KR20130134936A - Adhesive composition - Google Patents

Abstract

The present invention relates to an adhesive composition. The present invention provides the adhesive composition in which proper viscosity is maintained, and adhesive force, durability and water resistance etc. are excellently maintained while thickness uniformity is secured when being applied to an optical film. The adhesive composition can effectively attach a film with hydrophobicity and low moisture permeability to a polarized light device and exhibits excellent optical characteristics such as transparency etc.

Description

Adhesive composition

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

The polarizing plate which is an optical member applied to a liquid crystal display device etc. usually contains the protective film attached to one side or both sides of a polarizer. In some cases, the polarizing plate may have a structure in which a protective film is attached to one surface of the polarizer, and a layer having a function of the protective film and an additional optical function is stacked on the other surface.

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

As a protective film for light polarizers, a triacetyl cellulose (TAC) film is usually used, which is attached to the light polarizer through an aqueous polyvinyl alcohol-based adhesive or the like. By the way, the triacetyl cellulose film has a high moisture permeability, there is a problem that the polarizing plate is easily degraded under high temperature or high humidity conditions. Accordingly, there is an attempt to use a film having a low water vapor permeability as compared with a triacetyl cellulose film, for example, a thermoplastic saturated norbornene-based resin film or the like (eg, Patent Document 1). In addition, in addition, amorphous polyolefin film, polyester resin film, acrylic resin film, polycarbonate resin film, polysulfone resin film, alicyclic polyimide resin film or cyclic olefin (COP) resin film and the like Attempts have also been made. However, when the above film is attached to the polarizer using a conventional water-based adhesive or the like, sufficient adhesive strength is not obtained, and there is a problem that properties such as water resistance and heat resistance are inferior.

[Patent Document 1] Japanese Patent Application Laid-Open No. 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. In addition, the adhesive composition may be an adhesive composition for an optical film. The term adhesive composition for optical films, for example, laminates optical films such as a polarizer, a protective film for a polarizer, a polarizing plate, a retardation film, an anti-glare film, a wide viewing angle compensation film or a brightness enhancement film, or the optical film or its It may mean an adhesive composition used for attaching the laminate to an adherend such as a liquid crystal panel. The term polarizer means a functional film or sheet itself having a polarizing function, and the polarizing plate refers to an optical element having a structure in which a protective film for polarizer or another functional optical film or sheet is attached to one or both surfaces of the polarizer. Can mean.

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

In addition, the term "photocurable adhesive composition" can mean the adhesive composition which can be hardened | cured by irradiation of an electromagnetic wave, and can be an adhesive agent. In the above category of electromagnetic waves, microwaves, infrared (IR), ultraviolet (UV), X-rays and gamma rays, as well as alpha-particle beam (proton beam), Neutron beam (neutron) particle beams such as beams and electron beams, and the like.

The adhesive composition comprises 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 It 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 may secure the mechanical and thermal properties of the adhesive and improve 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 said compounds, the compound etc. which are respectively represented by following Chemical formulas 1-10 can be illustrated, for example.

[Formula 1]

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

(2)

In Formula 2, R ₃ and R ₄ each independently represent a hydrogen or an alkyl group, and n represents an integer of 2 to 20.

(3)

In Formula 3, R ₅ and R ₆ each independently represent a hydrogen or an alkyl group, and p represents an integer of 2 to 20.

[Chemical Formula 4]

In Formula 4, R ₇ and R ₈ each independently represent a hydrogen or an alkyl group, and q represents an integer of 2 to 20.

[Chemical Formula 5]

In Formula 5, R ₉ and R ₁₀ each independently represent a 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 a hydrogen or an alkyl group.

[Formula 7]

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

[Formula 8]

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

[Chemical Formula 9]

In Formula 9, R ₁₆ and R ₁₇ each independently represent a hydrogen or an alkyl group.

[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. In the above, the alkyl group may have a linear, branched or cyclic structure. In addition, the alkyl group may be optionally substituted with one or more substituents.

Substituents which may be optionally substituted in a specific functional group or compound herein, alkyl group, alkoxy group, alkenyl group, epoxy group, cyano group, carboxyl group, acryloyl group, methacryloyl group, acryloyloxy group, meta Cryloyloxy group or aryl group may be exemplified, but is not limited thereto.

