KR101603370B1 - Adhesive composition - Google Patents

Abstract

The present application relates to an adhesive composition. In this application, it is possible to provide an adhesive composition in which an appropriate viscosity is maintained and applied to, for example, an optical film to maintain excellent uniformity in thickness, adhesion, durability and water resistance. The above adhesive composition can effectively adhere a polarizing film to a film exhibiting, for example, hydrophobicity and low moisture permeability, and can provide an adhesive excellent in optical properties such as transparency.

Description

Adhesive composition [0001]

The present application relates to an adhesive composition, a polarizing plate and a liquid crystal display.

Polarizing plates, which are optical members applied to liquid crystal display devices and the like, usually include a protective film attached to one or both surfaces of a polarizer. The polarizing plate may have a structure in which a protective film is attached to one surface of the polarizer and the other surface thereof has a function of a protective film and an additional optical function.

In general, a polarizer is produced by treating a uniaxially stretched resin film dyed with a dichroic dye, mainly a polyvinyl alcohol film with boric acid, washing with water and drying, and then attaching a protective film.

As a protective film for a polarizer, a triacetyl cellulose (TAC) film is usually used, which is attached to the polarizer through an aqueous polyvinyl alcohol-based adhesive or the like. However, the triacetylcellulose film has a high moisture permeability and thus has a problem that the polarizing plate easily deteriorates under high temperature or high humidity conditions. Accordingly, there is an attempt to use a film having a lower moisture permeability than triacetylcellulose film, for example, a thermoplastic saturated norbornene resin film as a protective film (e.g., Patent Document 1). In addition, in addition to the above, it is possible to use an amorphous polyolefin film, a polyester resin film, an acrylic resin film, a polycarbonate resin film, a polysulfone resin film, an alicyclic polyimide resin film or a cyclic olefin (COP) Attempts to use it have also been made. However, when such a film is attached to a polarizer using an existing water-based adhesive or the like, sufficient adhesive strength can not be obtained, and properties such as water resistance and heat resistance deteriorate.

[Patent Document 1] JP-A-06-51117

The present application provides an adhesive composition, a polarizing plate and a liquid crystal display device.

Exemplary adhesive compositions of the present application may include alicyclic or aromatic epoxy compounds, linear epoxy compounds and diluents. The adhesive composition may be, for example, a photocurable adhesive composition. In addition, the adhesive composition may be a solvent-free adhesive composition. The adhesive composition may be an adhesive composition for an optical film. The term "adhesive composition for an optical film" is intended to encompass, for example, an optical film such as a polarizer, a polarizer protective film, a polarizing plate, a retardation film, an anti-glare film, a wide viewing angle compensation film, May mean an adhesive composition used for adhering a laminate to an adherend such as a liquid crystal panel or the like. The term polarizer refers to a functional film having a polarizing function or a sheet itself. The polarizing plate has an optical element having a structure in which a polarizing protective film or other functional optical film or sheet is attached to one or both surfaces of the polarizing element It can mean.

In one example, the adhesive composition can be used as an adhesive composition for a polarizer. The term " adhesive composition for polarizer " may mean, for example, an adhesive composition used for attaching a protective film or other optical film to a polarizer.

Further, the term " photocurable adhesive composition " may mean an adhesive composition which can be cured by irradiation with electromagnetic waves to be an adhesive. The categories of electromagnetic waves include, but are not limited to, microwaves, infrared (IR), ultraviolet (UV), X-rays and gamma rays, as well as alpha-particle beams, proton beams, neutron beams a particle beam such as a beam and an electron beam, and the like.

The adhesive composition includes an alicyclic epoxy compound or an aromatic epoxy compound. The term "alicyclic epoxy compound" may mean a compound containing at least one alicyclic epoxy group, wherein the "alicyclic epoxy group" includes an aliphatic saturated hydrocarbon ring, and the two carbon atoms constituting the ring are also May mean a functional group forming an epoxy group. In addition, the term " aromatic epoxy compound " may mean an aromatic compound containing at least one epoxy group.

The alicyclic or aromatic epoxy compound can ensure the mechanical and thermal properties of the adhesive and improve the durability of the optical film structure including the adhesive.

As the alicyclic epoxy compound, for example, epoxycyclohexylmethyl epoxycyclohexanecarboxylate compound; Epoxycyclohexanecarboxylate compounds of alkanediol; An epoxycyclohexylmethyl ester compound of dicarboxylic acid; Epoxycyclohexyl methyl ether compounds of polyethylene glycol; Epoxycyclohexyl methyl ether compounds of alkanediol; Diepoxy trispyrene compounds; Diepoxy monospiro compounds; Vinylcyclohexene diepoxide compounds; An epoxycyclopentyl ether compound or a diepoxy tricyclodecane compound, and the like. As the above-mentioned compounds, for example, compounds represented by the following general formulas (1) to (10) are exemplified.

[Chemical Formula 1]

In Formula 1, R ₁ and R ₂ each independently represent hydrogen or an alkyl group.

(2)

In the formula (2), R ₃ and R ₄ each independently represent hydrogen or an alkyl group, and n represents an integer of 2 to 20.

(3)

In the above formula (3), R ₅ and R ₆ each independently represent hydrogen or an alkyl group, and p represents an integer of 2 to 20.

[Chemical Formula 4]

In the formula (4), R ₇ and R ₈ each independently represent hydrogen or an alkyl group, and q represents an integer of 2 to 20.

[Chemical Formula 5]

In the formula (5), R ₉ and R ₁₀ each independently represent hydrogen or an alkyl group, and r represents an integer of 2 to 20.

[Chemical Formula 6]

In Formula 6, R ₁₁ and R ₁₂ each independently represent hydrogen or an alkyl group.

(7)

In Formula 7, R ₁₃ and R ₁₄ each independently represent hydrogen or an alkyl group.

[Chemical Formula 8]

In Formula 8, R ₁₅ represents hydrogen or an alkyl group.

[Chemical Formula 9]

In the above formula (9), R ₁₆ and R ₁₇ each independently represent hydrogen or an alkyl group.

