KR101666703B1 - Polarizing plate and display device comprising the same - Google Patents

Abstract

The present invention provides a polarizer comprising: a polarizer; An adhesive layer formed on at least one surface of the polarizer; And a film-type patterned retarder (FPR) film adhered on the adhesive layer, wherein the adhesive layer comprises an acrylic compound having at least one hydroxy substituent and a molecular weight of 120 g / mol or more; And an active energy ray-curable adhesive composition comprising a radical initiator, and an image display apparatus including the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a polarizing plate and an image display device including the polarizing plate.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polarizing plate and an image display apparatus including the polarizing plate, and more particularly, to an FPR film adhered to at least one surface of a polarizer through an adhesive layer having excellent adhesion to a polarizer and a FPR And a polarizing plate and an image display apparatus including the same.

An image display apparatus such as a liquid crystal display capable of realizing a stereoscopic image at present often includes an FPR (Film-type Patterned Retarder) film. The FPR film realizes a stereoscopic image by configuring the optical axes of the respective pattern regions in different directions so that the images transmitted to the left and right eyes of the viewer wearing polarized glasses are different.

In recent years, in order to reflect the need of the customer, it is required to reduce the thickness and weight of a liquid crystal display capable of realizing a stereoscopic image. To this end, an FPR film is attached to one surface of a polarizer through an adhesive, Have been actively studied.

On the other hand, the adhesive for a polarizing plate proposed so far is mainly an active energy ray-curable adhesive, and the active energy ray-curable adhesive mainly contains a low molecular weight acrylic compound having a hydroxy substituent such as 2-hydroxyethyl acrylate as a main component , And adhesion is ensured through hydrogen bonding. However, such a conventional adhesive for a polarizing plate has an excellent adhesive strength between a polarizer and a transparent protective film, but has a problem that the adhesive force is very weak when applied to the FPR film as described above.

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide a polarizer and a film-type patterned retarder (FPR) film on at least one side of the polarizer through an adhesive layer having excellent adhesion to a polarizer and a film- And an image display device including the same.

In one aspect, the present invention provides a polarizer comprising: a polarizer; An adhesive layer formed on at least one surface of the polarizer; And a film-type patterned retarder (FPR) film adhered on the adhesive layer, wherein the adhesive layer comprises an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent group; And an active energy ray curable adhesive composition comprising a radical initiator.

At this time, the acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent may be represented by the following formula (I) or (II).

(I)

Wherein R ₁ is C _{4 to} C ₈ alkyl, C _{4 to} C ₈ cycloalkyl, C _{4 to} C ₁₂ alkylcycloalkyl, C _{4 to} C ₁₂ cycloalkylalkyl, C _{5 to} C ₈ cycloalkylalkyl having at least one hydroxy substituent, _{- 14} alkyl, cycloalkyl alkyl, C _{7 ~ 12} phenylalkyl, or C _{7 - 12} phenoxy alkyl; R ₂ is hydrogen or C _{1 ~ 10} alkyl.

[Formula II]

In the above Formula Ⅱ], R ₃ is having at least one hydroxy substituent, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or Phenylene; R ₄ is C _{1 ~ 12} alkyl, C _{4 ~ 12} cycloalkyl, C _{4 ~ 12} alkylcycloalkyl, C _{4 ~ 12} cycloalkylalkyl, C _{5 ~ 14} alkyl and cycloalkyl-alkyl; R ₅ is hydrogen or C _{1 ~ 10} alkyl.

On the other hand, the active energy ray-curable adhesive composition comprises an acrylic compound having at least two benzene rings; And a carboxylic acid compound having at least one carbon-carbon unsaturated double bond.

More specifically, the active energy ray-curable adhesive composition may comprise 30 to 90 parts by weight of an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent, based on 100 parts by weight of the total composition; 5 to 50 parts by weight of an acrylic compound having at least two benzene rings; 1 to 30 parts by weight of a carboxylic acid compound having at least one carbon-carbon unsaturated double bond; And 0.1 to 10 parts by weight of a radical initiator.

At this time, the acrylic compound having at least two benzene rings may be represented by the following formula (III).

[Formula (III)

In the above formula (III), X ₁ is a single bond or -O-; R ₆ is a single bond, or C _1-10 alkylene; R ₇ and R ₈ are each independently a C _{1 ~ 10} aliphatic hydrocarbon chain, C _{4 ~ 14} aliphatic hydrocarbon ring, or C _{6 ~ 14} aromatic hydrocarbon ring; R ₉ and R ₁₀ are each independently selected from -OH, -C (= O) OH , -OC (= O) X 2 C (= O) OH, wherein X ₂ is C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or phenylene, and; R ₁₁ and R ₁₂ are each independently (meth) acryloyl or (meth) acryloyloxy; R ₁₃ and R ₁₄ are each independently a halogen atom or a C _{1 ~ 10} alkyl; a and b are each independently an integer of 0 to 2;

The carboxylic acid compound having at least one carbon-carbon unsaturated double bond may be represented by the following formula (IV).

[Formula IV]

In the above Formula Ⅳ], R ₁₅ is a single bond, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or phenylene, and; R ₁₆ is hydrogen, C _{1 ~ 6} carboxyalkyl, C _{1 ~ 6} (meth) acryloyl alkyl, C _{1 ~ 6} (meth) acryloyl oxyalkyl being one.

On the other hand, the active energy ray-curable adhesive composition preferably has a glass transition temperature of 50 DEG C or higher after curing.

The active energy ray-curable adhesive composition preferably has a viscosity of 10 to 200 cP.

On the other hand, it is preferable that the polarizer is a polyvinyl alcohol-based film in which iodine or a dichroic dye is adsorbed and oriented.

On the other hand, the polarizing plate of the present invention may further include a protective film on the opposite side of the surface of the polarizer on which the FPR (Film-type Patterned Retarder) film is formed.

In another aspect, the present invention provides an image display device including the polarizer.

The polarizing plate of the present invention is excellent in adhesion between the polarizer and the FPR film because the FPR film is attached to at least one surface of the polarizer through the adhesive layer having excellent adhesion to both the polarizer and the FPR film.

In addition, the polarizer of the present invention is excellent in the heat resistance reliability of the polarizer of the present invention including the high adhesive glass transition temperature of the adhesive layer, even in a high humidity environment.

Hereinafter, preferred embodiments of the present invention will be described. However, the embodiments of the present invention can be modified into various other forms, and the scope of the present invention is not limited to the embodiments described below. Further, the embodiments of the present invention are provided to more fully explain the present invention to those skilled in the art.

As a result of extensive research, the present inventors have found that when an adhesive layer is formed using an active energy ray-curable adhesive composition comprising an acrylic compound having a molecular weight of at least 120 g / mol and at least one hydroxy substituent group, And thus the present invention has been completed.

More specifically, the polarizer of the present invention comprises a polarizer; An adhesive layer formed on at least one surface of the polarizer; And a film-type patterned retarder (FPR) film adhered on the adhesive layer, wherein the adhesive layer comprises an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent and an active energy Curable adhesive composition according to the present invention.