As an alicyclic epoxy compound, For example, an epoxycyclohexylmethyl epoxycyclohexane carboxylate compound, the epoxycyclohexane carboxylate compound of an alkanediol, the epoxycyclohexylmethyl ester compound of dicarboxylic acid, or the epoxycyclohexylmethyl ether of an alkanediol Compounds, and the like, specifically, 7-oxabicyclo [4,1,0] heptan-3-carboxylic acid and (7-oxa-bicyclo [4,1,0] hepto-3-yl) methanol; Esterified product of R ₁ and R ₂ in Formula 1; Ester of 4-methyl-7-oxabicyclo [4,1,0] heptan-3-carboxylic acid with (4-methyl-7-oxa-bicyclo [4,1,0] hepto-3-yl) methanol Cargo (compound in which Formula ₁ , R ₁ is 4-CH ₃ , R ₂ is 4-CH ₃ ); Esters of 7-oxabicyclo [4,1,0] heptan-3-carboxylic acid with 1,2-ethanediol (compounds wherein R ₃ and R ₄ are hydrogen and n is 1 in Formula 3); Esters of (7-oxabicyclo [4,1,0] hepto-3-yl) methanol with adipic acid (compounds wherein R ₅ and R ₆ in the formula (4) are hydrogen and p is 2); Ester of (4-methyl-7-oxabicyclo [4,1,0] hepto-3-yl) methanol with adipic acid (in Formula 4, R ₅ and R ₆ are 4-CH ₃ , p is 2 compound); And etherified compounds of (7-oxabicyclo [4,1,0] hepto-3-yl) methanol with 1,2-ethanediol (wherein R ₉ and R ₁₀ in Formula 6 are hydrogen and r is 1) One or more selected from the group consisting of) can be exemplified.

As the alicyclic epoxy compound, for example, a bifunctional epoxy compound, i.e., a compound having two epoxy, may be used, and a compound in which the two epoxy groups are both alicyclic epoxy groups may be used, but is not limited thereto. .

As an aromatic epoxy compound, As an epoxy compound containing an aromatic group, For example, Bisphenol-type epoxy resins, such as bisphenol A epoxy, bisphenol F epoxy, bisphenol S epoxy, brominated bisphenol epoxy; Novolak-type epoxy resins such as phenol novolak-type epoxy resins and cresol novolak-type epoxy resins; Cresol epoxy resin or resorcinol glycidyl ether or the like may be used, but is not limited thereto.

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

As the linear epoxy compound, for example, an epoxy compound having an aliphatic epoxy group other than an alicyclic epoxy group, that is, an aliphatic epoxy compound may be used. As such a compound, For example, Polyglycidyl ether of aliphatic polyhydric alcohol; 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 oligomers or polymers obtained by vinyl polymerization of glycidyl acrylate or glycidyl methacrylate with other vinyl monomers, and in one example polyglycides of aliphatic polyhydric alcohols or their alkylene oxide adducts. Dyl ether may be used, but is not limited thereto.

As the aliphatic polyhydric alcohol, for example, an aliphatic polyhydric alcohol 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 may be exemplified. For example, ethylene Glycol, 1,2-propanediol, 1,3-propanediol, 2-methyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,4-butanediol, neopentyl Glycol, 3-methyl-2,4-pentanediol, 2,4-pentanediol, 1,5-pentanediol, 3-methyl-1,5-pentanediol, 2-methyl-2,4-pentanediol, 2 , 4-diethyl-1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 3,5-heptanediol, 1,8-octanediol, 2-methyl-1,8-octane 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.

In addition, as the alkylene oxide in the above, for example, alkylene oxide of 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 can be exemplified, for example 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 included in a ratio of 30 parts by weight to 300 parts by weight or 50 parts by weight to 250 parts by weight with respect to 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. By maintaining the weight ratio of the linear epoxy compound as described above, the viscosity of the composition can be maintained in an appropriate range, and the flexibility and adhesion of the adhesive can be maintained at an excellent level.

As the diluent included in the adhesive composition, for example, the viscosity at 25 ° C. is 30 cP or less, 25 cP or less, or 20 cP or less, and at least one or two or more functional groups capable of participating in a cationic reaction or a radical reaction The compound containing can be used. The lower limit of the viscosity at 25 ° C. of the diluent is not particularly limited, and may be, for example, about 1 cP.

As the diluent as described above, an epoxy diluent, a vinyl ether diluent, an oxetane diluent or an acrylic diluent may be exemplified.

As the epoxy-based diluent, for example, a compound represented by the following Formula 11 may be used.

[Formula 11]

R ^a to R ^f in Formula 11 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an oxiranyl group, an alkoxycarbonyl group or an alkyloxyranyl 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 with one or more substituents.

In the present specification, the term "alkoxycarbonyl group" may refer to a carbonyl group substituted with an alkoxy group as a monovalent moiety, unless otherwise specified, and the alkoxycarbonyl group is, for example, "-C (= O) -OR "(wherein R represents an alkyl group).

In addition, in this 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, linear, branched or cyclic, and may be optionally substituted with one or more substituents.

는, 그 부분이 모 화합물에 연결되는 것을 의미할 수 있다.).As used herein, unless otherwise specified, an "alkyloxyranyl group" may mean an oxiranyl group substituted with an alkyl group as a monovalent moiety, and for example, may be represented by the following Chemical Formula A (below). R in formula A is an alkyl group,

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

(A)

In one example, as the epoxy-based diluent, in Formula 11, 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, Two or three or more of R ^c to R ^f are hydrogen atoms, and the substituent which is not a hydrogen atom is an oxiranyl group, 2 to 12 carbon atoms, 2 to 8 carbon atoms or 2 to 4 alkenyl groups, 1 to 12 carbon atoms The compound may be an alkoxycarbonyl group containing 1 to 8, an alkoxy group having 1 to 4 carbon atoms or an alkyloxyranyl group including an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, but is not limited thereto. no.

