JP2020094214A - Compound, and photosensitive resin composition, photosensitive resin film and color filter which comprise that compound, as well as adhesive composition, adhesive film and polarizer which comprise that compound - Google Patents

Abstract

To provide a compound excellent in spectral characteristics.SOLUTION: The invention provides a compound of [3-13], for example. The invention also provides a photosensitive resin composition, an adhesive composition, a photosensitive resin film, an adhesive film, a color filter and a polarizer which comprise the compound.SELECTED DRAWING: None

Description

The present invention relates to a compound capable of strongly absorbing light in a very narrow region around 400 nm to 435 nm, a photosensitive resin composition containing the compound, a photosensitive resin film produced using the photosensitive resin composition, and a photosensitive resin film. And a pressure-sensitive adhesive composition containing the compound, a pressure-sensitive adhesive film produced using the pressure-sensitive adhesive composition, and a polarizing plate including the pressure-sensitive adhesive film.

The liquid crystal display device, which is one of the display devices, has advantages such as weight reduction, thinness, low cost, low power consumption driving, and excellent jointability with an integrated circuit, and is used for laptop computers, monitors and TV images. Its use range is expanding. Such a liquid crystal display device includes a lower substrate on which a black matrix (light shielding layer), a color filter, and an ITO pixel electrode are formed, an active circuit unit including a liquid crystal layer, a thin film transistor, and a storage capacitor layer, and an ITO pixel electrode. And an upper substrate on which is formed.

The color filter includes a black matrix (light-shielding layer) formed on a transparent substrate in a predetermined pattern to shield the boundaries between pixels, and a plurality of colors (usually red ( R), green (G), and blue (B) three primary colors) are arranged in a predetermined order, and a pixel portion is sequentially laminated.

The pigment dispersion method, which is one of the methods for realizing a color filter, is a photopolymerizable composition (hereinafter, a photosensitive resin composition) containing a pigment (colorant) on a transparent substrate provided with a black matrix. Is a method of forming a colored thin film by repeating a series of steps of coating, exposing the pattern of the form to be formed, removing the non-exposed portion with a solvent and thermally curing. The photosensitive resin composition used for producing a color filter by the pigment dispersion method generally comprises an alkali-soluble resin, a photopolymerization monomer, a photopolymerization initiator, an epoxy resin, a solvent and other additives (for example, Patent Document 1). The pigment dispersion method having the above characteristics is actively applied to manufacture LCDs for mobile phones, notebook computers, monitors, TVs and the like.

However, in recent years, in a photosensitive resin composition for a color filter using a pigment dispersion method having various advantages, it is difficult to make a pigment powder into a fine powder, and thus, in the composition. In order to stabilize the dispersed state of the pigment, various additives are required, which causes a problem that the process becomes very complicated. Further, the photosensitive resin composition (dispersion liquid) prepared by the pigment dispersion method has a drawback that storage and transportation conditions are difficult in order to maintain optimum quality.

In addition, in a color filter manufactured from the pigment-type photosensitive resin composition, there are limits on the brightness and the contrast ratio starting from the size of the pigment particles. In the case of a color image pickup device for an image sensor, smaller dispersion grain size is required for forming a fine pattern. In order to meet such demands, instead of a pigment, or together with a pigment, a photosensitive resin composition into which a dye that does not form particles is introduced is produced to provide a color filter having improved color characteristics such as brightness and contrast ratio. Although attempts to realize the dye-based photosensitive resin composition continue, the dye-type photosensitive resin composition has a problem that the durability is lower than that of the pigment-type photosensitive resin composition.

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

The polarizing plate is a polyvinyl alcohol (PVA) polarizer (or a “polarizing film”) that is stretched in a certain direction and has an iodine compound or a dichroic polarizing substance adsorbed and oriented, and its polarized light. And a polarizer protective film laminated to protect both sides of the child. Specifically, a polarizer protective film such as triacetyl cellulose (TAC) is provided on one surface of the polarizer, and a pressure-sensitive adhesive layer and a release film for bonding to the liquid crystal cell are provided on the protective film. The other surface of the polarizer is composed of a multilayer structure including a polarizer protection film and a surface protection film having a base material film and an adhesive layer laminated thereon.

In the step of attaching the polarizing plate having such a structure to the liquid crystal cell, the release film is peeled off from the pressure-sensitive adhesive layer, and when the role of the surface protective film is finished in the subsequent step, this is also peeled off. Since the release film and the surface protection film are made of a plastic material, they have high electric insulation and generate static electricity when peeled.

The static electricity generated in this manner induces problems such as foreign matter adsorbing to the optical member to contaminate the surface and unevenness due to misalignment of liquid crystal alignment, which may cause damage to thin film transistor (TFT) lines. There is. In particular, with the recent increase in the size of liquid crystal display device panels, the size of polarizing plates used in the manufacture of liquid crystal display devices has also increased, and the amount of static electricity generated has further increased as the process speed has increased. There is an urgent need to solve the problem against.

The present invention has been made in view of the above circumstances, and an object thereof is to provide a compound having excellent spectral characteristics.

Another object of the present invention is to provide a photosensitive resin composition containing a compound having excellent spectral characteristics. Still another object is to provide a photosensitive resin film manufactured using the photosensitive resin composition and a color filter including the photosensitive resin film.

Another object of the present invention is to provide a pressure-sensitive adhesive composition containing a compound having excellent spectral characteristics. Still another object is to provide a pressure-sensitive adhesive film produced using the pressure-sensitive adhesive composition and a polarizing plate including the pressure-sensitive adhesive film.

One embodiment of the present invention provides a compound represented by Chemical Formula 1 below.

In Formula 1,
M is Cu, Co, VO, Zn, Pt, or In,
L ^{1 to} L ⁴ are each independently *-C(=O)O-* or *-S(=O) ₂ NH-*,
R ^{1 to} R ⁴ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or A substituted or unsubstituted C2-C20 heteroaryl group,
R ^{5 to} R ¹² are each independently a hydrogen atom or a halogen atom.

L ^{1 to} L ⁴ are each independently *-C(═O)O-*, and R ^{1 to} R ⁴ are each independently represented by the following chemical formula 2.

In Formula 2,
R ¹³ is a halogen atom or a trifluoromethyl group,
n is an integer of 1 or 2.

Chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3.

In Chemical Formula 2-1 to Chemical Formula 2-3,
R ¹⁴ is a halogen atom or a trifluoromethyl group,
R ¹⁵ and R ¹⁶ are each independently a trifluoromethyl group,
R ¹⁷ and R ¹⁸ are each independently a halogen atom.

L ^{1 to} L ⁴ are each independently *-S(═O) ₂ NH-*, and R ^{1 to} R ⁴ are each independently a substituted or unsubstituted C ^{1 to} C 20 alkyl group. May be.

The compound is represented by any one of the following chemical formulas 3-1 to 3-13.

In Chemical Formula 3-1 to Chemical Formula 3-13,
M is Cu, Co, VO, Zn, Pt, or In.

Another embodiment provides a photosensitive resin composition including the compound, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

Yet another embodiment provides a photosensitive resin film manufactured using the photosensitive resin composition.

Yet another embodiment provides a color filter including the photosensitive resin film.

Yet another embodiment provides an adhesive composition including the compound, a binder resin, a curing agent, and a solvent.

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

Yet another embodiment provides an adhesive film produced using the adhesive composition.

Yet another embodiment provides a polarizing plate including the adhesive film.

Other specifics of aspects of the invention are included in the detailed description below.

According to the present invention, a compound having excellent spectral characteristics is provided.

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 thereby, and the present invention is defined only by the scope of the claims to be described later.

In the present specification, unless otherwise specified, the term “substituted” or “substituted” means that one or more hydrogen atoms in the functional groups of the present invention are halogen atoms (F, Br, Cl, or I), a hydroxy 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, each independently being 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 Substituted with one or more substituents selected from the group consisting of an unsubstituted alkynyl group, a substituted or unsubstituted alicyclic organic group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group Means that In addition, in this specification, C represents a carbon atom, for example, C1 means that the number of carbon atoms (carbon number) is 1. Therefore, the "C1-C10 alkyl group" means "an alkyl group having 1 to 20 carbon atoms".

In the present specification, unless otherwise specified, the “alkyl group” means a C1-C20 alkyl group, preferably a C1-C15 alkyl group, and the “cycloalkyl group” means a C3-C20 alkyl group. A cycloalkyl group, preferably a C3-C18 cycloalkyl group, an "alkoxy group" means a C1-C20 alkoxy group, preferably a C1-C18 alkoxy group, and an "aryl group". Means a C6-C20 aryl group, preferably a C6-C18 aryl group, and an "alkenyl group" means a C2-C20 alkenyl group, preferably a C2-C18 alkenyl group, The "alkylene group" means a C1-C20 alkylene group, preferably a C1-C18 alkylene group, and the "arylene group" means a C6-C20 arylene group, preferably a C6-C16 arylene group. Means

In this specification, unless otherwise specified, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible, and "(meth)acrylic acid" means "acrylic acid". Means that both "" and "methacrylic acid" are possible.

As used herein, the term “combination” means mixing or copolymerization, unless otherwise defined. Further, "copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

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

Further, in the present specification, unless otherwise defined, “*” means a moiety connected to the same or different atom or chemical formula.

Further, when a member is herein “above” another member, this means not only when one member is in contact with another member but also between two members. It also includes the case where other members are present.

In addition, in the present specification, when a certain part includes “a component”, this does not exclude other component, and may further include other component, unless there is a contrary description. Means

One embodiment of the present invention is a compound represented by Chemical Formula 1 below.

In Formula 1,
M is Cu, Co, VO, Zn, Pt, or In,
L ^{1 to} L ⁴ are each independently *-C(=O)O-* or *-S(=O) ₂ NH-*,
R ^{1 to} R ⁴ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or A substituted or unsubstituted C2-C20 heteroaryl group,
R ^{5 to} R ¹² are each independently a hydrogen atom or a halogen atom.

Here, the halogen atom is F, Cl, Br or I, and in the present embodiment, preferably F, Cl or Br, and more preferably F or Cl.

