KR102219053B1 - Polymer, photosensitive resin composition including the same, photosensitive resin layer, color filter and display device - Google Patents

Abstract

A polymer, a photosensitive resin composition comprising the polymer, a photosensitive resin film prepared using the photosensitive resin composition, a color filter including the photosensitive resin film, and a display device including the color filter are provided.

Description

Polymer, photosensitive resin composition containing the same, photosensitive resin film, color filter, and display device {POLYMER, PHOTOSENSITIVE RESIN COMPOSITION INCLUDING THE SAME, PHOTOSENSITIVE RESIN LAYER, COLOR FILTER AND DISPLAY DEVICE}

The present disclosure relates to a polymer, a photosensitive resin composition comprising the same, a photosensitive resin film manufactured using the photosensitive resin composition, a color filter including the photosensitive resin film, and a display device including the color filter.

A liquid crystal display device, which is one of the display devices, has advantages such as weight reduction, thinness, low cost, low power consumption, and excellent integration with integrated circuits, and thus its range of use is expanding for notebook computers, monitors and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter and an ITO pixel electrode are formed, an active circuit unit composed of a liquid crystal layer, a thin film transistor, and a capacitor layer, and an upper substrate on which an ITO pixel electrode is formed. The color filter is a black matrix layer formed in a predetermined pattern on a transparent substrate to block the boundary between pixels, and a plurality of colors (typically, red (R), green (G), blue (B)) to form each pixel. The three primary colors of )) are sequentially stacked in a predetermined order. In the pigment dispersion method, one of the methods of implementing a color filter, coating a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposing the pattern to be formed, and removing the unexposed part with a solvent. This is a method of forming a colored thin film by repeating a series of thermal curing processes. The colored photosensitive resin composition used to manufacture the color filter according to the pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerization monomer, a photoinitiator, a solvent and other additives, and may further include an epoxy resin. The pigment dispersion method as described above is actively applied to manufacture LCDs such as mobile phones, notebook computers, monitors, and TVs. However, in recent years, even in the photosensitive resin composition for color filters using the pigment dispersion method, which has various advantages, the micronization process of the powder is difficult, and even if it is dispersed, various additives are required because the dispersion state must be stable in the dispersion. It is very difficult, and furthermore, the pigment dispersion has a disadvantage that it is difficult to store and transport conditions because it must maintain an optimal quality state. In addition, in a color filter made of a pigment-type photosensitive resin composition, there is a limit of the brightness and contrast ratio resulting from the pigment particle size. Accordingly, there has been a need to develop a dye having heat resistance and chemical resistance similar to the pigment instead of the pigment.

For example, xanthene compounds have been structurally studied and red pigments using them have been developed. However, as described above, in a color filter made of a pigment-type photosensitive resin composition, there is a limit to the brightness and contrast ratio resulting from the pigment particle size. In addition, in the case of a color image sensor for an image sensor, a smaller dispersion particle size is required to form a fine pattern. In order to meet such demand, there is an attempt to implement a color filter with improved brightness and contrast ratio by introducing a dye that does not form particles instead of a pigment to prepare a photosensitive resin composition suitable for the dye. As it is not good and has poor heat resistance and chemical resistance, it is difficult to use it as a dye.

One embodiment is to provide a polymer having excellent solubility in an organic solvent, heat resistance, chemical resistance, pattern property, and surface wrinkle improvement effect.

Another embodiment is to provide a photosensitive resin composition comprising the polymer.

Another embodiment is to provide a photosensitive resin film prepared by using the photosensitive resin composition.

Another embodiment is to provide a color filter including the photosensitive resin film.

Another embodiment is to provide a display device including the color filter.

One embodiment provides a polymer including structural units represented by the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

R ¹ to R ⁶ and R ⁸ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

L ¹ , L ² , L ⁴ and L ⁵ are each independently a substituted or unsubstituted C1 to C20 alkylene group,

L ³ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, *-OC(=O)NH-*, *- O(C=O)-*, *-NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

X is represented by the following formula X-1 or formula X-2,

[Formula X-1]

[Formula X-2]

R ⁷ is a substituted or unsubstituted C11 to C20 alkyl group,

n is an integer from 0 to 3,

q1 and q2 are each independently an integer of 0 or 1.

The L ³ may be represented by Formula 2 below.

[Formula 2]

In Chemical Formula 2,

L ⁶ to L ¹⁰ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, and R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ⁶ to L ¹⁰ are not a single bond at the same time.

The L ³ may be a substituted or unsubstituted C1 to C20 alkylene group.

The L ³ may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

L ¹¹ to L ¹³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.

The L ¹¹ to L ¹³ may each independently be represented by a substituted or unsubstituted C1 to C10 alkylene group, the following Chemical Formula 3-1 or the following Chemical Formula 3-2.

[Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.

The L ³ may be represented by Formula 4 below.

[Formula 4]

In Chemical Formula 4,

L ¹⁴ to L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The L ³ may be represented by Formula 5 below.

[Formula 5]

In Chemical Formula 5,

L ¹⁷ and L ¹⁸ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group.

The polymer may further include structural units represented by Formulas 1-5 to 1-7 below.

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formula 1-5 to Formula 1-7,

R ¹ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹² and R ¹³ are each independently a substituted or unsubstituted C1 to C10 alkyl group,

L ¹⁹ and L ²⁰ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

m is an integer from 0 to 5.

The compound represented by Formula 1-1 may be represented by any one of Formula 1-1-1 to Formula 1-1-4 below.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

The polymer may have a maximum absorbance in a wavelength range of 500 nm to 600 nm.

Another embodiment provides a photosensitive resin composition comprising the polymer as a red dye.

The photosensitive resin composition may further include a binder resin, a photopolymerizable compound, a photoinitiator, and a solvent.

The photosensitive resin composition may further include a yellow dye.

The yellow dye may be a polymer containing a compound represented by Formula 6 below as a monomer.

[Formula 6]

In Formula 6,

R ¹⁴ and R ¹⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group, *-C(=O)OR' or *-OC(=O)R',

R'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, or a substituted or unsubstituted C6 to C20 aryl group,

However, any one of R ¹⁴ and R ¹⁵ includes a substituent represented by Formula 7 below,

[Formula 7]

(In Chemical Formula 7,

R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group)

R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group.

The polymer including the compound represented by Formula 6 as a monomer may include any one structural unit selected from the group consisting of structural units represented by Formula 6-1 to Formula 6-4 below.

[Formula 6-1]

[Chemical Formula 6-2]

[Chemical Formula 6-3]

[Formula 6-4]

In Formula 6-1 to Formula 6-4,

L ²¹ to L ²³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or *-L'-C(=O)O-L''-*,

Wherein L'and L'' are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R ¹⁶ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

The polymer including the compound represented by Formula 6 as a monomer may further include structural units represented by Formulas 8-1 and 8-2 below.

[Chemical Formula 8-1]

[Formula 8-2]

In Formula 8-1 and Formula 8-2,

R ¹⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ²⁴ is a substituted or unsubstituted C1 to C10 alkylene group.

The polymer containing the compound represented by Formula 6 as a monomer may include 40% to 60% by weight of any one structural unit selected from the group consisting of structural units represented by Formulas 6-1 to 6-4; 5% to 25% by weight of the structural unit represented by Formula 8-1; And 25% to 45% by weight of the structural unit represented by Formula 8-2.

The structural unit represented by Formula 6-1 may be any one selected from the group consisting of structural units represented by Formula 6-1-1 to Formula 6-1-14 below.

[Chemical Formula 6-1-1]

[Chemical Formula 6-1-2]

[Chemical Formula 6-1-3]

[Chemical Formula 6-1-4]

[Chemical Formula 6-1-5]

[Chemical Formula 6-1-6]

[Chemical Formula 6-1-7]

[Chemical Formula 6-1-8]

[Chemical Formula 6-1-9]

[Chemical Formula 6-1-10]

[Chemical Formula 6-1-11]

[Chemical Formula 6-1-12]

[Chemical Formula 6-1-13]

[Chemical Formula 6-1-14]

The structural unit represented by Formula 6-2 may be a structural unit represented by Formula 6-2-1 or Formula 6-2-2 below.

