KR102338286B1 - Photosensitive resin composition, photosensitive resin using the same and color filter - Google Patents

Abstract

(A) (a-1) a blue pigment, a blue dye, or a mixture thereof; (a-2) a yellow dye having a maximum absorption wavelength in a wavelength region of 360 nm to 390 nm and having a transmittance of 95% or more in a wavelength region of 450 nm to 900 nm; and (a-3) a colorant comprising a violet dye; (B) binder resin; (C) a photopolymerizable compound; (D) a photoinitiator; And (E) a photosensitive resin composition comprising a solvent, a photosensitive resin film and a color filter prepared using the photosensitive resin composition are provided.

Description

Photosensitive resin composition, photosensitive resin film and color filter using the same

The present disclosure relates to a photosensitive resin composition, a photosensitive resin film manufactured using the same, and a color filter.

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

A color filter includes a black matrix (light blocking layer) formed in a predetermined pattern on a transparent substrate to block light at the boundary between pixels, and a plurality of colors (typically, red (R), green (G), The pixel units in which the three primary colors of blue (B) are arranged in a predetermined order have a structure in which they are sequentially stacked.

The pigment dispersion method, which is one of the methods for implementing a color filter, involves coating a photopolymerizable composition containing a colorant on a transparent substrate provided with a black matrix, exposing the pattern to be formed, and then removing the unexposed area with a solvent. This is a method in which a colored thin film is formed by repeating a series of thermal curing processes. The colored photosensitive resin composition used for manufacturing a color filter according to the pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerization monomer, a photoinitiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method having the above characteristics is actively applied to the manufacture of LCDs such as mobile phones, notebook computers, monitors, and TVs.

However, in recent years, even in the photosensitive resin composition for a color filter using the pigment dispersion method, which has various advantages, the process of refining the powder is difficult and the dispersion state must be stable in the dispersion even after dispersion, so various additives are required and the process is also very difficult. In addition, the pigment dispersion has a disadvantage in that storage and transportation conditions are difficult to maintain optimal quality.

In addition, in a color filter made of a pigment-type photosensitive resin composition, there is a limit in luminance and contrast ratio resulting from the size of the pigment particle. In addition, in the case of a color imaging device for an image sensor, a smaller dispersed particle size is required to form a fine pattern. In order to meet this demand, attempts are being made to implement a color filter with improved color characteristics such as luminance and contrast by preparing a photosensitive resin composition incorporating a dye that does not form particles instead of or together with a pigment, but the dye type The photosensitive resin composition has a problem in that durability is inferior to that of the pigment-type photosensitive resin composition.

One embodiment is to provide a photosensitive resin composition having excellent luminance while implementing high color coordinates by minimizing the amount of colorant used.

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

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

One embodiment of the present invention is (A) (a-1) a blue pigment, a blue dye or a mixture thereof; (a-2) a yellow dye having a maximum absorption wavelength in a wavelength region of 360 nm to 390 nm and having a transmittance of 95% or more in a wavelength region of 450 nm to 900 nm; and (a-3) a colorant comprising a violet dye; (B) binder resin; (C) a photopolymerizable compound; (D) a photoinitiator; And (E) provides a photosensitive resin composition comprising a solvent.

The violet dye may be included in an amount of 0.1 wt% to 2 wt% based on the total amount of the photosensitive resin composition.

The violet dye may be represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

R ¹⁰¹ to R ¹⁰⁵ 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,

R ¹⁰⁶ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁰⁷ is a substituted or unsubstituted C3 to C20 alicyclic ring group or a substituted or unsubstituted C6 to C20 aryl group;

R ¹⁰⁸ to R ¹¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

n is an integer from 1 to 5;

L is represented by the following formula 1-3,

[Formula 1-3]

In Formula 1-3,

L ¹ is *-O(C=O)-* and

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, or a substituted or unsubstituted C6 to C20 aryl group.