The C1-C20 alkyl group may be a linear or branched alkyl group having 1 to 20 carbon atoms, and in the present embodiment, it is preferably a linear or branched alkyl group having 1 to 15 carbon atoms, More preferably, it is a linear or branched alkyl group having 1 to 10 carbon atoms, and even more preferably a branched alkyl group having 3 to 8 carbon atoms. Examples of the C1-C20 alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, Neopentyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group Group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-icosyl group and the like.

Examples of the C3-C20 cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and an adamantyl group.

Examples of the C6-C20 aryl group include a phenyl group and a naphthyl group.

C2-C20 heteroaryl means that the heteroaryl group has 2 to 20 carbon atoms. In the present embodiment, it is preferably heteroaryl having 3 to 20 carbon atoms, and more preferably heteroaryl having 3 to 14 carbon atoms. Examples of such a heteroaryl group include, for example, a furyl group, a thienyl group, a pyrrolyl group, a pyridyl group, a pyrimidinyl group, an imidazolyl group, a benzofuryl group, a benzothienyl group, an indolyl group, a quinolyl group, a thiazolyl group, an oxadiazolyl group, Examples thereof include a pyrazolyl group, an oxazolyl group and a benzoxazolyl group.

Among existing color filter resists, in the case of a blue resist, it is possible to add a part of violet coloring material to a blue pigment (mostly pigment blue 15:6; B15:6) for color coordinate adjustment and brightness increase. It is common. However, recently, in the color coordinates of the blue region for increasing the color reproduction rate, Bx tends to be smaller. In order to realize such a blue color filter having a high color reproducibility, a narrow transmission spectrum must be formed in the vicinity of 450 nm which is the wavelength of the blue LED of the light source, and for this reason, it has been conventionally used universally. In place of B15:6 (epsilon blue), B15:3 or B15:4 pigment of beta blue was used, and PWC (Pigment Weight Content/pigment-containing weight) was increased to obtain a resist having a reduced width of transmission spectrum. Directions for making are presented. However, in this case, as the content of the color material in the resist becomes higher, the brightness is much lower than that of the existing sRGB class blue, and this acts as a drawback during actual application.

On the other hand, the compound according to one embodiment has a spectroscopic property of strongly absorbing in a very narrow region of 400 nm to 435 nm. As a result, the color filter manufactured using the photosensitive resin composition containing the compound according to this embodiment as a colorant has excellent color reproducibility. Furthermore, the pressure-sensitive adhesive film produced using the pressure-sensitive adhesive composition containing the compound according to one embodiment as a dye has high color reproducibility and low reflectance.

Further, the compound according to one embodiment has a high solubility in an organic solvent while having a spectral characteristic of strongly absorbing light in a very narrow region of 400 nm to 435 nm. Accordingly, the compound according to this one embodiment is suitable because it is easily dissolved in an organic solvent when used as a colorant for a photosensitive resin composition and a dye for a pressure-sensitive adhesive composition.

In the chemical formula 1, the substituents (*-L ¹ -R ¹ , *-L ² -R ² , *-L ³ -R ³ , and *-L ⁴ -R ⁴ ) have a substitution position of ortho. It may be located at any position of meta and para. When the substitution position of the substituent is ortho, the absorption wavelength moves to the short wavelength side, and the solubility in the organic solvent improves, whereas when the substitution position of the substituent is para, the absorption wavelength shifts to the long wavelength side. Upon migration, the solubility in organic solvents becomes slightly lower. For example, the compound according to one embodiment exhibits a very strong absorbance at 400 nm to 435 nm, and preferably a very strong absorbance at 420 nm to 435 nm. Therefore, in consideration of the color reproducibility, color stability, light resistance, etc. of the composition containing the compound according to this embodiment as a colorant (pigment), the position of the substituent is para in one embodiment. preferable.

For example, the chemical formula 1 is represented by the following chemical formula 1-1.

In the chemical formula 1-1,
M is Cu, Co, VO, Zn, Pt, or In,
L ^{1 to} L ⁴ are each independently *-C(=O)O-* or *-S(=O) ₂ NH-*,
R ^{1 to} R ⁴ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or A substituted or unsubstituted C2-C20 heteroaryl group,
R ^{5 to} R ¹² are each independently a hydrogen atom or a halogen atom.

According to a preferred embodiment, in Formula 1, L ^{1 to} L ⁴ are each independently *-C(═O)O-*, and R ^{1 to} R ⁴ are each independently substituted or It is an unsubstituted C6-C20 aryl group. In the case where L ^{1 to} L ⁴ are each independently *-C(═O)O-*, the absorption wavelength of the compound according to one embodiment can shift to the longer wavelength side.

For example, in Chemical Formula 1, L ^{1 to} L ⁴ are each independently *-C(═O)O-*, and R ^{1 to} R ⁴ are each independently represented by Chemical Formula 2 below. It

In Formula 2,
R ¹³ is a halogen atom or a trifluoromethyl group,
n is an integer of 1 or 2.

When R ^{1 to} R ⁴ are each independently represented by Formula 2, the compound according to an embodiment may have high solubility in an organic solvent.

For example, the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3.

In Chemical Formula 2-1 to Chemical Formula 2-3,
R ¹⁴ is a halogen atom or a trifluoromethyl group,
R ¹⁵ and R ¹⁶ are each independently a trifluoromethyl group,
R ¹⁷ and R ¹⁸ are each independently a halogen atom.

For example, in Chemical Formula 1, L ^{1 to} L ⁴ may be each independently *-C(═O)O-*, and R ^{5 to} R ¹² may be each independently a hydrogen atom. ..

In Chemical Formula 1, L ^{1 to} L ⁴ are each independently *—C(═O)O—* and at least one or more of R ^{5 to} R ¹² is, for example, at least 2 or more is a halogen atom. In this case, the absorption wavelength of the compound according to one embodiment can be shifted to the longer wavelength side.

For example, in Chemical Formula 1, L ^{1 to} L ⁴ are each independently *-C(═O)O-*, R ⁵ and R ⁹ are each independently a halogen atom, and R ⁶ To R ⁸ and R ^{10 to} R ¹² may be each independently a hydrogen atom.

For example, in Chemical Formula 1, L ^{1 to} L ⁴ are each independently *-C(═O)O-*, and R ⁵ , R ⁶ , R ⁹ and R ¹⁰ are each independently halogen. An atom, and R ⁷ , R ⁸ , R ¹¹ and R ¹² may each independently be a hydrogen atom.

According to another preferred embodiment, in Formula 1, L ^{1 to} L ⁴ are each independently *-S(═O) ₂ NH-*, and R ^{1 to} R ⁴ are each independently. It may be a substituted or unsubstituted C1-C20 alkyl group. When L ^{1 to} L ⁴ are each independently *-S(═O) ₂ NH-*, the solubility of the compound according to an embodiment in an organic solvent can be further improved.

For example, in Chemical Formula 1, L ^{1 to} L ⁴ are each independently *-S(═O) ₂ NH-*, and R ^{5 to} R ¹² are each independently a hydrogen atom. Good.

For example, the compound according to one embodiment is represented by any one of Formulas 3-1 to 3-13 below, but is not necessarily limited thereto.

In Chemical Formula 3-1 to Chemical Formula 3-13,
M is Cu, Co, VO (V=O), Zn, Pt, or In.

According to a preferred embodiment, M is Zn, VO (V=O), or Cu.

According to another embodiment, the present invention provides a photosensitive resin composition including a compound represented by Chemical Formula 1, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. For example, the photosensitive resin composition may include the compound represented by Chemical Formula 1 as a colorant.

The compound represented by Chemical Formula 1 is preferably 0.01% by weight to 7% by weight, more preferably 0.1% by weight to 5% by weight, still more preferably 0.1% by weight, based on the weight of the photosensitive resin composition. 5 wt% to 3 wt% is included. By containing the compound represented by Chemical Formula 1 in such a range in the photosensitive resin composition, very high color reproduction is possible and an excellent process margin can be obtained.

For example, the colorant may further include a blue dye, a blue pigment, a red dye, a red pigment, or a combination thereof in addition to the compound represented by Chemical Formula 1.

The blue dye is represented by the following chemical formula 4.

In Formula 4,
R ²⁹ and R ³⁰ are each independently a substituted C1 to C20 alkyl group, or a substituted or unsubstituted C3 to C20 cycloalkyl group,
R ³¹ is a hydrogen atom or a halogen group,
R ³² is a hydrogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,
R ³³ is a C1 to C20 alkyl group substituted or unsubstituted with an acrylate group,
X ⁻ is represented by any one of the following chemical formulas A to C.

(In the chemical formula B, n3 is an integer of 0 to 10)
For example, the blue dye is represented by the following chemical formula 4-1 or chemical formula 4-2.

In Chemical Formula 4-1 and Chemical Formula 4-2,
X ⁻ is represented by any one of the following chemical formulas A to C.

(In the chemical formula B, n3 is an integer of 0 to 10)
Specifically, the blue dye is represented by Chemical Formula 4-1.

The compound represented by Chemical Formula 4-1 has improved heat resistance by containing a cyclohexyl group, and has improved light resistance by containing a methyl group in the phenyl group substituted by the nitrogen atom. Therefore, it is possible to provide a color filter which can realize high colors and can achieve high luminance characteristics, and also has excellent durability such as heat resistance and light resistance. In this specification, the lower the Bx value (based on the same By value) in the CIE color coordinates (Bx, By), the higher the realization of high color.

For example, the blue pigment may be an epsilon blue pigment. When using a blue pigment as a blue colorant according to an embodiment, it is more useful to use an epsilon blue pigment than a beta blue pigment to improve brightness.

For example, a blue pigment is C.I. I. Pigment Blue 15:6.

For example, red pigments include C.I. I. Red pigment 254, C.I. I. Red pigment 255, C.I. I. Red pigment 264, C.I. I. Red pigment 270, C.I. I. Red pigment 272, C.I. I. Red pigment 177, C.I. I. Red pigment 179, C.I. I. The red pigment 89 and the like may be used, but the invention is not limited thereto.

The colorant is preferably contained in an amount of 3% by weight to 20% by weight based on the weight of the photosensitive resin composition. When the colorant is contained in the photosensitive resin composition in such a range, high brightness at a high color coordinate (wide color gamut and high brightness) can be achieved.

The binder resin preferably contains an acrylic binder resin. The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units. ..