First, the adhesive layer of the present invention comprises an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent in order to adhere the polarizer and the FPR (Film-type Patterned Retarder) film; And an active energy ray curable adhesive composition comprising a radical initiator, and may be formed by methods well known in the art. For example, the active energy ray-curable composition may be applied to one side of the polarizer by a coating method well known in the art, such as spin coating, comma coating, bar coating, roll coating, gravure coating, blade coating, Followed by curing by irradiation with active energy rays.

The light source for irradiating the active energy ray is not particularly limited, but a light source capable of irradiating an active energy ray having a light emission distribution at a wavelength of 400 nm or less is preferable, and a light source such as low pressure, medium pressure, high pressure or ultra high pressure mercury lamp, , A microwave-excited mercury lamp or a metal halide lamp, and the like. The irradiation intensity of the active energy ray is determined depending on the composition of the composition and is not particularly limited, but it is preferable that the irradiation intensity in the wavelength range effective for activating the initiator is 0.1 mW / cm ² to 6,000 mW / cm ² . The irradiation time is controlled in accordance with the composition to be cured and is not particularly limited, but it is preferable that the integrated amount of light, which is a product of irradiation intensity and irradiation time, is set to 10 mJ / cm ² to 10,000 mJ / cm ² .

At this time, the acrylic compound having at least one hydroxy substituent group and having a molecular weight of 120 g / mol or more contained in the active energy ray-curable adhesive composition of the present invention is a component for realizing the adhesive force by hydrogen bonding and has a molecular weight of 120 is an acrylic compound having at least one hydroxy substituent group in the molecule and at least about 130 to 700 g / mol, more preferably about 140 to 500 g / mol, It can be used without any limitations. According to the studies of the present inventors, when the molecular weight of the acrylic compound having at least one hydroxy substituent is less than 120 g / mol, the adhesive force to the polarizer can be realized through the hydroxy substituent, It is not very good. That is, the liquid crystal of the FPR film is packed well between the liquid crystal molecules different from the surface of the general protective film, and the mobility of the surface molecules is deteriorated. Therefore, It is difficult to realize an adhesive force as a single molecule such as hydroxyethyl acrylate. However, as the molecular weight increases, the mobility of the adhesive increases, and the intermolecular affinity also improves, so that it becomes possible to realize the adhesive force with the FPR film.

For example, although not limited thereto, the acrylic compound having at least one hydroxy substituent and having a molecular weight of 120 g / mol or more may be represented by the following formula (I) or (II). On the other hand, they may be used alone or in combination.

(I)

Wherein R ₁ is C _{4 to} C ₈ alkyl, C _{4 to} C ₈ cycloalkyl, C _{4 to} C ₁₂ alkylcycloalkyl, C _{4 to} C ₁₂ cycloalkylalkyl, C _{5 to} C ₈ cycloalkylalkyl having at least one hydroxy substituent, _{- 14} alkyl, cycloalkyl alkyl, C _{7 ~ 12} phenylalkyl, or C _{7 - 12} phenoxy alkyl; R ₂ is hydrogen or C _{1 ~ 10} alkyl.

In the above R ₁ , the alkyl means a linear or branched hydrocarbon moiety, and examples thereof include, but are not limited to, butyl, pentyl, hexyl, heptyl, octyl and the like. On the other hand, the at least one hydroxy group may be substituted at any position within the alkyl, and the remaining one or more hydrogen atoms contained in the alkyl may be substituted with any substituent.

In the above-mentioned R ₁ , the cycloalkyl refers to a non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon moiety of a ring carbon, including, but not limited to, cyclopentyl, cyclohexyl, . On the other hand, the at least one hydroxy group may be substituted at any position within the cycloalkyl, and the remaining one or more hydrogen atoms contained in the cycloalkyl may be substituted with any substituent.

In the above R ₁ , the alkylcycloalkyl means that the alkyl is substituted with cycloalkyl, and examples thereof include, but are not limited to, methylcyclohexyl, ethylcyclohexyl, and propylcyclohexyl. On the other hand, the at least one hydroxy group may be substituted at any position within the alkylcycloalkyl, and the remaining one or more hydrogen atoms contained in the alkylcycloalkyl may be substituted with any substituent.

In the above-mentioned R ₁ , the cycloalkylalkyl means that the alkyl is substituted with cycloalkyl, and examples thereof include, but are not limited to, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like. On the other hand, the at least one hydroxy group may be substituted at any position within such cycloalkylalkyl, and the remaining one or more hydrogen atoms contained in the cycloalkylalkyl may be substituted with any substituent.

In the above-mentioned R ₁ , the alkylcycloalkylalkyl means that alkyl is substituted with alkylcycloalkyl. The alkylcycloalkylalkyl includes, but is not limited to, methylcyclohexylmethyl, methylcyclohexylethyl, methylcyclohexylpropyl, etc. For example. On the other hand, the at least one hydroxy group may be substituted at any position in the alkylcycloalkylalkyl, and the remaining one or more hydrogen atoms contained in the alkylcycloalkylalkyl may be substituted with any substituent.

In the above-mentioned R ₁ , the phenylalkyl means that alkyl is substituted with phenyl, and examples thereof include, but are not limited to, phenylmethyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl and the like . On the other hand, the at least one hydroxy group may be substituted at any position within the phenylalkyl, and the remaining one or more hydrogen atoms contained in the phenylalkyl may be substituted with any substituent.

In the above-mentioned R ₁ , the phenoxyalkyl means that phenoxy is substituted for alkyl, and it is not limited to phenoxymethyl, phenoxyethyl, phenoxypropyl, phenoxybutyl, phenoxypentyl And so on. On the other hand, the at least one hydroxy group may be substituted at any position in the phenoxyalkyl, and the remaining one or more hydrogen atoms contained in the phenoxyalkyl may be substituted with any substituent.

In the above-mentioned R ₂ , the alkyl means a linear or branched hydrocarbon moiety, and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, For example. The remaining one or more hydrogen atoms contained in the alkyl may be substituted with any substituent.

More specifically, the acrylic compound having at least one hydroxy substituent group represented by the above-mentioned formula (I) and having a molecular weight of 120 g / mol or more is not limited to, for example, 4-hydroxybutyl acrylate, 4 Hydroxypropyl methacrylate, 2-hydroxy-3-phenylpropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 4-hydroxycyclohexylmethacrylate, 4-hydroxycyclohexylmethacrylate, 4-hydroxycyclohexylmethacrylate, 4-hydroxycyclohexylmethacrylate, 4-hydroxycyclohexylmethacrylate, , 4-hydroxycyclohexylmethyl methacrylate, and the like. These may be used alone or in combination.

[Formula II]

In the above Formula Ⅱ], R ₃ is having at least one hydroxy substituent, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or Phenylene; R ₄ is C _{1 ~ 12} alkyl, C _{4 ~ 12} cycloalkyl, C _{4 ~ 12} alkylcycloalkyl, C _{4 ~ 12} cycloalkylalkyl, C _{5 ~ 14} alkyl and cycloalkyl-alkyl; R ₅ is hydrogen or C _{1 ~ 10} alkyl.

In R ₃ , the alkylene means a linear or branched divalent hydrocarbon moiety, and examples thereof include, but are not limited to, methylene, dimethylmethylene, ethylene, methylethylene, and the like. On the other hand, the at least one hydroxy group may be substituted at any position in the alkylene, and the remaining one or more hydrogen atoms contained in the alkylene may be substituted with any substituent.