As an epoxy-type diluent, the compound represented by following formula (12) can also be used.

[Chemical Formula 12]

In 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 general formula (B).

[Formula B]

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

May mean that part is linked to the parent compound.

In the present specification, the term "alkylene group" or "alkylidene group" is 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, unless otherwise specified. Or an alkylidene group. The alkylene group or alkylidene group may be, for example, linear, branched or cyclic, and may be optionally substituted with one or more substituents.

In one example, as the epoxy-based diluent, Formula 12 is R ^g , and in the substituent of Formula B, 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 1 to 12 carbon atoms. , A compound containing a substituent which is an alkylene group or an alkylidene group having 1 to 8 carbon atoms, or 1 to 4 carbon atoms can be used, but is not limited thereto.

As the vinyl ether diluent, for example, a compound of Formula 13 may be used.

[Chemical Formula 13]

In Formula 13, R ^h is an alkyl group, a hydroxyalkyl group or an alkyloxyalkyl group.

In one example, as the vinyl ether diluent, in Formula 13, R ^h is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, or 1 to 12, 1 to 8 carbon atoms or 1 to 4 carbon atoms. Or an alkyloxyalkyl group wherein 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 1 to 12 carbon atoms or 1 to 8 carbon atoms. A compound which is an alkyloxyalkyl group which is an alkylene group or an alkylidene group of 4 may be used, but is not limited thereto.

As the oxetane-based diluent, for example, a compound of Formula 14 may be used.

[Formula 14]

In Formula 14, R ⁱ is an alkyl group, and R ^j is a hydroxyalkyl group, an alkyloxyalkyl group or an alkyloxetanylalkyloxyalkyl group.

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

≪ RTI ID = 0.0 &

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

May mean that part is linked to the parent compound.

In one example, as the oxetane-based diluent, in Formula 14, R ⁱ is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, R ^j is 1 to 12 carbon atoms, or 1 to 8 carbon atoms A hydroxyalkyl group of 1 to 4, in the formula (B), R is an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, A is an alkylene group or alkylidene group having 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms R is an alkyloxyalkyl group or an alkyl group having 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms, and L ₁ and L ₂ are each independently 1 to 12 carbon atoms, 1 to 8 carbon atoms A compound which is an alkyloxetanylalkyloxyalkyl group which is an alkylene group or an alkylidene group of 4 may be used, but is not limited thereto.

As the acryl-based diluent, for example, the compound of formula 15 may be used.

[Formula 15]

In Formula 15, R ^k is hydrogen or an alkyl group, and R ¹ is a cation reactive functional group, and may be an epoxy group such as glycidyl group, vinyloxy group, or oxetanyl group.

As the acrylic diluent, in Formula 15, R ^k is hydrogen or an alkyl group having 1 to 4 carbon atoms, and R ¹ may be a compound which is an epoxy group such as glycidyl group, but is not limited thereto.

Such diluents may be included in the composition, for example, in an amount of 5 parts by weight to 200 parts by weight or 5 parts by weight to 150 parts by weight based on 100 parts by weight of the total weight of the epoxy compound, that is, the alicyclic or aromatic epoxy compound and the linear epoxy compound. Can be. In this ratio, the viscosity of the composition can be maintained at an appropriate level, and the physical properties of the final adhesive can be ensured.

The adhesive composition may further include a hydroxy curing agent. The term "hydroxy curing agent" means a compound containing at least one, for example, one to four hydroxy groups as a functional group capable of curing the adhesive composition.

Examples of the curing agent include aliphatic diols, polyether diols, polycarbonate diols, polycaprolactone diols, polyester diols, polyol compounds, and the like.

As the aliphatic diol in the above, for example, the compound of formula (16) can be used.

[Chemical Formula 16]

In 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-butane diol, 1,6-hexane diol, 1,8-octane diol, 1,9-nonane diol, 2-methyl-1,8-octane diol, or 3- Methyl-1,5-pentane diol and the like can be exemplified, but is not limited thereto.

As the polyether diol, for example, a compound represented by the following Chemical Formula 17 may 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 Formula 17 may be each independently a linear, branched or cyclic alkylene group or 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 addition, in Chemical Formula 17, t may be, for example, 1 to 8, 1 to 6, or 1 to 4.

As the chemical formula 17, di-, tri- or poly-ethylene glycol, di-, tri- or poly-propylene glycol, polytetramethylene glycol, polyhexamethylene glycol, polyheptamethylene glycol, polydecamethylene glycol, and the like can be exemplified. However, it is not limited thereto.

