test was excessive, but the durability was poor. Further, since the content of the antistatic agent (F) in the pressure-sensitive adhesive film of Comparative Example 3 was small, the antistatic agent did not deposit on the surface of the pressure-sensitive adhesive layer after the durability test, but the surface resistivity of the pressure-

As described above, the problems of the present invention were not solved in the adhesive films of Comparative Examples 1 to 3.

According to the present invention, it is possible to provide a pressure-sensitive adhesive which can form a pressure-sensitive adhesive layer which has an excellent antistatic performance with a surface resistivity of the pressure-sensitive adhesive layer of not higher than 1.0 x 10 ^{+ 9} ? /? And a pressure-sensitive adhesive film using the composition. Therefore, the pressure-sensitive adhesive film using the pressure-sensitive adhesive composition according to the present invention has excellent antistatic performance as a pressure-sensitive adhesive film for use in bonding a polarizing plate and a liquid crystal panel, and has great industrial value in terms of durability.

Claims (15)

A pressure-sensitive adhesive composition containing an acrylic polymer, (F) an antistatic agent, and (G) a crosslinking agent,
Wherein the acryl-
(A) n-butyl acrylate,
(B) at least one member selected from the group consisting of t-butyl acrylate, isobutyl acrylate, n-butyl methacrylate and methyl acrylate,
(C) at least one copolymerizable vinyl monomer containing a hydroxyl group and / or a carboxyl group,
(D) at least one copolymerizable vinyl monomer containing an aromatic group,
(E) a copolymer obtained by copolymerizing at least one selected from an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer, the acrylic polymer having a weight average molecular weight of 1,000,000 to 3,000,000,
Wherein the antistatic agent (F) contains an ionic compound having a melting point of 25 占 폚 or more and 90 占 폚 or less in an amount of 10 parts by weight or more and 60 parts by weight or less based on 100 parts by weight of the acrylic polymer,
Wherein the crosslinking agent (G) comprises at least one crosslinking agent selected from the group consisting of an isocyanate compound having three or more functional groups and an epoxy compound having two or more functional groups,
Wherein the pressure-sensitive adhesive composition further comprises (H) a monomer type or oligomer type silane coupling agent containing at least one functional group selected from an epoxy group, a mercapto group and an acid anhydride group,
Wherein the pressure-sensitive adhesive layer crosslinked with the pressure-sensitive adhesive composition has a surface resistivity of 1.0 x 10 ^{+ 9} ? /? Or less,
The pressure-sensitive adhesive layer was provided in a durability test under a test environment of 85 占 폚 占 750 hours or in a durability test under a test environment of 60 占 폚 占 90% RH 占 占 750 hours, Wherein the pressure-sensitive adhesive composition does not precipitate. The method according to claim 1,
(A) n-butyl acrylate in an amount of 40 to 89 parts by weight based on 100 parts by weight of the acryl-based polymer, and (B) t-butyl acrylate, isobutyl acrylate, n- (A) / (B) is in the range of 1.0 to 17.8 parts by weight, the ratio of (A) to (B) &Lt; / RTI &gt; 3. The method according to claim 1 or 2,
When the polarizing plate having a total thickness of 80 占 퐉 was bonded to a non-alkali glass via a pressure-sensitive adhesive layer having a thickness of 20 占 퐉 in which the pressure-sensitive adhesive composition was crosslinked, the pressure-sensitive adhesive layer had an adhesive force of 1.0 to 6.0 N / 25 mm ,
A test piece comprising a pressure-sensitive adhesive layer having a thickness of 20 占 퐉 bridged with the pressure-sensitive adhesive composition and having a total thickness of 80 占 퐉 and a thickness of 80 占 퐉 laminated on a non-alkali glass was subjected to a durability test under a test environment of 85 占 폚 for 750 hours , Or after providing it in a durability test under a test environment of 60 占 폚 占 90% RH 占 占 750 hr, there is no foaming and peeling. 3. The method according to claim 1 or 2,
(C) a copolymerizable vinyl monomer containing a hydroxyl group and / or a carboxyl group, with respect to 100 parts by weight of the total of (A), (B) and (D) And 0.1 to 5 parts by weight of at least one member selected from the group consisting of copolymerizable monomers,
(Meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 4-hydroxybutyl (Meth) acrylate, N-hydroxy (meth) acrylamide, N-hydroxymethyl (meth) acrylamide and N-hydroxyethyl
Wherein the copolymerizable monomer containing a carboxyl group is selected from the group consisting of (meth) acrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, 2- (meth) acryloyloxyethylhexahydrophthalic acid, 2- (Meth) acryloyloxyethylmaleic acid, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acryloyloxyethylsuccinic acid, carboxypolycaprolactone mono (Meth) acrylate, and 2- (meth) acryloyloxyethyl tetrahydrophthalic acid. The pressure-sensitive adhesive composition according to claim 1, 3. The method according to claim 1 or 2,
At least one selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer is at least one selected from the group consisting of an alkoxyalkyl (meth) acrylate, an alkoxypolyalkylene glycol mono (meth) acrylate, an N-vinyl substituted lactam, (Meth) acrylamide, dialkyl-substituted aminoalkyl (meth) acrylate, dialkyl-substituted (meth) acrylamide, (E) at least one selected from the group consisting of an alkoxy group-containing vinyl monomer and a nitrogen-containing vinyl monomer in an amount of 1 to 20 parts by weight based on 100 parts by weight of the pressure-sensitive adhesive composition. 3. The method according to claim 1 or 2,
Wherein the antistatic agent (F) is an ionic compound other than an alkali metal salt having a melting point of 25 占 폚 or more and 90 占 폚 or less. 3. The method according to claim 1 or 2,
Wherein an initial surface resistivity of the pressure-sensitive adhesive layer and a surface resistivity after being provided in a durability test under a test environment of 85 占 폚 占 750 hr are both 1.0 占 10 ^{+ 9} ? /? Or less. Characterized in that a pressure-sensitive adhesive layer formed by crosslinking the pressure-sensitive adhesive composition of any one of claims 1 to 3 is laminated on one side of a resin film. A pressure-sensitive adhesive film for a polarizing plate, wherein the pressure-sensitive adhesive film of claim 8 is used. 10. The method of claim 9,
Wherein the polarizing plate is used for bonding a polarizing plate and an in-cell panel. Sensitive adhesive layer / release film in which a pressure-sensitive adhesive layer obtained by crosslinking the pressure-sensitive adhesive composition of claim 1 or 2 is formed on one side of a release film to a thickness of 1 to 25 m. An optical film having a pressure-sensitive adhesive layer formed on at least one surface of an optical film, the pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to claim 1 or 2 laminated thereon, the release film / pressure-sensitive adhesive layer / optical film. A pressure-sensitive adhesive sheet comprising a pressure-sensitive adhesive layer formed by laminating a pressure-sensitive adhesive layer obtained by crosslinking the pressure-sensitive adhesive composition according to claim 1 or 2 on one side of a polarizing plate, wherein the pressure-sensitive adhesive layer is constituted of a releasing film / pressure-sensitive adhesive layer / polarizing plate. A liquid crystal panel comprising a polarizing plate on which a pressure-sensitive adhesive layer of claim 13 is formed. A polarizing plate on which the pressure-sensitive adhesive layer of claim 13 is formed is used.