KR102378562B1 - Adhesive composition, adhesive film using the same, polarizing plate and optical display device - Google Patents

Abstract

(상기 화학식 1에서, 각 치환기는 명세서에 정의된 바와 같다.)(1) a compound represented by the following formula (1); (2) acrylic binder resin; (3) curing agents; and (4) a pressure-sensitive adhesive composition including a solvent, an adhesive film prepared using the pressure-sensitive adhesive composition, a polarizing plate including the adhesive film, and an optical display device including the polarizing plate.
[Formula 1]

(In Formula 1, each substituent is as defined in the specification.)

Description

Adhesive composition, adhesive film, polarizing plate and optical display {ADHESIVE COMPOSITION, ADHESIVE FILM USING THE SAME, POLARIZING PLATE AND OPTICAL DISPLAY DEVICE}

The present disclosure relates to a pressure-sensitive adhesive composition, a pressure-sensitive adhesive film produced using the pressure-sensitive adhesive composition, a polarizing plate including the pressure-sensitive adhesive film, and an optical display device including the polarizing plate.

Liquid crystal display devices, which are one of the display devices, have advantages such as light weight, thinness, low cost, low power consumption, and excellent adhesion to integrated circuits, and thus their range of use is expanding for notebook computers, monitors, and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix (light blocking layer), a color filter, and an ITO pixel electrode are formed, an active circuit portion consisting of a liquid crystal layer, a thin film transistor, and a storage capacitor layer, and an upper substrate on which the ITO pixel electrode is formed. is composed

A liquid crystal display device (LCD) requires a liquid crystal cell containing liquid crystal and a polarizing plate, and an appropriate adhesive layer or adhesive layer for bonding them must be used.

In addition, the polarizing plate is stretched in a certain direction, and an iodine-based compound or a dichroic polarizing material is adsorbed and oriented to a polyvinyl alcohol (PVA) polarizer (or 'polarizing film'), and to protect both sides of the polarizer It includes a laminated polarizer protective film. Specifically, on one side of the polarizer, a polarizer protective film such as triacetyl cellulose (TAC), an adhesive layer and a release film to be bonded to the liquid crystal cell on the protective film are provided, and the other side of the polarizer is composed of a multilayer having a polarizer protective film and a surface protective film in which an adhesive layer is laminated on a base film.

In the process of attaching the polarizing plate of this structure to the liquid crystal cell, the release film is peeled from the pressure-sensitive adhesive layer, and when the role of the surface protection film is finished in the subsequent process, it is also peeled and removed. Since the release film and the surface protection film are made of a plastic material, they have high electrical insulation and generate static electricity during peeling.

The static electricity generated in this way causes a problem of contaminating the surface due to the adsorption of foreign substances to the optical member, a stain problem due to distortion of liquid crystal alignment, and there is a risk of causing damage to the thin film transistor (TFT) line. In particular, in recent years, as the LCD panel becomes larger, the size of the polarizing plate used in manufacturing the liquid crystal display is also enlarged, and the amount of static electricity is further increased as the speed of the process progresses.

One embodiment is to provide a pressure-sensitive adhesive composition comprising a compound having excellent color reproducibility.

Another embodiment is to provide a pressure-sensitive adhesive film prepared using the pressure-sensitive adhesive composition.

Another embodiment is to provide a polarizing plate including the adhesive film.

Another embodiment is to provide an optical display device including the polarizing plate.

One embodiment of the present invention is (1) a compound represented by the following formula (1); (2) acrylic binder resin; (3) curing agents; And (4) provides a pressure-sensitive adhesive composition comprising a solvent.

[Formula 1]

In Formula 1,

M is Zn, Co or Cu;

R ¹ to R ²⁰ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group or a substituted or unsubstituted C1 to C20 alkylester group;

provided that at least one or more of R ¹ to R ⁵ , at least one or more of R ⁶ to R ¹⁰ , at least one or more of R ¹¹ to R ¹⁵ , and at least one or more of R ¹⁶ to R ²⁰ are each independently not a hydrogen atom,

When one of R ¹ to R ⁵ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ⁶ to R ¹⁰ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ¹¹ to R ¹⁵ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ¹⁶ to R ²⁰ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group.

The compound represented by Formula 1 may be represented by Formula 2 below.

[Formula 2]

In Formula 2,

M is Zn, Co or Cu;

R ²¹ to R ²⁸ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted a cyclic sulfonamide group or a substituted or unsubstituted C1 to C20 alkylester group,

n1 to n8 are each independently an integer of 0 or 1, provided that 1 ≤ n1+n2 ≤ 2, 1 ≤ n3+n4 ≤ 2, 1 ≤ n5+n6 ≤ 2, 1 ≤ n7+n8 ≤ 2,

However, when R ²¹ , R ²³ , R ²⁵ and R ²⁷ are each independently a halogen atom or an unsubstituted C1 to C20 alkyl group, R ²² , R ²⁴ , R ²⁶ and R ²⁸ are each independently a halogen atom, substituted or unsubstituted A substituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkyl group an ester group, and n1 to n8 are each independently an integer of 1.

The compound may be represented by any one of the following Chemical Formulas 1-1 to 1-15 and Chemical Formulas 1-17 to 1-20.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

(In Formula 1-13,

R is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

m1 and m2 are each independently an integer from 0 to 20, provided that 4 ≤ m1+m2 ≤ 20)

[Formula 1-14]

[Formula 1-15]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

[Formula 1-20]

The compound represented by Formula 1 may be included in an amount of 0.001 wt% to 0.01 wt% based on the total amount of the pressure-sensitive adhesive composition.