In the above R ₃ , the alkenylene means a linear or branched saturated divalent hydrocarbon moiety, and examples thereof include, but are not limited to, ethenylene, propenylene, and the like. On the other hand, the at least one hydroxyl group may be substituted at any position in the alkenylene, and the remaining one or more hydrogen atoms contained in the alkenylene may be substituted with any substituent.

In the above-mentioned R ₃ , the cycloalkylene means a divalent nonaromatic hydrocarbon moiety of a ring carbon, and examples thereof include, but are not limited to, cyclopentylene, cyclohexylene, and the like. On the other hand, the at least one hydroxy group may be substituted at any position within the cycloalkylene, and the remaining one or more hydrogen atoms contained in the cycloalkylene may be substituted with any substituent.

In the above-mentioned R ₃ , the cycloalkenylene means a saturated divalent non-aromatic hydrocarbon moiety of a ring carbon, but is not limited to, cyclopentenylylene, cyclohexenylene, and the like . On the other hand, the at least one hydroxy group may be substituted at any position in the cycloalkenylene, and the remaining one or more hydrogen atoms contained in the cycloalkenylene may be substituted with any substituent.

In the above-mentioned R ₃ , the phenylene means a divalent benzene ring portion, and the at least one hydroxy group may be substituted at any position in the phenylene, and the remaining one or more hydrogen The atom may be substituted with any substituent.

In the above-mentioned R ₄ , the alkyl refers to a linear or branched hydrocarbon moiety and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, For example. Meanwhile, at least one hydrogen atom contained in the alkyl may be substituted with any substituent.

In the above-mentioned R ₄ , the cycloalkyl means a cyclic non-aromatic monocyclic, bicyclic or tricyclic hydrocarbon moiety, and includes, but is not limited to, cyclopentyl, cyclohexyl, and the like . On the other hand, at least one hydrogen atom contained in the cycloalkyl may be substituted with any substituent.

In the above-mentioned R ₄ , the alkylcycloalkyl means that alkyl is substituted for the cycloalkyl, and examples thereof include methylcyclohexyl, ethylcyclohexyl, and propylcyclohexyl. Meanwhile, at least one hydrogen atom contained in the alkylcycloalkyl may be substituted with any substituent.

In the above R ₄ , the cycloalkylalkyl means that cycloalkylalkyl is substituted with alkyl, and examples thereof include cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl and the like. Meanwhile, at least one hydrogen atom contained in the cycloalkylalkyl may be substituted with any substituent.

In the above-mentioned R ₄ , the alkylcycloalkylalkyl means that the alkylcycloalkyl is bound to the alkyl, and the alkylcycloalkylalkyl is not limited thereto, and examples thereof include methylcyclohexylmethyl, methylcyclohexylethyl, methylcyclohexylpropyl and the like. For example. Meanwhile, at least one hydrogen atom contained in the alkylcycloalkylalkyl may be substituted with any substituent.

In the above-mentioned R ₅ , the alkyl refers to a linear or branched hydrocarbon moiety and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, For example. The remaining one or more hydrogen atoms contained in the alkyl may be substituted with any substituent.

More specifically, the acrylic compound having at least one hydroxy substituent group represented by the above-mentioned formula (II) and having a molecular weight of 120 g / mol or more is not limited to, for example, 2-acryloyloxy- Hydroxyethyl 2-methyl-2-propyl hexanoate, 2-methacryloyloxy-1-hydroxyethyl 2-methyl-2-propyl hexanoate, 2- acryloyloxy- Ethyl 2-methyl-2-propyl hexanoate, 2-methacryloyloxy-1-hydroxymethyl ethyl 2-methyl-2-propyl hexanoate and the like. These may be used alone or in combination.

In addition, the radical initiator contained in the active energy ray-curable adhesive composition of the present invention is intended to enhance the curing rate by promoting radical polymerization. As the radical initiator, radical initiators generally used in the related art Can be used without limitation.

More specifically, the radical initiator can be, for example, 1-hydroxy-cyclohexyl-phenyl-ketone, 2-hydroxy- (2-hydroxy-2-methyl-1-phenyl-1-propanone) Methyl-2-methyl-1-propanone, methylbenzoylformate, oxy-phenyl-acetic acid -2- [2-oxo-2- Phenyl-acetoxy-ethoxy] -ethyl ester, oxy-phenyl-acetic acid 2- [2-hydroxy- 2-hydroxy-ethoxy] -ethyl ester, alpha-dimethoxy-alpha-phenylacetophenone, 2- Benzyl-2- (dimethylamino) -1- [4- (4-morpholinyl) phenyl] -1- -1-butanone), 2-methyl-1- [4- ( (Methylthio) phenyl] -2- (4-morpholinyl) -1-propanone), di (2,4,6-trimethylbenzoyl) -phosphine oxide, phosphine oxide, phenylbis (2,4,6-trimethylbenzoyl) -phosphine oxide, ) -Phosphine oxide (phenylbis (2,4,6-trimethylbenzoyl) -phosphine oxide). Particularly, in the present invention, phenylbis (2,4,6-trimethylbenzoyl) -phosphine oxide may be preferably used.

The active energy ray-curable adhesive composition of the present invention may further comprise an acrylic compound having at least two benzene rings. At this time, the acrylic compound having at least two benzene rings is added to improve the glass transition temperature of the adhesive composition of the present invention, and is an acrylic compound having at least two benzene rings. This is possible. In the case where a benzene ring having a high molecular density is contained in the molecule as described above, since the molecular density in the molecule is high, a higher glass transition temperature can be obtained, and furthermore, the adhesive layer becomes more dense and harder, Can also be improved. In addition, when the benzene ring is contained in the molecule, the intermolecular affinity between the FPR film and the liquid crystal molecule is improved, so that the adhesive force can be further improved.

On the other hand, it is preferable that the acrylic compound having at least two benzene rings has at least one hydrophilic functional group such as a hydroxyl group or a carboxyl group in the molecule. In this case, since the hydrophilic functional group makes hydrogen bonding with the hydroxyl group in the adhesive layer to make the adhesive layer harder, the glass transition temperature of the adhesive layer can be further raised, and furthermore, the adhesive layer can be further densified to further improve the water resistance to be.

For example, although not limited thereto, the acrylic compound having at least two benzene rings may be represented by the following formula (III).

 [Formula (III)

In the above formula (III), X ₁ is a single bond or -O-; R ₆ is a single bond, or C _1-10 alkylene; R ₇ and R ₈ are each independently a C _{1 ~ 10} aliphatic hydrocarbon chain, C _{4 ~ 14} aliphatic hydrocarbon ring, or C _{6 ~ 14} aromatic hydrocarbon ring; R ₉ and R ₁₀ are each independently selected from -OH, -C (= O) OH , -OC (= O) X 2 C (= O) OH, wherein X ₂ is C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or phenylene, and; R ₁₁ and R ₁₂ are each independently (meth) acryloyl or (meth) acryloyloxy; R ₁₃ and R ₁₄ are each independently a halogen atom or a C _{1 ~ 10} alkyl; a and b are each independently an integer of 0 to 2;

In the R ₆ , the alkylene means a linear or branched divalent hydrocarbon moiety, and examples thereof include methylene, dimethylmethylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, Heptamethylene, nonamethylene, decamethylene, and the like. Among them, methylene or dimethylmethylene is particularly preferable. The at least one hydrogen atom contained in the alkylene may be substituted with any substituent.