[Chemical Formula 6-2-1]

[Chemical Formula 6-2-2]

The structural unit represented by Formula 6-3 may be a structural unit represented by Formula 6-3-1 or Formula 6-3-2 below.

[Chemical Formula 6-3-1]

[Chemical Formula 6-3-2]

The structural unit represented by Formula 6-4 may be a structural unit represented by Formula 6-4-1 or Formula 6-4-2 below.

[Chemical Formula 6-4-1]

[Chemical Formula 6-4-2]

The photopolymerizable monomer may include a bifunctional (meth) acrylate monomer and a 6 functional (meth) acrylate monomer.

The bifunctional (meth)acrylate-based monomer may be represented by the following formula (9).

[Formula 9]

In Formula 9,

R ²⁰ and R ²¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ²⁵ to L ²⁷ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

p1 and p2 are each independently an integer of 1 to 10, but 11≦p1+p2≦20.

The six-functional (meth) acrylate-based monomer may be represented by the following formula (10).

[Formula 10]

In Chemical Formula 10,

R ²² to R ²⁷ are each independently represented by the following formula (11),

[Formula 11]

In Formula 11,

p3 is an integer of 0 to 2.

The p3 may be an integer of 1 or 2.

The binder resin may include an acrylic binder resin, a cardo binder resin, or a combination thereof.

The photosensitive resin composition may further include a pigment.

The photosensitive resin composition is a quencher, malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent containing a vinyl group or a (meth)acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator Or it may further include a combination thereof.

Another embodiment provides a photosensitive resin film prepared by using the photosensitive resin composition.

Another embodiment provides a color filter including the photosensitive resin film.

Another embodiment provides a display device including the color filter.

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

The polymer according to the embodiment has excellent solubility in organic solvents, excellent fluorescence control and spectral compatibility, and has excellent heat resistance and chemical resistance by using a photosensitive resin composition including a colorant including the compound as a component. Color filters can be manufactured. In addition, the photosensitive resin composition according to the embodiment may further include a polymer containing an azo compound as a monomer as a yellow dye, so that the color filter having excellent luminance and contrast ratio, and a display device such as a liquid crystal display device including the same It may be usefully used in production, and by using a photopolymerizable monomer having a long chain rather than a short chain, it is possible to improve the wrinkles on the pattern surface while maintaining the sensitivity of the pattern.

1 is a photograph of a pattern surface prepared from a composition according to Example 7.
2 is a photograph of the pattern surface prepared from the composition according to Example 8.
3 is a photograph of a patterned surface prepared from a composition according to Example 9.
4 is an SEM photograph of a photosensitive resin film prepared from a composition according to Example 9.
5 is a pattern photograph taken to confirm the straightness of the pattern prepared from the composition according to Example 9.

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

Unless otherwise specified in the specification, "substituted" to "substituted" means that at least one hydrogen atom in the functional groups of the present invention is a halogen atom (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 from each other, and each independently a C1 to C10 alkyl group), an amidino group, Hydrazine group, hydrazone group, carboxyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted alicyclic organic group, substituted or unsubstituted aryl group, And it means substituted with one or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group.

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

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

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

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

In the present specification, the cardo-based resin refers to a resin in which one or more functional groups selected from the group consisting of the following Formulas 12-1 to 12-11 are included in the backbone of the resin.

In the present specification, unless otherwise defined, “ethylenically unsaturated double bond” refers to “carbon-carbon double bond”, and ethylenically unsaturated monomer refers to a monomer including the ethylenically unsaturated double bond.

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

One embodiment provides a polymer including structural units represented by the following Chemical Formulas 1-1 to 1-4.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

R ¹ to R ⁶ and R ⁸ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

L ¹ , L ² , L ⁴ and L ⁵ are each independently a substituted or unsubstituted C1 to C20 alkylene group,

L ³ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, *-OC(=O)NH-*, *- O(C=O)-*, *-NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,

X is represented by the following formula X-1 or formula X-2,

[Formula X-1]

[Formula X-2]

R ⁷ is a substituted or unsubstituted C11 to C20 alkyl group,

n is an integer from 0 to 3,

q1 and q2 are each independently an integer of 0 or 1.

As described above, in a color filter made of a pigment-type photosensitive resin composition, there is a limit to the brightness and contrast ratio resulting from the pigment particle size. In addition, in the case of a color image sensor for an image sensor, a smaller dispersion particle size is required to form a fine pattern. In order to meet such demands, attempts to implement a color filter having improved brightness and contrast ratio and a display device including the same by introducing a dye that does not form particles instead of a pigment to prepare a photosensitive resin composition suitable for the dye are being continued.

In general, the xanthene-based compound has a separate charge, and the photosensitive resin composition including the same has low solubility in organic solvents such as PGMEA, and has low heat resistance and chemical resistance, and thus there is a limit to use as a colorant in the photosensitive resin composition. However, in one embodiment, the xanthene compound is polymerized to include the structural units represented by Formulas 1-2 to 1-4 together with the structural units represented by Formula 1-1. It is possible to improve the solubility of the structure, and furthermore, since the structural unit represented by Formula 1-1 has a dimer form connected with a functional linking group, it is excellent in fluorescence control and spectral compatibility, and by using a photosensitive resin composition containing it as a red dye ( A color filter having improved heat resistance and chemical resistance than conventional xanthene-based compounds or polymer dyes can be manufactured.

In particular, since the polymer according to an embodiment includes the structural unit represented by Formula 1-3, which is a structural unit derived from a long-chain acrylate monomer, the double bond at the end of the structural unit represented by Formula 1-1 It can exist as it is, without becoming angry. The structural unit represented by Formula 1-1 is derived from a xanthene monomer each having an acrylate group, that is, a double bond at both ends. When the xanthene monomer undergoes a polymerization reaction with a short chain acrylate monomer, the All of the acrylate groups at both ends of the xanthene monomer participate in the polymerization reaction, resulting in gelation of the final product, making it impossible to obtain a crude liquid into the composition. However, according to one embodiment, the xanthene monomer causes a polymerization reaction with a long chain acrylate monomer (e.g., lauryl (meth) acrylate), and only one acrylate group at both ends participates in the polymerization reaction. And, since the remaining acrylate groups do not participate in the polymerization reaction, gelation does not occur, and thus, it is possible to prepare liquid with a photosensitive resin composition, and ultimately, it becomes possible to manufacture a photosensitive resin composition for color filters having excellent heat resistance and chemical resistance. That is, the structural unit represented by Formula 1-1 includes a double bond at the terminal. When using the polymer according to an embodiment, a polymer containing a xanthene-based structural unit not including a double bond at the terminal It is possible to manufacture a color filter having superior heat resistance and chemical resistance than when used.

For example, L ³ may be represented by Formula 2 below.

[Formula 2]

In Chemical Formula 2,

L ⁶ to L ¹⁰ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, and R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ⁶ to L ¹⁰ are not a single bond at the same time.

For example, L ³ may be a substituted or unsubstituted C1 to C20 alkylene group.

For example, L ³ may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

L ¹¹ to L ¹³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.

For example, the L ¹¹ to L ¹³ may each independently be represented by a substituted or unsubstituted C1 to C10 alkylene group, the following formula 3-1 or the following formula 3-2.

[Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,

L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.

For example, L ³ may be represented by Formula 4 below.

[Formula 4]

In Chemical Formula 4,

L ¹⁴ to L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.

For example, L ³ may be represented by Formula 5 below.

[Formula 5]

In Chemical Formula 5,

L ¹⁷ and L ¹⁸ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

R ^x is a substituted or unsubstituted C1 to C10 alkyl group.

The polymer may further include structural units represented by Formulas 1-5 to 1-7 below.