The pressure-sensitive adhesive composition may further include a silane coupling agent, an antistatic agent, a UV absorber, a cationic initiator, a release agent, or a combination thereof.

The pressure-sensitive adhesive composition, based on the total amount of the pressure-sensitive adhesive composition, 0.001% by weight to 0.01% by weight of the compound represented by Formula 1; 70% to 85% by weight of the acrylic binder resin; 0.1 wt% to 1 wt% of the curing agent; and the remaining amount of the solvent.

Another embodiment provides an adhesive film prepared using the pressure-sensitive adhesive composition.

Another embodiment provides a polarizing plate including the adhesive film.

Another embodiment provides an optical display device including the polarizing plate.

The specific details of other aspects of the invention are included in the detailed description below.

The pressure-sensitive adhesive composition according to one embodiment does not cause discoloration even when exposed to a high temperature and high humidity environment for a long time, so it has excellent color stability and durability, and has excellent heat resistance or heat resistance. Accordingly, the pressure-sensitive adhesive film produced by using the pressure-sensitive adhesive composition has excellent durability, and the polarizing plate including the pressure-sensitive adhesive film having excellent durability may also have excellent durability and color stability.

Hereinafter, embodiments of the present invention will be described in detail. However, this is provided as an example, and the present invention is not limited thereto, and the present invention is only defined by the scope of the claims to be described later.

Unless otherwise specified herein, "substituted" to "substituted" means that at least one hydrogen atom in the functional group of the present invention is a halogen atom (F, Br, Cl or I), a hydroxyl group, a nitro group, a cyano group, an amino group ( NH ₂ , NH(R ²⁰⁰ ) or N(R ²⁰¹ )(R ²⁰² ), wherein R ²⁰⁰ , R ²⁰¹ and R ²⁰² are the same or different from each other, and each independently a C1 to C10 alkyl group), an amidino group, A hydrazine group, a hydrazone group, a carboxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, And it means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

Unless otherwise specified herein, "alkyl group" means a C1 to C20 alkyl group, specifically means a C1 to C15 alkyl group, and "cycloalkyl group" means a C3 to C20 cycloalkyl group, specifically C3 to C18 cycloalkyl group, "alkoxy group" means a C1 to C20 alkoxy group, specifically means a C1 to C18 alkoxy group, "aryl group" means a C6 to C20 aryl group, specifically C6 to refers to a C18 aryl group, “alkenyl group” refers to a C2 to C20 alkenyl group, specifically refers to a C2 to C18 alkenyl group, and “alkylene group” refers to a C1 to C20 alkylene group, specifically C1 to C18 alkylene group, “arylene group” means C6 to C20 arylene group, specifically, C6 to C16 arylene group.

Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" is "acrylic acid" and "methacrylic acid" It means both are possible.

Unless otherwise defined herein, "combination" means mixing or copolymerization. Also, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymerization or random copolymerization.

Unless otherwise defined in the chemical formulas in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded to the position.

In addition, unless otherwise defined in the present specification, "*" means a moiety connected to the same or different atoms or chemical formulas.

Also, in the present specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.

Also, in the present specification, when a part "includes" a certain component, it means that other components may be further included, rather than excluding other components, unless otherwise stated.

One embodiment is (1) a compound represented by the following formula (1); (2) acrylic binder resin; (3) curing agents; And (4) provides a pressure-sensitive adhesive composition comprising a solvent.

Hereinafter, each component will be described in detail.

A compound represented by Formula 1

The pressure-sensitive adhesive composition according to an embodiment includes a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

M is Zn, Co or Cu;

R ¹ to R ²⁰ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group or a substituted or unsubstituted C1 to C20 alkylester group;

provided that at least one or more of R ¹ to R ⁵ , at least one or more of R ⁶ to R ¹⁰ , at least one or more of R ¹¹ to R ¹⁵ , and at least one or more of R ¹⁶ to R ²⁰ are each independently not a hydrogen atom,

When one of R ¹ to R ⁵ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ⁶ to R ¹⁰ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ¹¹ to R ¹⁵ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group;

When one of R ¹⁶ to R ²⁰ is a halogen atom or an unsubstituted C1 to C20 alkyl group, the other four are a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted a cyclic C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkylester group.

For example, the compound may be represented by Formula 2.

[Formula 2]

In Formula 2,

M is Zn, Co or Cu;

R ²¹ to R ²⁸ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted a cyclic sulfonamide group or a substituted or unsubstituted C1 to C20 alkylester group,

n1 to n8 are each independently an integer of 0 or 1, provided that 1 ≤ n1+n2 ≤ 2, 1 ≤ n3+n4 ≤ 2, 1 ≤ n5+n6 ≤ 2, 1 ≤ n7+n8 ≤ 2,

However, when R ²¹ , R ²³ , R ²⁵ and R ²⁷ are each independently a halogen atom or an unsubstituted C1 to C20 alkyl group, R ²² , R ²⁴ , R ²⁶ and R ²⁸ are each independently a halogen atom, substituted or unsubstituted A substituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, a sulfonic acid group, a substituted or unsubstituted sulfonamide group, or a substituted or unsubstituted C1 to C20 alkyl group an ester group, and n1 to n8 are each independently an integer of 1.

