KR20170022436A - Adhesive Composition and Polarizing Plate Comprising the Same - Google Patents

Abstract

The present invention provides an adhesive composition comprising an ultraviolet ray absorbent having an acrylic copolymer and a polyalkylene glycol group, a polarizing plate comprising the same, and a liquid crystal display device. The adhesive composition according to the present invention can simultaneously satisfy ultraviolet barrier properties and durability.

Description

[0001] The present invention relates to a pressure-sensitive adhesive composition and a polarizing plate comprising the same. ≪

The present invention relates to a pressure-sensitive adhesive composition and a polarizing plate comprising the same, and more particularly, to a pressure-sensitive adhesive composition excellent in ultraviolet barrier property and durability, a polarizing plate including the same, and a liquid crystal display device.

2. Description of the Related Art A liquid crystal display device (LCD) includes a liquid crystal cell and a liquid crystal panel including a polarizing plate bonded to both sides of the liquid crystal cell via a pressure sensitive adhesive layer. The polarizing plate is composed of a polarizer and a protective film laminated on both sides thereof.

The adhesive for the bonding of the liquid crystal cell and the polarizing plate should simultaneously satisfy the properties such as adhesiveness to the substrate, light resistance prevention property, heat resistance and anti-wet heat resistance as well as reworkability.

In recent years, a cycloolefin-based or acrylate-based low moisture-permeable protective film having a thin film of a polarizer protective film and having no ultraviolet ray shielding effect is used. Therefore, in order to suppress the liquid crystal deformation due to ultraviolet rays introduced from external light or backlight, A method of imparting an ultraviolet shielding function has been proposed. Specifically, a method of adding an ultraviolet absorber to the pressure-sensitive adhesive composition has been attempted. However, in this case, the ultraviolet light shielding function is provided, but the ultraviolet absorber is bleed out to the glass substrate of the liquid crystal cell, and the durability such as heat resistance is deteriorated.

In order to solve this problem, Korean Patent Laid-Open No. 10-2014-0074581 discloses a pressure-sensitive adhesive composition comprising an acrylic copolymer containing an ultraviolet absorbing copolymerizable monomer having a specific ultraviolet absorbing group and a copolymerizable functional group. However, in the case of the pressure-sensitive adhesive composition, gelation and excessive crosslinking may occur during copolymerization of the ultraviolet-absorbing copolymerizable monomer, so that the light leakage characteristic may be deteriorated by the change of the photoelastic coefficient.

Korean Patent Publication No. 10-2014-0074581

Disclosure of Invention Technical Problem [8] The present invention has been made in view of the above problems, and it is an object of the present invention to provide a pressure-sensitive adhesive composition excellent in ultraviolet barrier property and durability.

Another object of the present invention is to provide a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

It is still another object of the present invention to provide a liquid crystal display having the polarizing plate on at least one side of a liquid crystal cell.

On the other hand, the present invention provides a pressure-sensitive adhesive composition comprising an acrylic copolymer and an ultraviolet absorber having a polyalkylene glycol group.

In one embodiment of the present invention, the polyalkylene glycol group may be a polyethylene glycol group or a polypropylene glycol group.

In one embodiment of the present invention, the ultraviolet absorber having a polyalkylene glycol group is at least one selected from the group consisting of benzophenone, benzotriazole, benzotriazine, hydroxyphenyltriazine, benzamide, benzoate, cyanoacrylate, A quinine-based (quinine-based, quinine-based, quaternary ammonium, quaternary ammonium, quaternary ammonium, quaternary ammonium, quaternary ammonium salt, quinine compounds. < / RTI >

On the other hand, the present invention provides a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

On the other hand, the present invention provides a liquid crystal display in which the polarizing plate is provided on at least one surface of a liquid crystal cell.

The pressure-sensitive adhesive composition according to the present invention can simultaneously satisfy the ultraviolet barrier property and the durability by including an ultraviolet absorber having a polyalkylene glycol group excellent in compatibility with an acrylic copolymer.

Hereinafter, the present invention will be described in more detail.