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formula 1-5 to Formula 1-7,

R ¹ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹² and R ¹³ are each independently a substituted or unsubstituted C1 to C10 alkyl group,

L ¹⁹ and L ²⁰ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

m is an integer from 0 to 5.

The compound represented by Formula 1-1 may be represented by any one of Formula 1-1-1 to Formula 1-1-4 below.

[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

The polymer may have a maximum absorbance in a wavelength range of 500 nm to 600 nm.

The polymer may have a weight average molecular weight of 5000 g/mol to 20000 g/mol.

Another embodiment provides a photosensitive resin composition comprising the polymer as a red dye.

The photosensitive resin composition may further include a binder resin, a photopolymerizable compound, a photoinitiator, and a solvent.

Hereinafter, the components will be described in detail.

coloring agent

In addition to the polymer (red dye), the colorant may further include a yellow dye.

The yellow dye may be a polymer containing a compound represented by Formula 6 below as a monomer.

[Formula 6]

In Formula 6,

R ¹⁴ and R ¹⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group, *-C(=O)OR' or *-OC(=O)R',

R'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, or a substituted or unsubstituted C6 to C20 aryl group,

However, any one of R ¹⁴ and R ¹⁵ includes a substituent represented by the following formula (7),

[Formula 7]

(In Chemical Formula 7,

R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group)

R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group.

The compound represented by Formula 6 is an azo-based compound, has excellent yellow spectral properties and a high molar absorption coefficient, and has excellent solubility in organic solvents. Furthermore, since any one of R ¹⁴ and R ¹⁵ , which is a substituent of the compound represented by Formula 6, is necessarily represented by Formula 7 (including a substituted or unsubstituted acrylate group), the compound represented by Formula 6 is used as a monomer. When the polymer contained as (monomer) is used as a yellow dye, it becomes possible to manufacture a color filter excellent in heat resistance, chemical resistance, and processability.

The polymer including the compound represented by Formula 6 as a monomer may include any one structural unit selected from the group consisting of structural units represented by Formula 6-1 to Formula 6-4 below.

[Formula 6-1]

[Chemical Formula 6-2]

[Chemical Formula 6-3]

[Formula 6-4]

In Formula 6-1 to Formula 6-4,

L ²¹ to L ²³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or *-L'-C(=O)O-L''-*,

Wherein L'and L'' are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,

R ¹⁶ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

The polymer including the compound represented by Formula 6 as a monomer may further include structural units represented by Formulas 8-1 and 8-2 below.

[Chemical Formula 8-1]

[Formula 8-2]

In Formula 8-1 and Formula 8-2,

R ¹⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ²⁴ is a substituted or unsubstituted C1 to C10 alkylene group.

The polymer containing the compound represented by Formula 6 as a monomer may include 40% to 60% by weight of any one structural unit selected from the group consisting of structural units represented by Formulas 6-1 to 6-4; 5% to 25% by weight of the structural unit represented by Formula 8-1; And 25% to 45% by weight of the structural unit represented by Formula 8-2.

For example, the structural unit represented by Formula 6-1 may be any one selected from the group consisting of structural units represented by Formula 6-1-1 to Formula 6-1-14 below.

[Chemical Formula 6-1-1]

[Chemical Formula 6-1-2]

[Chemical Formula 6-1-3]

[Chemical Formula 6-1-4]

[Chemical Formula 6-1-5]

[Chemical Formula 6-1-6]

[Chemical Formula 6-1-7]

[Chemical Formula 6-1-8]

[Chemical Formula 6-1-9]

[Chemical Formula 6-1-10]

[Chemical Formula 6-1-11]

[Chemical Formula 6-1-12]

[Chemical Formula 6-1-13]

[Chemical Formula 6-1-14]

For example, the structural unit represented by Formula 6-2 may be a structural unit represented by Formula 6-2-1 or Formula 6-2-2 below.

[Chemical Formula 6-2-1]

[Chemical Formula 6-2-2]

For example, the structural unit represented by Formula 6-3 may be a structural unit represented by Formula 6-3-1 or Formula 6-3-2 below.

[Chemical Formula 6-3-1]

[Chemical Formula 6-3-2]

For example, the structural unit represented by Formula 6-4 may be a structural unit represented by Formula 6-4-1 or Formula 6-4-2 below.

[Chemical Formula 6-4-1]

[Chemical Formula 6-4-2]

The colorant may further include a pigment.

The pigment may include a blue pigment, a violet pigment, a red pigment, a green pigment, a yellow pigment, and the like.

Examples of the blue pigment include C.I. Blue pigment 15:6, C.I. Blue pigment 15, C.I. Blue pigment 15:1, C.I. Blue pigment 15:2, C.I. Blue pigment 15:3, C.I. Blue pigment 15:4, C.I. Blue pigment 15:5, C.I. Blue pigment 16, C.I. Blue pigment 22, C.I. Blue pigment 60, C.I. Blue pigment 64, C.I. Blue pigment 80 or a combination thereof.

Examples of the violet pigment include C.I. Violet pigment 1, C.I. Violet pigment 19, C.I. Violet pigment 23, C.I. Violet pigment 27, C.I. Violet pigment 28, C.I. Violet pigment 29, C.I. Violet pigment 30, C.I. Violet pigment 32, C.I. Violet Pigment 37, C.I. Violet pigment 40, C.I. Violet pigment 42, C.I. Violet pigment 50 or a combination thereof.

Examples of the red pigment include perylene-based pigments, anthraquinone-based pigments, azo-based pigments, diazo-based pigments, quinacridone-based pigments, and anthracene-based pigments. Specific examples of the red pigment include perylene pigment, quinacridone pigment, naphthol AS, citamine pigment, anthraquinone (sudan I, II, III, R), vis azo ), benzopyran, etc. are mentioned.

Examples of the green pigment include C.I. Pigment Green 58, C.I. And halogenated phthalocyanine-based pigments such as Pigment Green 59.

Examples of the yellow pigment include C.I. Pigment Yellow 139, C.I. Pigment Yellow 138, C.I. Pigment yellow 150, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

The pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.

The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.

The solid pigment is 1% to 20% by weight, such as 8% to 20% by weight, such as 8% to 15% by weight, such as 10% to 20% by weight, such as 10% to 20% by weight, based on the total amount of the pigment dispersion. It may be included in 15% by weight.

Nonionic dispersants, anionic dispersants, cationic dispersants, and the like may be used as the dispersant. Specific examples of the dispersant include polyalkylene glycol and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, alkyl amines, etc., and these may be used alone or in combination of two or more.

For example, the commercially available products of the dispersant are BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc. from EFKA Chemical; Zeneka's Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; Alternatively, there are PB711 and PB821 of Ajinomoto.

The dispersant may be included in an amount of 1% to 20% by weight based on the total amount of the pigment dispersion. When the dispersant is included within the above range, the photosensitive resin composition has excellent dispersibility because it can maintain an appropriate viscosity, and thus, optical, physical and chemical quality can be maintained when the product is applied.

As a solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol (mono) methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like may be used.

Binder resin

The binder resin may include an acrylic binder resin, a cardo binder resin, or a combination thereof. For example, the binder resin may be an acrylic binder resin.

The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable therewith, and is a resin comprising at least one acrylic repeating unit.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxy group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or a combination thereof.

The first ethylenically unsaturated monomer may be included in an amount of 5% to 50% by weight, such as 10% to 40% by weight, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzylmethylether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxy butyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth)acrylate and phenyl (meth)acrylate; Unsaturated carboxylic acid amino alkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; Vinyl cyanide compounds such as (meth)acrylonitrile; Unsaturated amide compounds such as (meth)acrylamide; And the like, and these may 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 meth Acrylate copolymer, (meth)acrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like, but are not limited thereto, and these may be used alone or in combination of two or more. have.

The weight average molecular weight of the acrylic binder resin may be 3,000 g/mol to 150,000 g/mol, such as 5,000 g/mol to 50,000 g/mol, such as 20,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the acrylic binder resin is within the above range, the physical and chemical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and adhesion with the substrate is excellent when manufacturing a color filter.