For example, the compound may be represented by any one of the following Chemical Formulas 1-1 to 1-15 and Chemical Formulas 1-17 to 1-20.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

In Formula 1-13,

R is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

m1 and m2 are each independently an integer from 0 to 20, provided that 4 ≤ m1+m2 ≤ 20.

[Formula 1-14]

[Formula 1-15]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

[Formula 1-20]

The pressure-sensitive adhesive film prepared using the pressure-sensitive adhesive composition according to an embodiment includes the compound represented by Formula 1 having a maximum absorption wavelength of 400 nm to 450 nm, and thus diffuse reflection generated in the panel by light entering from the outside, that is, due to reflection It is possible to improve the visibility deterioration problem. Reflectance measurement for improving visibility may be measured using a spectrophotometer. That is, the level at which the light entering the panel from the outside deteriorates visibility due to diffuse reflection generated by particles inside the panel can be displayed through the reflectance.

The compound represented by Formula 1 may be included in an amount of 0.001 wt% to 0.01 wt% based on the total amount of the pressure-sensitive adhesive composition (based on the solid content of the pressure-sensitive adhesive composition, 0.01 wt% to 0.03 wt%).

The acrylic binder resin may be included in an amount of 70 wt% to 85 wt%, such as 70 wt% to 80 wt%, based on the total amount of the pressure-sensitive adhesive composition (90 wt% to 97 wt% based on the pressure-sensitive adhesive composition solid content).

The acrylic binder resin constituting the pressure-sensitive adhesive composition may include a first (meth)acrylate copolymer and/or a second (meth)acrylate copolymer.

The first (meth)acrylate copolymer and the second (meth)acrylate copolymer may have different functional groups.

The first (meth)acrylate copolymer may form a matrix of the pressure-sensitive adhesive film and provide at least one of a hydroxyl group and a carboxylic acid group to allow the pressure-sensitive adhesive composition to self-cur.

The first (meth)acrylate copolymer may include at least one of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylic monomer having a carboxylic acid group; And it may be a copolymer of a monomer mixture comprising a monomer copolymerizable with them (hereinafter, "first copolymerization monomer"). At least one of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylate monomer having a carboxylic acid group in the monomer mixture may be included in an amount of 10 mol% or less, specifically 0.01 mol% to 5 mol%. In the above range, when included together with the second (meth)acrylate copolymer, it is possible to implement an adhesive film that can be used in flexible devices with good flexibility and bendability.

The (meth)acrylate monomer having a hydroxyl group may enable self-curing and/or increase the adhesive force of the adhesive film and increase the durability of the adhesive film. The (meth)acrylate monomer having a hydroxyl group may be included in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol% of the monomer mixture. In the above range, the adhesive strength and durability of the pressure-sensitive adhesive film may be improved, and the aging of the pressure-sensitive adhesive composition may be accelerated.

A (meth)acrylate monomer having a hydroxyl group includes a (meth)acrylate monomer having a C1 to C20 alkyl group having at least one hydroxyl group, a (meth)acrylic monomer having a C3 to C20 cycloalkyl group having at least one hydroxyl group, and at least one hydroxyl group It may include at least one of (meth)acrylate monomers having a C6 to C20 aromatic group. Specifically, the (meth)acrylate monomer having a hydroxyl group is 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxy Butyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 1,4-cyclohexanedimethanol mono (meth) acrylate, 1-chloro-2-hydroxypropyl (meth) acrylate, diethylene At least one of glycol mono (meth) acrylate, 2-hydroxy-3-phenyloxypropyl (meth) acrylate, 4-hydroxycyclopentyl (meth) acrylate, and 4-hydroxycyclohexyl (meth) acrylate may include These may be included alone or in mixture of two or more.

A (meth)acrylate monomer having a carboxylic acid group can be made self-curable. The (meth)acrylate monomer having a carboxylic acid group may be included in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol% of the monomer mixture. In the above range, there is no risk of corrosion to the adherend because the acidity of the adhesive film is not high, the resistance can be lowered, and the reliability of the adhesive film can be increased. The (meth)acrylate monomer having a carboxylic acid group may include (meth)acrylic acid, but is not limited thereto.

The first copolymerization monomer is copolymerized with at least one of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylate monomer having a carboxylic acid group to form a first (meth)acrylate copolymer, and the matrix of the adhesive film It can form or provide additional functions.

The first copolymerization monomer may include a (meth)acrylate monomer having an alkyl group. The (meth)acrylate monomer having an alkyl group may be included in the (meth)acrylate copolymer to form a matrix of the adhesive film and increase the mechanical strength of the adhesive film. The (meth)acrylate monomer having an alkyl group may be included in an amount of 50 mol% to 99.99 mol%, specifically 50 mol% to 95 mol%, 95 mol% to 99.9 mol%, 55 mol% to 90 mol%, 60 mol% to 85 mol% in the monomer mixture. . Within the above range, the mechanical strength of the adhesive film may be increased. The (meth)acrylate monomer having an alkyl group may include (meth)acrylic acid ester having an unsubstituted C4 to C12 alkyl group. Specifically, the (meth) acrylate monomer having an alkyl group is n-butyl (meth) acrylate, t-butyl (meth) acrylate, iso-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) ) acrylate, 2-ethylhexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, iso-octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate , but may include one or more of dodecyl (meth) acrylate, but is not limited thereto. These may be included alone or in mixture of two or more.