An embodiment of the present invention relates to a pressure-sensitive adhesive composition comprising an acrylic copolymer and an ultraviolet absorber having a polyalkylene glycol group.

In one embodiment of the present invention, the polyalkylene glycol group is a polymer of an alkylene glycol having 2 to 5 carbon atoms, particularly a polyethylene glycol group or a polypropylene glycol group.

In one embodiment of the present invention, the ultraviolet absorber having a polyalkylene glycol group is at least one selected from the group consisting of benzophenone, benzotriazole, benzotriazine, hydroxyphenyltriazine, benzamide, benzoate, cyanoacrylate, A quinine series, a quinine series, a quinine series, a quinine series, a nitroaniline series, a salicylate series, a cinnamate series, an oxanilide series, a coumarin series, a flavone series, a dansyl amide series, quinine compounds, especially benzophenone compounds, benzotriazole compounds, hydroxyphenyltriazine compounds or benzoate compounds. These ultraviolet absorbers may be used alone or in combination of two or more.

In one embodiment of the present invention, the ultraviolet absorber having a polyalkylene glycol group may include at least one member selected from the group consisting of compounds represented by the following general formulas (1) and (2).

[Chemical Formula 1]

 (2)

In the above formula, n is an integer of 1 to 700, preferably an integer of 4 to 200.

In one embodiment of the present invention, the ultraviolet absorbent having the polyalkylene glycol group is commercially available or can be easily prepared by reacting a polyalkylene glycol diglycidyl ether with an ultraviolet absorbent known in the art . For example, it can be prepared by reacting a conventional ultraviolet absorber with a polyalkylene glycol diglycidyl ether in the presence of a catalyst such as triethylamine (TEA), as shown in the following reaction scheme (1).

[Reaction Scheme 1]

In the above formula, n is an integer of 1 to 700, preferably an integer of 4 to 200.

In one embodiment of the present invention, the ultraviolet absorbent having the polyalkylene glycol group not only provides an ultraviolet ray blocking effect, but also has excellent compatibility with the acrylic copolymer due to the polyalkylene glycol group, Bleed-out phenomenon can be prevented. Thus, durability (heat resistance and anti-wet heat) can be improved, and optical characteristics and tackiness can be stabilized.

In one embodiment of the present invention, the ultraviolet absorbent having the polyalkylene glycol group is preferably contained in an amount of 0.2 to 2.0 parts by weight based on 100 parts by weight of the acrylic copolymer. If the content of the ultraviolet absorber is less than 0.2 parts by weight, the effect of ultraviolet ray shielding is insufficient. If the content of the ultraviolet absorber is more than 2.0 parts by weight, residual components that are not participating in the reaction are present.

In one embodiment of the present invention, the acrylic copolymer may include a (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms and a polymerizable monomer having a crosslinkable functional group.

The (meth) acrylate means acrylate and methacrylate.

Specific examples of the (meth) acrylate monomer having an alkyl group of 1 to 12 carbon atoms include n-butyl (meth) acrylate, 2-butyl (meth) acrylate, (Meth) acrylate, ethyl (meth) acrylate, methyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl Acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate and lauryl (meth) acrylate. Of these, n-butyl acrylate, Or a mixture thereof. These may be used alone or in combination of two or more.

The polymerizable monomer having a crosslinkable functional group is a component for imparting durability and breaking property by reinforcing the cohesive strength or adhesive strength of the pressure-sensitive adhesive composition by chemical bonding with the following crosslinking agent, and examples thereof include a monomer having a hydroxy group, Monomers having an amide group, monomers having a tertiary amine group, etc. These monomers may be used alone or in admixture of two or more.

Examples of the monomer having a hydroxy group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl Hydroxypropyleneglycol (meth) acrylate, hydroxyalkylene glycol having 2 to 4 carbon atoms in the alkylene group (e.g., methoxyethyl (meth) acrylate, Hydroxybutyl vinyl ether, 8-hydroxyoctyl vinyl ether, 9-hydroxynonyl (meth) acrylate, 4-hydroxybutyl vinyl ether, Vinyl ether, and 10-hydroxydecyl vinyl ether. Of these, 2-hydroxyethyl (meth) acrylate or 4-hydroxybutyl vinyl ether is preferable.