The acid value of the acrylic binder resin may be 15 mgKOH/g to 60 mgKOH/g, such as 20 mgKOH/g to 50 mgKOH/g　. When the acid value of the acrylic binder resin is within the above range, the resolution of the pixel pattern is excellent.

The cardo-based binder resin may include a repeating unit represented by Formula 12 below.

[Formula 12]

In Formula 12,

R ²⁸ and R ²⁹ are each independently a hydrogen atom or a substituted or unsubstituted (meth)acryloyloxyalkyl group,

R ³⁰ and R ³¹ are each independently a hydrogen atom, a halogen atom, or a substituted or unsubstituted C1 to C20 alkyl group,

Z ¹ is a single bond, O, CO, SO ₂ , CR ³² R ³³ , SiR ³⁴ R ³⁵ (here, R ³² to R ³⁵ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or the following Any one of the linking groups represented by Formula 12-1 to Formula 12-11,

[Chemical Formula 12-1]

[Formula 12-2]

[Chemical Formula 12-3]

[Chemical Formula 12-4]

[Formula 12-5]

(In Formula 12-5,

R ^a is a hydrogen atom, an ethyl group, C ₂ H ₄ Cl, C ₂ H ₄ OH, CH ₂ CH=CH ₂ or a phenyl group.)

[Chemical Formula 12-6]

[Chemical Formula 12-7]

[Chemical Formula 12-8]

[Chemical Formula 12-9]

[Chemical Formula 12-10]

[Chemical Formula 12-11]

Z ² is an acid dianhydride residue,

p4 and p5 are each independently an integer of 0 to 4.

The cardo-based binder resin may include a functional group represented by Formula 13 below at at least one of both ends.

[Formula 13]

In Chemical Formula 13,

Z ³ may be represented by the following Chemical Formula 13-1 to Chemical Formula 13-7.

[Chemical Formula 13-1]

(In Formula 13-1, R ^b and R ^c are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group.)

[Formula 13-2]

[Chemical Formula 13-3]

[Formula 13-4]

[Chemical Formula 13-5]

(In Formula 13-5, R ^d is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, a C1 to C20 alkylamine group, or a C2 to C20 alkenylamine group.)

[Formula 13-6]

[Chemical Formula 13-7]

The cardo-based binder resin may be, for example, a fluorene-containing compound such as 9,9-bis(4-oxyranylmethoxyphenyl)fluorene; Benzene tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, benzophenone tetracarboxylic dianhydride, pyromellitic dianhydride, cyclobutane tetracarboxylic dianhydride, perylene tetracarboxylic dianhydride , Anhydride compounds such as tetrahydrofuran tetracarboxylic acid dianhydride and tetrahydrophthalic acid anhydride; Glycol compounds such as ethylene glycol, propylene glycol, and polyethylene glycol; Alcohol compounds such as methanol, ethanol, propanol, n-butanol, cyclohexanol, and benzyl alcohol; Solvent compounds such as propylene glycol methyl ethyl acetate and N-methyl pyrrolidone; Phosphorus compounds such as triphenylphosphine; And two or more of amine or ammonium salt compounds such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

When the cardo-based binder resin is used together with the above-described acrylic binder resin, it is possible to obtain a photosensitive resin composition having excellent adhesion and high resolution and high luminance characteristics.

The weight average molecular weight of the cardo-based binder resin may be 500 g/mol to 50,000 g/mol, for example, 3,000 g/mol to 30,000 g/mol. When the weight average molecular weight of the cardo-based binder resin is within the above range, a pattern can be formed well without residues when manufacturing a color filter, there is no loss of film thickness during development, and a good pattern can be obtained.

The cardo-based binder resin may have an acid value of 100 mgKOH/g to 140 mgKOH/g.

Photopolymerization Monomer

The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

Since the photopolymerizable monomer has the 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 formation process.

For example, the photopolymerizable monomer may include a bifunctional (meth)acrylate-based monomer and a six-functional (meth)acrylate-based monomer.

The bifunctional (meth)acrylate-based monomer may be represented by the following Formula 9, and the six-functional (meth)acrylate-based monomer may be represented by the following Formula 10.

[Formula 9]

In Formula 9,

R ²⁰ and R ²¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,

L ²⁵ to L ²⁷ are each independently a substituted or unsubstituted C1 to C10 alkylene group,

p1 and p2 are each independently an integer of 1 to 10, but 11≦p1+p2≦20.

[Formula 10]

In Chemical Formula 10,

R ²² to R ²⁷ are each independently represented by the following formula (11),

[Formula 11]

In Formula 11,

p3 is an integer of 0 to 2.

For example, p3 may be an integer of 1 or 2.

When p3 is an integer of 1 or 2, it has a longer chain than when p3 is an integer of 0, thereby improving pattern surface wrinkles. In a typical photosensitive resin composition, heat curing occurs through post-baking after development in a color filter process. At this time, when the difference in the hardening degree of the upper and lower portions of the pattern increases, surface wrinkles occur. In this case, the surface wrinkles are usually improved by using an initiator that is fast-curing and an initiator with low sensitivity, but this method lacks the sensitivity of the pattern, and pattern tearing and resolution deterioration appear. However, when a 6-functional (meth)acrylate-based monomer having a long chain is used as the photopolymerizable monomer, the sensitivity of the pattern is maintained as compared to the case of using a 6-functional (meth)acrylate-based monomer having a short chain. While doing so, pattern tearing does not occur, and while maintaining resolution, surface wrinkles can be improved.

Commercially available products of photopolymerizable monomers are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ^®, the same M-111 ^®, the same M-114 ^®; KAYARAD TC-110S ^® of Nihon Kayaku Co., Ltd., TC-120S ^®, etc.; Osaka yukki the like Kagaku Kogyo (main)社of ^{V-158 ®, V-2311} ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ^®, copper or the like M-240 ^®, the same M-6200 ^®; KAYARAD HDDA ^® , HX-220 ^® , R-604 ^{® of} Nihon Kayaku Co., Ltd.; Osaka Yuki Kagaku High School Co., Ltd.'s V-260 ^® , V-312 ^® , and V-335 HP ^® are listed. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ^®, the same M-400 ^®, the same M-405 ^®, the same M-450 ^®, Dong M -710 ^® , M-8030 ^® , M-8060 ^®, etc.; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^{®, ®} copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka Yuki Kayaku High School Co., Ltd.'s V-295 ^® , East-300 ^® , East-360 ^® , East-GPT ^® , East-3PA ^® , East-400 ^®, etc. no. The above products can be used alone or in combination of two or more.

The photopolymerizable monomer may be used after treatment with an acid anhydride in order to impart better developability.

Light polymerization Initiator

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, for example, an acetophenone compound, a benzophenone compound, a thioxanthone compound, a benzoin compound, a triazine compound, an oxime compound, or a combination thereof. Can be used.

Examples of the acetophenone-based compound include 2,2'-diethoxy acetophenone, 2,2'-dibutoxy acetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloro acetophenone, pt -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropane-1 -One, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, and the like.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, 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.

Examples of the thioxanthone-based compound include thioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- And chloro thioxanthone.

Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyldimethylketal, and the like.

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-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-(naphtho-1-yl)-4, 6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-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, etc. are mentioned.

Examples of the oxime-based compound include O-acyloxime-based compounds, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime )-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone, O-ethoxycarbonyl-α-oxyamino-1-phenylpropan-1-one Etc. can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 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-oneoxime-O-acetate, 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime- O-acetate, etc. are mentioned.

In addition to the above compounds, the photopolymerization initiator may be 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.

The photopolymerization initiator may be used together with a photosensitizer that absorbs light and becomes excited, and then transmits the energy to cause a chemical reaction.