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxy groups and/or hydroxy groups, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, Itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer is contained in an amount of preferably 5% by weight to 50% by weight, more preferably 10% by weight to 40% by weight, based on the weight of the acrylic binder resin.

The second ethylenically unsaturated monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzylmethylether; methyl(meth)acrylate, ethyl(meth)acrylate, butyl(meth)acrylate, Unsaturated carboxylic acid ester compounds such as 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate and phenyl (meth)acrylate; 2-aminoethyl (meth ) Unsaturated carboxylic acid aminoalkyl ester compounds such as acrylate and 2-dimethylaminoethyl (meth)acrylate; carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; unsaturated carboxylic acid glycidyl esters such as glycidyl (meth)acrylate Examples thereof include compounds; vinyl cyanide compounds such as (meth)acrylonitrile; unsaturated amide compounds such as (meth)acrylamide; and the like, and these can be used alone or in combination of two or more.

Specific examples of the acrylic binder resin include (meth)acrylic acid/benzyl methacrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene copolymer, (meth)acrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate. Examples thereof include copolymers and (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymers, but are not limited to these and may be used alone or in combination of two or more. You may. For example, examples of the acrylic binder resin include RY-25 manufactured by Showadenko.

The weight average molecular weight of the acrylic binder resin is preferably 3,000 g/mol to 150,000 g/mol, more preferably 5,000 g/mol to 50,000 g/mol, and further preferably 20,000 g/mol. mol-30,000 g/mol. When the weight average molecular weight of the acrylic binder resin is within such a range, a photosensitive resin composition having excellent physical and chemical physical properties can be obtained. Therefore, such a photosensitive resin composition is suitable. It has various viscosities and has excellent adhesion to the substrate during the production of the color filter.

The acid value of the acrylic binder resin is preferably 15 mgKOH/g to 60 mgKOH/g, more preferably 20 mgKOH/g to 50 mgKOH/g. When the acid value of the acrylic binder resin is within such a range, the pixel pattern resolution is excellent.

The binder resin is contained in the photosensitive resin composition in an amount of preferably 0.5% by weight to 20% by weight, more preferably 1% by weight to 15% by weight, and further preferably 2% by weight to 10% by weight. .. When the binder resin is contained in such a range, the developability is excellent at the time of manufacturing the color filter, the crosslinkability is improved, and the excellent surface smoothness can be obtained.

As the photopolymerizable compound, a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond can be used.

Since the photopolymerizable compound has an ethylenically unsaturated double bond, it is possible to form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern forming step. it can.

Specific examples of the photopolymerizable compound include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate. 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, penta Erythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate , Bisphenol A epoxy (meth)acrylate, ethylene glycol monomethyl ether (meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, novolac epoxy (meth)acrylate and the like.

Examples of commercially available photopolymerizable compounds are as follows. Examples of monofunctional esters of (meth)acrylic acid include Aronix M-101 (registered trademark, abbreviated below), Toray Gosei Chemical Industry Co., Ltd., M-111, M-114, etc.; Nippon Kayaku ( KAYARAD TC-110S (registered trademark, hereinafter abbreviated), TC-120S, etc.; Osaka Organic Chemical Industry Co., Ltd. V-158 (registered trademark, abbreviated), V-2311 and the like. Examples of the bifunctional ester of (meth)acrylic acid include Aronix M-210 (registered trademark, abbreviated below), M-240, M-6200, and the like manufactured by Toagosei Kagaku Kogyo Co., Ltd.; Nippon Kayaku ( KAYARAD HDDA (registered trademark, abbreviated below), HX-220, R-604 and the like; Osaka Organic Chemical Industry V-260 (registered trademark, abbreviated below), V-312, V -335 and the like. Examples of trifunctional esters of (meth)acrylic acid include Aronix M-309 (registered trademark, abbreviated below) manufactured by Toagosei Kagaku Kogyo Co., Ltd., M-400, M-405 and M-450. M-710, M-8030, M-8060 and the like; KAYARAD TMPTA (registered trademark, abbreviated below) manufactured by Nippon Kayaku Co., Ltd., DPCA-20, -30, -60, and -120. Etc.; V-295 (registered trademark, abbreviated below), -300, -360, -GPT, -3PA, -400, etc. of Osaka Organized Chemicals Co., Ltd. These products can be used alone or in combination of two or more.

The photopolymerizable compound may be used after being treated with an acid anhydride in order to impart more excellent developability.

The photopolymerizable compound is contained in an amount of preferably 1% by weight to 15% by weight, more preferably 5% by weight to 10% by weight, based on the weight of the photosensitive resin composition. When the photopolymerizable compound is contained in such a range in the photosensitive resin composition, excellent reliability can be obtained because the photosensitive resin composition can be sufficiently cured during exposure in the pattern forming step. And also has excellent developability in an alkaline developer.

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, and includes, for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds, or these. Can be used.

Examples of the acetophenone-based compound include 2,2′-diethoxyacetophenone, 2,2′-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyl. Dichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, 2-benzyl-2- Dimethylamino-1-(4-morpholinophenyl)-butan-1-one and the like can be mentioned.

Examples of benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4′-bis(dimethylamino)benzophenone, 4,4′-bis( Diethylamino)benzophenone, 4,4′-dimethylaminobenzophenone, 4,4′-dichlorobenzophenone, 3,3′-dimethyl-2-methoxybenzophenone and the like can be mentioned.

Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl4,6-bis(trichloromethyl)-s-triazine, 2-(3′,4′-dimethoxystyryl)- 4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6 -Bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, Bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphth-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphth-1-yl) -4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, 2-4-bis(trichloromethyl)-6-(4-methoxystyryl) )-S-Triazine and the like.

Examples of the oxime compound include O-acyl oxime compound, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime). Use of 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one, etc. You can Specific examples of O-acyl oxime compounds include 1,2-octanedione and 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-yl-phenyl)-butane-1. -One, 1-(4-phenylsulfanylphenyl)-butane-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione 2-oxime-O -Benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate and the like.

The photopolymerization initiator can include an oxime-based initiator and an acetophenone-based initiator at the same time. In this case, curing efficiency can be increased and an excellent process margin can be secured as compared with the case where only one type of photopolymerization initiator is used. Further, in this case, the oxime-based initiator is contained in a larger amount than the acetophenone-based initiator. When the content of the oxime-based initiator is equal to or smaller than that of the acetophenone-based initiator, the sensitivity is low (excellent in sensitivity) and a desired CD (Critical Dimension/critical value number) can be realized.

As the photopolymerization initiator, other than the above compounds, a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, a biimidazole compound, a fluorene compound, or the like can be used.

The photopolymerization initiator may be used together with a photosensitizer that causes a chemical reaction by absorbing light and being in an excited state and then transmitting the energy.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like.

The photopolymerization initiator is contained in an amount of 0.01% by weight to 5% by weight, preferably 0.1% by weight to 1% by weight, based on the weight of the photosensitive resin composition. When the photopolymerization initiator is contained in such a range in the photosensitive resin composition, the photosensitive resin composition can be sufficiently cured at the time of exposure in the pattern forming step, and excellent reliability can be obtained. The pattern has excellent heat resistance, light resistance and chemical resistance, and also has excellent resolution and adhesiveness, and can prevent a decrease in transmittance due to an unreacted initiator.

As the solvent, a substance that is compatible with the colorant containing the compound represented by Chemical Formula 1, the binder resin, the photopolymerizable compound, and the photopolymerization initiator and does not react can be used.

Examples of the solvent include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether and tetrahydrofuran; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol dimethyl ether. Glycol ethers such as; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, diethyl cellosolve acetate; methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol Carbitols such as diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl Ketones such as 2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone and 2-heptanone; saturated aliphatic monocarboxylic acids such as ethyl acetate, acetic acid-n-butyl and isobutyl acetate. Acid alkyl esters; Lactic acid esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Methyl methoxyacetate, Ethyl methoxyacetate, Butyl methoxyacetate, Methyl ethoxyacetate , Alkoxyacetic acid alkyl esters such as ethyl ethoxyacetate; Methyl 3-oxypropionate, 3-Oxypropionic acid alkyl esters such as ethyl 3-oxypropionate; Methyl 3-methoxypropionate, Ethyl 3-methoxypropionate, 3-Alkoxypropionic acid alkyl esters such as ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropiones such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate Acid alkyl esters; methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, etc. Which 2-alkoxypropionic acid alkyl esters; 2-oxy-2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, 2-methoxy-2 -Monooxymonocarboxylic acid alkyl esters of alkyl 2-alkoxy-2-methylpropionates such as methyl methylpropionate and ethyl 2-ethoxy-2-methylpropionate; ethyl 2-hydroxypropionate, 2-hydroxy- Esters such as ethyl 2-methylpropionate, ethyl hydroxyacetate, and methyl 2-hydroxy-3-methylbutanoate; ketone ester such as ethyl pyruvate; and N-methylformamide, N,N-dimethyl. Formamide, N-methylformanilad, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzylethylether, dihexylether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, Examples thereof include high boiling point solvents such as 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate and phenyl cellosolve acetate.

Among these, preferably, in consideration of compatibility and reactivity, ketones such as cyclohexanone; glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; 2-hydroxy. Esters such as ethyl propionate; carbitols such as diethylene glycol monomethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.

The solvent is contained in the balance, preferably 40 to 80% by weight, and more preferably 50 to 75% by weight, based on the weight of the photosensitive resin composition. When the photosensitive resin composition contains the solvent in such a range, the photosensitive resin composition has an appropriate viscosity, and thus the processability is excellent at the time of manufacturing the color filter.

The photosensitive resin composition may further contain an epoxy compound in order to improve the adhesion to the substrate.

Examples of epoxy compounds include phenol novolac epoxy compounds, tetramethylbiphenyl epoxy compounds, bisphenol A type epoxy compounds, alicyclic epoxy compounds, or combinations thereof.

The epoxy compound is contained in an amount of preferably 0.01% by weight to 20% by weight, more preferably 0.1% by weight to 10% by weight, based on the weight of the photosensitive resin composition. When the photosensitive resin composition contains the epoxy compound in such a range, the adhesiveness and the storage stability are excellent.

Further, the photosensitive resin composition may further contain a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group or an epoxy group in order to improve the adhesiveness to the substrate.