As the polycarbonate diol, for example, a polycarbonate of polytetrahydrofuran, a polycarbonate of 1,6-hexanediol, or a compound of Formula 18 may be used. For example, a compound of Formula 18 may be used. have.

[Chemical Formula 18]

In Formula 18, Q and W are each independently a divalent hydrocarbon group having 2 to 12 carbon atoms, U is the same structure as Q or W, y is an integer of 2 to 150, z is an integer of 0 to 150 , y + z is 2 to 200.

The polycarbonate diol of the formula (18) can be produced, for example, by a known method such as a transesterification reaction of a diol compound and a carbonate compound or a polycondensation reaction of a diol compound and phosgene. In this case, as the diol compound used, 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol, 1,9-nonanediol or 2-methyl-1,8-octane Diol and the like, but is not limited thereto.

As polycaprolactone diol, for example, polycaprolactone diol obtained by reacting ε-caprolactone and diol can be used. In this case, as the diol, ethylene glycol, polyethylene glycol, propylene glycol, polypropylene glycol, tetramethylene glycol, polytetrimethylene glycol, 1,2-polybutylene glycol, 1,6-hexanediol, neopentyl glycol, 1, 4- cyclohexane dimethanol, 1, 4- butanediol, etc. can be illustrated.

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

In the present application, the term polyol compound may mean a compound having three or more hydroxyl groups. As a polyol compound, the polyether polyol etc. which modified | denatured the polyhydric alcohol with the cyclic ether compound can be illustrated. Examples of the polyol compound include trimethylolpropane, glycerin, pentaerythritol, sorbitol, sucrose or quodolol, and the like, and as the cyclic ether compound, ethylene oxide (EO), propylene oxide ( PO), butylene oxide, tetrahydrofuran and the like can be exemplified. Examples of the polyether polyols include ethylene oxide modified trimethylolpropane, propylene oxide modified trimethylolpropane, tetrahydrofuran modified trimethylolpropane, ethylene oxide modified glycerin, propylene oxide modified glycerin, tetrahydrofuran modified glycerin, and ethylene. Oxide modified pentaerythritol, propylene oxide modified pentaerythritol, tetrahydrofuran modified pentaerythritol, ethylene oxide modified sorbitol, propylene oxide modified sorbitol, ethylene oxide modified sucrose, propylene oxide modified sucrose or Ethylene oxide modified kudorol may be exemplified, but is not limited thereto.

In one example, as the curing agent, an aliphatic diol or a polyether polyol may be used among the compounds, and for example, a polyether polyol of Chemical Formula 17 may be used, but is not limited thereto.

The adhesive composition may include a hydroxy-based curing agent in an amount of 0.3 parts by weight to 3 parts by weight based on 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 hydroxyl equivalent of the curing agent in an amount of 0.001 equivalent to 1 equivalent relative to 1 equivalent of the epoxy group of the total epoxy compound included in the composition. By adjusting the content of the curing agent as described above, it is possible to maintain excellent workability and adhesive strength of the adhesive.

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

The kind of photocationic initiator is not specifically limited, For example, well-known photocationic initiators, such as an aromatic diazonium salt, an aromatic iodine aluminum salt, an aromatic sulfonium salt, or an iron-arene complex, can be used, for example, aromatic Sulfonium salts may be used, but are not limited thereto.

The adhesive composition may include 0.01 to 10 parts by weight or 0.1 to 3 parts by weight based on 100 parts by weight of the total weight of the epoxy compound, for example, the total epoxy compound present in the composition. Can be. If the content of the photocationic initiator is too small, there is a fear that sufficient curing does not proceed, and if too large, the content of the ionic substance after curing increases, resulting in high hygroscopicity of the adhesive, inferior durability, or conjugate acid (conjugate acid). ) Is formed, which is disadvantageous in terms of optical durability, and corrosion may occur depending on the substrate, so that an appropriate content range can be selected in consideration of this point.

The adhesive composition may further contain a suitable radical initiator if necessary, for example, when the diluent or the like contains a radical polymerizable functional group. As a radical initiator, an optical radical initiator can be used as an initiator which can induce a radical polymerization reaction etc. by irradiation of an electromagnetic wave, for example.

As the photo-radical initiator, for example, benzoin, hydroxy ketone, amino ketone or phosphine oxide-based photoinitiator and the like can be used, and in one example, benzoin, benzoin methyl ether, benzoin ethyl ether , Benzoin isopropyl ether, benzoin n-butyl ether, benzoin isobutyl ether, acetophenone, dimethylanino acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2 -Phenylacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1one, 1-hydroxycyclohexylphenylketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpho Lino-propan-1-one, 4- (2-hydroxyethoxy) phenyl-2- (hydroxy-2-propyl) ketone, benzophenone, p-phenylbenzophenone, 4,4'-diethylaminobenzo Phenone, dichlorobenzophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-aminoanthraquinone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chloro Thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, benzyldimethyl ketal, acetophenone dimethyl ketal, p-dimethylamino benzoic acid ester, oligo [2-hydroxy-2-methyl-1- [ 4- (1-methylvinyl) phenyl] propanone] or 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and the like can be used.