In Formula 1-2, L may be represented by any one of Formulas 1-3-1 to 1-3-5.

[Formula 1-3-1]

[Formula 1-3-2]

[Formula 1-3-3]

[Formula 1-3-4]

[Formula 1-3-5]

In Formulas 1-3-1 to 1-3-5,

R ¹¹¹ is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted acyl group,

R ¹¹² to R ¹¹⁴ are each independently a hydroxyl group or a substituted or unsubstituted C1 to C10 alkyl group, provided that at least one of ^{R 112} and R ^{113 is a hydroxyl group,}

R ¹¹⁵ is a substituted or unsubstituted C1 to C10 alkyl group,

o and p are each independently an integer from 1 to 3, provided that 2 ≤ o + p ≤ 5;

q is an integer from 0 to 4.

In the violet dye represented by Formula 1-2, R ¹⁰⁶ is a hydrogen atom, R ¹⁰⁷ is a substituted or unsubstituted adamantyl group, R ¹⁰⁸ to R ¹¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group and L may be represented by Formula 1-3-1.

The yellow dye may be an azo dye.

The yellow dye may be included in an amount of 0.01 wt% to 1 wt% based on the total amount of the photosensitive resin composition.

The yellow dye may be included in an amount less than that of the violet dye, and the violet dye may be included in an amount less than that of the blue colorant.

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

The photosensitive resin composition may include, based on the total amount of the photosensitive resin composition, 2 wt% to 40 wt% of the colorant; 3 wt% to 20 wt% of the binder resin; 1 wt% to 10 wt% of the photopolymerizable compound; 0.1 wt% to 5 wt% of the photopolymerization initiator and the remaining amount of the solvent may be included.

The photosensitive resin composition may further include an epoxy compound, a silane coupling agent, a surfactant, or a combination thereof.

The photosensitive resin composition may have a Bx value of 0.148 or less when the By value is 0.0510 in the CIE color coordinate.

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

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

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

The photosensitive resin composition according to the exemplary embodiment minimizes the amount of blue pigment, thereby realizing a low Bx color coordinate in a high-color blue resist and preventing a decrease in luminance.

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

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

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

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

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

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

In this specification, the CIE color coordinates refer to the CIE1931 color coordinates.

As used herein, the cardo-based resin refers to a resin in which one or more functional groups selected from the group consisting of the following Chemical Formulas 10-1 to 10-11 are included in the backbone of the resin.

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

One embodiment is (A-1) a blue colorant; (A-2) a yellow dye having a maximum absorption wavelength in a wavelength range of 360 nm to 390 nm and having a transmittance of 95% or more in a wavelength range of 450 nm to 900 nm; (A-3) violet dye; (B) binder resin; (C) a photopolymerizable compound; (D) a photoinitiator; And (E) provides a photosensitive resin composition comprising a solvent.

In the case of blue resists among existing color filter resists, it is common to add some violet colorant to the blue pigment to adjust color coordinates and increase luminance. However, in recent years, the new blue color coordinate for increasing color gamut has a tendency to become smaller in Bx. In order to implement a blue color filter having such a high color gamut, a narrow transmission spectrum should be created around 450 nm, which is the wavelength of the blue LED, which is the light source. etc.) instead of beta blue (eg, CI Pigment Blue 15:3, CI Pigment Blue 15:4, etc.), the direction of producing a resist with a reduced width of the transmission spectrum by increasing the PWC is also suggested. However, in this case, there is a problem that the existing luminance is very low.