Examples of silane coupling agents include trimethoxysilylbenzoic acid, γmethacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γisocyanatopropyltriethoxysilane, γglycidoxypropyltrimethoxysilane, β Epoxycyclohexylethyltrimethoxysilane, vinylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxy Propylmethyldiethoxysilane, 3-glycidoxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropyltrimethoxysilane , 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2- (Aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-tri Ethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-chloropropyltrimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltriamine Methoxysilane, bis(triethoxysilylpropyl) tetrasulfide, 3-isocyanatopropyltriethoxysilane and the like can be mentioned, and these can be used alone or in combination of two or more.

The silane coupling agent is preferably contained in an amount of 0.01% by weight to 10% by weight, more preferably 0.05% by weight to 5% by weight, based on the weight of the photosensitive resin composition. When the photosensitive resin composition contains the silane coupling agent in such a range, the adhesiveness and the storage stability are excellent.

In addition, the photosensitive resin composition may further include a surfactant, if necessary, for the purpose of improving coating properties and preventing defect formation.

Examples of the surfactant include BM-1000 (registered trademark, abbreviated below) manufactured by BM Chemie, BM-1100 and the like; Megafac F142D (registered trademark, abbreviated below) manufactured by Dainippon Ink and Chemicals, Inc. F172, F173, F183, F554, etc.; Fluorard FC-135 (registered trademark, abbreviated below) of Sumitomo 3M Ltd., FC-170C, FC-430, FC-431, etc.; Asahi Glass (shares) ) Surflon S-112 (registered trademark, abbreviated below), S-113, S-131, S-141, S-145 and the like; SH-28PA (registered trademark, Toray Silicone Co., Ltd.) (Hereinafter abbreviated), -190, -193, SZ-6032, SF-8428, and other commercially available fluorine-based surfactants can be used.

The surfactant may be used in an amount of 0.001% by weight to 5% by weight based on the weight of the photosensitive resin composition. When the photosensitive resin composition contains the surfactant within such a range, coating uniformity is ensured, unevenness does not occur, and wettability with respect to the glass substrate is excellent.

Further, the photosensitive resin composition may be added with a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.

According to another embodiment, a photosensitive resin film manufactured using the photosensitive resin composition according to one embodiment is provided.

The pattern forming process in the photosensitive resin film is as follows.

Applying a photosensitive resin composition onto a supporting substrate by spin coating, slit coating, inkjet printing, etc.; drying the applied photosensitive resin composition to form a photosensitive resin composition film; The method includes the steps of exposing the photosensitive resin composition film to light; developing the exposed photosensitive resin composition film with an alkaline aqueous solution to produce a photosensitive resin film; and heat treating the photosensitive resin film. Since the conditions in the process are well known in the art, detailed description thereof will be omitted in this specification.

According to yet another embodiment, a color filter including a photosensitive resin film is provided.

According to still another embodiment, there is provided a pressure-sensitive adhesive composition including a compound represented by Formula 1, a binder resin, a curing agent, and a solvent.

According to still another embodiment, an adhesive film manufactured using the adhesive composition is provided.

Hereinafter, a pressure-sensitive adhesive composition and a pressure-sensitive adhesive film according to an embodiment of the present invention will be described.

The pressure-sensitive adhesive composition according to one embodiment includes the compound represented by Chemical Formula 1 (as a colorant) having a maximum absorption wavelength of 400 nm to 435 nm, so that diffuse reflection generated in the panel by external light, that is, The problem of reduced visibility due to reflection can be improved. The reflectance measurement for improving visibility can be measured by a spectrocolorimeter. That is, it is possible to display, by the reflectance, a level at which the visibility of the light entering the panel from the outside decreases due to the diffused reflection generated by the particles inside the panel.

The compound represented by Chemical Formula 1 is preferably contained in an amount of 0.001% by weight to 0.01% by weight based on the weight of the adhesive composition (0.01% by weight based on the solid content of the adhesive composition). 0.03% by weight).

The binder resin may be an acrylic binder resin, and the acrylic binder resin is preferably 65% by weight to 85% by weight, more preferably 70% by weight to 80% by weight, based on the weight of the pressure-sensitive adhesive composition. Included (90 wt% to 98 wt% based on the solid content of the pressure-sensitive adhesive composition).

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

The functional groups of the first (meth)acrylate copolymer and the second (meth)acrylate copolymer may be different from each other.

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

The first (meth)acrylate copolymer is one or more of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylic monomer having a carboxylic acid group; and a monomer copolymerizable therewith. It may be a copolymer of a monomer mixture containing a monomer (hereinafter, referred to as “first copolymerized monomer”). Among the monomer mixture, one or more of the (meth)acrylate monomer having a hydroxyl group and the (meth)acrylate monomer having a carboxylic acid group may be used based on the total mol number of the monomer mixture. The content is preferably 10 mol% or less, more preferably 0.01 mol% to 5 mol%. When included in such a range together with the second (meth)acrylate copolymer, it is possible to realize a pressure-sensitive adhesive film that is excellent in flexibility and bending property and can be used in a flexible device.

The (meth)acrylate monomer having a hydroxyl group can be self-curable and/or can enhance the adhesive strength of the adhesive film and enhance the durability of the adhesive film. The (meth)acrylate monomer having a hydroxyl group is contained in an amount of preferably 5 mol% or less, more preferably 0.01 mol% to 5 mol% based on the total mol number of the monomer mixture. By being included in such a range, there may be an effect that the adhesive strength and durability of the adhesive film are improved and the aging of the adhesive composition is accelerated.

The (meth)acrylate monomer having a hydroxyl group has a (meth)acrylate monomer having a C1 to C20 alkyl group having one or more hydroxyl groups, and a C3 to C20 cycloalkyl group having one or more hydroxyl groups ( One or more of a (meth)acrylic monomer and a (meth)acrylate monomer having a C6 to C20 aromatic group having one or more hydroxyl groups can be included. Specifically, the (meth)acrylate monomer having a hydroxyl group includes 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, and 4-hydroxybutyl (meth). ) Acrylate, 6-hydroxyhexyl(meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate, 1-chloro-2-hydroxypropyl(meth)acrylate, diethylene glycol mono(meth)acrylate, 2-hydroxy-3. -One or more of phenyloxypropyl (meth)acrylate, 4-hydroxycyclopentyl (meth)acrylate, and 4-hydroxycyclohexyl (meth)acrylate. These are contained alone or as a mixture of two or more kinds.

The (meth)acrylate monomer having a carboxylic acid group can be made self-curable. The (meth)acrylate monomer having a carboxylic acid group is contained in an amount of preferably 5 mol% or less, more preferably 0.01 mol% to 5 mol%, based on the total mol number of the monomer mixture. By being included in such a range, the acidity of the adhesive film is not high, there is no risk of corrosion on the adherend, the resistance can be reduced, and the reliability of the adhesive film can be improved. 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. Copolymers can be formed to form a matrix for adhesive films and to provide additional functionality.

The first copolymerization monomer may include a (meth)acrylate monomer having an alkyl group. The (meth)acrylate monomer having an alkyl group can be included in the (meth)acrylate copolymer to form a matrix of the pressure-sensitive adhesive film and enhance the mechanical strength of the pressure-sensitive adhesive film. The (meth)acrylate monomer having an alkyl group is preferably 50 mol% to 99.99 mol%, more preferably 50 mol% to 95 mol%, further preferably 55 mol% to the total mol number of the monomer mixture. 99.9 mol%, particularly preferably 55 mol% to 90 mol%, most preferably 60 mol% to 85 mol%. By being included in such a range, the mechanical strength of the pressure-sensitive adhesive film can be increased. The (meth)acrylate monomer having an alkyl group can include a (meth)acrylic acid ester having an unsubstituted C4 to C12 alkyl group. Specifically, the (meth)acrylate monomer having an alkyl group includes n-butyl(meth)acrylate, t-butyl(meth)acrylate, iso-butyl(meth)acrylate, pentyl(meth)acrylate, hexyl( Of (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, iso-octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate It can include, but is not limited to, one or more of these. These are contained alone or as a mixture of two or more kinds.

The first copolymerization monomer further contains at least one of a (meth)acrylate monomer having an alicyclic group and a (meth)acrylate monomer having a heteroalicyclic group, thereby providing an adhesive property. It is also possible to further increase the pencil hardness of the polarizing plate including the film.

The (meth)acrylate monomer having an alicyclic group is contained in the first (meth)acrylate copolymer, and the polarizing film having the pressure-sensitive adhesive film for a polarizing plate adhered together with the second (meth)acrylate copolymer. The pencil hardness of the polarizing plate on the adhesive film of the plate can be increased. Specifically, in the polarizing plate to which the pressure-sensitive adhesive film for polarizing plate is adhered, the pencil hardness of the polarizing plate on the adhesive film may be 2H or more, and more specifically 2H to 3H. In such a range, even if the polarizing plate is adhered to the liquid crystal panel such as a glass material with the adhesive film for polarizing plate, the pencil hardness is significantly reduced as compared with the case where the polarizing plate is adhered to the liquid crystal panel without the adhesive film. Instead, 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 a heteroalicyclic group described below, and is included in the adhesive for polarizing plates. The creep at 25° C. of the film can be reduced and the creep at 85° C. can be increased. Particularly, the (meth)acrylate monomer having an alicyclic group and the (meth)acrylate monomer having a heteroalicyclic group each have a homopolymer glass transition temperature of preferably 30° C. or higher, more preferably 40. By setting the temperature to be in the range of ℃ to 180 ℃, the creep of the adhesive film at 25 ℃ can be reduced and the creep at 85 ℃ can be increased. In the monomer mixture, the (meth)acrylate monomer having an alicyclic group:the (meth)acrylic monomer having a heteroalicyclic group may be used in a molar ratio of 1:0.25 to 1:2. Included in the ratio. By being included in such a range, the cohesive force or strength at room temperature may be increased. Alternatively, there may be a stress relaxation effect and a deflection improving effect on the polarizing film at high temperature.

The (meth)acrylate monomer having an alicyclic group is contained in an amount of preferably 1 mol% to 30 mol%, more preferably 5 mol% to 20 mol% based on the total mol number of the monomer mixture. By being included in such a range, the pencil hardness of the polarizing plate on the pressure-sensitive adhesive film can be increased and the cohesive force can be increased.