Examples of the monomer having a carboxyl group include monovalent acids such as (meth) acrylic acid and crotonic acid; Dicarboxylic acids such as maleic acid, itaconic acid, and fumaric acid, and monoalkyl esters thereof; 3- (meth) acryloylpropionic acid; A succinic anhydride ring-opening addition adduct of 2-hydroxyalkyl (meth) acrylate in which the alkyl group has 2 to 4 carbon atoms, anhydrous succinic ring opening adduct of a hydroxyalkylene glycol (meth) acrylate having 2 to 4 carbon atoms in the alkylene group , And compounds obtained by ring-opening addition of succinic anhydride to a caprolactone adduct of 2-hydroxyalkyl (meth) acrylate in which the alkyl group has 2-3 carbon atoms. Of these, (meth) acrylic acid is preferable.

Examples of the monomer having an amide group include (meth) acrylamide, N-isopropyl acrylamide, N-tertiary butyl acrylamide, 3-hydroxypropyl (meth) acrylamide, 4-hydroxybutyl (Meth) acrylamide, 8-hydroxyoctyl (meth) acrylamide and 2-hydroxyethylhexyl (meth) acrylamide. Of these, (meth) acrylamide is preferable.

Examples of the monomer having a tertiary amine group include N, N- (dimethylamino) ethyl (meth) acrylate, N, N- (diethylamino) ethyl (meth) ) Acrylate, and the like.

The polymerizable monomer having a crosslinkable functional group is preferably contained in an amount of 0.05 to 10 parts by weight, more preferably 0.1 to 8 parts by weight, based on 100 parts by weight of the (meth) acrylate monomer having an alkyl group having 1-12 carbon atoms. When the content is less than 0.05 part by weight, the cohesive force of the pressure-sensitive adhesive becomes small and durability may be deteriorated. When the content is more than 10 parts by weight, a high gel fraction may lower the adhesive strength and cause durability problems.

The acrylic copolymer may further contain other polymerizable monomers other than the monomers in an amount not lowering the adhesive strength, for example, 10% by weight or less based on the total amount.

The method for producing the acrylic copolymer is not particularly limited, and it can be produced by methods such as bulk polymerization, solution polymerization, emulsion polymerization or suspension polymerization which are generally used in the art, and solution polymerization is preferable. In addition, a solvent, a polymerization initiator, a chain transfer agent for molecular weight control and the like which are usually used in polymerization can be used.

The acrylic copolymer generally has a weight average molecular weight (in terms of polystyrene) measured by Gel Permeation Chromatography (GPC) of usually 50,000 to 2,000,000, preferably 1,000,000 to 2,000,000.

The pressure-sensitive adhesive composition according to one embodiment of the present invention may further include a crosslinking agent and a silane coupling agent.

The crosslinking agent is a component for reinforcing the cohesive force of the pressure-sensitive adhesive by properly crosslinking the copolymer, and the kind thereof is not particularly limited. Examples thereof include isocyanate compounds and epoxy compounds, which may be used alone or in combination of two or more.

Examples of the isocyanate compound include tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethyl xylene diisocyanate , Diisocyanate compounds such as naphthalene diisocyanate; An adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate compound in which 3 moles of a diisocyanate compound is self-condensed, a diisocyanate obtained from 2 moles of 3 moles of a diisocyanate compound And multifunctional isocyanate compounds containing three functional groups such as burette, triphenylmethane triisocyanate and methylene bistriisocyanate in which the remaining one mole of diisocyanate is condensed in urea.