[Chemical formula 10]

In Formula 10, R ₁₈ represents hydrogen or an alkyl group.

The term "alkyl group" as used herein may mean an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, unless otherwise specified. The alkyl group may have a linear, branched or cyclic structure. In addition, the alkyl group may be optionally substituted by one or more substituents.

Examples of the substituent which may be optionally substituted in the specific functional group or compound in the present invention include an alkyl group, an alkoxy group, an alkenyl group, an epoxy group, a cyano group, a carboxyl group, an acryloyl group, a methacryloyl group, A chloro group, a chloro group, a chloro group,

Examples of the alicyclic epoxy compound include epoxycyclohexylmethyl epoxycyclohexanecarboxylate compounds, epoxycyclohexanecarboxylate compounds of alkanediol, epoxycyclohexylmethyl ester compounds of dicarboxylic acids or epoxycyclohexylmethyl ethers of alkanediol Specifically, 7-oxabicyclo [4,1,0] heptane-3-carboxylic acid and (7-oxa-bicyclo [4,1,0] hept- (Compound in which R < ₁ > and R < ₂ > are hydrogen in the above formula (1)); Ester of 4-methyl-7-oxabicyclo [4,1,0] heptane-3-carboxylic acid with (4-methyl-7-oxa-bicyclo [ Cargo (in the formula 2, R ₁ is 4-CH ₃ and R ₂ is 4-CH ₃ ); An esterified product of 7-oxabicyclo [4,1,0] heptane-3-carboxylic acid and 1,2-ethanediol (compound of Formula 3 wherein R ₃ and R ₄ are hydrogen and n is 1); (7-oxabicyclo [4,1,0] hept-3-yl) methanol and adipic acid (compound of formula 4 wherein R ₅ and R ₆ are hydrogen and p is 2); (4-methyl-7-oxabicyclo [4,1,0] hept-3-yl) methanol and adipic acid (wherein R ₅ and R ₆ are 4-CH ₃ and p is 2); And ethers of (7-oxabicyclo [4,1,0] hept-3-yl) methanol and 1,2-ethanediol in which R ₉ and R ₁₀ are hydrogen and r is 1 ) May be exemplified.

As the alicyclic epoxy compound, for example, a bifunctional epoxy compound, that is, a compound having two epoxies can be used, and a compound in which both epoxy groups are all alicyclic epoxy groups can be used, but the present invention is not limited thereto .

Examples of the aromatic epoxy compound include aromatic compounds such as bisphenol A epoxy, bisphenol F epoxy, bisphenol S epoxy, brominated bisphenol epoxy, and the like; Novolak type epoxy resins such as phenol novolak type epoxy resins and cresol novolak type epoxy resins; Cresol epoxy resin, resorcinol glycidyl ether, and the like, but are not limited thereto.

The linear epoxy compound contained in the adhesive composition can serve to improve the flexibility and adhesive force of the adhesive after curing while maintaining the viscosity of the adhesive composition at an appropriate level, for example.

As the linear epoxy compound, for example, an epoxy compound having an aliphatic epoxy group rather than an alicyclic epoxy group, that is, an aliphatic epoxy compound can be used. Such compounds include, for example, polyglycidyl ethers of aliphatic polyhydric alcohols; Polyglycidyl ethers of alkylene oxide adducts of aliphatic polyhydric alcohols; Polyglycidyl ethers of polyester polyols of aliphatic polyhydric alcohols and aliphatic polyvalent carboxylic acids; Polyglycidyl ethers of aliphatic polyvalent carboxylic acids; Polyglycidyl ethers of polyester polycarboxylic acids of aliphatic polyhydric alcohols and aliphatic polyvalent carboxylic acids; Dimers, oligomers or polymers obtained by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate; Or an oligomer or polymer obtained by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers can be exemplified. In one example, an aliphatic polyhydric alcohol or polyglycidyl Diesters may be used, but are not limited thereto.

Examples of the aliphatic polyhydric alcohols include aliphatic polyhydric alcohols having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms, for example, ethylene 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,4-butanediol, neopentyl Pentanediol, 2-methyl-2,4-pentanediol, 2-methyl-2,4-pentanediol, Pentanediol, 1,6-hexanediol, 1,7-heptanediol, 3,5-heptanediol, 1,8-octanediol, 2-methyl- Aliphatic diols such as diol, 1,9-nonanediol, and 1,10-decanediol; Alicyclic diols such as cyclohexane dimethanol, cyclohexanediol, hydrogenated bisphenol A and hydrogenated bisphenol F; Trimethylol ethane, trimethylol propane, hexitol, pentitol, glycerin, polyglycerin, pentaerythritol, dipentaerythritol, tetramethylol propane and the like.

Examples of the alkylene oxides include alkylene oxides having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, For example, ethylene oxide, propylene oxide, or butylene oxide may be used.

Examples of the aliphatic polycarboxylic acid include aliphatic polycarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, dodecanedioic acid, , 2-methyladipic acid, 3-methyladipic acid, 3-methylpentanedioic acid, 2-methyloctanedioic acid, 3,8-dimethyldecanedioic acid, 3,7-dimethyldecanedioic acid, Dicarboxylic acid, 1,2-cyclopentanedicarboxylic acid, 1,3-cyclopentanedicarboxylic acid, 1,2-cyclohexanedicarboxylic acid, 1,3-cyclohexanedicarboxylic acid, 1 , 4-cyclohexanedicarboxylic acid, 1,4-dicarboxylmethylene cyclohexane, 1,2,3-propanetricarboxylic acid, 1,2,3,4-butanetetracarboxylic acid, 1,2 , 3,4-cyclobutanetetracarboxylic acid, and the like, but are not limited thereto.

The linear epoxy compound may be contained in an amount of 30 to 300 parts by weight or 50 to 250 parts by weight based on 100 parts by weight of the alicyclic or aromatic epoxy compound. Unless otherwise specified, the unit weight portion in the present specification may mean a weight ratio between the respective components. The weight ratio of the linear epoxy compound can be maintained as described above so that the viscosity of the composition can be maintained in an appropriate range and the flexibility and adhesive force of the adhesive can be maintained at a good level.