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

"Alicyclic group" means a non-heteroalicyclic group that does not contain nitrogen, oxygen, or sulfur heteroatoms. "Heterocycle" means two or more alicyclic groups linked by one or more carbon atoms in common.

Specifically, the (meth)acrylic acid ester having a substituted or unsubstituted C5-C20 single ring or heterocyclic alicyclic group is cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentanyl ( It can include one or more of (meth)acrylate, methylcyclohexyl (meth)acrylate, dicyclopentenyl (meth)acrylate. These are contained alone or as a mixture of two or more kinds.

The (meth)acrylate monomer having a heteroalicyclic group can reduce 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 a heteroalicyclic group is contained in an amount of preferably 1 mol% to 30 mol%, more preferably 5 mol% to 20 mol% with respect to the total mol number of the monomer mixture. By being included in such a range, the modulus of the pressure-sensitive adhesive film at 30° C. may be increased, and the cohesive force may be increased.

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

The first copolymerized monomer is one or more of a (meth)acrylic acid ester having a C1-C3 alkyl group, a monomer having an amide group, and a monomer having an aromatic group. It may further include. 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 one or more of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylate monomer having a carboxylic acid group, 0.01 mol% to It may be a copolymer of 5 mol% and an alkyl group-containing (meth)acrylate monomer of 95 mol% to 99.99 mol%. In another embodiment, the first (meth)acrylate copolymer is one or more 0.01 mol% of a (meth)acrylate monomer having a hydroxyl group and a (meth)acrylate monomer having a carboxylic acid group. ~ 5 mol%, (meth) acrylate monomer having an alkyl group 50 mol% to 95 mol%, (meth) acrylate monomer having an alicyclic group 1 mol% to 30 mol%, having a heteroalicyclic group (meth) It may be a copolymer of 1 mol% to 30 mol% of an acrylate monomer. In such a range, high cohesive strength and high strength effect can be obtained.

The second (meth)acrylate copolymer forms the matrix of the adhesive film and provides one or more of epoxy groups and oxetane groups to allow the adhesive composition to self-cure without a cross-linking agent. ..

The second (meth)acrylate copolymer is one or more of a (meth)acrylic monomer having an epoxy group and a (meth)acrylic monomer having an oxetane group; and is copolymerizable with these. It may be a copolymer of a monomer mixture containing a monomer (hereinafter, "second copolymerized 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 is 10 mol% or less, specifically 0.01 mol%. ~ 5 mol% is included. In such a range, when it is included with the first (meth)acrylate copolymer, it is possible to realize an adhesive film which has good flexibility, bending property, hardness, processability and reliability and which can be used in a flexible device. ..

The (meth)acrylate monomer having an epoxy group may be self-curable and/or may have an effect of improving cohesive strength and reliability. The (meth)acrylic monomer having an epoxy group is contained in the monomer mixture in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol%. In such a range, there may be an effect that the curing is quick and the reliability is improved. The (meth)acrylic monomer having an epoxy group may be glycidyl (meth)acrylate.

The (meth)acrylate monomer having an oxetane group can be self-curable and/or can achieve the effect of improving cohesive strength and reliability. The (meth)acrylate monomer having an oxetane group is contained in the monomer mixture in an amount of 5 mol% or less, specifically 0.01 mol% to 5 mol%. In such a range, there may be an effect that the curing is quick and the reliability is improved. Examples of the (meth)acrylate monomer having an oxetane group include oxetanyl (meth)acrylate, oxetanylmethyl (meth)acrylate, (3-methyl-3-oxetanyl)methyl (meth)acrylate, and (3-ethyl-3-oxetanyl). It may be methyl (meth)acrylate or the like.

The second copolymerization monomer is copolymerized with at least one of a (meth)acrylate monomer having an epoxy group and a (meth)acrylate monomer having an oxetane group to form a matrix of an adhesive film. Or can provide additional functionality.

The second copolymerizable monomer may include a (meth)acrylate monomer having an alkyl group. The second copolymerization monomer further comprises at least one of a (meth)acrylate monomer having an alicyclic group and a (meth)acrylate monomer having a heteroalicyclic group, thereby providing an adhesive property. It is also possible to further increase the pencil hardness of the polarizing plate including the film. Specific types 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 As described for the copolymerization monomer.

In one embodiment, the second (meth)acrylate copolymer comprises one or more of an epoxy group-containing (meth)acrylate monomer and an oxetane group-containing (meth)acrylate monomer in an amount of 0.01 mol% or more. It may be a copolymer of 5 mol% and 95 mol% to 99.9 mol% of a (meth)acrylate monomer having an alkyl group. In another embodiment, the second (meth)acrylate copolymer is 0.01 mol% of one or more of a (meth)acrylate monomer having an epoxy group and a (meth)acrylate monomer having an oxetane group. ˜5 mol%, (meth)acrylate monomer having an alkyl group 50 mol% to 95 mol%, (meth)acrylate monomer having an alicyclic group 1 mol% to 30 mol%, and a heteroalicyclic group It may be a copolymer with 1 to 30 mol% of a (meth)acrylate monomer. In such a range, there may be an effect that the curing is quick and the reliability is improved.

The glass transition temperature of each of the first (meth)acrylate copolymer and the second (meth)acrylate copolymer is preferably −55° C. to −5° C., more preferably −50° C. to −30° C. is there. The weight average molecular weights of the first (meth)acrylate copolymer and the second (meth)acrylate copolymer are each preferably 200,000 g/mol to 1,500,000 g/mol, more preferably 500, It is 000 g/mol-1,000,000 g/mol. The acid value of each of the first (meth)acrylate copolymer and the second (meth)acrylate copolymer is preferably 5 mgKOH/g or less, more preferably 0.01 mgKOH/g to 3 mgKOH/g. .. Within such a range, the effect of inhibiting corrosion can be directly or indirectly achieved on the adherend.

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

The curing agent may be a thermosetting agent or is used to enhance 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 compound, an aziridine compound, etc. are mentioned, These can be used individually or in mixture of 2 or more types.

Examples of the isocyanate compound include diisocyanate compounds such as tolylene diisocyanate, xylene diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4-diphenylmethane diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, tetramethylxylene diisocyanate and naphthalene diisocyanate; trimethylolpropane and the like. Of 1 mol of the polyhydric alcohol compound, an adduct obtained by reacting 3 mol of the diisocyanate compound, an isocyanurate body obtained by self-condensing 3 mol of the diisocyanate compound, and 1 mol of the remaining diisocyanate urea obtained from 2 mol of 3 mol of the diisocyanate compound. Examples thereof include a burette body in which diisocyanate is condensed, triphenylmethane triisocyanate, and a polyfunctional isocyanate compound having three functional groups such as methylenebistriisocyanate.

Examples of the aziridine compound include N,N'-toluene-2,4-bis(1-aziridinecarboxamide), N,N'-diphenylmethane-4,4'-bis(1-aziridinecarboxamide), triethylenemelamine, bis. Examples include isophthaloyl-1-(2-methylaziridine), tri-1-aziridinylphosphine oxide, and the like.

In addition to the isocyanate compound and the aziridine compound, melamine compounds may be used alone or in admixture of two or more.

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

The curing agent is preferably contained in an amount of 0.1% by weight to 1% by weight, more preferably 0.1% by weight to 0.5% by weight, based on the total amount of the adhesive composition (solid content of the adhesive composition. The content of 0.3 to 1.0% by weight is preferable in terms of adhesive strength or cohesiveness. When the amount of 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 force of the pressure-sensitive adhesive is slightly reduced (incomplete curing) due to the insufficient degree of crosslinking, resulting in durability such as floating. When the curing agent exceeds 1% by weight with respect to the total amount of the pressure-sensitive adhesive composition, compatibility may be slightly reduced and surface migration may occur, resulting in cross-linking. The reaction may proceed excessively and the adhesive strength may be slightly reduced, which may cause a problem in residual stress relaxation.

The solvent improves the coating property of the pressure-sensitive adhesive composition and can prevent the self-curing reaction of the pressure-sensitive adhesive composition. As the solvent, an ordinary 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 is preferably a balance amount with respect to the pressure-sensitive adhesive composition, for example, a total amount of the pressure-sensitive adhesive composition. 10 to 40% by weight, more preferably 10 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.

The description of the silane coupling agent is as described above, and the silane coupling agent is preferably 0.01% by weight to 0.1% by weight, more preferably 0.01% by weight, based on the total amount of the pressure-sensitive adhesive composition. % To 0.05% by weight (0.1% to 0.3% by weight based on the solid content of the pressure-sensitive adhesive composition).

The antistatic agent suppresses the generation of static electricity during reprocessing of the pressure-sensitive adhesive film, and may include a usual antistatic agent. The antistatic agent is contained in an amount of 1% by weight to 5% by weight, for example, 1% by weight to 3% by weight, based on the total amount of the adhesive composition (1.0% by weight based on the solid content of the adhesive composition. 5.0% by weight). When the antistatic agent is contained within the range, it is preferable in terms of chargeability. If the antistatic agent is contained 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 slightly reduced. If so, the physical properties of the pressure-sensitive adhesive composition are deteriorated to increase the manufacturing 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 have a slightly low compatibility with the pressure-sensitive adhesive and may lack durability, and the ionic liquid has a large fluidity in the pressure-sensitive adhesive composition and has a little antistatic performance due to aging. It may decrease. In short, it is preferable to include an ionic solid that is solid at room temperature (25° C.) in consideration of durability and stability of antistatic property over time.

For example, the antistatic agent may be todecylpyridinium hexafluorophosphate (KOEI), lithium bistrifluoromethanesulfonimide (3M), tri-n-butylmethylammonium bis-(trifluoromethanesulfonyl)imide (3M), or the like. However, the present invention is not limited to this, and two or more kinds may be mixed and used.

The ultraviolet absorber may have an absorption wavelength of 380 to 420 nm. Here, the “absorption wavelength” can refer to the “maximum absorption wavelength”.

When the pressure-sensitive adhesive composition includes an ultraviolet absorber having an absorption wavelength range, it can exhibit a transmittance of 5% or less in a region of 400 nm or less, thereby providing a polarizing plate described below and a display device including the same. Has the advantage that it can be prevented from being damaged by external ultraviolet rays.