The adhesive composition may include, for example, a ratio of 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 included in the adhesive composition. A ratio can be suitably changed according to the specific example of the compound which has a radically polymerizable functional group, etc., for example.

The adhesive composition may also further include, if necessary, additives such as UV stabilizers, antioxidants, colorants, reinforcing agents, fillers, antifoaming agents, surfactants, optical thickeners and plasticizers, etc. have.

The adhesive composition may, for example, have a coating viscosity at room temperature, such as about 23 ° C. or about 25 ° C., of 60 cP or less, 50 cP or less, 40 cP or less, 30 cP or less, or less than 30 cP. The term coating viscosity may refer to the viscosity of the adhesive composition, ie coating liquid, at the time when it is applied to the coating process to form an adhesive. The coating viscosity of an adhesive composition can be adjusted by adjusting the kind and / or ratio of the said diluent, etc., for example. The lower limit of the coating viscosity of the adhesive composition is not particularly limited, and may be, for example, about 5 cP or about 10 cP.

The present application also relates to a polarizing plate. An exemplary polarizer comprises a polarizer; And a protective film attached to one or both surfaces of the polarizer by an adhesive. The adhesive agent affixing the said protective film can be formed, for example by hardening the said adhesive composition previously described.

The kind of polarizer contained in a polarizing plate is not specifically limited, For example, the general polarizer known in this field, such as a polyvinyl alcohol-type polarizer, can be employ | adopted without a restriction | limiting.

The 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 in a polyvinyl alcohol-based resin film. Polyvinyl alcohol-type resin which comprises a polarizer can be obtained by gelatinizing polyvinylacetate-type resin, for example. In this case, the polyvinylacetate-based resin that can be used may include not only a homopolymer of vinyl acetate but also a copolymer of vinyl acetate and other comonomers copolymerizable with the above. Examples of the comonomers include, but are not limited to, unsaturated carboxylic acids, olefins, vinyl ethers, unsaturated sulfonic acids, and a mixture of two or more kinds of acrylamides having an ammonium group. The degree of gelation of the polyvinyl alcohol-based resin may be about 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. In addition, 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.

Polyvinyl alcohol-type resin is formed into a film, and can be used as a raw film of a polarizer. The method of forming a polyvinyl alcohol-type resin into a film is not specifically limited, The general method known in this field can be used. The thickness of the raw film formed into a polyvinyl alcohol-based resin is not particularly limited, and may be appropriately controlled within, for example, 1 µm to 150 µm. In consideration of ease of stretching and the like, the thickness of the master film can be controlled to 10 ㎛ or more.

The polarizer is stretched (ex. Uniaxial or biaxially stretched) of a polyvinyl alcohol-based resin film; Staining and adsorption of dichroic pigments; Boric acid treatment; And water washing step. As the dichroic dye, iodine or a dichroic organic dye may be used.

The kind of protective film attached to one side or both sides of the polarizer by the adhesive is not particularly limited. As a protective film, For example, a cellulose film (ex, triacetyl cellulose (TAC)), an amorphous polyolefin film, a polyester resin film, an acrylic resin film, a polycarbonate resin film, a polysulfone resin film, A film such as an alicyclic polyimide resin film or a cyclic olefin (COP) resin film can be used. When the protective film is attached to both sides of the polarizer, at least one film is an amorphous polyolefin film, polyester resin film, acrylic resin film, polycarbonate resin film, polysulfone resin film, alicyclic polyimide resin It may be composed of a film or a cyclic olefin (COP) -based resin film and the like, but is not limited thereto.

When a protective film is affixed on both surfaces of a polarizer, the said 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. As shown in FIG. 1, in the polarizing plate 1 of the present application, one surface of the polarizer 11 has a cellulose-based film 13 such as triacetyl cellulose (TAC) attached by an adhesive 12a, and the other surface thereof. The film of other types besides a cellulose film, for example, the acryl-type film 14 etc. may be affixed with the adhesive agent 12b. In addition, as shown in FIG. 2, the same kind of protective films 14a and 14b may be attached to both surfaces of the polarizer 11 by the adhesives 12a and 12b of the present application. In this case, the protective films 14a and 14b may be selected from films other than cellulose-based films, for example, acrylic films and the like.

The adhesive may exhibit excellent adhesion even when pretreatment using NaOH is not performed on a cellulose-based film such as triacetyl cellulose (TAC), which is a conventional polarizer protective film, and also has a moisture permeability compared to the cellulose-based film. Falls, exhibits hydrophobicity, exhibits hydrophilicity, and is difficult to attach with polarizers; polyester resin film; acrylic resin film; polycarbonate resin film; polysulfone resin film; alicyclic polyimide resin film Or excellent adhesiveness can also be exhibited with respect to a cyclic olefin (COP) type resin film.