Examples of the diluent contained in the adhesive composition include one or more functional groups capable of participating in a cationic reaction or a radical reaction and having a viscosity at 25 DEG C of 30 cP or less, 25 cP or 20 cP or less, May be used. The lower limit of the viscosity of the diluent at 25 캜 is not particularly limited, and may be, for example, about 1 cP.

Examples of the diluent include an epoxy type diluent, a vinyl ether type diluent, an oxetane type diluent, and an acrylic type diluent.

As the epoxy diluent, for example, a compound represented by the following formula (11) may be used.

(11)

In the formula (11), R ^a to R ^f are each independently a hydrogen atom, an alkyl group, an alkenyl group, an oxiranyl group, an alkoxycarbonyl group or an alkyloxiranyl group.

The term "alkenyl group" as used herein may mean an alkenyl group having 2 to 20 carbon atoms, 2 to 16 carbon atoms, 2 to 12 carbon atoms, 2 to 8 carbon atoms, or 2 to 4 carbon atoms unless otherwise specified. The alkenyl group may have a linear, branched or cyclic structure. In addition, the alkenyl group may be optionally substituted by one or more substituents.

The term " alkoxycarbonyl group " as used herein may mean a carbonyl group substituted with an alkoxy group as a monovalent residue, unless otherwise specified, and examples of the alkoxycarbonyl group include " -C (= O) -OR "(wherein R represents an alkyl group).

In the present specification, the term "alkoxy group" may be an alkoxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms unless otherwise specified. The alkoxy group may be, for example, straight-chain, branched-chain or cyclic, and may be optionally substituted by one or more substituents.

는, 그 부분이 모 화합물에 연결되는 것을 의미할 수 있다.).In the present specification, the term "alkyloxiranyl" may mean an oxiranyl group substituted with an alkyl group as a monovalent residue unless otherwise specified, and may be represented by, for example, the following formula (A) In formula (A), R is an alkyl group,

May mean that the moiety is linked to the parent compound).

(A)

In one example, the epoxy-based diluent is a compound wherein R ^a and R ^b are each independently hydrogen or an alkyl group, for example, an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, R ^c is a to R ^f 2, one or three or more hydrogen atoms of the substituents other than hydrogen atoms are oxiranyl group, having 2 to 12 carbon atoms, having 2 to 8 carbon atoms or an alkenyl group, having 1 to 12 carbon atoms, having a carbon number of 2 to 4 carbon atoms An alkoxycarbonyl group having 1 to 8 carbon atoms, an alkoxycarbonyl group having 1 to 4 carbon atoms, or an alkyloxiranyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or an alkyl group having 1 to 4 carbon atoms may be used, no.

As the epoxy diluent, a compound represented by the following general formula (12) may also be used.

[Chemical Formula 12]

In the above formula (12), R ^g may be an alkyloxyalkyl group.

In the present specification, the alkyloxyalkyl group may mean, for example, a substituent represented by the following formula (B).

[Chemical Formula B]

는, 그 부분이 모 화합물에 연결되는 것을 의미할 수 있다.Wherein R is an alkyl group, A is an alkylene group or an alkylidene group,

May mean that the moiety is linked to the parent compound.

The term "alkylene group" or "alkylidene group" as used herein means an alkylene group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, Or an alkylidene group. The alkylene or alkylidene group may be, for example, linear, branched or cyclic, and may optionally be substituted by one or more substituents.

In one example of the above epoxy-based diluents is the abovementioned formula (12) is R ^g, wherein R is an alkyl group having 1 to 12 carbon atoms, having 1 to 8 carbon atoms, having from 1 to 4 carbon atoms in a substituent of the formula B, A has from 1 to 12 carbon atoms , An alkylene group having 1 to 8 carbon atoms, and an alkylidene group having 1 to 4 carbon atoms, but the present invention is not limited thereto.

As the vinyl ether diluent, for example, a compound represented by the following formula (13) may be used.

[Chemical Formula 13]

In the above formula (13), R ^h is an alkyl group, a hydroxyalkyl group or an alkyloxyalkyl group.

In one example, the vinyl ether diluent is a compound wherein R ^h is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms, or an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms And R is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms and 1 to 4 carbon atoms, and A is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, 1 to 8 carbon atoms, An alkylene group having 1 to 4 carbon atoms or an alkyloxyalkyl group having an alkylidene group can be used, but the present invention is not limited thereto.

As the oxethane-based diluent, for example, a compound represented by the following formula (14) may be used.

[Chemical Formula 14]

In the above formula (14), R ⁱ is an alkyl group, and R ^j is a hydroxyalkyl group, alkyloxyalkyl group or alkyloxetanylalkyloxyalkyl group.

In the present specification, the alkyloxetanylalkyloxyalkyl group may mean a substituent represented by the following formula (C) unless otherwise specified.

≪ RTI ID = 0.0 &

는, 그 부분이 모 화합물에 연결되는 것을 의미할 수 있다.Wherein R is an alkyl group, L ₁ and L ₂ are each independently an alkylene group or an alkylidene group,

May mean that the moiety is linked to the parent compound.

In one example, okse tangye diluent with, and in the formula 14 R ⁱ is an alkyl group having 1 to 12 carbon atoms, having 1 to 8 carbon atoms or having from 1 to 4, R ^j is from 1 to 12 carbon atoms, having 1 to 8 carbon atoms or carbon atoms Wherein R is an alkyl group having 1 to 12 carbon atoms and 1 to 8 carbon atoms and A is an alkylene group or alkylidene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, 1 to 4 carbon atoms, An alkyloxyalkyl group or an alkyloxyalkyl group of the above formula (C) wherein R is a C 1-12, C 1-8 or C 1-4 alkyl group, L ₁ and L ₂ each independently represent a C 1-12, a C 1-8, 4, or an alkyloxetanylalkyloxyalkyl group, which is an alkylidene group, but is not limited thereto.

As the acrylic diluent, for example, a compound represented by the following formula (15) may be used.