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

The cationic initiator may be, but is not limited to, a cationic photopolymerization initiator, and cationic photoinitiators generally used in the art can be used. For example, an onium salt or its derivative that releases a Lewis acid upon irradiation with light can be given. Such a compound is represented by the general formula [X] ^x+ [Y] ^x- and is in a salt form composed of a cation and an anion. Specific examples of the cation include aromatic diazonium salts and aromatic iodonium salts. , Aromatic halonium salts, aromatic sulfonium salts and the like. Specific examples of the anion include tetrafluoroborate (BF ₄ ), hexafluorophosphate (PF ₆ ), hexafluoroantimonate (SbF ₆ ), hexafluoro. Examples include arsenate (AsF ₆ ), hexachloroantimonate (SbCl ₆ ), and the like. These cationic photopolymerization initiators can be used alone or in combination of two or more.

The content of the cationic initiator is not particularly limited, but is, for example, 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, with respect to the total amount of the adhesive composition. Includes parts by weight. When the amount of the cation initiator is less than 0.01 parts by weight based on the total amount of the pressure-sensitive adhesive composition, the colored adhesive composition may be insufficiently cured, and it may be difficult to obtain sufficient adhesive force and adhesive force. If the amount of the initiator exceeds 10 parts by weight with respect to the total amount of the pressure-sensitive adhesive composition, the hygroscopicity may increase due to excessive content of the ionic substance in the adhesive layer, and the durability may slightly deteriorate.

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

In addition to these components, the pressure-sensitive adhesive composition may include a reworking agent, an adhesive agent, an adhesive agent, an adhesive agent, a cohesive force, a viscosity, an elastic modulus, a glass transition temperature, etc. It may further contain additives such as a property imparting resin, an antioxidant, a leveling agent, a surface lubricant, an antifoaming agent, a filler and a light stabilizer.

Additives can 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 such a range, the thickness of the pressure-sensitive adhesive film can be easily adjusted, the pressure-sensitive adhesive film can be even, and the coating surface can be uniform.

Yet another embodiment provides a polarizing plate including an adhesive film.

The method for producing the pressure-sensitive adhesive film is not particularly limited and can be produced by a usual method. For example, it can be applied to the production of an adhesive film using the adhesive composition.

For example, the pressure-sensitive adhesive composition described above is coated on a polarizer protective film by a fluid casting method, a bar coater, an air knife, an gravure, a reverse roll, or a kiss roll. Direct application by a suitable spreading method using a coating method such as a spray method, a spray method, or a blade method, followed by drying (thermosetting) to form a pressure-sensitive adhesive layer, and then laminating with a polarizing plate. It can be manufactured.

In addition, after forming an adhesive film on the silicone-coated release film by the same coating method as above, by using a roll pressure bonding device, a silicone-coated release film having different peeling force is laminated and adhered. After the agent transfer tape is manufactured, it can be used by adhering it to a polarizing plate.

The pressure-sensitive adhesive film can be formed by thermosetting, but when a UV-curable compound and a photopolymerization initiator (such as the above-mentioned cationic photopolymerization initiator) are used as a crosslinking agent, a polarizing plate is laminated. After that, it can be produced by irradiating ultraviolet rays from the release film side, or by laying a silicone-coated release film having a different peeling force using a roll pressure bonding device, and then irradiating ultraviolet rays (photocuring). ..

The thickness of the adhesive film is not particularly limited, but may be 5 μm to 30 μm, for example 7 μm to 20 μm, for example 10 μm to 15 μm. When the thickness of the adhesive film is within such a range, it is preferable in terms of adhesiveness and durability, and there is an advantage that it can be applied to a thin element.

In a 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 caused to the polarizing plate or an element in which the polarizing plates are joined is prevented, and a transmittance of a wavelength of 455 nm or more is 40% or more. However, there is an advantage that it is possible to prevent the phenomenon that the blue luminance decreases.

Yet another embodiment provides an optical display device including a color filter and/or a polarizing plate including a photosensitive resin film.

The optical display device is an image display device, and may be a liquid crystal display device, an OLED, a flexible display, or the like, but is not limited thereto, and all applicable image display devices known in the art may be used. It can be illustrated.

For example, the optical display device may be a liquid crystal display device. Generally, the 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 the polarizing plate according to one embodiment. The color filter may be a color filter according to an embodiment. For example, the optical display device may include a polarizing plate in which the pressure-sensitive adhesive layer according to the embodiment is laminated on at least one surface of the color filter according to the embodiment.

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

<Synthesis of Compound Represented by Chemical Formula 1>
The central metals M of the compounds synthesized in Synthesis Examples 1 to 13 below are all Zn. In the following examples, Ac is an acetyl group _{(CH 3 (C = O)} -) means.

The molecular weight of each compound obtained in the following Synthesis Examples 1 to 14, Comparative Synthesis Example 1 and Comparative Synthesis Example 2 was measured by mass spectrometry (MALDI-TOF). The measurement results of the molecular weight are shown in each synthesis example.

[Synthesis Example 1: Synthesis of compound represented by chemical formula 3-1]
To a round bottom flask, 30 g (0.2 mol) of terephthalaldehyde acid and 600 g of propionic acid were sequentially added and stirred. After adding 13.5 g (0.2 mol) of pyrrole to the reaction product in the round bottom flask, the temperature of the reaction product was raised to 80° C. and stirred for 1 hour. The reaction was then heated to 130° C. and stirred for 90 minutes before terminating the reaction. The obtained reaction product was cooled to room temperature (23° C.), 300 g of acetone was added to the reaction product, the mixture was stirred at room temperature for 1 hour, and the generated precipitate was filtered using a filter. Then, the solid compound on the filter was collected, washed with acetone, and then dried to obtain 8.3 g of the intermediate (A).

Under a nitrogen atmosphere, 3 g (3.8 mmol) of the intermediate (A) obtained above and 30 g of SOCl ₂ were added to a round bottom flask, and then the mixture was stirred at 80° C. for 12 hours, and then excess SOCl ₂ was distilled. Removed by. Thereafter, 45 g of chloroform was added to the round bottom flask, and 2.96 g (18.24 mmol) of 2-hydroxybenzotrifluoride and 1.85 g (18.24 mmol) of triethylamine were further added, followed by stirring at room temperature for 24 hours. After completion of the reaction, the reaction product was washed with 10% NaCl solution and deionized water, and extracted with chloroform. Then, the solvent was removed from the extract by distillation, and the obtained reaction product was subjected to column chromatography to obtain 0.99 g of the intermediate (B).

0.9 g (0.66 mmol) of the intermediate (B) obtained above and 45 g of chloroform were sequentially added to a round bottom flask, and the mixture was stirred at 60°C. Zn(OAc) ₂ (363 mg, 1.98 mmol) and 7 g of methanol were sequentially added to another round bottom flask and stirred at room temperature to dissolve Zn(OAc) ₂ . Then, the Zn(OAc) ₂ solution was added to the round bottom flask containing the intermediate (B), and the mixture was stirred for 2 hours. After the reaction was completed, the reaction product was allowed to cool to room temperature, then the reaction product was extracted with methylene chloride, and the extract was washed with 10% NaCl and deionized water. The solvent was removed from the extract by distillation, the obtained reaction product was dissolved in a minimum amount of methylene chloride, and the methylene chloride solution was gradually added dropwise to 100 g of acetonitrile to form a precipitate. The obtained precipitate was filtered, washed with acetonitrile, and then dried to obtain 0.81 g (yield: 86%) of a porphyrin compound represented by the following chemical formula 3-1.

(M=Zn, MALDI-TOF: 1428 m/z)
[Synthesis Example 2: Synthesis of compound represented by chemical formula 3-2]
To a round bottom flask, 1 g (0.73 mmol) of the intermediate (B) obtained above and 300 g of chloroform were sequentially added and stirred. After adding 214 mg (1.61 mmol) of N-chlorosuccinimide to this round bottom flask, it heated at 60 degreeC. After the reaction was completed, the reaction product was allowed to cool to room temperature, extracted with chloroform, and the extract was washed with 10% NaCl and deionized water. Then, the solvent was removed from the extract by distillation, and the obtained reaction product was subjected to column chromatography to obtain 0.47 g of the intermediate (C).

0.9 g (0.66 mmol) of the intermediate (C) produced above and 45 g of chloroform were sequentially added to a round bottom flask, and the mixture was stirred at 60°C. Zn(OAc) ₂ (363 mg, 1.98 mmol) and 7 g of methanol were sequentially added to another round-bottomed flask, and the mixture was stirred at room temperature to dissolve Zn(OAc) ₂ . Then, the Zn(OAc) ₂ solution was added to the round bottom flask containing the intermediate (B), and the mixture was stirred for 2 hours. After completion of the reaction, the reaction product was allowed to cool to room temperature, extracted with methylene chloride, and the extract was washed with 10% NaCl and deionized water. The solvent was removed from the extract by distillation, the obtained reaction product was dissolved in a minimum amount of methylene chloride, and then gradually dropped into 100 g of acetonitrile to form a precipitate. The precipitate was filtered, washed with acetonitrile, and then dried to obtain 0.39 g (yield: 79%) of a porphyrin compound represented by the following chemical formula 3-2.

(M=Zn, MALDI-TOF: 1496 m/z)
[Synthesis Example 3: Synthesis of compound represented by chemical formula 3-3]
1 g (0.73 mmol) of the intermediate (B) obtained above and 100 g of 1,1,2,2-tetrachloroethane were sequentially added to a round bottom flask and stirred. After adding N-chlorosuccinimide (526 mg, 3.94 mmol) to this round bottom flask, it heated at 100 degreeC. After completion of the reaction, the reaction product was allowed to cool to room temperature, the solvent was removed by distillation, the obtained reaction product was extracted with chloroform, and the extract was washed with 10% NaCl and deionized water. did. Then, the solvent was removed from the extract by distillation, and the obtained reaction product was subjected to column chromatography to obtain 0.69 g of the intermediate (D).