Examples of the photosensitizer include tetraethylene glycol bis-3-mercapto propionate, pentaerythritol tetrakis-3-mercapto propionate, dipentaerythritol tetrakis-3-mercapto propionate, etc. Can be mentioned.

menstruum

The solvent has compatibility with a polymer, a pigment, a binder resin, a photopolymerizable monomer, and a photopolymerization initiator according to an exemplary embodiment, but does not react.

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; Glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; Carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; Saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; Lactate esters such as methyl lactate and ethyl lactate; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl methoxy acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxypropionic acid alkyl esters such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as 2-oxy methyl propionate, 2-oxy ethyl propionate, and 2-oxy propionate propyl; 2-alkoxy propionic acid alkyl esters such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methyl propionic acid esters such as 2-oxy-2-methyl methyl propionate and 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- Monooxy monocarboxylic acid alkyl esters of alkyl 2-alkoxy-2-methyl propionate such as ethyl methyl propionate; Esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl methyl butanoate; Ketone acid esters such as ethyl pyruvate, etc., and also N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, N,N-dimethylacetamide , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, capronic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid High boiling point solvents such as ethyl, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among these, in consideration of compatibility and reactivity, ketones such as cyclohexanone are preferred; Glycol ethers such as ethylene glycol monoethyl ether; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; 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 may be used.

Other additives

The photosensitive resin composition may include malonic acid in order to prevent unevenness or spots during application, to improve leveling performance, and to prevent generation of residues due to undeveloped images; 3-amino-1,2-propanediol; Silane-based coupling agents having reactive substituents such as carboxyl group, methacryloyl group, isocyanate group, and epoxy group; Leveling agents; Fluorine-based surfactant; It may further contain additives such as a radical polymerization initiator.

Examples of the silane-based coupling agent include trimethoxysilyl benzoic acid, γ-methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, and γ-gly Cidoxy propyl trimethoxysilane, β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more.

The silane-based coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane-based coupling agent is included within the above range, adhesion and storage properties are excellent.

The photosensitive resin composition may further include an epoxy compound to improve adhesion with the substrate.

Examples of the epoxy compound include a phenol novolac epoxy compound, a tetramethyl biphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be included in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight, based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is included within the above range, adhesion and storage properties are excellent.

In addition, the photosensitive resin composition may further include a surfactant to improve coating properties and prevent defects from being generated, if necessary.

A fluorine-based surfactant may be used as the surfactant, and examples of the fluorine-based surfactant include DIC's F-482, F-484, F-478, and F-554, but are not limited thereto.

The surfactant may be used in an amount of 0.001 to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is included within the above range, coating uniformity is ensured, stains do not occur, and wetting properties for the glass substrate are excellent.

The photosensitive resin composition may further include a quencher. A quencher refers to a molecule capable of quenching the fluorescence of a fluorescent molecule, and usually, a dye having a property of absorbing light is used. The mechanism of quenching is known to occur through aggregation of dyes such as fluorescence resonance energy transfer (FRET), photo-induced electron transfer and H-dimer formation.

All dyes can be quenching dyes as long as they can cover the fluorescence of the highest absorption wavelength or the entire fluorescence spectrum of the fluorescent dye to be used. , Benzylidene dyes, cyanine dyes, phthalocyanine dyes, azaporphyrin dyes, indigo dyes, xanthene dyes, and the like. For example, the matting agent may be an anthraquinone-based dye.

In addition, a certain amount of other additives such as antioxidants and stabilizers may be added to the photosensitive resin composition within a range that does not impair physical properties.

According to another embodiment, a color filter manufactured by using the photosensitive resin composition is provided.

The pattern formation process in the color filter is as follows.

Applying the photosensitive resin composition onto a supporting substrate by spin coating, slit coating, inkjet printing, or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film to light; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to prepare a photosensitive resin film; And a step of heat treating the photosensitive resin film. Since the above process conditions are widely known in the art, detailed descriptions thereof will be omitted herein.

According to another embodiment, a display device including the color filter is provided.

The display device may be, for example, a liquid crystal display (LCD).

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

(Synthesis of compounds)

Synthesis example 1: Synthesis of a compound represented by Formula E-1

(1) 3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide 8.1 g, 56 g 2-propanol and 2.9 g 2 Add -(ethylamino)ethanol and stir at room temperature for 3 hours. After obtaining a precipitate using ether, an intermediate is obtained by drying. Into the N, N '-Dimethyl-1,6- hexanediamine 0.5 equivalents of water and the resulting intermediate was reacted for one day at 80 ℃, to give the intermediate product.

(2) The intermediate product was reacted with isocyanatoethyl methacrylate in a chloroform solvent to obtain a compound represented by the following formula E-1.

[Formula E-1]

Maldi-tof MS: 1296 m/z

Synthesis example 2: Synthesis of a compound represented by Formula E-2

(1) 3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide 8.1 g, 56 g 2-propanol and 2.9 g 2 Add -(ethylamino)ethanol and stir at room temperature for 3 hours. After obtaining a precipitate using ether, an intermediate is obtained by drying. Into the N, N '-Diethyl-1,6- hexanediamine 0.5 equivalents of water and the resulting intermediate was reacted for one day at 80 ℃, to give the intermediate product.

(2) The intermediate product was reacted with isocyanatoethyl methacrylate in a chloroform solvent to obtain a compound represented by the following formula E-2.

[Formula E-2]

Maldi-tof MS: 1325 m/z

compare Synthesis example 1: Synthesis of a compound represented by Formula C-1

Add 56g 2-propanol and 1.46g diethylamine to 8.1g 3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide at room temperature Stir for 3 hours at. After obtaining a precipitate with ether, it is dried to obtain Intermediate 1.

3',6'-Dichlorospiro[3 H -2,1-benzoxathiol-3,9'-[9 H ]xanthene]-1,1-dioxide 8.1g, 56g 2-propanol and 1.78g 2-(ethylamino ) Add ethanol and stir at room temperature for 3 hours. After obtaining a precipitate using ether, it is dried to obtain intermediate 2.

Of the intermediate 1 and the mixture of intermediate 2 each by one equivalent of N, N '-Diethyl-1,6- hexanediamine 1 equivalent to and to the resulting compound by reaction with isocyanatoethyl methacrylate reacting the compound represented by the formula C-1 Got it.

[Chemical Formula C-1]

Maldi-tof MS: 1154 m/z

compare Synthesis example 2: Synthesis of a compound represented by Formula C-2

10 g of compound A (CAS No. 77545-45-0) was added to a reactor and dissolved with 100 g of 2-propanol. After adding 7.2 g of diethylamine, the mixture was stirred at 80°C for 8 hours. The reaction was cooled and 800 mL of water was added to form a precipitate. The obtained precipitate was suction filtered and further washed with water. The filtrate was dried to obtain 9.9 g (84% yield) of a compound represented by Chemical Formula C-2.

Maldi-tof MS: 478.2 m/z

Evaluation 1: Solubility

0.5 g of compounds represented by the above formulas E-1, E-2, C-1 and C-2 were added to a diluting solvent (MeOH, CH ₂ Cl ₂ , Cyclohexanone), respectively, and the solution was added to a mix rotor (manufactured by iuchi Corporation). MIXROTAR VMR-5) was stirred at 25° C. and 100 rpm for 1 hour, and the results of confirming the dissolved state (dissolved compound content) of the compound are shown in Table 1 below.

Solubility evaluation criteria

X: solubility less than 1 wt%

○: Solubility 1 wt% or more and less than 5 wt%

◎: solubility 5wt% or more

Dissolved compound content (% by weight) Chloroform Diacetone alcohol Formula E-1 ◎ ◎ Formula E-2 ◎ ◎ Formula C-1 ○ ○ Formula C-2 X X

( Polymer Manufacturing-red dye)

With the composition shown in Table 2 below, a polymer was prepared. Specifically, 1.5 g of a photoinitiator V601 (Wako) (AIBN), which is a photopolymerization initiator, was added to a 100 ml beaker, and then each monomer was sequentially added in the weight% shown in Table 1 below. 72 g of DAA (diacetone alcohol) was added thereto, and a solution was prepared by stirring for 30 minutes until the monomer and photopolymerization initiator were completely dissolved. In order to proceed with the graft reaction, 54 g of DAA was added to a 250 ml three-neck glass reactor equipped with a cooler and a nitrogen tube, and the temperature was raised to 85° C. and nitrogen bubbling was performed. Next, the previously prepared solution was added dropwise to the reactor for 3 hours, and the reaction was performed at the same temperature for 9 hours, and then the temperature was lowered to room temperature and the reaction was terminated. The graft reaction was carried out under a nitrogen atmosphere.