The adhesive agent to which the said protective film is affixed can have thickness of 10 micrometers or less, 7 micrometers or less, or 5 micrometers or less, for example, exceeding 0 micrometer.

The method for producing the polarizing plate is not particularly limited. For example, a method of forming an adhesive layer by forming a layer of the adhesive composition in advance through a pre-coating method and then laminating the polarizer and the protective film through the adhesive layer and curing the layer of the adhesive composition, or manufacturing a polarizing plate. The method of laminating a polarizer and a protective film by applying the droplet system etc. which are normally used for this, and the method of hardening an adhesive composition, etc. can be used.

The manner of curing the adhesive composition is also not particularly limited, and for example, a method of irradiating an appropriate electromagnetic wave, such as ultraviolet rays, may be used so that the reaction of the initiator in the adhesive composition can be induced. In the above, the irradiation conditions of the electromagnetic wave, for example, the electromagnetic wave in the UV B region can be irradiated with a light amount of about 500 mJ / cm ² to 1,500 mJ / cm ² and illuminance of 150 mW / cm ² to 400 mW / cm ² But it is not limited thereto.

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

The kind of liquid crystal panel contained in a liquid crystal display device is not specifically limited. For example, F various passive matrix systems including, but not limited to, TN (Twisted Neumatic), STN (Super Twisted Neumatic), F (ferroelectric), PD (polymer dispersed LCD), and the like; Various active matrix schemes including two terminals and three terminals; Both known liquid crystal panels, including IPS mode panels and VA mode panels, can be applied. The kind of other components included in the liquid crystal display device and a method of manufacturing the same are not particularly limited, and general structures in this field may be employed without limitation.

In the present application, an appropriate viscosity can be maintained, for example, an adhesive composition can be provided that can be applied to an optical film to maintain excellent adhesion, durability and water resistance while maintaining thickness uniformity. The adhesive composition can, for example, effectively attach a film showing hydrophobicity and low moisture permeability to a polarizer, and can provide an adhesive excellent in optical properties such as transparency.

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

Hereinafter, the composition will be described in detail through 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

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

<Evaluation criteria of viscosity>

(Circle): When the viscosity in 25 degreeC is less than 30 cP

(Triangle | delta): When the viscosity in 25 degreeC is 30 cP-50 cP

Ｘ: viscosity at 25 ° C. exceeds 50 cP

2. Peel force  evaluation

A polarizing plate having a structure including a protective film prepared in Examples or Comparative Examples, a layer of an adhesive composition, a polyvinyl alcohol-based polarizer, a layer of an adhesive composition, and a protective film was attached to a glass plate using a double-sided tape, and the length was 2 cm. After cutting to be, lamination was carried out so that each layer of the polarizing plate was completely pressed. Thereafter, the ultraviolet irradiation, annealing and aging processes described in Examples or Comparative Examples were carried out. Subsequently, peeling force was evaluated using the UTM equipment, peeling a protective film in the longitudinal direction of a polarizing plate at a peeling angle of 90 degrees and a peeling speed of 5 mm / sec from a polarizer.

Peeling force evaluation criteria

(Circle): When peeling force is 200 gf / 2cm or more

(Triangle | delta): When peeling force is 150 gf / 2cm or more and is less than 200 gf / 2cm

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

3. Evaluation of water resistance

A specimen prepared by cutting the polarizing plate prepared in Example or Comparative Example to have a horizontal size of 2 cm and a vertical size of 5 cm was placed in a thermostat at 60 ° C., and water resistance was evaluated according to the following criteria.

<Water resistance evaluation standard>

(Circle): When there is no change in the external appearance of a polarizing plate for 8 hours or more, and peeling does not arise.

(Triangle | delta): When there is no change in the external appearance of a polarizing plate for 4 hours or more, and peeling does not arise.

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

4. Evaluation of Optical Properties

Test to maintain the polarizing plate prepared in Example or Comparative Example for 10 hours in a horizontal size of 10 cm, cut to a size of 15 cm in an oven at 80 ℃ (heat resistance test) and A test (moisture heat durability test) for 100 hours at 60 ° C. and 90% relative humidity conditions was performed, respectively, to determine whether the polarizer was good or bad, and the optical properties were evaluated according to the following criteria. In the above, the case where the iodine aggregation phenomenon and yellowing did not generate | occur | produce in the polarizing plate after each test was made into favorable, and the case where any of the above generate | occur | produced was evaluated as defective.

<Optical Characteristic Evaluation Criteria>

○: When both polarizers are satisfactory in the heat resistance test and the moisture resistance test.

(Triangle | delta): When a fault arises in a polarizing plate in a heat resistant durability test or a moisture resistant heat resistance test

Ｘ: When the polarizer is defective in the heat resistance test and the moisture resistance test.