The first copolymerization monomer may further include at least one of a (meth)acrylate monomer having an alicyclic group and a (meth)acrylate monomer having a heteroalicyclic group, thereby further increasing the pencil hardness of the polarizing plate including the adhesive film.

The (meth)acrylate monomer having the alicyclic group is included in the first (meth)acrylate copolymer, and together with the second (meth)acrylate copolymer, the adhesive film of the polarizing plate to which the adhesive film for the polarizing plate is adhered It is possible to increase the pencil hardness of the upper polarizing plate. Specifically, in the polarizing plate to which the adhesive film for a polarizing plate is adhered, the pencil hardness of the polarizing plate on the adhesive film may be 2H or more, more specifically, 2H to 3H. In the above range, even if the polarizing plate is adhered to a liquid crystal panel such as a glass material as an adhesive film for a polarizing plate, the pencil hardness is not significantly reduced compared to the case where the polarizing plate is adhered to a liquid crystal panel without an adhesive film, so that the polarizing plate can be used in an optical display device. In addition, the (meth)acrylate monomer having an alicyclic group is included in the (meth)acrylate copolymer together with the (meth)acrylate monomer having the following heteroalicyclic group, thereby lowering the creep at 25°C of the adhesive film for a polarizing plate and 85 At °C, creep can be increased. In particular, when the (meth)acrylate monomer having an alicyclic group and the (meth)acrylate monomer having a heteroalicyclic group are homopolymers, respectively, the glass transition temperature is 30°C or more, specifically 40°C to 180°C. Creep can be lowered at °C and creep can be increased at 85 °C. The (meth)acrylate monomer having the alicyclic group in the monomer mixture: the (meth)acrylic monomer having the heteroalicyclic group may be included in a molar ratio of 1:0.25 to 1:2. In the above range, there may be an effect of increasing cohesion or strength at room temperature. Alternatively, there may be a stress relaxation effect and an effect of improving the warpage of the polarizing film at high temperatures.

The (meth)acrylate monomer having the alicyclic group may be included in an amount of 1 mol% to 30 mol%, specifically 5 mol% to 20 mol% of the monomer mixture. In the above range, there may be an effect of increasing the pencil hardness of the polarizing plate on the pressure-sensitive adhesive film and increasing the cohesive force.

The (meth)acrylate monomer having an alicyclic group may include a (meth)acrylic acid ester having a substituted or unsubstituted C5 to C20 monocyclic or heterocyclic alicyclic group.

The "alicyclic group" means a non-heteroalicyclic group that does not contain a heteroatom of nitrogen, oxygen or sulfur. The "heterocycle" means that two or more alicyclic groups share one or more carbon atoms and are connected.

Specifically, the (meth)acrylic acid ester having a substituted or unsubstituted C5 to C20 monocyclic or heterocyclic alicyclic group is cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, dicyclopentanyl (meth) It may include at least one of acrylate, methylcyclohexyl (meth)acrylate, and dicyclopentenyl (meth)acrylate. These may be included alone or in mixture of two or more.

The (meth)acrylate monomer having a heteroalicyclic group may lower the creep at 25°C and increase the creep at 85°C together with the (meth)acrylate monomer having an alicyclic group.

The (meth)acrylate monomer having the heteroalicyclic group may be included in an amount of 1 mol% to 30 mol%, specifically 5 mol% to 20 mol% of the monomer mixture. In the above range, the modulus at 30° C. of the adhesive film may be increased, and there may be an effect of increasing the cohesive force.

The (meth)acrylate monomer having a heteroalicyclic group may include a (meth)acrylic acid ester having a C4 to C9 heteroalicyclic group containing at least one of nitrogen, oxygen, or sulfur. Specifically, the (meth)acrylate monomer having the heteroalicyclic group may include (meth)acryloylmorpholine, but is not limited thereto.

The first copolymerization monomer may further include at least one of a (meth)acrylic acid ester having a C1 to C3 alkyl group, a monomer having an amide group, and a monomer having an aromatic group. Specifically, the monomer may include, but is not limited to, methyl (meth) acrylate, (meth) acrylamide, benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, styrene, and the like.

In one embodiment, the first (meth) acrylate copolymer comprises 0.01 mol% to 5 mol% of at least one of the (meth)acrylate monomer having the hydroxyl group and the (meth)acrylate monomer having the carboxylic acid group and the alkyl group It may be a copolymer of 95 mol% to 99.99 mol% of a (meth)acrylate monomer having. In another embodiment, the first (meth)acrylate copolymer is 0.01 mol% to 5 mol% of at least one of the (meth)acrylate monomer having the hydroxyl group and the (meth)acrylate monomer having the carboxylic acid group, the alkyl group A copolymer of 50 mol% to 95 mol% of a (meth)acrylate monomer having, 1 mol% to 30 mol% of a (meth)acrylate monomer having an alicyclic group, and 1 mol% to 30 mol% of a (meth)acrylate monomer having the heteroalicyclic group can be In the above range, there may be a high cohesive force and high strength effect.

The second (meth)acrylate copolymer may form a matrix of the pressure-sensitive adhesive film and provide at least one of an epoxy group and an oxetane group to allow the pressure-sensitive adhesive composition to self-cur without a crosslinking agent.