(Unit: wt%, based on solid content) Monomer type Manufacturing Example 1 Manufacturing Example 2 Manufacturing Example 3 Manufacturing Example 4 Comparative Preparation Example 1 Comparative Preparation Example 2 Synthesis Example 1 40 - 40 40 - 40 Synthesis Example 2 - 40 - - - - Comparative Synthesis Example 1 - - - - 40 - Methacrylic acid 15 15 15 15 15 15 mono(2-acryloyloxyethyl)succinate 5 5 5 5 5 5 Lauryl methacrylate 13 13 13 13 10 - Dicyclopentanyl methacrylate 19 19 19 9 19 19 Phenyl maleimide - - - 10 - - Methyl methacryate 4.5 4.5 6.0 4.5 4.5 17.5 AIBN 3.5 3.5 2.0 3.5 3.5 3.5 Molecular weight (Mw, g/mol) 11000 11000 20000 14000 11000 Gelation

( Polymer Manufacture-yellow dye)

Manufacturing example 5

(Reaction Scheme)

(1) In a 125 mL Erlenmeyer flask, stir 3.12 g of 4-aminobenzoic acid, 75.6 ml of DI water, and 17.28 ml of HCl (35%) under an icebath. 14.4ml of sodium nitrite aqueous solution (1mM) was added dropwise and stirred under an icebath for 3 hours. Add 4.35g of ethyl cyanoacetate and 4.97g of ethylhexylamine and reflux reaction at 110℃ for 2 hours. Add 5g of ethylaetoacetate and 3.76g of piperidine and send the reaction overnight under reflux. After TLC check, the pyridone compound (1) is synthesized by washing with acid and water several times.

(2) After 4.722 g of pyridone compound (1) was added to 20 ml of DI water, NaOH aqueous solution was added and dissolved (pH8). The dissolved pyridone compound (1) was added to the 125ml Erlenmeyer flask containing 4-aminobenzoic acid, and the pH was adjusted to neutral with sodium carbonate (10%) aqueous solution. After filter purification with water, it is vacuum-dried to give compound (2).

(3) 5.5g of compound (2) was put into a 250ml flask, 2.09g of GMA, 2.16g of TBAB, and 70ml of acetonitrile were added, and then overnignt reaction was carried out under reflux at 90℃. After work-up with MC/water, yellow monomer 1 is synthesized by column purification. ( ¹ H NMR(DMSO): 15.02(s, 1H), 8.1(m, 1H), 7.94(m, 1H), 7.73(m, 1H), 7.55(m, 1H), 6.65(m, 1H), 6.17(m, 1H), 4.7(m, 1H), 4.3(m, 2H), 3.9(m, 2H), 2.03(s, 1H) 1.73(m, 3H), 1.96(m, 3H), 1.81( m, 1H), 1.28 (m, 8H), 0.91 (m, 6H))

(4) To synthesize a polymer containing 50% by weight of yellow monomer 1, 15% by weight of methacrylic acid (Daejeonghwa Geum), and 35% by weight of benzyl methacrylate (Hitach) as monomers, respectively.

Specifically, 1.5 g of the initiator V601 (Wako) was added to a 100 ml beaker, and then 50% by weight of yellow monomer 1, 15% by weight of methacrylic acid (Daejeonghwa Geum) and benzylmetha Crylate (Hitach) was added in sequence at a rate of 35% by weight. A monomer solution was prepared by adding 72 g of CYCLOHEXANONE as a solvent and stirring for 30 minutes until the dye monomer and initiator were completely dissolved. In order to proceed with the polymerization reaction, 54 g of a solvent was added to a 250 ml glass reactor equipped with a cooler, and the temperature was raised to 85° C., and the monomer solution prepared above was added dropwise to the reactor for 3 hours. After completion of the dropping, the reaction was performed at the same temperature for 9 hours, and then the temperature was lowered to room temperature and the reaction was terminated. The polymerization reaction was carried out under a nitrogen atmosphere. The weight average molecular weight measured by Waters' Gel Permission Chromatography (GPC) was 10,800 g/mol.

Manufacturing example 6

(Reaction Scheme)

(1) Stir in a 20 mL vial with 1.5 g of isobutyl 4-aminobenzoate, 32 ml of DI water, and 7.5 ml of HCl (35%) in an icebath. 6ml of sodium nitrite aqueous solution (1mM) was added dropwise and stirred under an icebath for 3 hours. 1.46 g of pyridone compound (7) was added to 20 ml of DI water, and then NaOH aqueous solution was added and dissolved (pH8). The dissolved pyridone compound (7) was added to the 20 mL vial containing isobutyl 4-aminobenzoate, and the pH was adjusted to neutral with sodium carbonate (10%) aqueous solution. After filter purification with water, it is vacuum-dried to give compound (8).

(2) 1 g of compound (8) was added to a 100 ml flask, 0.766 g of TEA, 0.154 g of DMAP, 0.457 g of acryloyl chloride, and 10 ml of acetonitrile were added, followed by an overnignt reaction at RT. After work-up with MC/water, yellow monomer 2 is synthesized by column purification. ( ¹ H NMR(DMSO): 14.38(s, 1H), 8.03(m, 1H), 7.85(m, 1H), 7.8(m, 1H), 7.6(m, 1H), 6.5(m, 1H), 6.26(m, 1H), 5.94(m, 1H), 4.4(m, 2H), 4.1(m, 2H), 3.9(s, 2H), 2.64(m, 1H), 2.01(s, 1H), 1.73 (m, 3H), 1.21 (m, 6H))

(3) To synthesize a polymer containing 50% by weight of yellow monomer 2, 15% by weight of methacrylic acid (Daejeonghwa Geum), and 35% by weight of benzyl methacrylate (Hitach) as monomers, respectively. The weight average molecular weight measured by Waters' Gel Permission Chromatography (GPC) was 9,900 g/mol.

(Synthesis of photosensitive resin composition)

Example 1 to Example 9, Comparative example 1 and Comparative example 2

In the composition shown in Table 3 and Table 4 below, a photopolymerization initiator was added to the solvent and stirred at room temperature for 1 hour to dissolve. Then, a binder resin and a photopolymerizable monomer were added, and the mixture was stirred at room temperature for 1 hour. Here, other additives were added and stirred at room temperature for 1 hour. Here, with the polymer (red dye) prepared in Preparation Examples 1 to 4 and Comparative Preparation Example 1, and the monomer (red dye) prepared in Comparative Synthesis Example 2, optionally prepared in Preparation Examples 5 and 6 After adding one polymer (yellow dye) and stirring at room temperature for 2 hours, the solution was filtered three times to remove impurities, and according to Examples 1 to 9, Comparative Examples 1 and 2 A photosensitive resin composition was prepared. Components used in the preparation of the photosensitive resin composition are as follows.