According to one embodiment, while lowering Bx, a yellow dye that cuts the Violet region so as to have advantageous luminance compared to when beta blue is used is used, but the violet dye is used together with the yellow dye. (Based on the same By) In order to lower Bx, the content of the colorant must be lowered. In one embodiment, by using the violet dye together with the blue colorant and the yellow dye, the total amount of the colorant can be greatly reduced. However, in the prior art, when the amount of the colorant used was reduced, a luminance deterioration problem occurred and became a problem. It is common not to use a common blue color filter and yellow dye together because the transmission and absorption spectra overlap, but according to one embodiment, the transmittance is adjusted according to the wavelength of the yellow dye to absorb mainly the wavelength region of 420 nm or less. , so that the transmittance in the wavelength region after 450 nm is 95% or more, it is possible to minimize the luminance loss of the main spectrum from the light source. When a blue color filter is manufactured by using such a yellow dye together with the violet dye, the short-wavelength region that irritates the eyes is blocked, so that the eyesight protection effect is also obtained. In addition, by using the yellow dye according to an embodiment for a colorant (dye or pigment) that is not suitable for high color coordinates due to high luminance compared to existing blue pigments but large Bx, luminance can be further increased while realizing high color coordinates.

Hereinafter, each component will be described in detail.

(A) Colorant

The colorant is (a-1) a blue pigment, a blue dye, or a mixture thereof; (a-2) a yellow dye having a maximum absorption wavelength in a wavelength region of 360 nm to 390 nm and having a transmittance of 95% or more in a wavelength region of 450 nm to 900 nm; and (a-3) a violet dye, and may be included in an amount of 2 wt% to 40 wt% based on the total amount of the photosensitive resin composition according to an embodiment.

(a-1) blue dye, blue pigment or mixtures thereof

The blue dye may be represented by Formula 2 below.

[Formula 2]

In Formula 2,

R ¹ and R ² are each independently a substituted C1 to C20 alkyl group or a substituted or unsubstituted C3 to C20 cycloalkyl group,

R ³ is a hydrogen atom or a halogen group,

R ⁴ is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,

R ⁵ is a C1 to C20 alkyl group unsubstituted or substituted with an acrylate group,

X ^- is represented by any one of the following formulas A to C.

[Formula A]

SO ₃ ^-

[Formula B]

(in Formula B, n3 is an integer from 0 to 10)

[Formula C]

For example, the blue dye may be represented by the following Chemical Formula 3 or Chemical Formula 4.

[Formula 3]

[Formula 4]

In Formulas 3 and 4,

X ^- is represented by any one of the following formulas A to C.

[Formula A]

SO ₃ ^-

[Formula B]

(in Formula B, n3 is an integer from 0 to 10)

[Formula C]

Specifically, the blue dye may be represented by Formula 3 above.

The compound represented by Formula 3 may have improved heat resistance by including a cyclohexyl group, and light resistance may be improved by having a phenyl group substituted for a nitrogen atom include a methyl group, so that not only high brightness in high color coordinates but also heat resistance, It is possible to provide a color filter having excellent durability such as light resistance.

For example, the blue pigment may be an epsilon blue pigment. When a blue pigment is used as a blue colorant according to an exemplary embodiment, it is helpful to use an epsilon blue pigment rather than a beta blue pigment to improve luminance.

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

The blue dye or blue pigment may be a derivative combined with an organic polymer.

The blue dye, blue pigment, or mixtures thereof may be included in an amount of 1.5 wt% to 15 wt%, such as 2 wt% to 10 wt%, based on the solid content, based on the total amount of the photosensitive resin composition according to an embodiment. When included in the above range, it is possible to achieve high luminance in high color coordinates.

(a-2) yellow dye

The yellow dye has a maximum absorption wavelength in a wavelength region of 360 nm to 390 nm, and transmittance in a wavelength region of 450 nm to 900 nm is 95% or more.