The second (meth)acrylate copolymer may include at least one of a (meth)acrylic monomer having an epoxy group and a (meth)acrylic monomer having an oxetane group; And it may be a copolymer of a monomer mixture comprising a monomer copolymerizable with them (hereinafter, "second copolymerization monomer"). One or more of the (meth)acrylate monomer having an epoxy group and the (meth)acrylate monomer having an oxetane group in the monomer mixture may be included in an amount of 10 mol% or less, specifically 0.01 mol% to 5 mol%. In the above range, when included together with the first (meth)acrylate copolymer, it is possible to implement an adhesive film that can be used in flexible devices with good flexibility, bendability, hardness, fairness, and reliability.

The (meth)acrylate monomer having the epoxy group may realize the effect of making it possible to self-curing and/or improving cohesion and reliability. The (meth)acrylic monomer having the epoxy group may be included in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol% of the monomer mixture. In the above range, there may be an effect of improving fast curing and reliability. The (meth)acrylic monomer having the epoxy group may be glycidyl (meth)acrylate or the like.

The (meth)acrylate monomer having the oxetane group may be capable of self-curing and/or may implement the effect of improving cohesion and reliability. The (meth)acrylate monomer having the oxetane group may be included in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol% of the monomer mixture. In the above range, there may be an effect of improving fast curing and reliability. The (meth) acrylate monomer having the oxetane group is oxetanyl (meth) acrylate, oxetanylmethyl (meth) acrylate, (3-methyl-3-oxetanyl) methyl (meth) acrylate, ( 3-ethyl-3-oxetanyl)methyl (meth)acrylate and the like.

The second copolymerization monomer may be copolymerized with one or more of the (meth)acrylate monomer having the epoxy group and the (meth)acrylate monomer having the oxetane group to form a matrix of the adhesive film or provide an additional function.

The second copolymerization monomer may include a (meth)acrylate monomer having an alkyl group. The second copolymerized monomer may further include at least one of a (meth)acrylate monomer having an alicyclic group and a (meth)acrylate monomer having a heteroalicyclic group, thereby further increasing the pencil hardness of the polarizing plate including the adhesive film. Specific types of each of the (meth)acrylate monomer having an alkyl group, the (meth)acrylate monomer having an alicyclic group, and the (meth)acrylate monomer having a heteroalicyclic group are the same as described above in the first copolymerization monomer.

In one embodiment, the second (meth) acrylate copolymer is 0.01 mol% to 5 mol% of at least one of the (meth)acrylate monomer having the epoxy group and the (meth)acrylate monomer having the oxetane group, the alkyl group It may be a copolymer of 95 mol% to 99.9 mol% of a (meth)acrylate monomer having. In another embodiment, the second (meth) acrylate copolymer is 0.01 mol% to 5 mol% of at least one of the (meth)acrylate monomer having the epoxy group and the (meth)acrylate monomer having the oxetane group, the alkyl group 50 mol% to 95 mol% of a (meth)acrylate monomer having may be synthetic. In the above range, there may be an effect of improving fast curing and reliability.

The glass transition temperature of the first (meth)acrylate copolymer and the second (meth)acrylate copolymer may be -55°C to -5°C, respectively, and specifically -50°C to -30°C. The weight average molecular weight of the first (meth) acrylate copolymer and the second (meth) acrylate copolymer may be 200,000 g/mol to 1,500,000 g/mol, specifically 500,000 g/mol to 1,000,000 g/mol, respectively. there is. The first (meth)acrylate copolymer and the second (meth)acrylate copolymer may each have an acid value of 5 mgKOH/g or less, more specifically 0.01 mgKOH/g to 3 mgKOH/g. Within the above range, it is possible to implement the effect of inhibiting corrosion protection directly or indirectly on the adherend.

The first (meth)acrylate copolymer and the second (meth)acrylate copolymer may be prepared by polymerizing a monomer mixture in a conventional polymerization method, respectively. Polymerization methods may include conventional methods known to those skilled in the art. For example, the (meth)acrylate copolymer may be prepared by adding an initiator to the monomer mixture, and then performing general copolymer polymerization, for example, suspension polymerization, emulsion polymerization, solution polymerization, and the like. The polymerization temperature may be 65° C. to 70° C. The polymerization time may be 6 hours to 8 hours. The initiator is an azo polymerization initiator; and/or peroxides such as benzoyl peroxide or acetyl peroxide may be used.

The curing agent may be a thermosetting agent, and is used to strengthen the cohesive force of the pressure-sensitive adhesive by appropriately crosslinking the acrylic binder resin, and the type thereof is not particularly limited. For example, an isocyanate-based compound, an aziridine-based compound, etc. may be mentioned, and these may be used alone or in combination of two or more.

Examples of the isocyanate-based compound include tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene diisocyanate, diisocyanate compounds such as naphthalene diisocyanate; An adduct obtained by reacting 3 moles of a diisocyanate compound with 1 mole of a polyhydric alcohol compound such as trimethylolpropane, an isocyanurate product obtained by self-condensing 3 moles of a diisocyanate compound, and a diisocyanate obtained from 2 moles of 3 moles of a diisocyanate compound The polyfunctional isocyanate compound etc. which contain three functional groups, such as the biuret body which the remaining 1 mol diisocyanate condensed to urea, triphenylmethane triisocyanate, and methylene bistriisocyanate, etc. are mentioned.