(A) binder resin

(A-1) Acrylic binder resin (RY-25, Showadenko company)

(A-2) Acrylic binder resin (CRG-1000S, SMS company)

(B) Photopolymerization Monomer

(B-1) DPHA (Nippon KAYAKU)

(B-2) KAYARAD DPCA-30(Nippon KAYAKU)

(B-3) KAYARAD DPCA-120(Nippon KAYAKU)

(B-4) ABPE-20 (Shin-nakamura company)

(C) Light polymerization Initiator

(C-1) SPI-03 (Samyang Corporation)

(C-2) OXE-01 (Basf company)

(D) colorant

(D-1) Polymer according to Preparation Example 1

(D-2) Polymer according to Preparation Example 2

(D-3) Polymer according to Preparation Example 3

(D-4) Polymer according to Preparation Example 4

(D-5) Polymer according to Comparative Preparation Example 1

(D-6) Monomer according to Comparative Synthesis Example 2

(D-7) C.I. pigment red 254 (SANYO company)

(D-8) C.I. pigment red 177 (SANYO company)

(D-9) Polymer according to Preparation Example 5

(D-10) Polymer according to Preparation Example 6

(E) solvent

Propylene glycol monomethyl ethyl acetate (PGMEA, sigma-aldrich company)

(G) other additives

(G-1) Fluorine surfactant (F-554, DIC company)

(G-2) Matting agent (ORASOL 330, BASF company)

(Unit: wt%) Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Comparative Example 1 Comparative Example 2 Binder resin A-1 2.2 2.2 2.2 2.2 2.2 2.2 2.2 2.2 A-2 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Photopolymerizable monomer B-1 3.2 3.2 3.2 3.2 3.2 3.2 3.2 3.2 B-2 - - - - - - - - B-3 - - - - - - - - B-4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Photopolymerization initiator C-1 1.0 1.0 1.0 1.0 1.0 1.0 1.0 1.0 C-2 0.4 0.4 0.4 0.4 0.4 0.4 0.4 0.4 coloring agent D-1 10.1 - - - 10.1 10.1 - - D-2 - 10.1 - - - - - - D-3 - - 10.1 - - - - - D-4 - - - 10.1 - - - - D-5 - - - - - - 10.1 - D-6 - - - - - - - 10.1 D-7 39.8 39.8 39.8 39.8 34.8 34.8 39.8 39.8 D-8 - - - - - - - - D-9 - - - - 5.0 - - - D-10 - - - - - 5.0 - - menstruum 41.7 41.7 41.7 41.7 41.7 41.7 41.7 41.7 Other additives G-1 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 G-2 - - - - - - - -

(Unit: wt%) Example 7 Example 8 Example 9 Binder resin A-1 1.508 1.499 1.494 Photopolymerizable monomer B-1 5.413 - - B-2 - 5.382 - B-3 - - 5.362 Photopolymerization initiator C-1 0.305 0.338 0.360 coloring agent D-1 5.333 5.167 5.167 D-2 - - - D-3 - - - D-4 - - - D-5 - - - D-6 - - - D-7 D-8 33.235 33.236 33.237 D-9 22.562 22.593 22.592 D-10 - - - menstruum 29.213 29.275 29.278 Other additives G-1 0.2 0.2 0.2 G-2 2.306 2.309 2.308

Evaluation 2: Evaluation of luminance characteristics

The color characteristics of the color filter specimens prepared using the photosensitive resin compositions prepared in Examples 1 to 9 and Comparative Examples 1 and 2 were added for 30 minutes in a convection oven at 230°C. The color change before/after baking by baking was measured using a spectrophotometer (MCPD3000 manufactured by Otsuka Electronics), and the results are shown in Table 5 below.

Evaluation 3: Chemical resistance evaluation

The color filter specimens prepared using the photosensitive resin compositions prepared in Examples 1 to 9, Comparative Examples 1 and 2 were immersed in a pattern of NMP solution at 90° C. for 10 minutes to evaluate the chemical resistance of the PI solution. . Chemical resistance was evaluated by the color change of the color filter pattern before and after immersion of the NMP solution and whether the color filter pattern was peeled off after the immersion of the stripper. The change in color characteristics of the color filter pattern was measured using a spectrophotometer (MCPD3000 of Otsuka Electronics Co., Ltd.), and whether the color filter pattern was peeled off was evaluated with an optical microscope. The evaluation results are shown in Table 5 below.

Evaluation 4: Heat resistance evaluation

The patterns of the color filter specimens prepared using the photosensitive resin compositions prepared in Examples 1 to 9 and Comparative Examples 1 and 2 were heat-treated in an oven at 230° C. for 30 minutes to evaluate heat resistance. Heat resistance was evaluated by the color change of the color filter pattern before and after heat treatment, and the color change was measured using a spectrophotometer (MCPD3000 of Otsuka Electronics Co., Ltd.), and the results are shown in Table 5 below.

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Comparative Example 1 Comparative Example 2 Color difference after post baking (Δ Eab*) 2.0 1.9 1.9 1.4 2.1 2.1 2.2 1.9 2.0 3.5 5.35 Corrected luminance after post baking (%) 102.1 102.4 102.2 102.3 102.9 102.9 103.1 102.4 102.4 100 100 Chemical resistance (Δ Eab*) 1.9 1.8 1.1 1.9 1.9 1.9 2.0 1.8 1.8 5.2 6.37 Heat resistance (Δ Eab*) 1.5 1.6 1.5 0.9 1.5 1.6 1.7 1.2 1.1 4.3 7.21

Through Table 5, the photosensitive resin compositions of Examples 1 to 9 including a polymer (red dye) according to an embodiment were compared with Comparative Examples 1 and 2 not including the polymer, and brightness, etc. It can be seen that not only the color characteristics of the product, but also heat resistance and chemical resistance are excellent. In particular, it can be confirmed that the luminance becomes more excellent when another yellow polymer is additionally used as a colorant together with the polymer according to the embodiment.

Evaluation 5: pattern wrinkle evaluation

The photosensitive resin composition prepared in Examples 7 to 9 was coated using a MIKASA coating machine at an rpm capable of exhibiting a certain thickness for each specimen, followed by pre-baking on a 90°C hot plate, and an exposure machine The pattern exposure was performed under exposure conditions of Dose: 40mJ and Gap: 200㎛, and development was performed to indicate the pattern. The developer was used by diluting a Na ₂ CO ₃ solution, and the time (second) (BP) of the pattern appearance was measured. At this time, the BP should be at least 40 seconds or less. Pattern formation was completed by baking the pattern substrate on which development was completed at 230° C. for 20 minutes. The completed pattern was zoomed 500 times through an optical microscope to measure the width of the confirmed pattern. The pattern to be confirmed was carried out by measuring the size with an optical microscope at 100 μm wide, and the results are shown in Table 6 and FIGS. 1 to 5 below.

Example 7 Example 8 Example 9 CD(100㎛) 101.54 101.28 100.88 Resolution 10 12 10

From Table 6 and FIGS. 1 to 3, when a compound having a long chain acrylate group is used as the photopolymerizable monomer, it is shown that there is an excellent effect on improving wrinkles on the pattern surface than when using a compound having a short chain acrylate group. I can confirm. In addition, from FIGS. 4 and 5, in the case of the photosensitive resin composition further comprising a matting agent, it can be seen that developability and pattern straightness are further improved.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims, the detailed description of the invention, and the accompanying drawings. It is natural to fall within the scope of the invention.