[Chemical Formula 15]

In the above formula (15), R ^k is hydrogen or an alkyl group, and R ¹ is a cation-reactive functional group, such as an epoxy group, a vinyloxy group or an oxetanyl group such as a glycidyl group.

As the acrylic diluent, compounds represented by the general formula (15) wherein R ^k is hydrogen or an alkyl group having 1 to 4 carbon atoms and R ¹ is an epoxy group such as a glycidyl group may be used, but the present invention is not limited thereto.

The diluent may be included in the composition in an amount of 5 to 200 parts by weight or 5 to 150 parts by weight based on 100 parts by weight of the total amount of the epoxy compound, that is, the alicyclic or aromatic epoxy compound and the linear epoxy compound . At such a ratio, the viscosity of the composition can be maintained at an appropriate level and the physical properties of the final adhesive can be secured.

The adhesive composition may further comprise a hydro-hardening agent. The term " hydroxyl clock curing agent " means a compound containing at least one, for example, one to four, hydroxy groups as a functional group capable of curing the above adhesive composition.

As the curing agent, an aliphatic diol, a polyether diol, a polycarbonate diol, a polycaprolactone diol, a polyester diol or a polyol compound and the like can be exemplified.

As the aliphatic diol, for example, a compound represented by the following formula (16) may be used.

[Chemical Formula 16]

In the above formula (16), A is an alkylene group or an alkylidene group.

In Formula 16, A may be, for example, a linear or branched alkylene or alkylidene group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, or 1 to 8 carbon atoms.

Examples of the diol compound represented by Formula 16 include 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 2-methyl- Methyl-1,5-pentanediol, and the like, but are not limited thereto.

As the polyether diol, for example, a compound represented by the following general formula (17) can be used.

[Chemical Formula 17]

In Formula 17, X and Y are each independently an alkylene group or an alkylidene group, and t represents an integer of 1 to 10.

X and Y in the formula (17) are, for example, independently a linear, branched or cyclic alkylene group or an alkylidene group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms have.

In Formula 17, t may be, for example, 1 to 8, 1 to 6, or 1 to 4.

Examples of the compound represented by the formula (17) include di-, tri- or poly-ethylene glycol, di-, tri- or poly-propylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol or polydecamethylene glycol But is not limited thereto.

As the polycarbonate diol, for example, a polycarbonate of polytetrahydrofuran, a polycarbonate of 1,6-hexanediol, or a compound of the following formula (18) can be used. For example, a compound of the formula have.

[Chemical Formula 18]

Wherein Q and W are each independently a divalent hydrocarbon group of 2 to 12 carbon atoms, U has the same structure as Q or W, y is an integer of 2 to 150, and z is an integer of 0 to 150 , and y + z is 2 to 200.

The polycarbonate diol represented by the above formula (18) can be produced by a known method such as, for example, ester exchange reaction of a diol compound and a carbonate compound or polycondensation reaction of a diol compound and phosgene. In this case, the diol compounds to be used include 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,9- Diol, and the like, but are not limited thereto.

As the polycaprolactone diol, for example, polycaprolactone diol obtained by reacting? -Caprolactone with a diol can be used. Examples of the diol in this case include ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetramethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1,4-cyclohexane dimethanol, 1,4-butane diol and the like.

As the polyester diol, for example, a polymer of an aliphatic diol compound and an aliphatic dicarboxylic acid compound can be used. In this case, as the aliphatic diol compound, for example, a diol compound of the above-mentioned formula (16) can be used, and examples of the aliphatic dicarboxylic acid compound include malonic acid, succinic acid, glutaric acid, adipic acid, .

The term polyol compound in the present application may mean a compound having three or more hydroxy groups. Examples of the polyol compound include a polyether polyol obtained by modifying a polyhydric alcohol with a cyclic ether compound. Examples of the polyol compound include trimethylol propane, glycerin, pentaerythritol, sorbitol, sucrose, and quadrolol. Examples of the cyclic ether compound include ethylene oxide (EO), propylene oxide PO), butylene oxide or tetrahydrofuran. Examples of the polyether polyol include ethylene oxide modified trimethylol propane, propylene oxide modified trimethylol propane, tetrahydrofuran modified trimethylol propane, ethylene oxide modified glycerin, propylene oxide modified glycerin, tetrahydrofuran modified glycerin, ethylene Ethylene oxide modified sucrose, ethylene oxide modified sucrose, propylene oxide modified sucrose, or propylene oxide modified sucrose, or an ethylene oxide modified pentaerythritol, an ethylene oxide modified pentaerythritol, an oxide modified pentaerythritol, a propylene oxide modified pentaerythritol, a tetrahydrofuran modified pentaerythritol, Ethylene oxide modified quadrrol, and the like, but the present invention is not limited thereto.

In one example, as the hardener, an aliphatic diol or polyether polyol or the like may be used among the above compounds, and for example, the polyether polyol of the above formula (17) may be used, but the present invention is not limited thereto.

The adhesive composition may contain 0.3 to 3 parts by weight of the hydroxy-clockwise curing agent relative to 100 parts by weight of the total weight of the epoxy compound, for example, the alicyclic or aromatic epoxy compound and the linear epoxy compound. In another example, the adhesive composition may include an amount such that the hydroxyl group equivalent of the curing agent is from 0.001 to 1 equivalent based on 1 equivalent of the epoxy group of the total epoxy compound contained in the composition. By adjusting the content of the curing agent as described above, the workability and adhesive strength of the adhesive can be kept excellent.

The adhesive composition may further comprise a photo cationic initiator. The term " photo cationic initiator " means a compound capable of initiating cationic polymerization by irradiation with electromagnetic waves or a compound capable of generating a compound capable of initiating cationic polymerization by irradiation of electromagnetic waves.

The kind of the photo cationic initiator is not particularly limited and a known photo cationic initiator such as an aromatic diazonium salt, an aromatic iodo aluminum salt, an aromatic sulfonium salt or an iron-arene complex can be used. For example, Sulfonium salts may be used, but are not limited thereto.