In the above-mentioned R ₇ and R ₈ , the aliphatic hydrocarbon chain may be a linear or branched saturated or unsaturated trivalent hydrocarbon moiety of 1 to 10, or 1 to 8, or 1 to 4 carbon atoms, Alkane chains such as a trivalent, methane chain, ethane chain, propane chain, butane chain, pentane chain, hexane chain, heptane chain, octane chain, nonane chain and decane chain, etc., For example. do. The at least one hydrogen atom contained in the aliphatic hydrocarbon chain may be substituted with any substituent.

Further, in the above R ₇ and R ₈ , the aliphatic hydrocarbon ring may be saturated or unsaturated nonaromatic trivalent monocyclic, saturated or unsaturated, having 4 to 14, or 4 to 10, or 4 to 6 ring carbon atoms, But not limited to, a cycloalkane ring such as a trivalent, cyclopentane ring, or a cyclohexane ring, or a trivalent ring such as a trivalent cyclopentene ring, a cyclohexene ring, a cyclohexene ring, And cycloalkene rings such as rings. The at least one hydrogen atom contained in the aliphatic hydrocarbon ring may be substituted with any substituent.

In the above R ₇ and R ₈ , the aromatic hydrocarbon ring means a trivalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon moiety having 6 to 14, or 6 to 12, ring atoms, But are not limited to, trivalent, benzene ring, naphthalene ring, anthracene ring, biphenyl ring and the like. The at least one hydrogen atom contained in the aromatic hydrocarbon ring may be substituted with any substituent.

On the other hand, the R ₇ and R ₈ are, but are not limited to, each independently, among the C _{1 ~ 10} a, it is preferable an aliphatic hydrocarbon chain, more preferably from C _{1 ~ 8} aliphatic hydrocarbon chain, C _{1 ~ 4} More preferably an aliphatic hydrocarbon chain.

In the above R ₉ and R ₁₀ , the alkylene of X _{2 means} a straight or branched divalent hydrocarbon moiety of methylene, ethylene or the like; Alkenylene means straight or branched saturated divalent hydrocarbon moieties such as ethenylene, propenylene and the like; Cycloalkylene means a divalent non-aromatic hydrocarbon ring moiety such as cyclopentylene, cyclohexylene and the like; Cycloalkenylene means a saturated divalent non-aromatic hydrocarbon ring moiety such as cyclopentenylene, cyclohexenylene, and the like. On the other hand, at least one hydrogen atom of the alkylene, alkenylene, cycloalkylene, cycloalkenylene, and phenylene may be substituted with any substituent.

On the other hand, in the above R ₉ and R _10, wherein X ₂ is preferably Among them, a C _1-6 alkylene, the alkylene is a C _{1 ~ 4} are more preferable.

In the above R ₁₁ and R ₁₂ , the (meth) acryloyl means acryloyl or methacryloyl; The (meth) acryloyloxy means acryloyloxy or methacryloyloxy.

In the above-mentioned R ₁₃ and R ₁₄ , the alkyl means a linear or branched hydrocarbon moiety, and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, Neal and the like are examples. The remaining one or more hydrogen atoms contained in the alkyl may be substituted with any substituent.

More specifically, the acrylic compound having at least two benzene rings contained in the active energy ray-curable adhesive composition of the present invention is not limited to the following. For example, compounds represented by the following formulas (III-1) to -6]. ≪ / RTI > These may be used alone or in combination.

[Formula (III-1)

[Formula (III-2)

[Formula (III-3)

[Formula (III-4)

[Formula III-5]

[Formula III-6]

In addition, the active energy ray-curable adhesive composition of the present invention may further comprise a carboxylic acid compound having at least one carbon-carbon unsaturated double bond. At this time, the carboxylic acid compound having at least one carbon-carbon unsaturated double bond is added in order to further improve the adhesive strength of the present invention and is a carboxylic acid compound having at least one carbon-carbon unsaturated double bond, It is possible to use without. As described above, when a carboxylic acid compound is contained, since a carboxyl group having a high affinity for water has a moisture and hydrogen bond, a hydrogen bonding site can be ensured. Therefore, .

On the other hand, in the carboxylic acid compound having at least one carbon-carbon unsaturated double bond, it is preferable that the carbon-carbon unsaturated double bond exists in the side chain and the carbon-carbon unsaturated double bond present in the side chain is conjugated with the carboxy group Do. Here, the side chain (side chain) means a hydrocarbon branch branched from the main chain of the above compound. In this case, radical polymerization can be performed more advantageously.

For example, but not limited to, the carboxylic acid compound having at least one carbon-carbon unsaturated double bond may be represented by the following formula (IV).

[Formula IV]

In the above Formula Ⅳ], R ₁₅ is a single bond, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or phenylene, and; R ₁₆ is one oxyalkylene hydrogen, C _{1 ~ 6} carboxyalkyl, C _{1 ~ 6} (meth) alkyl, C _{1 ~ 6} (meth) acryloyl.

Here, in R ₁₅ , the alkylene means a straight or branched divalent hydrocarbon moiety such as methylene, ethylene or the like; Alkenylene means straight or branched saturated divalent hydrocarbon moieties such as ethenylene, propenylene and the like; Cycloalkylene means a divalent non-aromatic hydrocarbon ring moiety such as cyclopentylene, cyclohexylene and the like; Cycloalkenylene means a saturated divalent non-aromatic hydrocarbon ring moiety such as cyclopentenylene, cyclohexenylene, and the like. On the other hand, at least one hydrogen atom of the alkylene, alkenylene, cycloalkylene, cycloalkenylene, and phenylene may be substituted with any substituent.

In R ₁₆ , the carboxyalkyl means that carboxy such as carboxymethyl, carboxyethyl or carboxypropyl is substituted by alkyl; The (meth) acryloylalkyl means that acryloyl or methacryloyl such as acryloylmethyl, acryloylethyl, methacryloylmethyl or methacryloylethyl is substituted with alkyl; The (meth) acryloyloxyalkyl is preferably acryloyloxy or methacryloyloxyalkyl such as acryloyloxymethyl, acryloyloxyethyl, methacryloyloxymethyl or methacryloyloxyethyl, Substituted " On the other hand, at least one hydrogen atom of the carboxyalkyl, (meth) acryloylalkyl, and (meth) acryloyloxyalkyl may be substituted with any substituent.

More specifically, although not limited thereto, the carboxylic acid compound having at least one carbon-carbon unsaturated double bond may be a compound represented by the following formulas (IV-1) to (IV-5). These may be used alone or in combination.

[Formula IV-1]

[Formula IV-2]

[Formula IV-3]

[Formula IV-4]

[Formula IV-5]

On the other hand, the active energy ray-curable adhesive composition comprises an acrylic compound having a molecular weight of at least 120 g / mol having at least one hydroxy substituent group; An acrylic compound having at least two benzene rings; A carboxylic acid compound having at least one carbon-carbon unsaturated double bond; And a radical initiator.