Thereafter, 0.9 g (0.66 mmol) of the intermediate (D) produced above and 45 g of chloroform were sequentially added to a round bottom flask and stirred at 60°C. Zn(OAc) ₂ (363 mg, 1.98 mmol) and 7 g of methanol were sequentially added to another round-bottomed flask, and the mixture was stirred at room temperature to dissolve Zn(OAc) ₂ . Then, the Zn(OAc) ₂ solution was added to the round bottom flask containing the intermediate (B), and the mixture was stirred for 2 hours. After the reaction was completed, the reaction product was allowed to cool to room temperature, extracted with methylene chloride, and the extract was washed with 10% NaCl and deionized water. After removing the solvent from the extract by distillation, the obtained reaction product was dissolved in a minimum amount of methylene chloride, and the methylene chloride solution was gradually added dropwise to 100 g of acetonitrile to form a precipitate. The obtained precipitate was filtered, washed with acetonitrile, and then dried to obtain 0.57 g (yield: 79%) of a porphyrin compound represented by the following chemical formula 3-3.

(M=Zn, MALDI-TOF: 1564 m/z)
[Synthesis Example 4: Synthesis of compound represented by chemical formula 3-4]
A porphyrin-based compound represented by the following chemical formula 3-4 was performed in the same manner as in Synthesis Example 1 except that 3,5-bis(trifluoromethyl)phenol was used instead of 2-hydroxybenzotrifluoride. 0.78 g (yield: 79%) was obtained.

(M=Zn, MALDI-TOF: 1700 m/z)
[Synthesis Example 5: Synthesis of compound represented by chemical formula 3-5]
Porphyrin-based compound 0 represented by the following chemical formula 3-5 was performed in the same manner as in Synthesis Example 2 except that 3,5-bis(trifluoromethyl)phenol was used instead of 2-hydroxybenzotrifluoride. 0.69 g (yield: 74%) was obtained.

(M=Zn, MALDI-TOF: 1768 m/z)
[Synthesis Example 6: Synthesis of compound represented by Chemical Formula 3-6]
Porphyrin-based compound 0 represented by the following chemical formula 3-6 was performed in the same manner as in Synthesis Example 3 except that 3,5-bis(trifluoromethyl)phenol was used instead of 2-hydroxybenzotrifluoride. 0.59 g (yield: 69%) was obtained.

(M=Zn, MALDI-TOF: 1836 m/z)
[Synthesis Example 7: Synthesis of compound represented by chemical formula 3-7]
The same procedure as in Synthesis Example 1 was carried out except that 2-fluorophenol was used instead of 2-hydroxybenzotrifluoride, and 1.5 g of a porphyrin-based compound represented by the following chemical formula 3-7 (yield: 88 %) was obtained.

(M=Zn, MALDI-TOF: 1228 m/z)
[Synthesis Example 8: Synthesis of compound represented by chemical formula 3-8]
The same method as in Synthesis Example 2 was performed except that 2-fluorophenol was used instead of 2-hydroxybenzotrifluoride, and 0.92 g of a porphyrin compound represented by the following chemical formula 3-8 (yield: 75 %) was obtained.

(M=Zn, MALDI-TOF: 1296 m/z)
[Synthesis Example 9: Synthesis of compound represented by chemical formula 3-9]
The same procedure as in Synthesis Example 3 was carried out except that 2-fluorophenol was used instead of 2-hydroxybenzotrifluoride, and 0.71 g of a porphyrin compound represented by the following chemical formula 3-9 (yield: 79 %) was obtained.

(M=Zn, MALDI-TOF: 1364 m/z)
[Synthesis Example 10: Synthesis of compound represented by chemical formula 3-10]
The same procedure as in Synthesis Example 1 was carried out except that 2,6-difluorophenol was used instead of 2-hydroxybenzotrifluoride, and 1.3 g of a porphyrin compound represented by the following chemical formula 3-10 (yield: : 84%) was obtained.

(M=Zn, MALDI-TOF: 1300 m/z)
[Synthesis Example 11: Synthesis of compound represented by chemical formula 3-11]
The same procedure as in Synthesis Example 2 was repeated except that 2,6-difluorophenol was used instead of 2-hydroxybenzotrifluoride, and 1.05 g of a porphyrin compound represented by the following chemical formula 3-11 (yield: : 75%) was obtained.

(M=Zn, MALDI-TOF: 1368 m/z)
[Synthesis Example 12: Synthesis of compound represented by chemical formula 3-12]
The same procedure as in Synthesis Example 3 was carried out except that 2,6-difluorophenol was used instead of 2-hydroxybenzotrifluoride, and 0.55 g of porphyrin compound represented by the following chemical formula 3-12 (yield: : 72%) was obtained.

(M=Zn, MALDI-TOF: 1436 m/z)
[Synthesis Example 13: Synthesis of compound represented by Chemical Formula 3-13]
To a round bottom flask, 30 g (0.283 mol) of benzaldehyde and 600 g of propionic acid were sequentially added and stirred. After adding 18.9 g (0.283 mol) of pyrrole to the stirred reaction product, the temperature of the reaction product was raised to 80° C. and stirred for 1 hour. The reaction was then heated to 130° C. and stirred for 90 minutes before terminating the reaction. The obtained reaction product was allowed to cool to room temperature, 300 g of acetone was added, the mixture was stirred at room temperature for 1 hour, and the generated precipitate was filtered using a filter. Then, the solid compound on the filter was collected, washed with acetone, and dried to obtain 11.3 g of the intermediate (E).

11.3 g (18.4 mmol) of the intermediate (E) obtained above was added to a round bottom flask, 50 g of chlorosulfonic acid and 200 g of methylene chloride were sequentially added, and then the mixture was stirred at room temperature for 5 hours. .. After completion of the reaction, the solvent and chlorosulfonic acid were removed from the reaction product by distillation, and 2-ethylhexylamine (14.3 g, 110.4 mmol) was added to 100 g of the reaction product, followed by stirring at room temperature for 24 hours. After the reaction was completed, the obtained reaction product was washed with 10% NaCl solution and deionized water, and extracted with methylene chloride. Then, the solvent was removed from the extract by distillation, and the obtained reaction product was subjected to column chromatography to obtain 5.1 g of the intermediate (F).

Then, 0.9 g (0.66 mmol) of the intermediate (F) produced above and 45 g of chloroform were sequentially added to a round bottom flask, and the mixture was stirred at 60°C. Zn(OAc) ₂ (363 mg, 1.98 mmol) and 7 g of methanol were sequentially added to another round bottom flask and stirred at room temperature to dissolve Zn(OAc) ₂ . Then, the Zn(OAc) ₂ solution was added to the round bottom flask containing the intermediate (F), and then stirred for 2 hours. After the reaction was completed, the reaction product was allowed to cool to room temperature, extracted with methylene chloride, and the extract was washed with 10% NaCl and deionized water. After removing the solvent from the extract by distillation, the obtained reaction product was dissolved in a minimum amount of methylene chloride, and the methylene chloride solution was gradually added dropwise to 100 g of acetonitrile to form a precipitate. The precipitate was filtered, washed with acetonitrile, and then dried to obtain 2.5 g (yield: 90%) of a porphyrin compound represented by the following chemical formula 3-13.

(M=Zn, MALDI-TOF: 1378 m/z)
[Synthesis Example 14: Synthesis of compound represented by Chemical Formula 3-14]
3.2 g (2.58 mmol) of the intermediate (F) obtained above and 160 g of chloroform were sequentially added to a round bottom flask, and the mixture was stirred at 60°C. 1.42 g (7.74 mmol) of Zn(OAc) ₂ and 30 g of methanol were sequentially added to another round bottom flask, and the mixture was stirred at room temperature to dissolve Zn(OAc) ₂ . Then, the Zn(OAc) ₂ solution was added to the round bottom flask containing the intermediate (B), and then the mixture was stirred for 2 hours for reaction. After completion of the reaction, the reaction product was allowed to cool to room temperature (23° C.), extracted with methylene chloride, and the extract was washed with 10% NaCl and deionized water. After removing the solvent from the extract by distillation, the obtained reaction product was dissolved in a minimum amount of methylene chloride, and the methylene chloride solution was gradually added dropwise to 100 g of acetonitrile to form a precipitate. The precipitate was filtered, washed with acetonitrile, and then dried to obtain 3.1 g (yield: 92%) of a compound represented by the following chemical formula 3-14.

(M=Zn, MALDI-TOF: 1200 m/z)
[Comparative Synthesis Example 1: Synthesis of compound represented by chemical formula C-1]
3.5 g of a porphyrin-based compound represented by the following chemical formula C-1 was performed in the same manner as in Synthesis Example 1 except that 4-(trifluoromethyl)benzaldehyde was used instead of 2-hydroxybenzotrifluoride. (Yield: 91%) was obtained.

(MALDI-TOF: 948m/z)
[Comparative Synthesis Example 2: Synthesis of compound represented by chemical formula C-2]
The same procedure as in Synthesis Example 1 was carried out except that 2-ethylhexylamine was used instead of 2-hydroxybenzotrifluoride, and 1.6 g of a porphyrin-based compound represented by the following chemical formula C-2 (yield: 90 %) was obtained.

<Evaluation 1: Maximum absorption wavelength and solubility>
Maximum absorption wavelength (λ _max ) in cyclohexanone of each compound obtained in Synthesis Example 1 to Synthesis Example 14, Comparative Synthesis Example 1 and Comparative Synthesis Example 2 and solubility in propylene glycol 1-monomethyl ether 2-acetate (PGMEA) Is shown in Table 1 below. Solubility was evaluated based on the following solubility evaluation criteria, at room temperature (20° C.), whether 10 g of each compound can be dissolved in 1000 cm ³ of solvent (PGMEA).

Solubility Evaluation Criteria O: 10 g of the compound dissolves in 1000 cm ³ of PGMEA.

X: 10 g of the compound does not dissolve in PGMEA 1000 cm ³ .

From Table 1, it was found that the compound according to the present embodiment has the highest absorbance in the narrow wavelength region band of 420 nm to 435 nm and the excellent solubility in the organic solvent.

<Synthesis of photosensitive resin composition>
[Examples 1 to 14, Comparative Example 1 and Comparative Example 2]
The components shown below were mixed in the compositions shown in Tables 2 and 3 to prepare photosensitive resin compositions according to Examples 1 to 14, Comparative Example 1 and Comparative Example 2.