Examples of the epoxy compound include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, polypropylene glycol Hexanediol diglycidyl ether, polytetramethylene glycol diglycidyl ether, glycerol diglycidyl ether, glycerol triglycidyl ether, glycerol diglycidyl ether, glycerol diglycidyl ether, Diglycerol polyglycidyl ether, polyglycerol polyglycidyl ether, resorcinol diglycidyl ether, 2,2-dibromoneopentyl glycol diglycidyl ether, trimethylol propane triglycidyl ether, pentaerythritol Polyglycidyl ether, sorbitol polyglycidyl ether, adipic acid diglycidyl ester, phthalic acid diglycidyl ester, tris (glycidyl) isocyanurate N, N ', N'-tetraglycidyl-m-glycidoxyethyl isocyanurate, 1,3-bis (N, N-glycidylaminomethyl) cyclohexane, Xylylenediamine, and the like.

In addition, an isocyanate compound, an epoxy compound, and a melamine compound may be used alone or in admixture of two or more.

Examples of the melamine-based compound include hexamethylol melamine, hexamethoxymethyl melamine, and hexabutoxymethyl melamine.

The amount of the crosslinking agent is preferably 0.1 to 5 parts by weight, more preferably 0.1 to 2 parts by weight based on 100 parts by weight of the acrylic copolymer. If the content is less than 0.1 part by weight, the cohesive force becomes small due to insufficient crosslinking, resulting in deterioration of durability such as peeling and deterioration of cutability. If the content is more than 5 parts by weight, excessive crosslinking reaction may cause problems in relaxation of residual stress have.

The type of the silane coupling agent is not particularly limited, and examples thereof include vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3- Glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethylethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3- Methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxy Silane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) Propylmethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane Silane, 3-triethoxysilyl-N- (1,3-dimethylbutylidene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis (triethoxysilylpropyl) tetrasulfide, 3-isocyanate propyltriethoxysilane, and the like. These may be used alone or in combination of two or more.

The amount of the silane coupling agent is preferably 0.01 to 5 parts by weight, more preferably 0.1 to 5 parts by weight, based on 100 parts by weight of the acrylic copolymer. When the content is less than 0.01 part by weight, the amount is too small and durability is not expected to be improved. If the content is more than 5 parts by weight, the cohesive strength is excessively increased.

The pressure-sensitive adhesive composition according to one embodiment of the present invention may further contain additives such as a tackifier resin, antioxidant, antistatic agent, antistatic agent, antioxidant, antistatic agent, An antioxidant, a corrosion inhibitor, a leveling agent, a surface lubricant, a dye, a pigment, a defoaming agent, a filler, a light stabilizer, an antistatic agent and the like.

The pressure-sensitive adhesive composition of the present invention can be used not only as a pressure-sensitive adhesive for a polarizing plate for bonding with a liquid crystal cell but also as a pressure-sensitive adhesive for a surface protective film. In addition, it can be used not only as a protective film, a reflective sheet, a structural adhesive sheet, a photographic adhesive sheet, a lane marking adhesive sheet, an optical adhesive product, an electronic component adhesive, but also a general commercial adhesive sheet product or a medical patch.

One embodiment of the present invention relates to a polarizing plate in which a pressure-sensitive adhesive layer composed of the pressure-sensitive adhesive composition is laminated.

The thickness of the pressure-sensitive adhesive layer can be adjusted according to the adhesive force, and is preferably 3 to 100 탆, more preferably 10 to 100 탆.

Such a polarizing plate can be applied to all ordinary liquid crystal display devices, and concretely, a liquid crystal display device including a liquid crystal panel in which a polarizing plate in which the pressure-sensitive adhesive layer is laminated is bonded to at least one surface of a liquid crystal cell can be constituted.

Therefore, one embodiment of the present invention relates to a liquid crystal display device provided with the polarizing plate on at least one surface of a liquid crystal cell.

Hereinafter, the present invention will be described more specifically with reference to Examples, Comparative Examples and Experimental Examples. It should be apparent to those skilled in the art that these examples, comparative examples and experimental examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.

Manufacturing example  1: Preparation of acrylic copolymer

90 parts by weight of n-butyl acrylate (BA), 8 parts by weight of methyl acrylate (MA), 1 part by weight of acrylic acid (AA) and 2 parts by weight of acrylic acid (AA) were charged in a 1 L reactor equipped with a cooling device, -Hydroxyethyl acrylate (2-HEA) was added thereto, and 100 parts by weight of ethyl acetate (EAc) was added as a solvent. Nitrogen gas was then purged for one hour to maintain oxygen at 72 < 0 > C to remove oxygen. After the mixture was homogeneously mixed, 0.07 part by weight of azobisisobutyronitrile (AIBN) was added as a reaction initiator and reacted for 8 hours to prepare an acrylic copolymer.