The adhesive composition may contain 0.01 to 10 parts by weight or 0.1 to 3 parts by weight of the photo cationic initiator relative to 100 parts by weight of the total weight of the epoxy compound, for example, the total epoxy compound present in the composition . If the content of the photo cationic initiator is too small, there is a fear that sufficient curing will not proceed. If the content is too large, the content of the ionic substance after curing will increase to increase the hygroscopicity of the adhesive and deteriorate durability, ) Is formed, which is disadvantageous from the viewpoint of optical durability, and corrosion may occur depending on the base material. Therefore, an appropriate content range can be selected in consideration of this point.

The adhesive composition may further comprise, if necessary, an appropriate radical initiator when, for example, the diluent or the like contains a radically polymerizable functional group. As the radical initiator, for example, a photo radical initiator can be used as an initiator capable of inducing a radical polymerization reaction or the like by irradiation of an electromagnetic wave.

As the photo radical initiator, for example, benzoin, hydroxy ketone, amino ketone or phosphine oxide photoinitiators may be used. In one example, benzoin, benzoin methyl ether, benzoin ethyl ether , Benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethyl anino acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy- Methyl-1 - [4- (methylthio) phenyl] -2-morpholinone, 2-methyl- (2-hydroxy-2-propyl) ketone, benzophenone, p-phenylbenzophenone, 4,4'-diethylaminobenzo 2-ethyl anthraquinone, 2-t-butyl anthraquinone, 2-amino anthraquinone, 2-methyl thioxanthone, 2-ethyl thioxanthone, 2- 2-methyl-1 - [(2-hydroxy-2-methyl-1- < / RTI > methyl) benzoic acid ester, 4- (1-methylvinyl) phenyl] propanone] or 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide.

The adhesive composition may contain the radical initiator in a proportion of, for example, 0.01 to 10 parts by weight or 0.1 to 5 parts by weight based on 100 parts by weight of the total weight of the total epoxy compound contained in the adhesive composition, The ratio can be appropriately changed depending on, for example, specific examples of the compound having a radically polymerizable functional group.

The adhesive composition may further comprise, in addition to the above-mentioned components, one or more additives such as ultraviolet stabilizer, antioxidant, colorant, reinforcing agent, filler, defoamer, surfactant, optical thickener and plasticizer have.

The adhesive composition may have a coating viscosity of 60 cP or less, 50 cP or less, 40 cP or less, 30 cP or less or 30 cP or less at room temperature, for example, at about 23 캜 or about 25 캜. The term coating viscosity may refer to the viscosity of the adhesive composition, i.e., the coating, at the time it is applied to the coating process to form the adhesive. The coating viscosity of the adhesive composition can be adjusted, for example, by adjusting the type and / or ratio of the diluent. The lower limit of the coating viscosity of the adhesive composition is not particularly limited, and may be, for example, about 5 cP or 10 cP.

The present application is also directed to a polarizing plate. An exemplary polarizer comprises a polarizer; And a protective film adhered to one or both surfaces of the polarizer by an adhesive. The adhesive to which the protective film is adhered can be formed, for example, by curing the above-described adhesive composition.

The type of the polarizer included in the polarizing plate is not particularly limited, and for example, general polarizers known in the art such as polyvinyl alcohol polarizers and the like can be employed without limitation.

A polarizer is a functional film or sheet capable of extracting only light vibrating in one direction from incident light while vibrating in various directions. The polarizer may be, for example, a form in which a dichroic dye is adsorbed and oriented on a polyvinyl alcohol-based resin film. The polyvinyl alcohol-based resin constituting the polarizer can be obtained by, for example, gelling a polyvinyl acetate-based resin. In this case, the polyvinyl acetate-based resin that can be used may include not only homopolymers of vinyl acetate but also copolymers of vinyl acetate and other comonomers copolymerizable therewith. Examples of the comonomer include, but are not limited to, one or more kinds of acrylamides having unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and ammonium groups. The degree of gelation of the polyvinyl alcohol-based resin may be generally from 85 mol% to 100 mol% or 98 mol% or more. The polyvinyl alcohol resin may be further modified. For example, polyvinyl formal or polyvinyl acetal modified with aldehydes may be used. The degree of polymerization of the polyvinyl alcohol-based resin may be about 1,000 to 10,000 or about 1,500 to 5,000.

A polyvinyl alcohol-based resin may be formed and used as the original film of the polarizer. The method of forming the polyvinyl alcohol-based resin is not particularly limited, and a general method known in this field can be used. The thickness of the original film formed of a polyvinyl alcohol-based resin is not particularly limited, and can be suitably controlled within a range of, for example, 1 m to 150 m. The thickness of the original film can be controlled to 10 mu m or more in consideration of easiness of drawing and the like.

The polarizer may be a film obtained by stretching a polyvinyl alcohol-based resin film (e.g., uniaxial or biaxial stretching); Dyeing and adsorption of dichroic dye; Boric acid treatment; And a water washing step. As the dichroic dye, iodine or dichroic organic dyes may be used.

The kind of the protective film to be adhered to the one side or both sides of the polarizer by the adhesive is not particularly limited. Examples of the protective film include a cellulose film (ex, triacetylcellulose (TAC)), amorphous polyolefin film, polyester resin film, acrylic resin film, polycarbonate resin film, polysulfone resin film, A film such as an alicyclic polyimide resin film or a cyclic olefin (COP) resin film can be used. When a protective film is attached to both surfaces of the polarizer, at least one film is preferably an amorphous polyolefin film, a polyester resin film, an acrylic resin film, a polycarbonate resin film, a polysulfone resin film, an alicyclic polyimide resin Film or a cyclic olefin (COP) based resin film, but the present invention is not limited thereto.

When a protective film is attached to both sides of the polarizer, the protective film may be the same kind or a different kind of film.