In order to implement the high color coordinates, the Bx value on the CIE color coordinates must be small. For this, there was a method to implement by using B15:3 or B15:4, which were redshifted from the existing B15:6, and increasing the content, but the problem is that in this case, the luminance is greatly reduced. In addition, although a violet colorant was added to increase the luminance in the existing sRGB class, in this case, the Bx value on the CIE color coordinates became large, so that it was impossible to implement the high color coordinates itself. However, according to one embodiment, instead of using such B15:3 and B15:4, a yellow colorant, specifically, a yellow dye, is used, and the transmittance according to the wavelength of the yellow dye is adjusted as described above to minimize luminance loss. can Furthermore, the yellow dye blocks a wavelength of 360 nm to 390 nm, that is, a short wavelength region, and the short wavelength generally stimulates the eye and is one of the causes of lowering of eyesight, so it may also have an eye protection effect.

The yellow dye may be an azo dye.

The yellow dye may be included in an amount of 0.01 wt% to 1 wt%, such as 0.05 wt% to 0.5 wt%, based on the total amount of the photosensitive resin composition according to an embodiment. When the yellow dye is included in the above range, it is possible to achieve high luminance in high color coordinates and maximize the effect of protecting eyesight. In this case, the yellow dye may be included in an amount less than that of the violet dye. When the yellow dye is included in an amount equal to or greater than that of the violet dye, there are problems in that luminance is lowered and a process margin is disadvantageous.

(A-3) Violet dye

The violet dye may be represented by the following Chemical Formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,

R ¹⁰¹ to R ¹⁰⁵ 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,

R ¹⁰⁶ is a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkoxy group or a substituted or unsubstituted C6 to C20 aryl group,

R ¹⁰⁷ is a substituted or unsubstituted C3 to C20 alicyclic ring group or a substituted or unsubstituted C6 to C20 aryl group;

R ¹⁰⁸ to R ¹¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,

n is an integer from 1 to 5;

L is represented by the following formula 1-3,

[Formula 1-3]

In Formula 1-3,

L ¹ is *-O(C=O)-* and

A is a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 alicyclic ring group, or a substituted or unsubstituted C6 to C20 aryl group.

In Formula 1-2, L may be represented by any one of Formulas 1-3-1 to 1-3-5.

[Formula 1-3-1]

[Formula 1-3-2]

[Formula 1-3-3]

[Formula 1-3-4]

[Formula 1-3-5]

In Formulas 1-3-1 to 1-3-5,

R ¹¹¹ is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted acyl group,

R ¹¹² to R ¹¹⁴ are each independently a hydroxyl group or a substituted or unsubstituted C1 to C10 alkyl group, provided that at least one of ^{R 112} and R ^{113 is a hydroxyl group,}

R ¹¹⁵ is a substituted or unsubstituted C1 to C10 alkyl group,

o and p are each independently an integer from 1 to 3, provided that 2 ≤ o + p ≤ 5;

q is an integer from 0 to 4.

For example, in the violet dye represented by Formula 1-2, R ¹⁰⁶ is a hydrogen atom, R ¹⁰⁷ is a substituted or unsubstituted adamantyl group, R ¹⁰⁸ to R ¹¹⁰ are each independently a substituted or unsubstituted C1 to It is a C20 alkyl group, and L may be represented by Formula 1-3-1.

The violet dye represented by Formula 1-1 is effective in significantly reducing the amount of the above-described blue colorant and yellow dye, and the violet dye represented by Formula 1-2 reduces the amount of the above-described blue colorant and yellow dye to a small extent. Instead, it is effective to increase the luminance even in high color coordinates.

The violet dye may be included in an amount of 0.1 wt% to 2 wt%, for example 0.2 wt% to 1 wt%, based on the total amount of the photosensitive resin composition according to an embodiment. When the violet dye is included in the above range, it is possible to reduce the amount of the above-mentioned blue dye, blue pigment, or mixtures thereof and yellow pigment, so that when the By value is 0.0510 in the high color coordinates, such as the CIE color coordinate, the Bx value is 0.148 or less. It is possible to achieve high luminance in the high color coordinates at the same time as being implemented.

(B) binder resin

The binder resin may include an acrylic binder resin, a cardo-based binder resin, or a combination thereof. for example,

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 including one or more acrylic repeating units.