Manufacturing example  2: Polyalkylene glycol groups  Preparation of ultraviolet absorber having

Manufacturing example  2-1

Polyethylene glycol diglycidyl ether (50 g, 0.1 mol, Sigma-Aldrich) having a molecular weight (Mw) of 500 and 2,4-dihydroxybenzophenone (10.7 g, 0.05 mol) were dissolved in 300 g of acetonitrile as a solvent And 1 g of triethylamine as a catalyst was added thereto. The resulting mixture was heated in N ₂ to 50 ℃ conditions was completed After the reaction was stirred for 12 hours. The resulting product was subjected to NMR measurement to confirm that all of the epoxy peaks disappeared, and then the solvent and the catalyst were removed by distillation under reduced pressure to prepare an ultraviolet absorber (60 g) having a polyethylene glycol group.

Manufacturing example  2-2

Except that polyethylene glycol diglycidyl ether (200 g, 0.1 mol, Sigma-Aldrich) having a molecular weight of 2,000 and 500 g of acetonitrile were used, to obtain an ultraviolet absorber having a polyethylene glycol group (210 g).

Manufacturing example  2-3

Except that polypropylene glycol diglycidyl ether having a molecular weight of 640 (64 g, 0.1 mol, Sigma-Aldrich) was used instead of the polypropylene glycol diglycidyl ether ).

Example  One:

(1) Production of pressure-sensitive adhesive composition

99 parts by weight of the acrylic copolymer obtained in Preparation Example 1, 1 part by weight of the ultraviolet absorber obtained in Production Example 2-1, Coronate-L (adduct of tolylene diisocyanate of trimethylolpropane, manufactured by Japan Polyurethane Industry Co., Ltd.) And 0.2 part by weight of KBM-403 (3-glycidoxypropyltrimethoxysilane, Shinetsu) as a silane coupling agent were mixed and diluted with ethyl acetate as an organic solvent to prepare a pressure-sensitive adhesive composition.

(2) Production of Polarizer with Adhesive

The pressure-sensitive adhesive composition prepared above was cured on a releasing film coated with silicone release agent to a thickness of 25 mu m and dried at 100 DEG C for 1 minute to form a pressure-sensitive adhesive layer. A release film was laminated on the pressure-sensitive adhesive layer to produce a pressure-sensitive adhesive sheet.

After peeling off the release film of the pressure-sensitive adhesive sheet thus prepared, an iodine-based polarizing plate having a thickness of 185 占 퐉 (a polarizing plate having an 80 占 퐉 protective film having no ultraviolet blocking function bonded to both sides of a 25 占 퐉 thick polarizing plate with an adhesive) Layer was laminated by a sticking process to produce a polarizer with a pressure-sensitive adhesive. The prepared polarizing plate was stored for a curing period under the conditions of 23 캜 and 60% RH.

Example  2:

A pressure-sensitive adhesive composition and a polarizing plate with a pressure-sensitive adhesive were prepared in the same manner as in Example 1, except that the ultraviolet absorber obtained in Preparation Example 2-2 was used.

Example  3:

A pressure-sensitive adhesive composition and a polarizing plate with a pressure-sensitive adhesive were prepared in the same manner as in Example 1, except that the ultraviolet absorber obtained in Preparation Example 2-3 was used.

Comparative Example  One:

A pressure-sensitive adhesive composition and a polarizing plate with a pressure-sensitive adhesive were prepared in the same manner as in Example 1, except that a compound represented by the following formula was used as an ultraviolet absorber.

Comparative Example  2:

A pressure-sensitive adhesive composition and a polarizing plate with a pressure-sensitive adhesive were prepared in the same manner as in Example 1 except that the acrylic copolymer obtained in Preparation Example 1 was used in an amount of 100 parts by weight and an ultraviolet absorber was not used.