5. Thermal shock  evaluation

Put the specimen prepared by cutting the polarizing plate prepared in Example or Comparative Example to have a horizontal size of 10 cm and a vertical size of 10 cm in a thermal shock oven, and maintained at -40 ℃ for 30 minutes, and then the temperature was The procedure was repeated 100 cycles, with one cycle of raising to 80 ° C. and holding for 30 minutes. Subsequently, after 100 cycles, agglomeration of iodine and excitation between each interface occurred in the polarizing plate were examined, and thermal shock was evaluated according to the following criteria.

<Thermal Shock Evaluation Criteria>

○: when no defect occurs in the polarizer after 100 cycles

(Triangle | delta): When lifting of the variable part within 1 mm occurs after 100 cycles

Note: After 100 cycles, more than 1 mm of lifting or iodine agglomeration occurs.

Example  One

Preparation of Adhesive Composition

Alicyclic epoxy compound (7-oxa-bicyclo [4,1,0] hetan-3-ylmethyl 7-oxa-bicyclo [4,1,0] heptane-3-carboxylate, ceoxide 2021P, manufactured by Daicel Corporation) And a linear epoxy compound (butanediol diglycidylether, Mirate BDGE, Miwon Chemical Co., Ltd.) in a weight ratio of 3: 2 (alicyclic epoxy compound: linear epoxy compound). Cyclohexene oxide is then added as a diluent in a ratio of 25 parts by weight to 100 parts by weight of the total weight of the alicyclic and linear epoxy compounds, and polyester polyols (D800, BASF) are added above the epoxy compounds. 1 part by weight based on 100 parts by weight of the total weight. Then add a cationic initiator (50 wt% propylene carbonate solution of Triacrylsulfonium hexafluoroantimonate, CPI 101A, San-Apro) to 2 parts by weight relative to 100 parts by weight of the total weight of the epoxy compound, and about 20 to 20 The adhesive composition was prepared by mixing for 30 minutes.

Preparation of Polarizer

An adhesive comprising a pre-treated triacetyl cellulose protective film, a polyvinyl alcohol polarizer and a biaxially stretched acrylic protective film sequentially laminated using the prepared adhesive composition, wherein the protective film and the polarizer are formed using the adhesive composition. It has a structure comprising a polarizing plate (hereinafter referred to as a polarizing plate structure 1) or a sequentially laminated biaxially stretched acrylic protective film, a polyvinyl alcohol-based polarizer and a biaxially stretched acrylic protective film, a protective film and a polarizer using the adhesive composition A polarizing plate (hereinafter, referred to as a polarizing plate structure 2) adhered with the formed adhesive was manufactured. Attachment of the polarizer and the protective film in the above was carried out in a droplet method using a ramilol. Specifically, after attaching a polarizer and a protective film with an adhesive composition, it is irradiated with ultraviolet (UV) light (B area, light amount: 1,000 mJ / cm ² , illuminance: 210 mW / cm ² ), and at 90 ° C. for about 1 to 3 minutes After annealing (aging) at room temperature for 1 day (aging) to prepare a polarizing plate.

Example  2

Instead of using an alicyclic epoxy compound, a bisphenol F type epoxy compound (liquid epoxy, TDF165, Kukdo Chemical Co., Ltd.) is used in a weight ratio of 1: 1 with the linear epoxy compound, and the diluent is a bisphenol F type epoxy compound. And a polarizing plate was manufactured in the same manner as in Example 1, except that 20 parts by weight based on 100 parts by weight of the total epoxy compound was used.

Example  3

A polarizing plate was manufactured in the same manner as in Example 1, except that the weight ratio of the alicyclic epoxy compound and the linear epoxy compound was changed to 1: 1.

Example  4

Change the weight ratio of the bisphenol F type epoxy compound and the linear epoxy compound to 1: 2 (bisphenol F type epoxy compound: the linear epoxy compound), and use 4-vinyl-1-cyclohexene diepoxide (instead of cyclohexene oxide as a diluent) 4-vinyl-1-cyclohexene diepoxide) was prepared in the same manner as in Example 2 except that the bisphenol F-type epoxy compound and the linear epoxy compound were used in an amount of 30 parts by weight based on 100 parts by weight.

Example  5

4-vinyl-1-cyclohexene 1,2-epoxide (4-vinyl-1-cyclohexene 1, 2- instead of 4-vinyl-1-cyclohexene diepoxide as a diluent epoxide) was prepared in the same manner as in Example 4 except that 10 parts by weight of the bisphenol F-type epoxy compound and 100 parts by weight of the total epoxy compound were manufactured.

Example  6

1-methyl-4- (2-methyloxirane-2-yl) -7-oxa-bicyclo [4 instead of 4-vinyl-1-cyclohexene diepoxide as diluent Total weight of 1,0] heptane (1-methyl-4- (2-methyloxiran-2-yl) -7-oxa-bicyclo [4,1,0] heptane) on bisphenol F-type epoxy compounds and linear epoxy compounds A polarizing plate was manufactured in the same manner as in Example 4, except that 100 parts by weight was used in an amount of 10 parts by weight.