1 and 2 are diagrams schematically showing a polarizing plate according to various examples of the present application. 1, in the polarizing plate 1 of the present application, a cellulose-based film 13 such as triacetylcellulose (TAC) is attached to one surface of a polarizer 11 by an adhesive 12a, A film other than a cellulose-based film, for example, an acrylic film 14 or the like may be adhered by an adhesive 12b. 2, the same type of protective films 14a and 14b may be attached to both sides of the polarizer 11 by means of the adhesives 12a and 12b of the present invention. In this case, the protective films 14a and 14b may be selected from films other than the cellulose-based film, for example, an acrylic film or the like may be used.

The adhesive can exhibit an excellent adhesive force even when the pretreatment using NaOH is not performed on a cellulose-based film such as triacetyl cellulose (TAC), which is commonly used as a protective film for existing polarizers, A polyester resin film, an acrylic resin film, a polycarbonate resin film, a polysulfone resin film, an alicyclic polyimide resin film, or the like, Or a cyclic olefin (COP) based resin film.

The adhesive to which the protective film is adhered may have a thickness of, for example, more than 0 占 퐉, 10 占 퐉 or less, 7 占 퐉 or 5 占 퐉 or less.

The method for producing the polarizing plate is not particularly limited. For example, a method of preliminarily forming a layer of an adhesive composition through a precoating method, then laminating a polarizer and a protective film through the adhesive layer, and curing the layer of the adhesive composition to form an adhesive layer, A method in which a polarizer and a protective film are laminated by applying a liquid droplet method or the like commonly used for curing the adhesive composition, or the like can be used.

The manner of curing the adhesive composition is not particularly limited. For example, a suitable electromagnetic wave, for example, a method of irradiating ultraviolet rays may be used so that the reaction of the initiator in the adhesive composition can be induced. The irradiation condition of the electromagnetic wave from the, for example, an electromagnetic wave of a UV B region can be irradiated with a light intensity of about 500 mJ / cm ² to 1,500 mJ / cm ² intensity and 150 mW / cm ² to 400 mW / cm ² of , But is not limited thereto.

The present application also relates to a liquid crystal display device. Exemplary liquid crystal display devices include, for example, a liquid crystal panel; And the polarizer attached to one side or both sides of the liquid crystal panel.

The type of the liquid crystal panel included in the liquid crystal display device is not particularly limited. For example, the present invention is not limited to the type, but various passive matrix methods including TN (Twisted Neumatic) type, STN (Super Twisted Neumatic) type, F (ferroelectric) type and PD (polymer dispersed LCD) type; Various active matrix systems including two-terminal and three-terminal; Any known liquid crystal panel including a horizontal mode (IPS mode) panel and a vertical mode (VA mode) panel can be applied. Other types of other structures included in the liquid crystal display device and the manufacturing method thereof are not particularly limited, and general structures in this field can be employed without any limitations.

In this application, it is possible to provide an adhesive composition in which an appropriate viscosity is maintained and applied to, for example, an optical film to maintain excellent uniformity in thickness, adhesion, durability and water resistance. The above adhesive composition can effectively adhere a polarizing film to a film exhibiting, for example, hydrophobicity and low moisture permeability, and can provide an adhesive excellent in optical properties such as transparency.

1 and 2 are sectional views schematically showing an exemplary polarizing plate.

Hereinafter, the composition will be described in detail by way of examples and comparative examples, but the scope of the composition is not limited by the following examples.

In the following Examples and Comparative Examples, physical properties were evaluated in the following manner.

1. Evaluation of Viscosity

The viscosity was measured while adjusting the angular velocity within a range of 5 to 50 rpm at room temperature by adding 11 mL of the adhesive composition to a viscosity measuring instrument (Toki Sangyo TV-22 viscometer).

<Evaluation Criteria of Viscosity>

?: When the viscosity at 25 占 폚 is less than 30 cP

?: A viscosity at 25 ° C of 30 cP to 50 cP

X: Viscosity at 25 캜 exceeds 50 cP

2. Exfoliation  evaluation

A polarizing plate having a structure including a protective film, a layer of an adhesive composition, a polyvinyl alcohol polarizer, a layer of an adhesive composition and a protective film prepared in Examples or Comparative Examples was attached to a glass plate using a double-sided tape, , And then lamination was performed so that each layer of the polarizing plate was completely pressed. Thereafter, irradiation, annealing and aging of the ultraviolet ray described in Examples and Comparative Examples were carried out. Then, the peel force was evaluated by peeling the protective film from the polarizer at a peeling angle of 90 degrees and a peeling rate of 5 mm / sec in the longitudinal direction of the polarizing plate using the UTM equipment.

<Peel strength evaluation standard>

○: When the peeling force is 200 gf / 2 cm or more

?: When the peel force is 150 gf / 2 cm or more and less than 200 gf / 2 cm

X: When the peel force is less than 100 gf / 2 cm

3. Evaluation of water resistance

The polarizing plates prepared in Examples and Comparative Examples were cut to a width of 2 cm and a length of 5 cm, and the specimens were placed in a thermostatic chamber at 60 ° C to evaluate the water resistance according to the following criteria.

<Water-resistance evaluation standard>

&Amp; cir &amp;: no change in appearance of the polarizing plate for more than 8 hours, no peeling or the like occurred

?: No change in appearance of the polarizing plate for 4 hours or more, and peeling or the like did not occur

X: When the appearance of the polarizing plate changes in less than 4 hours, or peeling occurs between the films

4. Evaluation of optical properties

Tests (heat resistance durability test) in which the polarizing plate prepared in Examples or Comparative Examples were kept in an oven at 80 ° C for 100 hours for a specimen produced by cutting the specimen so that the width and width of the specimen were 10 cm and 15 cm, respectively, and (Damp heat resistance durability test) in which the temperature was maintained at 60 DEG C and 90% relative humidity for 100 hours, respectively, to determine whether the polarizer was good or bad, and the optical characteristics were evaluated according to the following criteria. In the above, the case in which iodine aggregation and yellowing did not occur in the polarizing plate after each test was regarded as good, and the case where any one of the above occurred was evaluated as defective.