Experimental Example  1: Durability (heat resistance, Wet heat ) And ultraviolet Barrier property  evaluation

The physical properties of the polarizer with a pressure-sensitive adhesive prepared in the above Examples and Comparative Examples were measured by the following methods, and the results are shown in Table 1 below.

(1) Durability (heat resistance, Wet heat )

The produced polarizer with a pressure-sensitive adhesive was cut into a size of 90 mm x 170 mm, the release film was peeled off, and the optical absorption axis was perpendicularly attached to both surfaces of a glass substrate (110 mm x 190 mm x 0.7 mm). At this time, the applied pressure was 5 kg / cm < 2 >, and the clean room operation was performed so that bubbles or foreign matter would not occur. The heat resistance was evaluated by observing the occurrence of bubbles or peeling after being left at a temperature of 80 ° C for 1000 hours. The moisture resistance was evaluated by observing the occurrence of bubbles or peeling after being left at a temperature of 60 ° C and 90% RH for 1000 hours Respectively. At this time, the sample was allowed to stand at room temperature for 24 hours immediately before evaluating the state of the specimen.

<Evaluation Criteria>

○: Bubbles or peeling <5

X: 5 pieces &lt; bubble &

(2) ultraviolet rays Barrier property

The light transmittance of the prepared polarizer with a pressure-sensitive adhesive to a wavelength of 380 nm was measured using an ultraviolet ray spectrophotometer (V-7100 / VAF-7070, manufactured by Nippon Bunko).

Light transmittance (%) durability Heat resistance Wet heat Example 1 1.0 O O Example 2 1.1 O O Example 3 1.0 O O Comparative Example 1 2.2 X X Comparative Example 2 10 O O

As can be seen from the above Table 1, the pressure-sensitive adhesive compositions of Examples 1 to 4 comprising an ultraviolet absorber having a PEG or PPG group contained the pressure-sensitive adhesive composition of Comparative Example 1 containing an ultraviolet absorber having no PEG or PPG group and the ultraviolet absorber Compared with the pressure-sensitive adhesive composition of Comparative Example 2, which was not used, the light transmittance was remarkably lowered in the wavelength region of 380 nm, and ultraviolet ray shielding exhibited excellent heat and moisture and heat durability.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the invention. Do. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.

Accordingly, the actual scope of the invention is defined by the appended claims and their equivalents.

Claims (9)

An acrylic copolymer, and an ultraviolet absorber having a polyalkylene glycol group. The pressure-sensitive adhesive composition according to claim 1, wherein the polyalkylene glycol group is a polyethylene glycol group or a polypropylene glycol group. The ultraviolet absorber according to claim 1, wherein the ultraviolet absorbent having a polyalkylene glycol group is selected from the group consisting of benzophenone, benzotriazole, benzotriazine, hydroxyphenyltriazine, benzamide, benzoate, cyanoacrylate, Salicylate, cinnamate, oxanilide, coumarin, flavone, dansyl amide, and quinine. The term &quot; &Lt; / RTI &gt; and at least one compound selected from the group consisting of compounds. The pressure-sensitive adhesive composition according to claim 1, wherein the ultraviolet absorber having a polyalkylene glycol group comprises at least one selected from the group consisting of compounds represented by the following formulas (1) and (2):
[Chemical Formula 1]

(2)

In the above formula, n is an integer of 1 to 700. The pressure-sensitive adhesive composition according to claim 4, wherein n is an integer of 4 to 200. The pressure-sensitive adhesive composition according to claim 1, wherein the ultraviolet absorbent having the polyalkylene glycol group is contained in an amount of 0.2 to 2.0 parts by weight based on 100 parts by weight of the acrylic copolymer. The pressure-sensitive adhesive composition according to claim 1, further comprising a crosslinking agent and a silane coupling agent. A polarizing plate laminated with a pressure-sensitive adhesive layer comprising the pressure-sensitive adhesive composition according to any one of claims 1 to 7. A liquid crystal display device comprising the liquid crystal cell according to claim 8 on at least one surface thereof.