The active energy ray-curable adhesive composition may comprise 30 to 90 parts by weight of an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent, based on 100 parts by weight of the total composition; 5 to 50 parts by weight of an acrylic compound having at least two benzene rings; 1 to 30 parts by weight of a carboxylic acid compound having at least one carbon-carbon unsaturated double bond; And 0.1 to 10 parts by weight of a radical initiator.

More specifically, the content of the acrylic compound having a molecular weight of 120 g / mol or more having at least one hydroxy substituent is 30 to 90 parts by weight, preferably 40 to 80 parts by weight relative to 100 parts by weight of the total adhesive composition , And more preferably about 50 to 80 parts by weight. If the content of the acrylic compound having a molecular weight of at least 120 g / mol with at least one hydroxy substituent is less than the above range, it is difficult to secure the adhesive strength. If the content is larger than the above range, the glass transition temperature of the adhesive composition is lowered, .

The content of the acrylic compound having at least two benzene rings is 5 to 50 parts by weight, preferably 10 to 40 parts by weight, more preferably 10 to 30 parts by weight, based on 100 parts by weight of the total adhesive composition . If the content of the acrylic compound having at least two benzene rings is less than the above range, the glass transition temperature may be lowered and the heat resistance may be lowered. If the content is higher than the above range, the adhesive strength may be lowered.

The content of the carboxylic acid compound having at least one carbon-carbon unsaturated double bond is 1 to 30 parts by weight, preferably 1 to 25 parts by weight, more preferably 1 to 30 parts by weight per 100 parts by weight of the whole adhesive composition. 15 parts by weight. If the content of the carboxylic acid compound having at least one carbon-carbon unsaturated double bond is less than the above range, the adhesive strength can not be secured. If the content is higher than the above range, the storage stability may be deteriorated and the adhesive strength may be deteriorated.

The content of the radical initiator may be 0.1 to 10 parts by weight, preferably 1 to 5 parts by weight, more preferably 1 to 3 parts by weight based on 100 parts by weight of the total adhesive composition. When the content of the radical initiator satisfies the above-described numerical range, the curing of the adhesive can be smoothly performed.

On the other hand, the active energy ray-curable adhesive composition of the present invention can be used as needed in order to further improve the adhesive strength and water resistance An acrylic compound having an adamantane ring, an epoxy compound, a cationic initiator, and the like.

At this time, the acrylic compound having an adamantane ring is an acrylic compound having an adamantane ring and can be used without any particular limitation as long as it is capable of radical polymerization. For example, although not limited thereto, the acrylic compound having an adamantane ring may be represented by the following formula (V).

[Formula V]

Wherein in Formula Ⅴ], R ₁₇ is an alkylene group of a single bond, or C _{1 ~ 6;} R ₁₈ is hydrogen or C _{1 ~ 10} alkyl; R ₁₉ is a halogen atom or C _{1 ~ 10} alkyl; n is an integer of 1 to 3; m is an integer of 0 to 3;

In R ₁₇ , the alkylene means a linear or branched divalent hydrocarbon moiety, and examples thereof include methylene, dimethylmethylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, etc. For example. Meanwhile, at least one hydrogen atom contained in the alkylene may be substituted with any substituent.

In the above-mentioned R ₁₈ , the alkyl means a linear or branched hydrocarbon moiety, and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, For example. Meanwhile, at least one hydrogen atom contained in the alkyl may be substituted with any substituent.

In the above R ₁₉ , the alkyl means a linear or branched hydrocarbon moiety, and includes, but is not limited to, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, For example. Meanwhile, at least one hydrogen atom contained in the alkyl may be substituted with any substituent.

N is an integer of 1 to 3, more preferably 1, and m is an integer of 0 to 3, preferably 0 or 1.

More specifically, the acrylic compound having an adamantane ring may be, for example, 1-adamantanyl acrylate, 1-adamantanyl methacrylate, and the like. These may be used alone or in combination.

On the other hand, the content of the acrylic compound having the adamantane ring is 1 to 30 parts by weight, preferably 1 to 20 parts by weight, more preferably 1 to 15 parts by weight, based on 100 parts by weight of the total adhesive composition . When the above range is satisfied, the effect of improving the adhesive strength and water resistance is excellent.

The epoxy compound is not particularly limited as long as it has at least one epoxy group, and examples thereof include an aromatic epoxy compound, a hydrogenated epoxy compound, an alicyclic epoxy compound, and an epoxy group-containing (meth) have. These may be used alone or in combination of two or more.

On the other hand, the epoxy compound is not limited thereto, but is preferably an alicyclic epoxy compound. Here, the alicyclic epoxy compound refers to an epoxy compound having an epoxy group formed between two adjacent carbon atoms constituting an aliphatic hydrocarbon ring. Among them, at least two epoxy groups and at least two alicyclic rings Epoxy compounds such as 2- (3,4-epoxy) cyclohexyl-5,5-spiro- (3,4-epoxy) cyclohexane-m-dioxane, 3,4-epoxycyclohexylmethyl- -Epoxy cyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, vinylcyclohexanedioxide, bis (3,4- Epoxycyclohexylmethyl) adipate, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, exo-exobis (2,3-epoxycyclopentyl) ether, endo-exobis Pentyl) ether, 2,2-bis [4- (2,3-epoxypropoxy) cyclohexyl] propane, 2,6 (2,3-epoxypropoxycyclohexyl-p-dioxane), 2,6-bis (2,3-epoxypropoxy) norbornene, limonene dioxide, 2,2- Epoxycyclohexyl) propane, dicyclopentadienedioxide, 1,2-epoxy-6- (2,3-epoxypropoxy) hexahydro-4,7-methanoindane, p- (2,3- (2,3-epoxypropoxy) phenyl-5,6-epoxyhexahydro-4,7-methanone, o- (2,3-epoxy) (Cyclopentylphenyl-2,3-epoxypropyl ether), 1,2-bis [5- (1,2-epoxy) -4,7-hexahydro methano nanooxyl] ethane cyclopentenylphenyl glycidyl ether, More preferred are ethylenebis (3,4-epoxycyclohexane) ethylene glycol di (3,4-epoxycyclohexylmethyl) ether and ethylenebis (3,4-epoxycyclohexanecarboxylate) 4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate Particularly preferred.

On the other hand, the content of the epoxy compound may be 1 to 30 parts by weight, preferably 1 to 20 parts by weight, more preferably 1 to 15 parts by weight based on 100 parts by weight of the whole adhesive composition. When the above range is satisfied, the effect of improving the adhesive strength and water resistance is excellent.

The cationic initiator is a compound which generates an acid (H +) by an active energy ray. Examples of the cationic initiator that can be used in the present invention include a sulfonium salt or an iodonium salt . Specific examples of the photoacid generator containing a sulfonium salt or an iodonium salt include diphenyl (4-phenylthio) phenylsulfonium hexafluoroantimonate (Diphenyl (4- phenylthio) phenylsulfonium hexafluoroantimonate), diphenyl (4-phenylthio) phenylsulfonium hexafluorophosphate, phenyl (4- (2-methylpropyl) phenyl] -iodonium hexa (2-methylpropyl) phenyl] -iodonium hexafluorophosphate, (thiodi-4,1-phenylene) bis (diphenylsulfonium) dihexafluoroantimonate ((Thiodi- 4,1-phenylene) bis (diphenylsulfonium) dihexafluoroantimonate and thiodi-4,1-phenylene bis (diphenylsulfonium) bis (diphenylsulfonium) dihexafluoroantimonate) dihexafluorophosphate), but is limited to at least one selected from the group consisting of The.