Example  7

Instead of 4-vinyl-1-cyclohexene diepoxide, 2-ethylhexyl glycidyl ether was used as a diluent, compared to 100 parts by weight of the total weight of the bisphenol F-type epoxy compound and the linear epoxy compound. A polarizing plate was manufactured in the same manner as in Example 4 except that the weight part was used.

Example  8

The same procedure as in Example 1 was carried out except that 3-ethyl-3-hydroxymethyl oxetane was used instead of cyclohexene oxide as 100 parts by weight based on 100 parts by weight of the total weight of the alicyclic epoxy compound and the linear epoxy compound. A polarizing plate was prepared.

Example  9

Instead of 4-vinyl-1-cyclohexene diepoxide, glycidyl methacrylate was used as a diluent to 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. In addition, a polarizing plate was prepared in the same manner as in Example 4 except that a radical initiator (Irgacure 184) was added in an amount of 3 parts by weight based on 100 parts by weight of the glycidyl methacrylate.

Example  10

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

Comparative Example  One

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

Comparative Example  2.

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

Comparative Example  3.

Except not using an alicyclic epoxy compound, a polarizing plate was prepared in the same manner as in Example 1.

Comparative Example  4.

Except not using a linear epoxy compound, a polarizing plate was prepared in the same manner as in Example 1.

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 triacetylcellulose protective film and polarizer in polarizing plate structure 1
Peeling force (acrylic): Peeling force between the acrylic protective film and the polarizer in the polarizing plate 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 triacetylcellulose protective film and polarizer in polarizing plate structure 1
Peeling force (acrylic): Peeling force between the acrylic protective film and the polarizer in the polarizing plate 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, wherein the coating viscosity at 25 ° C. is 60 cP or less. The cycloaliphatic epoxy compound according to claim 1, further comprising: 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; A photocurable adhesive composition which is an epoxycyclopentyl ether compound or a diepoxy tricyclo decane compound. The method of claim 1, wherein the aromatic epoxy compound is a bisphenol type epoxy resin; Novolac type epoxy resins; The photocurable adhesive composition which is cresol epoxy resin or resorcinol glycidyl ether. The method of claim 1, wherein the linear epoxy compound is selected from 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 with another vinyl monomer. The photocurable adhesive composition of claim 1, wherein the linear epoxy compound is included in a ratio of 30 parts by weight to 300 parts by weight with respect to 100 parts by weight of the alicyclic or aromatic epoxy compound. The photocurable adhesive composition according to claim 1, wherein the diluent is a compound having a viscosity at 25 ° C of 30 cP or less and having at least one functional group capable of participating in a cationic reaction or a radical reaction. The photocurable adhesive composition of claim 1, wherein the diluent is a compound represented by the following general formula (11):
(11)

v
R ^a to R ^f in Formula 11 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an oxiranyl group, an alkoxycarbonyl group or an alkyloxyranyl group. The photocurable adhesive composition of claim 1, wherein the diluent is a compound represented by Formula 12:
[Chemical Formula 12]

In Formula 12, R ^g is an alkyloxyalkyl group. The photocurable adhesive composition of claim 1, wherein the diluent is a compound represented by the following Chemical Formula 13.
[Chemical Formula 13]

In Formula 13, R ^h is an alkyl group, a hydroxyalkyl group or an alkyloxyalkyl group. The photocurable adhesive composition of claim 1, wherein the diluent is a compound represented by Formula 14:
[Chemical Formula 14]

In Formula 14, R ⁱ is an alkyl group, and R ^j is a hydroxyalkyl group, an alkyloxyalkyl group or an alkyloxetanylalkyloxyalkyl group. The photocurable adhesive composition of claim 1, wherein the diluent is a compound represented by Formula 15:
[Chemical Formula 15]

In Formula 15, R ^k is hydrogen or an alkyl group, and R ¹ is an epoxy group, a vinyloxy group, or an oxetanyl group. The photocurable adhesive composition of claim 1, wherein the diluent is included in a ratio of 5 parts by weight to 200 parts by weight based on 100 parts by weight of the total weight of the alicyclic or aromatic epoxy compound and the linear epoxy compound. The photocurable adhesive composition according to claim 1, further comprising a hydroxy-based curing agent. The photocurable adhesive composition of claim 13, wherein the curing agent is a compound of Formula 17:
[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 photocationic initiator. The photocurable adhesive composition of claim 1 further comprising a radical initiator. A polarizer; And a protective film attached to one or both surfaces of the polarizer by an adhesive formed by curing the adhesive composition of claim 1. 18. The polarizing plate according to claim 17, wherein the adhesive has a thickness of more than 0 mu m and more than 10 mu m. A liquid crystal panel; And a polarizing plate of claim 17 attached to one side or both sides of the liquid crystal panel.

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