Specifically, after dissolving the photopolymerization initiator in the solvent, the mixture was stirred at room temperature for 2 hours, the binder resin and the photopolymerizable compound were added thereto, and the mixture was stirred at room temperature for 2 hours. Next, a colorant and other additives were added to the obtained reaction product, and the mixture was stirred at room temperature for 1 hour. Next, the photosensitive resin composition was manufactured by filtering the obtained product 3 times and removing impurities.

[(A) Colorant]
(A-1) Compound of Synthesis Example 1 (Compound represented by Chemical Formula 3-1)
(A-2) Compound of Synthesis Example 2 (Compound represented by Chemical Formula 3-2)
(A-3) Compound of Synthesis Example 3 (Compound represented by Chemical Formula 3-3)
(A-4) Compound of Synthesis Example 4 (Compound represented by Chemical Formula 3-4)
(A-5) Compound of Synthesis Example 5 (Compound represented by Chemical Formula 3-5)
(A-6) Compound of Synthesis Example 6 (compound represented by Chemical Formula 3-6)
(A-7) Compound of Synthesis Example 7 (Compound represented by Chemical Formula 3-7)
(A-8) Compound of Synthesis Example 8 (Compound represented by Chemical Formula 3-8)
(A-9) Compound of Synthesis Example 9 (Compound represented by Chemical Formula 3-9)
(A-10) Compound of Synthesis Example 10 (Compound represented by Chemical Formula 3-10)
(A-11) Compound of Synthesis Example 11 (Compound represented by Chemical Formula 3-11)
(A-12) Compound of Synthesis Example 12 (compound represented by the chemical formula 3-12)
(A-13) Compound of Synthesis Example 13 (Compound represented by Chemical Formula 3-13)
(A-14) Compound of Synthesis Example 14 (Compound represented by Chemical Formula 3-14)
(A-15) Compound of Comparative Synthesis Example 1 (compound represented by the chemical formula C-1)
(A-16) Compound of Comparative Synthesis Example 2 (compound represented by the chemical formula C-2)
(A-17) C.I. I. Pigment Blue 15:6 pigment dispersion liquid (SANYO Co.; pigment solid content 20%)
[(B) Binder resin]
Acrylic binder resin (RY-25, Showadenko)
[(C) Photopolymerizable compound]
Dipentaerythritol hexaacrylate (DPHA) (Nippon Kayaku Co., Ltd.)
[(D) Photopolymerization Initiator]
(D-1) Oxime compound (NCI831, adeka company)
(D-2) Acetophenone compound (IRG369, Basf)
[(E) solvent]
(E-1) Propylene glycol methyl ether acetate (PGMEA) (Kyowa Co., Ltd.)
(E-2) Ethylene glycol dimethyl ether (EDM) (Kyowa)
[(F) Additive]
γ-glycidoxypropyltrimethoxysilane (S-510, Chisso Co.).

<Evaluation 2: Luminance of photosensitive resin film>
On the degreased and washed 1 mm-thick glass substrate, the photosensitive resin compositions produced in Examples 1 to 14, Comparative Example 1 and Comparative Example 2 were applied under the conditions of 250 rpm to 350 rpm, and a hot plate at 90°C was used. After drying for 2 minutes, a coating film having a thickness of 2 μm was obtained. Subsequently, the entire surface of the coating film was exposed using a high-pressure mercury lamp having a main wavelength of 365 nm under the condition of 50 mJ/cm ² , and then washed with KOH developer (111-fold diluted solution) with a developing machine. Development was carried out for 60 seconds under the condition of liquid/developing solution=1/0.8, followed by washing with water for 60 seconds again to give a development history. Then, it was dried in a hot air circulation type drying oven at 230° C. for 20 minutes to obtain a color test piece (Color Chip).

The prepared color test piece was evaluated for color characteristics based on the C light source using a spectrophotometer (MCPD3000, Otsuka electronic Co., Ltd.), and the brightness (Bx/By=0.148/0.048) was used as a reference for the luminance (Bx/By=0.148/0.048). Y) (%) was calculated and the results are shown in Table 4 below.

From Table 4, it is found that when the compound according to the present embodiment is used, sufficiently excellent brightness and high color can be realized even with a small amount.

<Synthesis of adhesive composition>
[Example 15]
Acrylic binder resin (PL-8540; SAIDEN chemistry) 78.583% by weight, isocyanate curing agent (H-AL; Zirker ceramics) 0.236% by weight, aziridine curing agent (HDU-P25) 0.145% by weight %, 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% Then, 0.004 wt% of the compound of Synthesis Example 1 and the balance of the solvent (MEK) (19.644 wt%) were mixed to produce a pressure-sensitive adhesive composition for a polarizing plate of Example 15.

[Example 16]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 2 was used instead of the compound of Synthesis Example 1.

[Example 17]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Synthesis Example 3 was used instead of the compound of Synthesis Example 1.

[Example 18]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Synthesis Example 4 was used instead of the compound of Synthesis Example 1.

[Example 19]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 5 was used instead of the compound of Synthesis Example 1.

[Example 20]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 6 was used instead of the compound of Synthesis Example 1.

[Example 21]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Synthesis Example 7 was used instead of the compound of Synthesis Example 1.

[Example 22]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 8 was used instead of the compound of Synthesis Example 1.

[Example 23]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 9 was used instead of the compound of Synthesis Example 1.

[Example 24]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 10 was used instead of the compound of Synthesis Example 1.

[Example 25]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 11 was used instead of the compound of Synthesis Example 1.

[Example 26]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Synthesis Example 12 was used instead of the compound of Synthesis Example 1.

[Example 27]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 13 was used instead of the compound of Synthesis Example 1.

[Example 28]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15 except that the compound of Synthesis Example 14 was used instead of the compound of Synthesis Example 1.

[Comparative Example 3]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Comparative Synthesis Example 1 was used instead of the compound of Synthesis Example 1.

[Comparative Example 4]
A pressure-sensitive adhesive composition for a polarizing plate was produced in the same manner as in Example 15, except that the compound of Comparative Synthesis Example 2 was used instead of the compound of Synthesis Example 1.

<Evaluation 3: Color reproduction and reflectance of adhesive film>
[1. Measurement of color reproduction rate]
The pressure-sensitive adhesive compositions according to Examples 15 to 28 and Comparative Examples 3 and 4 were applied to a 1 mm glass substrate so as to have a thickness of 2 μm, and then dried at 90° C. for 4 minutes at 23° C. and 55% relative humidity. Aged for 24 hours to produce an adhesive film. After the pressure-sensitive adhesive film was attached to one surface of the panel (the side opposite to the backlight), the color reproduction rate was measured using a spectrophotometer (SR-3, Topcon), and the results are shown in the table below. 5 shows. The color reproduction rate is a value calculated by measuring the chromaticity of the above compound in an adhesive film produced using an adhesive composition containing the compound produced in the above Synthesis Example.

[2. Measurement of reflectance]
The pressure-sensitive adhesive compositions according to Examples 15 to 28 and Comparative Examples 3 and 4 were applied to a 1 mm glass substrate so as to have a thickness of 2 μm, and then dried at 90° C. for 4 minutes at 23° C. and 55% relative humidity. Aged for 24 hours to produce an adhesive film. This adhesive film is bonded to a QD (quantum dot) panel, a C light source (C-Light spectrum) is applied using a spectrocolorimeter (CM-2600D, Konica Minolta Co., Ltd.), and reflectance at a wavelength of 550 nm is measured. The measurement was performed, and the results are shown in Table 5 below.

As is clear from Table 5, the example to which the compound according to the present embodiment is applied has a higher color reproduction rate and a higher effect of reducing the reflectance than the comparative example to which the compound according to the present embodiment is not applied. I found out.

Although the preferred embodiment of the present invention has been described above, the present invention is not limited to this, and various modifications may be made within the scope of the claims, the detailed description of the invention and the accompanying drawings. Of course, this is also within the scope of the invention.

Claims (12)

A compound represented by the following chemical formula 1:

In Chemical Formula 1,
M is Cu, Co, VO, Zn, Pt, or In,
L ^{1 to} L ⁴ are each independently *-C(=O)O-* or *-S(=O) ₂ NH-*,
R ^{1 to} R ⁴ are each independently a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C6 to C20 aryl group, or A substituted or unsubstituted C2-C20 heteroaryl group,
R ^{5 to} R ¹² are each independently a hydrogen atom or a halogen atom. L ^{1 to} L ⁴ are each independently *-C(=O)O-*,
The compound according to claim 1, wherein R ^{1 to} R ⁴ are each independently represented by the following chemical formula 2:

In the chemical formula 2,
R ¹³ is a halogen atom or a trifluoromethyl group,
n is an integer of 1 or 2. The compound according to claim 2, wherein the chemical formula 2 is represented by any one of the following chemical formulas 2-1 to 2-3.

In Chemical Formula 2-1 to Chemical Formula 2-3,
R ¹⁴ is a halogen atom or a trifluoromethyl group,
R ¹⁵ and R ¹⁶ are each independently a trifluoromethyl group,
R ¹⁷ and R ¹⁸ are each independently a halogen atom. L ^{1 to} L ⁴ are each independently *-S(=O) ₂ NH-*,
The compound according to claim 1, wherein R ^{1 to} R ⁴ are each independently a substituted or unsubstituted C1 to C20 alkyl group. The compound according to claim 1, wherein the compound is represented by any one of the following Chemical Formulas 3-1 to 3-13:





In Chemical Formula 3-1 to Chemical Formula 3-13,
M is Cu, Co, VO, Zn, Pt, or In. A photosensitive resin composition containing the compound according to claim 1, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. A photosensitive resin film produced using the photosensitive resin composition according to claim 6. A color filter comprising the photosensitive resin film according to claim 7. A pressure-sensitive adhesive composition comprising the compound according to any one of claims 1 to 5, a binder resin, a curing agent, and a solvent. The pressure-sensitive adhesive composition according to claim 9, wherein the pressure-sensitive adhesive composition further contains a silane coupling agent, an antistatic agent, an ultraviolet absorber, a cationic initiator, a release agent, or a combination thereof. An adhesive film produced using the adhesive composition according to claim 9. A polarizing plate comprising the adhesive film according to claim 11.