&Lt; Evaluation Criteria of Optical Properties &

○: When both the heat resistance durability test and the anti-wet heat durability test are all good

△: When the polarizer is defective in the heat resistance durability test or the anti-wet heat durability test

X: When the polarizer is defective in heat resistance durability test and anti-wet heat durability test

5. Thermal shock  evaluation

The polarizing plates prepared in Examples and Comparative Examples were cut to a size of 10 cm in width and 10 cm in length, placed in a heat-shocked oven, maintained at -40 ° C. for 30 minutes, The temperature was raised to 80 DEG C and kept for 30 minutes to form one cycle, and the above procedure was repeated for 100 cycles. Next, after 100 cycles, it was examined whether the iodine aggregation occurred in the polarizing plate and whether there was a crease between each interface, and the thermal shock resistance was evaluated according to the following criteria.

&Lt; Criteria for evaluation of thermal shock property &

&Amp; cir &amp;: No defect occurred in the polarizer after 100 cycles

?: When a variable portion within 1 mm occurs after 100 cycles

X: Variable sticking or iodine aggregation exceeding 1 mm after 100 cycles

Example  One

Preparation of adhesive composition

Cycloaliphatic epoxy compounds such as 7-oxa-bicyclo [4,1,0] hetan-3-ylmethyl 7-oxa-bicyclo [4,1,0] heptane-3-carboxylate, Celloxide 2021P, And a linear epoxy compound (butanediol diglycidylether, Mirate BDGE, Miwon Chemical) were mixed in a weight ratio of 3: 2 (alicyclic epoxy compound: linear epoxy compound). Then, cyclohexene oxide as a diluent is added in a proportion of 25 parts by weight based on 100 parts by weight of the total amount of the alicyclic and linear epoxy compounds, and the polyester polyol (D800, manufactured by BASF) 1 part by weight based on 100 parts by weight of the total weight. Subsequently, 2 parts by weight of a cationic initiator (50 wt% propylene carbonate solution of triacrylsulfonium hexafluoroantimonate, CPI 101A, San-Apro) was added in an amount of 2 parts by weight based on 100 parts by weight of the total weight of the epoxy compound, The adhesive composition was prepared by mixing for 30 minutes.

Production of Polarizer

A polyvinyl alcohol polarizer, and a biaxially stretched acrylic protective film, wherein the protective film and the polarizer are formed using the adhesive composition formed using the adhesive composition, (Hereinafter referred to as &quot; polarizing plate structure 1 &quot;) or a biaxially stretched acrylic protective film sequentially laminated, a polyvinyl alcohol polarizer and a biaxially stretched acrylic protective film, wherein the protective film and the polarizer use the adhesive composition (Hereinafter referred to as &quot; polarizing plate structure 2 &quot;). The attachment of the polarizer and the protective film was carried out in a droplet manner using a lamell roll. Specifically, after the polarizer and the protective film are adhered with an adhesive composition, ultraviolet rays (B region, light quantity: 1,000 mJ / cm ² , illuminance: 210 mW / cm ² ) After the annealing, aging was performed at room temperature for 1 day to prepare a polarizing plate.

Example  2

Instead of using an alicyclic epoxy compound, a bisphenol F type epoxy compound (liquid epoxy, TDF165, National Kagaku Kagaku) was used in a weight ratio of 1: 1 with a linear epoxy compound and bisphenol F type epoxy compound And linear epoxy compound was used in an amount of 20 parts by weight relative to 100 parts by weight of the total weight of the polarizing plate and the linear epoxy compound.

Example  3

Except that the weight ratio of the alicyclic epoxy compound and the linear epoxy compound was changed to 1: 1, to prepare a polarizing plate.

Example  4

The weight ratio of bisphenol F type epoxy compound and linear epoxy compound was changed to 1: 2 (bisphenol F type epoxy compound: linear epoxy compound), and 4-vinyl-1-cyclohexene diepoxide 4-vinyl-1-cyclohexene diepoxide) was used in an amount of 30 parts by weight based on 100 parts by weight of the total weight of the bisphenol F type epoxy compound and the linear epoxy compound, to prepare a polarizing plate.

Example  5

Vinyl-1-cyclohexene 1,2-epoxide (4-vinyl-1-cyclohexene diepoxide) was used instead of 4-vinyl-1-cyclohexene diepoxide as a diluent, Epoxide was used in an amount of 10 parts by weight based on 100 parts by weight of the total weight of the bisphenol F type epoxy compound and the linear epoxy compound, to prepare a polarizing plate.

Example  6

Instead of 1-methyl-4- (2-methyloxiran-2-yl) -7-oxa-bicyclo [4 , 1, 0] heptane (1-methyl-4- (2-methyloxiran-2-yl) -7-oxa-bicyclo [4,1,0] heptane) was added to the total weight of bisphenol F type epoxy compound and linear epoxy compound Was used in an amount of 10 parts by weight based on 100 parts by weight of the polarizing plate.

Example  7

2-ethylhexyl glycidyl ether was used instead of 4-vinyl-1-cyclohexene diepoxide as a diluent in an amount of 10 parts by weight based on 100 parts by weight of the total weight of bisphenol F type epoxy compound and linear epoxy compound The procedure of Example 4 was repeated to prepare a polarizing plate.

Example  8

Except that 100 parts by weight of 3-ethyl-3-hydroxymethyloxetane was used as a diluent instead of cyclohexene oxide in the total weight of 100 parts by weight of the alicyclic epoxy compound and the linear epoxy compound, To prepare a polarizing plate.

Example  9

Instead of 4-vinyl-1-cyclohexene diepoxide as a diluent, 10 parts by weight of glycidyl methacrylate was added to 100 parts by weight of the total weight of bisphenol F type epoxy compound and linear epoxy compound And a radical initiator (Irgacure 184) was added in an amount of 3 parts by weight based on 100 parts by weight of the above glycidyl methacrylate, to thereby prepare a polarizing plate.

Example  10

A polarizing plate was prepared in the same manner as in Example 1 except that ethylene glycol vinyl ether was used as a diluent instead of cyclohexene oxide in an amount of 50 parts by weight based on 100 parts by weight of the total amount of an alicyclic epoxy compound and a linear epoxy compound.