On the other hand, the content of the cationic initiator may be 0.1 to 10 parts by weight, preferably 1 to 8 parts by weight, more preferably 1 to 5 parts by weight based on 100 parts by weight of the whole adhesive composition. When the content is included in the content of the above numerical range, there is an advantage that the adhesive strength is improved as compared with the case where it is not included or does not satisfy the above numerical range.

Meanwhile, in the active energy ray-curable adhesive composition of the present invention, the total adhesive composition preferably has a glass transition temperature of 50 ° C or higher after curing, and may be, for example, 50 to 500 ° C or 50 to 200 ° C. The polarizer produced by using the adhesive composition having the glass transition temperature in the above-described numerical range has an advantage of excellent heat resistance.

In the active energy ray-curable adhesive composition of the present invention, the total adhesive composition preferably has a viscosity of 10 to 200 cP or 20 to 100 cP or so. When the viscosity of the adhesive composition satisfies the above-described numerical value range, the adhesive layer can be formed to have a small thickness, and a low viscosity can be obtained, which is advantageous in workability.

The adhesive layer formed by the active energy ray-curable adhesive composition of the present invention preferably has a thickness of about 0.1 to 20 mu m, preferably about 0.1 to 10 mu m, or about 0.1 to 5 mu m. When the thickness of the adhesive layer is less than 0.1 mu m, the uniformity and the adhesive force of the adhesive layer may be lowered. If the thickness of the adhesive layer exceeds 10 mu m, the appearance of the polarizer may be wrinkled.

Next, the polarizer of the present invention can use a polarizer known in the art, for example, a polyvinyl alcohol-based film in which an iodine or a dichroic dye is adsorbed and oriented. At this time, the production method of the polarizer is also not particularly limited, and for example, the polyvinyl alcohol film can be washed, swollen, dyed, washed, drawn, complemented, and dried.

On the other hand, when the polarizer is a polyvinyl alcohol-based film, the polyvinyl alcohol-based film can be used without any particular limitation as long as it contains a polyvinyl alcohol resin or a derivative thereof. At this time, derivatives of the polyvinyl alcohol resin include, but are not limited to, polyvinyl formal resins and polyvinyl acetal resins. Alternatively, the polyvinyl alcohol-based film may be a commercially available polyvinyl alcohol-based film commonly used in the art for producing polarizers, such as P30, PE30, PE60 manufactured by Kuraray Co., Ltd., M3000 M6000 manufactured by Nippon Synthetic Chemical Industry Co., .

On the other hand, the polyvinyl alcohol film is not limited to this, but the degree of polymerization is preferably about 1,000 to 10,000, and preferably about 1,500 to 5,000. When the degree of polymerization satisfies the above range, molecular motion is free and can be mixed with iodine or a dichroic dye or the like in a flexible manner.

Next, the FPR (Film-type Patterned Retarder) film of the present invention is structured such that the optical axes of the respective pattern regions are formed in different directions so that the images transmitted to the left and right eyes of the viewer wearing polarized glasses are different, Various FPR (Film-type Patterned Retarder) films commonly used in the art can be used. For example, various optical films described in Japanese Laid-Open Patent Publication No. 2005-049865, Korean Patent Publication No. 2010-0089782, Korean Patent No. 0967899, Korean Patent No. 1204135, and the like can be used.

The polarizing plate of the present invention may further include a protective film on one side of the polarizer, if necessary. More specifically, in the polarizing plate of the present invention, a protective film may be attached to the opposite side of the surface of the polarizer on which the FPR (Film-type Patterned Retarder) film is formed.

The protective film is used for supporting and protecting the polarizer. The protective film may be a protective film of various materials generally known in the art, for example, a cellulose-based film, a polyethylene terephthalate (PET) film, An olefin polymer (COP, cycloolefin polymer) film, an acrylic film, and the like can be used without limitation. Of these, it is particularly preferable to use an acrylic film in consideration of optical characteristics, durability, economical efficiency and the like.

On the other hand, the acrylic film usable in the present invention can be obtained by molding a molding material containing a (meth) acrylate resin as a main component by extrusion molding. In this case, the (meth) acrylate-based resin contains a resin containing a (meth) acrylate-based unit as a main component, and includes not only a homopolymer resin composed of a (meth) acrylate- But also a copolymer resin in which other monomer units are copolymerized and a blend resin in which another resin is blended with the above-mentioned (meth) acrylate resin.

On the other hand, the (meth) acrylate-based unit may be, for example, an alkyl (meth) acrylate-based unit. Here, the alkyl (meth) acrylate-based unit means both an alkyl acrylate-based unit and an alkyl methacrylate-based unit, and the alkyl (meth) acrylate-based alkyl group preferably has 1 to 10 carbon atoms , More preferably from 1 to 4 carbon atoms.

Examples of the monomer unit copolymerizable with the (meth) acrylate-based monomer unit include a styrene-based monomer unit, a maleic anhydride-based monomer unit, and a maleimide-based monomer unit. Examples of the styrene-based monomer include, but are not limited to, styrene and? -Methylstyrene. The maleic anhydride monomer includes, but is not limited to, maleic anhydride, cyclohexylmaleic acid Examples of the maleimide-based monomer include, but are not limited to, maleimide, N-methylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide and the like For example. These may be used alone or in combination.

On the other hand, in the case of the acryl-based film, a primer layer may be included on one side for imparting slipperiness and improving adhesion to the radical-curable composition. At this time, the primer layer may be formed by applying a coating solution containing a water-dispersible polymer resin, water-dispersible fine particles, and water on an acrylic film using a bar coating method, a gravure coating method, and the like. The water-dispersible polymer resin may be, for example, water-dispersed polyurethane resin, water-dispersed acrylic resin, water-dispersed polyester resin, or a combination thereof, and the water-dispersible fine particles may be inorganic fine particles such as silica, titania, alumina, zirconia Organic fine particles made of a silicone resin, a fluorine resin, a (meth) acrylic resin, a crosslinked polyvinyl alcohol and a melamine resin, or a combination thereof may be used, but the present invention is not limited thereto.

On the other hand, if necessary, the acrylic film may be subjected to a surface treatment for improving the adhesive strength. For example, at least one surface of the optical film may be subjected to at least one surface treatment selected from the group consisting of alkali treatment, corona treatment, Can be performed.

The attachment of the polarizer and the protective film may be performed by coating an adhesive on the surface of the polarizer or the protective film using a roll coater, a gravure coater, a bar coater, a knife coater or a capillary coater, A method of laminating by laminating at room temperature or a method of UV irradiation after laminating. As the adhesive, various adhesives for polarizing plates used in the related art, for example, a polyvinyl alcohol adhesive, a polyurethane adhesive, an acrylic adhesive, a cationic or radical adhesive, and the like can be used without limitation.