Examples of the aziridine-based compound include N,N'-toluene-2,4-bis(1-aziridinecarboxamide), N,N'-diphenylmethane-4,4'-bis(1-aziridinecarboxamide). mide), triethylene melamine, bisisoprothaloyl-1-(2-methylaziridine) and tri-1-aziridinylphosphine oxide, and the like.

In addition, the isocyanate-based compound and the aziridine-based compound together with the melamine-based compound may be used alone or in combination of two or more.

Examples of the melamine-based compound include hexamethylolmelamine, hexamethoxymethylmelamine, and hexabutoxymethylmelamine.

The curing agent is included in an amount of 0.1% to 1% by weight, for example, 0.1% to 0.5% by weight based on the total amount of the pressure-sensitive adhesive composition (including 0.3% to 1.0% by weight based on the solid content of the pressure-sensitive adhesive composition) of adhesive strength or cohesiveness It is preferable in terms of When the curing agent is less than 0.1% by weight based on the total amount of the pressure-sensitive adhesive composition, the adhesive strength or cohesive strength of the pressure-sensitive adhesive is slightly lowered (incomplete curing) due to insufficient crosslinking degree to cause deterioration in durability such as moxibustion and may impair cutability, and the curing agent When it exceeds 1% by weight based on the total amount of the pressure-sensitive adhesive composition, the compatibility may be slightly lowered and surface migration may occur, the crosslinking reaction may proceed too much, so that the adhesive strength may be somewhat lowered, and a problem may occur in relieving residual stress.

The solvent may improve the coatability of the pressure-sensitive adhesive composition and inhibit the self-curing reaction of the pressure-sensitive adhesive composition. As the solvent, a conventional solvent known to those skilled in the art can be used. For example, the solvent may include any one or more of methyl ethyl ketone, ethyl acetate, and toluene, and the remaining amount relative to the pressure-sensitive adhesive composition, for example, 10% to 40% by weight, such as 10% by weight, based on the total amount of the pressure-sensitive adhesive composition % to 30% by weight.

The pressure-sensitive adhesive composition may further include a silane coupling agent, an antistatic agent, a UV absorber, a cationic initiator, a release agent, or a combination thereof.

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxy propyl tri Methoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3- Glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltri Methoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3 -Aminopropylmethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N -Phenyl-3-aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis(triethoxysilylpropyl)tetra Sulfide, 3-isocyanate propyltriethoxysilane, etc. are mentioned, These can be used individually or in mixture of 2 or more types.

The silane coupling agent may be included in an amount of 0.01 wt% to 0.1 wt%, such as 0.01 wt% to 0.05 wt%, based on the total amount of the pressure-sensitive adhesive composition (0.1 wt% to 0.3 wt% based on the pressure-sensitive adhesive composition solid content).

The antistatic agent suppresses the generation of static electricity during rework of the adhesive film, and may include a conventional antistatic agent. The antistatic agent may be included in an amount of 1 wt% to 5 wt%, such as 1 wt% to 3 wt% (1.0 wt% to 5.0 wt% based on the pressure-sensitive adhesive composition solid content) based on the total amount of the pressure-sensitive adhesive composition. When the antistatic agent is included within the above range, it is preferable in terms of electrification. When the antistatic agent is included in an amount of less than 1% by weight based on the total amount of the pressure-sensitive adhesive composition, the antistatic effect may be somewhat reduced, and when included in an amount of more than 5% by weight based on the total amount of the pressure-sensitive adhesive composition, the physical properties of the pressure-sensitive adhesive composition are reduced and manufactured will increase the cost.

For example, the antistatic agent may be an ionic antistatic agent. The ionic antistatic agent may be an alkali metal salt, an ionic liquid or an ionic solid. However, the alkali metal salt may lack compatibility with the pressure-sensitive adhesive and may lack durability, and the ionic liquid has high fluidity in the pressure-sensitive adhesive fired material, and thus the antistatic performance may be somewhat reduced according to changes over time. In other words, it is preferable to include an ionic solid in a solid state at room temperature (25° C.

For example, the antistatic agent is dodecylpyridinium hexafluorophosphate (KOEI), lithium bistrifluoromethanesulfonimide (3M), tri-n-butylmethylammonium bis-(trifluoromethanesulfonyl)imide (3M), etc., but is not limited thereto, and two or more types may be mixed and used.

The ultraviolet absorber may have an absorption wavelength of 380 to 420 nm. Here, the "absorption wavelength" may refer to a "maximum absorption wavelength".

When the pressure-sensitive adhesive composition includes an ultraviolet absorber having the absorption wavelength range, it may exhibit a transmittance of 5% or less in a wavelength region of 400 nm or less, thereby preventing a polarizing plate and a device including the same from being damaged by external ultraviolet rays. There are advantages that can be

The ultraviolet absorber is not limited thereto, as long as it satisfies the above-described absorption wavelength range, and ultraviolet absorbers commonly used in the art may be applied. For example, the ultraviolet absorber may be 2-hydroxy-3((4-methoxyphenyl)diazenyl)-5-methylbenzylmethacrylate or 2-hydroxy-5-methoxy-3-(5-trifluoromethyl )-2H-benzo[d][1,2,3]triazol-2-yl)benzyl methacrylate, but is not limited thereto as long as the absorption wavelength is satisfied.