Claims (31)

Polymers containing structural units represented by the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
R ¹ to R ⁶ and R ⁸ to R ¹¹ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,
L ¹ , L ² , L ⁴ and L ⁵ are each independently a substituted or unsubstituted C1 to C20 alkylene group,
L ³ is a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, a substituted or unsubstituted C6 to C20 arylene group, *-OC(=O)NH-*, *- O(C=O)-*, *-NR ^X -* or a combination thereof, wherein R ^x is a substituted or unsubstituted C1 to C10 alkyl group,
X is represented by the following formula X-1 or formula X-2,
[Formula X-1]

[Formula X-2]

R ⁷ is a substituted or unsubstituted C11 to C20 alkyl group,
n is an integer from 0 to 3,
q1 and q2 are each independently an integer of 0 or 1.
The method of claim 1,
The L ³ is a polymer represented by the following formula (2):
[Formula 2]

In Chemical Formula 2,
L ⁶ to L ¹⁰ are each independently a single bond, a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C20 cycloalkylene group, *-OC(=O)NH-*, *-O( C=O)-* or *-NR ^X -*, and R ^x is a substituted or unsubstituted C1 to C10 alkyl group, provided that L ⁶ to L ¹⁰ are not a single bond at the same time.
The method of claim 2,
The L ³ is a substituted or unsubstituted C1 to C20 alkylene group.
The method of claim 2,
The L ³ is a polymer represented by the following formula (3):
[Formula 3]

In Chemical Formula 3,
L ¹¹ to L ¹³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C3 to C10 cycloalkylene group, or a combination thereof.
The method of claim 4,
The L ¹¹ to L ¹³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a polymer represented by the following formula 3-1 or the following formula 3-2:
[Formula 3-1]

[Chemical Formula 3-2]

In Formulas 3-1 and 3-2,
L ^a to L ^c are each independently a substituted or unsubstituted C1 to C5 alkylene group.
The method of claim 2,
The L ³ is a polymer represented by the following formula (4):
[Formula 4]

In Chemical Formula 4,
L ¹⁴ to L ¹⁶ are each independently a substituted or unsubstituted C1 to C10 alkylene group.
The method of claim 2,
The L ³ is a polymer represented by the following formula (5):
[Formula 5]

In Chemical Formula 5,
L ¹⁷ and L ¹⁸ are each independently a substituted or unsubstituted C1 to C10 alkylene group,
R ^x is a substituted or unsubstituted C1 to C10 alkyl group.
The method of claim 1,
The polymer further comprises a structural unit represented by the following Chemical Formulas 1-5 to 1-7:
[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formula 1-5 to Formula 1-7,
R ¹ is a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group,
R ¹² and R ¹³ are each independently a substituted or unsubstituted C1 to C10 alkyl group,
L ¹⁹ and L ²⁰ are each independently a substituted or unsubstituted C1 to C10 alkylene group,
m is an integer from 0 to 5.
The method of claim 1,
The compound represented by Formula 1-1 is a polymer represented by any one of Formulas 1-1-1 to 1-1-4 below.
[Formula 1-1-1]

[Formula 1-1-2]

[Formula 1-1-3]

[Formula 1-1-4]

The method of claim 1,
The polymer is a polymer having a maximum absorbance in the wavelength range of 500nm to 600nm.
A photosensitive resin composition comprising the polymer of any one of claims 1 to 10 as a red dye.
The method of claim 11,
The photosensitive resin composition further comprises a binder resin, a photopolymerizable monomer, a photopolymerization initiator, and a solvent.
The method of claim 11,
The photosensitive resin composition further comprises a yellow dye photosensitive resin composition.
The method of claim 13,
The yellow dye is a photosensitive resin composition that is a polymer containing a compound represented by the following Formula 6 as a monomer:
[Formula 6]

In Formula 6,
R ¹⁴ and R ¹⁵ are each independently a substituted or unsubstituted C1 to C20 alkyl group, *-C(=O)OR' or *-OC(=O)R',
R'is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C2 to C10 alkenyl group, or a substituted or unsubstituted C6 to C20 aryl group,
However, any one of R ¹⁴ and R ¹⁵ includes a substituent represented by Formula 7 below,
[Formula 7]

(In Chemical Formula 7,
R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group)
R ¹⁶ is a substituted or unsubstituted C1 to C20 alkyl group.
The method of claim 14,
The polymer comprising the compound represented by Formula 6 as a monomer is a photosensitive resin composition comprising any one structural unit selected from the group consisting of structural units represented by Formulas 6-1 to 6-4:
[Formula 6-1]

[Chemical Formula 6-2]

[Chemical Formula 6-3]

[Formula 6-4]

In Formula 6-1 to Formula 6-4,
L ²¹ to L ²³ are each independently a substituted or unsubstituted C1 to C10 alkylene group, a substituted or unsubstituted C6 to C20 arylene group, or *-L'-C(=O)O-L''-*,
Wherein L'and L'' are each independently a substituted or unsubstituted C1 to C5 alkylene group or a substituted or unsubstituted C6 to C12 arylene group,
R ¹⁶ and R ¹⁸ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
R ¹⁷ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group.
The method of claim 15,
The polymer comprising the compound represented by Formula 6 as a monomer further comprises a structural unit represented by Formula 8-1 and Formula 8-2:
[Chemical Formula 8-1]

[Formula 8-2]

In Formula 8-1 and Formula 8-2,
R ¹⁹ is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
L ²⁴ is a substituted or unsubstituted C1 to C10 alkylene group.
The method of claim 16,
The polymer containing the compound represented by Formula 6 as a monomer,
40% to 60% by weight of any one structural unit selected from the group consisting of structural units represented by Chemical Formulas 6-1 to 6-4;
5% to 25% by weight of the structural unit represented by Formula 8-1; And
25% to 45% by weight of the structural unit represented by Formula 8-2
Photosensitive resin composition comprising a.
The method of claim 15,
The structural unit represented by Formula 6-1 is any one selected from the group consisting of structural units represented by Formula 6-1-1 to Formula 6-1-14 below.
[Chemical Formula 6-1-1]

[Chemical Formula 6-1-2]

[Chemical Formula 6-1-3]

[Chemical Formula 6-1-4]

[Chemical Formula 6-1-5]

[Chemical Formula 6-1-6]

[Chemical Formula 6-1-7]

[Chemical Formula 6-1-8]

[Chemical Formula 6-1-9]

[Chemical Formula 6-1-10]

[Chemical Formula 6-1-11]

[Chemical Formula 6-1-12]

[Chemical Formula 6-1-13]

[Chemical Formula 6-1-14]

The method of claim 15,
The structural unit represented by Formula 6-2 is a structural unit represented by Formula 6-2-1 or Formula 6-2-2 below.
[Chemical Formula 6-2-1]

[Chemical Formula 6-2-2]

The method of claim 15,
The structural unit represented by Formula 6-3 is a structural unit represented by Formula 6-3-1 or Formula 6-3-2 below.
[Chemical Formula 6-3-1]

[Chemical Formula 6-3-2]

The method of claim 15,
The structural unit represented by Formula 6-4 is a structural unit represented by Formula 6-4-1 or Formula 6-4-2 below.
[Chemical Formula 6-4-1]

[Chemical Formula 6-4-2]

The method of claim 12,
The photopolymerizable monomer is a photosensitive resin composition comprising a bifunctional (meth) acrylate monomer and a 6 functional (meth) acrylate monomer.
The method of claim 22,
The bifunctional (meth)acrylate-based monomer is a photosensitive resin composition represented by the following formula (9):
[Formula 9]

In Formula 9,
R ²⁰ and R ²¹ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group,
L ²⁵ to L ²⁷ are each independently a substituted or unsubstituted C1 to C10 alkylene group,
p1 and p2 are each independently an integer of 1 to 10, but 11≦p1+p2≦20.
The method of claim 22,
The six-functional (meth) acrylate-based monomer is a photosensitive resin composition represented by the following formula (10):
[Formula 10]

In Chemical Formula 10,
R ²² to R ²⁷ are each independently represented by the following formula (11),
[Formula 11]

In Formula 11,
p3 is an integer of 0 to 2.
The method of claim 24,
The p3 is an integer of 1 or 2 photosensitive resin composition.
The method of claim 12,
The binder resin is a photosensitive resin composition comprising an acrylic binder resin, a cardo binder resin, or a combination thereof.
The method of claim 12,
The photosensitive resin composition is a photosensitive resin composition further comprising a pigment.
The method of claim 12,
The photosensitive resin composition is a matting agent, malonic acid, 3-amino-1,2-propanediol, a silane-based coupling agent containing a vinyl group or a (meth)acryloxy group, a leveling agent, a surfactant, a radical polymerization initiator, or Photosensitive resin composition further comprising a combination.
A photosensitive resin film prepared by using the photosensitive resin composition of claim 11.
A color filter comprising the photosensitive resin film of claim 29.
A display device comprising the color filter of claim 30.

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