The polarizing plate of the present invention as described above can be advantageously applied to an image display apparatus. The image display device may be, for example, a liquid crystal panel and a three-dimensional image display device including polarizing plates provided on both sides of the liquid crystal panel. At least one of the polarizing plates may be a polarizing plate according to the present invention. At this time, the type of the liquid crystal panel included in the stereoscopic image display device is not particularly limited. The types of the other constituent elements constituting the stereoscopic image display device, for example, the types of the upper and lower substrates (e.g., color filter substrate or array substrate) are not particularly limited, .

Hereinafter, the present invention will be described in detail with reference to specific examples.

Manufacturing example  1 - Preparation of Acrylic Protective Film

A resin composition obtained by uniformly mixing poly (N-cyclohexylmaleimide-co-methylmethacrylate), styrene-maleic anhydride copolymer resin and phenoxystyrene resin at a weight ratio of 100: 2.5: To an extruder was fed to an extruder of 24φ substituted with nitrogen and melted at 250 ° C to prepare a raw material pellet.

The styrene-maleic anhydride copolymer resin was a mixture of 85% by weight of styrene and 15% by weight of maleic anhydride, Dylaeck 332 (trade name, manufactured by Nippon Polyurethane Industry Co., Ltd.) , And poly (N-cyclohexylmaleimide-co-methylmethacrylate) resin had a content of N-cyclohexylmaleimide of 6.5% by weight by NMR analysis.

The obtained raw material pellets were dried in vacuo, melted in an extruder at 260 占 폚, passed through a coat hanger type T-die, and a film having a thickness of 150 占 퐉 was produced through a chrome casting roll and a drying roll. The film was stretched at a rate of 170% using a pylot stretching machine at 125 DEG C in the MD direction using the speed difference of rolls to produce an acrylic film.

The acrylic film prepared through the above process was subjected to corona treatment, and then a primer composition having a solid content of 10% by weight prepared by diluting CK-PUD-F (dim light urethane dispersion) with pure water on one side of the acrylic film was coated with oxazoline 20 parts by weight of a crosslinking agent (Nippon Catalyst Co., Ltd., WS700) was coated on the primer composition in # 7 bar and stretched in the TD direction at 130 캜 using a tenter to obtain a primer composition having a primer layer thickness of 300 nm A film was prepared.

Manufacturing example  2 - FPR ( Film - type Patterned Retarder ) Production of film

The composition for forming a photo alignment layer was coated on one surface of a TAC substrate (refractive index: 1.49, thickness: 80,000 nm) to a thickness of about 1,000 Å after drying, and dried in an oven at 80 ° C for 2 minutes. As the composition for forming a photo alignment film, a mixture of a polynorbornene (molecular weight (Mw) = 150,000) having a cinnamate group represented by the following formula (A) and an acrylic monomer was mixed with a photoinitiator (Irgacure 907) (Polynorbornene: acrylic monomer: photoinitiator = 2: 1: 0.25 (weight ratio)) was prepared by dissolving the mixture in a toluene solvent such that the solid content concentration of polynorbornene was 2 wt%.

Then, a pattern mask in which stripe-shaped light transmitting portions having a width of about 450 mu m and light blocking portions alternately formed on the upper and lower sides and the left and right sides were placed on the dried composition, The polarizing element having the two regions formed therein was positioned. Thereafter, while the TAC substrate on which the photo alignment layer was formed was moved at a speed of about 3 m / min, ultraviolet rays of 300 mW / cm < ² > were irradiated to the composition for photo alignment layer through the polarizing element plate and the pattern mask for about 30 seconds And the alignment treatment was carried out. Subsequently, a liquid crystal layer was formed on the alignment layer subjected to alignment treatment. Specifically, 70 parts by weight of a multifunctional polymerizable liquid crystal compound represented by the following formula (B) as a liquid crystal composition and 30 parts by weight of a monofunctional polymerizable liquid crystal compound represented by the following formula (C), and a proper amount of a photoinitiator after the liquid crystal composition was applied so that a dry thickness of about 1㎛ and oriented according to the orientation of the lower alignment layer, by irradiating ultraviolet 300mW / cm ² for about 10 seconds, cross-linking and polymerizing the liquid crystal, of the lower alignment layers A liquid crystal layer having first and second regions having optical axes orthogonal to each other according to the orientation was formed.

(A)

[Chemical Formula B]

≪ RTI ID = 0.0 &

Manufacturing example  3 - Preparation of adhesive composition

(1) Adhesive composition A

70 parts by weight of 4-hydroxybutylacrylate (molecular weight: 144 g / mol), 4,4 '- (((propane-2,2-diylbis (4,1- phenylene) 20 parts by weight of bis (1- (methacryloyloxy) propane-3,2-diyl) bis (oxy)) bis (4-oxobutanoic acid) and 10 parts by weight of itaconic acid , 3 parts by weight of a radical initiator Irgacure 819 (Ciba) was added to prepare an adhesive composition A.

(2) Adhesive composition B

57.4 parts by weight of 2-hydroxybutylacrylate (molecular weight 144 g / mol), 4,4 '- ((((propane-2,2-diylbis (4,1-phenylene) 16.4 parts by weight of bis (1- (methacryloyloxy) propane-3,2-diyl) bis (oxy)) bis (4-oxobutanoic acid), 8.1 parts by weight of itaconic acid, 8.1 parts by weight of hexylmethyl-3,4-epoxycyclohexanecarboxylate, and 10 parts by weight of 1-adamantanyl methacrylate were added 3 parts by weight of a radical initiator Irgacure 819 (Ciba) And 5 parts by weight of PF6 (Lambson) were added to prepare an adhesive composition B.

(3) Adhesive composition C

70 parts by weight of 2-hydroxyethyl acrylate (molecular weight: 116 g / mol), 4,4 '- ((((propane-2,2-diylbis (4,1-phenylene) 20 parts by weight of bis (1- (methacryloyloxy) propane-3,2-diyl) bis (oxy)) bis (4-oxobutanoic acid) and 10 parts by weight of itaconic acid , And 3 parts by weight of a radical initiator Irgacure 819 (Ciba) were added to prepare an adhesive composition C.

(4) Adhesive composition D

57.4 parts by weight of 2-hydroxyethyl acrylate (molecular weight: 116 g / mol), 4,4 '- ((((propane-2,2-diylbis (4,1-phenylene) 16.4 parts by weight of bis (1- (methacryloyloxy) propane-3,2-diyl) bis (oxy)) bis (4-oxobutanoic acid), 8.1 parts by weight of itaconic acid, 8.1 parts by weight of methyl-3,4-epoxycyclohexanecarboxylate and 10 parts by weight of 1-adamantanyl methacrylate were added 3 parts by weight of a radical initiator Irgacure 819 (Ciba) and 10 parts by weight of a cationic initiator PF6 (Lambson) were added to prepare an adhesive composition D. [

The specific structures of the compounds used in the above adhesive compositions A to D are shown in Table 1 below.

name rescue 2-hydroxybutyl acrylate

2-hydroxyethyl acrylate

Bis (1- (methacryloyloxy) propane-3,2-diyl) bis (4-methoxyphenyl) ) Bis (oxy)) bis (4-oxobutanoic acid)

Itaconic acid

3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate

1-adamantanyl methacrylate

Example  One

The adhesive composition A was coated on both sides of a polyvinyl alcohol polarizing element in which iodine was adsorbed and aligned with a sphere and then the acrylic film produced in Production Example 1 was laminated on one side of the polarizing element, The FPR film was laminated on the other side (the liquid crystal layer was brought into contact with the adhesive), and then the thickness of the final adhesive layer was set to 4 to 6 占 퐉 and passed through a laminator. Then, a polarizing plate was prepared by irradiating ultraviolet rays of 900 mJ / cm ² using a metal halide lamp on the surface of the acrylic film laminated.