Comparative Example  One

A polarizing plate was produced in the same manner as in Example 1 except that cyclohexene oxide as a diluent was not used.

Comparative Example  2.

A polarizing plate was produced in the same manner as in Example 4 except that cyclohexene oxide as a diluent was not used.

Comparative Example  3.

A polarizing plate was produced in the same manner as in Example 1 except that no alicyclic epoxy compound was used.

Comparative Example  4.

A polarizing plate was produced in the same manner as in Example 1 except that no linear epoxy compound was used.

The measured results are summarized in Tables 1 and 2 below.

Example One 2 3 4 5 6 7 8 9 10 Viscosity ○ ○ ○ ○ ○ ○ ○ ○ ○ ○ Peel force TAC ○ ○ ○ ○ ○ ○ △ ○ ○ △ acryl ○ ○ ○ △ ○ △ △ ○ ○ ○ Water resistance Polarizer Structure 1 ○ ○ ○ ○ ○ ○ ○ ○ ○ △ Polarizer structure 2 ○ ○ ○ ○ ○ ○ ○ ○ ○ △ optics
characteristic Polarizer Structure 1 ○ ○ ○ ○ ○ ○ ○ ○ ○ ○ Polarizer structure 2 ○ ○ ○ ○ ○ △ △ ○ ○ ○ Thermal shock
characteristic Polarizer Structure 1 ○ ○ ○ ○ △ △ △ ○ ○ △ Polarizer structure 2 ○ ○ ○ ○ △ △ △ ○ ○ △ Peeling force (TAC): Peeling force between the triacetyl cellulose protective film and the polarizer in the polarizer structure 1
Peeling force (Acrylic): peeling force between polarizer and acrylic protective film in polarizer structure 2

Comparative Example One 2 3 4 Viscosity X X ○ △ Peel force TAC ○ ○ △ X acryl ○ ○ X X Water resistance Polarizer Structure 1 ○ ○ ○ ○ Polarizer structure 2 ○ ○ △ ○ optics
characteristic Polarizer Structure 1 X △ △ △ Polarizer structure 2 △ △ △ X Thermal shock
characteristic Polarizer Structure 1 ○ ○ X ○ Polarizer structure 2 X X X ○ Peeling force (TAC): Peeling force between the triacetyl cellulose protective film and the polarizer in the polarizer structure 1
Peeling force (Acrylic): peeling force between polarizer and acrylic protective film in polarizer structure 2

1, 2: polarizer
11: Polarizer
12a, 12b: Adhesive
13, 14, 14a, 14b: protective film

Claims (19)

Alicyclic or aromatic epoxy compounds; Linear epoxy compounds; And a diluent having a viscosity at 25 DEG C of 30 cP or less and having at least one functional group capable of participating in a cationic reaction or a radical reaction,
Wherein the linear epoxy compound is contained in an amount of 30 to 300 parts by weight based on 100 parts by weight of the alicyclic or aromatic epoxy compound,
The diluent is a compound represented by the following general formula (12), (13) or (15), and is contained in an amount of 5 to 200 parts by weight relative to 100 parts by weight of the total weight of the alicyclic or aromatic epoxy compound and the linear epoxy compound.
Wherein the coating viscosity at 25 DEG C is 50 cP or less.
[Chemical Formula 12]

Wherein R ^g is an alkyloxyalkyl group;
[Chemical Formula 13]

In the above formula (13), R ^h is an alkyl group, a hydroxyalkyl group or an alkyloxyalkyl group;
[Chemical Formula 15]

Wherein R ^k is hydrogen or an alkyl group, and R ¹ is an epoxy group, a vinyloxy group or an oxetanyl group. The method according to claim 1, wherein the alicyclic epoxy compound is an epoxycyclohexylmethyl epoxycyclohexanecarboxylate compound; Epoxycyclohexanecarboxylate compounds of alkanediol; An epoxycyclohexylmethyl ester compound of dicarboxylic acid; Epoxycyclohexyl methyl ether compounds of polyethylene glycol; Epoxycyclohexyl methyl ether compounds of alkanediol; Diepoxy trispyrene compounds; Diepoxy monospiro compounds; Vinylcyclohexene diepoxide compounds; An epoxy cyclopentyl ether compound or a diepoxy tricyclodecane compound. The epoxy resin composition according to claim 1, wherein the aromatic epoxy compound is a bisphenol-type epoxy resin; Novolak type epoxy resins; Cresol epoxy resin or resorcinol glycidyl ether. The composition of claim 1, wherein the linear epoxy compound is selected from the group consisting of polyglycidyl ethers of aliphatic polyhydric alcohols; Polyglycidyl ethers of alkylene oxide adducts of aliphatic polyhydric alcohols; Polyglycidyl ethers of polyester polyols of aliphatic polyhydric alcohols and aliphatic polyvalent carboxylic acids; Polyglycidyl ethers of aliphatic polyvalent carboxylic acids; Polyglycidyl ethers of polyester polycarboxylic acids of aliphatic polyhydric alcohols and aliphatic polyvalent carboxylic acids; Dimers, oligomers or polymers obtained by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate; Or an oligomer or polymer obtained by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate and other vinyl monomers. delete delete delete delete delete delete delete delete The photocurable adhesive composition of claim 1, further comprising a hydroxystyrene curing agent. 14. The photocurable adhesive composition of claim 13, wherein the curing agent is a compound of formula (17): &lt; EMI ID =
[Chemical Formula 17]

In Formula 17, X and Y are each independently an alkylene group or an alkylidene group, and t is an integer of 1 to 10. The photocurable adhesive composition of claim 1, further comprising a photo cationic initiator. The photocurable adhesive composition of claim 1, further comprising a radical initiator. A polarizer; And a protective film attached to one side or both sides of the polarizer by an adhesive formed by curing the adhesive composition of claim 1. The polarizing plate according to claim 17, wherein the adhesive has a thickness of more than 0 탆 and not more than 10 탆. A liquid crystal panel; And a polarizer attached to one side or both sides of the liquid crystal panel.

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