The cationic initiator may be a cationic photopolymerization initiator, but is not limited thereto, and a cationic photoinitiator generally used in the art may be used. For example, an onium salt or a derivative thereof that releases a Lewis acid upon irradiation with light is mentioned. Such a compound is in the form of a salt consisting of a cation and an anion, represented by the general formula [X] ^{x +} [Y] ^x- , and specific examples of the cation include an aromatic diazonium salt, an aromatic iodonium salt, an aromatic halonium salt, an aromatic sulfonium salt, and the like. Specific examples of the anion include tetrafluoroborate (BF ₄ ), hexafluorophosphate (PF ₆ ), hexafluoroantimonate (SbF ₆ ), hexafluoroarusenate (AsF ₆ ), hexa Chloroantimonate (SbCl ₆ ), and the like. These cationic photoinitiators can be used individually or in mixture of 2 or more types.

The content of the cationic initiator is not particularly limited, but may be included, for example, in an amount of 0.01 parts by weight to 10 parts by weight, for example, 0.1 parts by weight to 5 parts by weight, based on the solid content, based on the total amount of the pressure-sensitive adhesive composition. When the cationic initiator is less than 0.01 parts by weight based on the total amount of the pressure-sensitive adhesive composition, curing of the colored adhesive composition may be insufficient to obtain sufficient adhesion and adhesion, and when the cationic initiator exceeds 10 parts by weight based on the total amount of the pressure-sensitive adhesive composition, the adhesive The hygroscopicity may increase due to an excessive content of the ionic material in the layer, and thus durability may be somewhat reduced.

The release agent may be an alkyd-based release agent, a silicone-based release agent, a fluorine-based release agent, an unsaturated ester-based release agent, a polyolefin-based release agent, or a wax-based release agent. For example, it may be preferable in terms of heat resistance to use an alkyd-based release agent, a silicone-based release agent, or a fluorine-based release agent as the release agent, but is not limited thereto. The release agent may be included in an amount of 0.01 wt% to 0.1 wt% based on the total amount of the pressure-sensitive adhesive composition.

In addition to the above components, the pressure-sensitive adhesive composition is a reworking agent, adhesion-imparting resin, antioxidant, leveling agent in order to control the required adhesive force, cohesive force, viscosity, elastic modulus, glass transition temperature, etc. according to the use. , may further contain additives such as a surface lubricant, an antifoaming agent, a filler, and a light stabilizer.

The additive may be added by appropriately adjusting the content within a range that does not impair the effects of the present invention.

The pressure-sensitive adhesive composition according to an embodiment may have a viscosity of 1,000 cPs to 4,000 cPs at 25°C. In the above range, it may be easy to adjust the thickness of the pressure-sensitive adhesive film, there is no stain on the pressure-sensitive adhesive film, and the coating surface may have a uniform effect.

Another embodiment provides a pressure-sensitive adhesive film prepared using the above-described pressure-sensitive adhesive composition.

Another embodiment provides a polarizing plate including the adhesive film.

The manufacturing method of the adhesive film is not particularly limited, and may be manufactured by a conventional method. For example, it may be applied to the production of an adhesive film using the pressure-sensitive adhesive composition.

For example, the above-described pressure-sensitive adhesive composition on the polarizer protective film by a flow casting method, a bar coater, an air knife (air knife), gravure (gravure), reverse roll (reverse roll), kiss roll (kiss roll), spray ( Spray) or a blade method, etc., directly applied in an appropriate development method, dried (thermal curing) to form an adhesive layer, and then laminated with a polarizing plate.

In addition, after forming an adhesive film on the silicone-coated release film by the same application method as above, it was laminated with a silicone-coated release film having different peeling force using a roll compression device to prepare an adhesive transfer tape, and then applied to a polarizing plate. It can be used by sticking.

The pressure-sensitive adhesive film may be formed through thermal curing, but when an ultraviolet curable compound and a photopolymerization initiator (such as the cationic photopolymerization initiator described above) are used as a crosslinking agent, after laminating a polarizing plate, ultraviolet rays are irradiated from the release film side, or roll compression bonding It can also be manufactured by irradiating (photocuring) ultraviolet rays after laminating a silicone-coated release film having different peel strength using a device.

The thickness of the pressure-sensitive adhesive film is not particularly limited, but may be 5 μm to 30 μm, such as 7 μm to 20 μm, such as 10 μm to 15 μm. When the thickness of the pressure-sensitive adhesive film is within the above range, it is preferable in terms of adhesion and durability, and there is an advantage that it can be applied to a thin device.

In the polarizing plate having an adhesive film on at least one surface, the polarizing plate may have a transmittance of 5% or less at a wavelength of 400 nm or less, and a transmittance of 40% or more at a wavelength of 455 nm or more.

Since the polarizing plate has a transmittance of 5% or less at a wavelength of 400 nm or less, damage to the polarizing plate or an element to which the polarizing plate is bonded can be prevented, and since the transmittance of a wavelength of 455 nm or more is 40% or more, the blue luminance is reduced. There are advantages to avoiding

Another embodiment provides an optical display device including the polarizing plate.

The optical display device is an image display device, and may include a liquid crystal display device, an OLED, a flexible display, and the like, but is not limited thereto, and all image display devices known in the art that can be applied may be exemplified.

For example, the optical display device may be a liquid crystal display device. In general, a liquid crystal display device includes a backlight (BLU), a polarizing plate, a thin film transistor (TFT), a liquid crystal cell, a color filter, and a polarizing plate, and the polarizing plate may be a polarizing plate according to an exemplary embodiment. For example, the optical display device may be provided with a polarizing plate on which an adhesive layer according to an embodiment is laminated.