Example  2

A polarizing plate was produced in the same manner as above except that B was used instead of the adhesive composition A.

Comparative Example  One

A polarizing plate was produced in the same manner as above except that C was used in place of the adhesive composition A.

Comparative Example  2

A polarizing plate was produced in the same manner as above except that D was used in place of the adhesive composition A.

Experimental Example  1 - of the polarizer Peel force  evaluation

The peeling forces of the polarizing plates produced in the above Examples and Comparative Examples were measured and shown in Table 2 below. Specifically, the polarizing plates prepared in the above Examples and Comparative Examples were cut to a width of 20 mm and a length of 100 mm. Then, polarizing elements and FPRs at speeds of 300 mm / min and 90 degrees with a Texture Analyzer (Stable Micro Systems TA-XT Plus) The peeling force between the films was measured. When the peel force is 1.4 N / 2 cm or more, it is indicated by o, when the peel force is 1.0 N / 2 cm or more and 1.4 N / 2 cm or less, and when the peel force is less than 1.0 N / 2 cm,

Experimental Example  2 - The adhesive layer  Glass transition temperature measurement

The glass transition temperature of the adhesive layer of the polarizing plate prepared in the above Examples and Comparative Examples was measured and shown in Table 2 below. Specifically, after separating the adhesive layer of the polarizing plate prepared under the above-described curing conditions, the temperature was elevated to -30 to 200 ° C using a differential scanning calorimeter (DSC Mettler) to adjust the glass transition temperature in the second run Respectively.

division Composition Peel force Glass transition temperature (캜) Example 1 A ○ 50 Example 2 B ◎ 50 Comparative Example 1 C X 85 Comparative Example 2 D X 80

As can be seen from the above Table 2, Example 1 produced using the adhesive composition A of the present invention shows excellent adhesion between the polarizing element and the FPR film, and the adhesive composition B of the present invention It can be seen that the contact force between the polarizing element and the FPR film is further improved. However, as in Comparative Examples 1 and 2, it can be seen that the polarizing plate manufactured using the adhesive compositions C to D has a very weak adhesive force between the polarizing element and the FPR film.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, It will be obvious to those of ordinary skill in the art.

Claims (11)

A polarizer; An adhesive layer formed on at least one surface of the polarizer; And an FPR (Film-type Patterned Retarder) film adhered on the adhesive layer,
Wherein the adhesive layer comprises an acrylic compound having a molecular weight of 120 g / mol or more and 700 g / mol or less and having at least one hydroxy substituent group; And an active energy ray curable adhesive composition comprising a radical initiator,
Wherein the active energy ray curable composition is an acrylic compound having at least two benzene rings; And a carboxylic acid compound having at least one carbon-carbon unsaturated double bond. The method according to claim 1,
Wherein the acrylic compound having at least one hydroxy substituent and having a molecular weight of 120 g / mol or more is represented by the following formula (I) or (II).
(I)

Wherein R ₁ is C _{4 to} C ₈ alkyl, C _{4 to} C ₈ cycloalkyl, C _{4 to} C ₁₂ alkylcycloalkyl, C _{4 to} C ₁₂ cycloalkylalkyl, C _{5 to} C ₈ cycloalkylalkyl having at least one hydroxy substituent, _{- 14} alkyl, cycloalkyl alkyl, C _{7 ~ 12} phenylalkyl, or C _{7 - 12} phenoxy alkyl; R ₂ is hydrogen or C _{1 ~ 10} alkyl.

[Formula II]

In the above Formula Ⅱ], R ₃ is having at least one hydroxy substituent, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or Phenylene; R ₄ is C _{1 ~ 12} alkyl, C _{4 ~ 12} cycloalkyl, C _{4 ~ 12} alkylcycloalkyl, C _{4 ~ 12} cycloalkylalkyl, C _{5 ~ 14} alkyl and cycloalkyl-alkyl; R ₅ is hydrogen or C _{1 ~ 10} alkyl.
delete The method according to claim 1,
Wherein the active energy ray-curable adhesive composition comprises 30 to 90 parts by weight of an acrylic compound having a molecular weight of 120 g / mol or more and having at least one hydroxy substituent, based on 100 parts by weight of the total composition; 5 to 50 parts by weight of an acrylic compound having at least two benzene rings; 1 to 30 parts by weight of a carboxylic acid compound having at least one carbon-carbon unsaturated double bond; And 0.1 to 10 parts by weight of a radical initiator. The method according to claim 1,
Wherein the acrylic compound having at least two benzene rings is represented by the following formula (III).
[Formula (III)

In the above formula (III), X ₁ is a single bond or -O-; R ₆ is a single bond, or C _1-10 alkylene; R ₇ and R ₈ are each independently a C _1-10 aliphatic hydrocarbon chain, a C ₁₄ aliphatic hydrocarbon ring, or a C _6-14 aromatic hydrocarbon ring; R ₉ and R ₁₀ are each independently selected from -OH, -C (= O) OH , -OC (= O) X 2 C (= O) OH, wherein X ₂ is C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _4-6 cycloalkylene, C _4-6 cycloalkenylene, or phenylene; R ₁₁ and R ₁₂ are each independently (meth) acryloyl or (meth) acryloyloxy; R ₁₃ and R ₁₄ are each independently a halogen atom or C _1-10 alkyl; a and b are each independently an integer of 0 to 2; The method according to claim 1,
The carboxylic acid compound having at least one carbon-carbon unsaturated double bond is represented by the following formula (IV).
[Formula IV]

In the above Formula Ⅳ], R ₁₅ is a single bond, C _{1 ~ 6} alkylene, C _{2 ~ 6} alkenylene, C _{4 ~ 6} cycloalkylene, C _{4 ~ 6} cycloalkyl alkenylene, or phenylene, and; R ₁₆ is hydrogen, C _1-6 carboxyalkyl, C _1-6 (meth) acryloylalkyl, or C _1-6 (meth) acryloyloxyalkyl. The method according to claim 1,
Wherein the active energy ray-curable adhesive composition has a glass transition temperature after curing of 50 DEG C or more and 500 DEG C or less. The method according to claim 1,
Wherein the active energy ray-curable adhesive composition has a viscosity of 10 to 200 cP.
The method according to claim 1,
Wherein the polarizer is a polyvinyl alcohol-based film in which iodine or a dichroic dye is adsorbed and oriented.
The method according to claim 1,
And a protective film is attached on the opposite side of the surface of the polarizer on which the FPR (Film-type Patterned Retarder) film is formed.
An image display apparatus comprising the polarizing plate of any one of claims 1, 2 and 4 to 10.