Hereinafter, the present invention will be described in more detail with reference to examples, but the following examples are only preferred examples of the present invention, and the present invention is not limited to the following examples.

(synthesis of dyes)

Synthesis Example 1: Synthesis of dye represented by Formula 1-1

[Scheme 1]

(1) Put 4-t-butylbenzaldehyde (16.2 g, 0.1 mol), propionic acid 100 g, and pyrrole (6.71 g, 0.1 mol) in a round-bottom flask, raise the temperature to 130° C., and stir for 6 hours. When the reaction is completed, the temperature is lowered to room temperature, and 100 g of acetone is added thereto and stirred. The resulting solid compound was filtered through a filter, washed with acetone, and dried to synthesize a porphyrin intermediate (4.2 g, 20%).

(2) Put the intermediate (4.2g, 5mmol) and 80g of chloroform in a round-bottom flask, stir at 60℃, add zinc acetate (2.75g, 15mmol) to another round-bottom flask, add 53g of methanol, and stir . At this time, it should be stirred until zinc acetate is completely dissolved, and when zinc acetate is completely dissolved, it is added to the intermediate and stirred at 60° C. for 3 hours, and then the reaction is terminated. It is extracted using chloroform, washed with water, and filtered. After the filtrate was distilled, 50 g of acetone was added thereto, stirred at room temperature for 1 hour, and then filtered again to obtain a porphyrin-based dye (3.1 g, 69%) (900 m/z).

(Synthesis of adhesive composition)

Example 1

Acrylic binder resin (PL-8540; SAIDEN Chemical) 78.583 wt%, isocyanate-based curing agent (H-AL; Zirka ceramic) 0.236 wt%, aziridine-based curing agent (HDU-P25; manufacturer) 0.145 wt%, release agent (MAC-2101) Soken) 0.028 wt%, antistatic agent (FC-4400L; 3M) 1.336 wt%, silane coupling agent (KBM-403; shinetsu) 0.024 wt%, compound of Synthesis Example 1 0.004 wt% and solvent (MEK) balance ( 19.644 wt%) was mixed to prepare a pressure-sensitive adhesive composition for a polarizing plate of Example 1.

Comparative Example 1

A pressure-sensitive adhesive composition for a polarizing plate of Comparative Example 1 was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 1 was not used.

Evaluation: Color gamut and reflectance of adhesive film

1. Measurement of color gamut

After applying the composition according to Example 1 and Comparative Example 1, the composition was dried at 90 ° C. for 4 minutes, aged at 23 ° C. and 55% relative humidity for 24 hours to prepare an adhesive film, which was attached to one side of the panel (opposite to the backlight). Then, the color gamut was measured using a spectrophotometer (SR-3, Topcon), and the results are shown in Table 1 below.

2. Reflectance Measurement

The adhesive film prepared using the adhesive composition obtained in Example 1 and Comparative Example 1 was bonded to the QD panel, and C-Light spectrum was applied using a spectrophotometer (CM-2600D, Minolta). The reflectance was measured, and the results are shown in Table 1 below.

(unit: %) color gamut reflectivity Example 1 89.7 10.85 Comparative Example 1 88.2 12.04

As can be seen in Table 1, Example 1 to which the compound of Synthesis Example 1 is applied, compared to Comparative Example 1 to which the compound of Synthesis Example 1 is not applied, it can be confirmed that the color reproducibility is high and the reflectance is also reduced.

Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims, the detailed description of the invention, and the accompanying drawings, and this is also It goes without saying that it falls within the scope of the invention.

Claims (9)

(1) a compound represented by any one of Formulas 1-1 to 1-15 and Formulas 1-17 to 1-20;
(2) acrylic binder resin;
(3) curing agents; and
(4) solvent
A pressure-sensitive adhesive composition comprising:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

[Formula 1-13]

(In Formula 1-13,
R is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
m1 and m2 are each independently an integer from 0 to 20, provided that 4 ≤ m1+m2 ≤ 20)
[Formula 1-14]

[Formula 1-15]

[Formula 1-17]

[Formula 1-18]

[Formula 1-19]

[Formula 1-20]

In Formulas 1-1 to 1-15 and Formulas 1-17 to 1-20,
M is Zn, Co or Cu.
delete delete According to claim 1,
The compound represented by any one of Formulas 1-1 to 1-15 and Formulas 1-17 to 1-20 is included in an amount of 0.001% by weight to 0.01% by weight based on the total amount of the pressure-sensitive adhesive composition.
According to claim 1,
The pressure-sensitive adhesive composition further comprises a silane coupling agent, an antistatic agent, a UV absorber, a cationic initiator, a release agent, or a combination thereof.
According to claim 1,
The pressure-sensitive adhesive composition is based on the total amount of the pressure-sensitive adhesive composition,
0.001 wt% to 0.01 wt% of a compound represented by any one of Formulas 1-1 to 1-15 and Formulas 1-17 to 1-20;
70% to 85% by weight of the acrylic binder resin;
0.1 wt% to 1 wt% of the curing agent; and
the remaining amount of the solvent
A pressure-sensitive adhesive composition comprising a.
An adhesive film prepared by using the pressure-sensitive adhesive composition of any one of claims 1 and 4 to 6 .
A polarizing plate comprising the adhesive film of claim 7.
An optical display device comprising the polarizing plate of claim 8.