The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl 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 wt% to 50 wt%, for example 10 wt% to 40 wt%, based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene, α-methylstyrene, vinyltoluene or vinylbenzylmethyl ether; Methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (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 a 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 A acrylate copolymer, (meth)acrylic acid/benzylmethacrylate/styrene/2-hydroxyethyl methacrylate copolymer, etc. may be mentioned, 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, physical and chemical properties of the photosensitive resin composition are excellent, the viscosity is appropriate, and the adhesion to the substrate is excellent in manufacturing the color filter.

The acid value of the acrylic binder resin may be 15 mgKOH/g to 60 mgKOH/g, for example, 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 be represented by the following Chemical Formula 10.

[Formula 10]

In the formula (10),

R ¹⁰¹ and R ¹⁰² are each independently a hydrogen atom or a substituted or unsubstituted (meth)acryloyloxy alkyl group,

R ¹⁰³ and R ¹⁰⁴ 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 ¹⁰⁷ R ¹⁰⁸ , SiR ¹⁰⁹ R ¹¹⁰ (wherein R ¹⁰⁷ to R ¹¹⁰ are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group) or Any one of the linking groups represented by Formulas 10-1 to 10-11,

[Formula 10-1]

[Formula 10-2]

[Formula 10-3]

[Formula 10-4]

[Formula 10-5]

(In Formula 10-5,

R ^z 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.)

[Formula 10-6]

[Formula 10-7]

[Formula 10-8]

[Formula 10-9]

[Formula 10-10]

[Formula 10-11]

Z ² is an acid anhydride residue or an acid dianhydride residue,

z1 and z2 are each independently an integer from 0 to 4.

The weight average molecular weight of the cardo-based binder resin may be 500 g/mol to 50,000 g/mol, for example, 1,000 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 without a residue when manufacturing the light shielding layer, there is no loss of film thickness during development, and a good pattern can be obtained.

The cardo-based binder resin may include a functional group represented by the following Chemical Formula 11 at at least one of both ends.

[Formula 11]

In the above formula (11),

Z ³ may be represented by the following Chemical Formulas 11-1 to 11-7.

[Formula 11-1]

(In Formula 11-1, R ^h and R ⁱ are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, an ester group, or an ether group.)

[Formula 11-2]

[Formula 11-3]

[Formula 11-4]

[Formula 11-5]

(In Formula 11-5, R ^j is O, S, NH, a substituted or unsubstituted C1 to C20 alkylene group, C1 to C20 alkylamine group, or C2 to C20 alkenylamine group.)

[Formula 11-6]

[Formula 11-7]

The cardo-based binder resin may include, for example, a fluorene-containing compound such as 9,9-bis(4-oxiranylmethoxyphenyl)fluorene; Benzenetetracarboxylic acid dianhydride, naphthalenetetracarboxylic acid dianhydride, biphenyltetracarboxylic acid dianhydride, benzophenonetetracarboxylic acid dianhydride, pyromellitic dianhydride, cyclobutanetetracarboxylic acid dianhydride, phenol anhydride compounds such as rylenetetracarboxylic acid dianhydride, tetrahydrofurantetracarboxylic acid dianhydride, and tetrahydrophthalic 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 methylethyl acetate and N-methylpyrrolidone; phosphorus compounds such as triphenylphosphine; and amine or ammonium salt compounds such as tetramethylammonium chloride, tetraethylammonium bromide, benzyldiethylamine, triethylamine, tributylamine, and benzyltriethylammonium chloride.

When the binder resin includes a cardo-based binder resin, the photosensitive resin composition has excellent developability, and has excellent sensitivity during photocuring, so that fine pattern formation is excellent.

The binder resin may be included in an amount of 3 wt% to 20 wt%, for example 5 wt% to 15 wt%, based on the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent developability and improved crosslinking properties can be obtained when manufacturing a color filter, thereby obtaining excellent surface smoothness.

(C) photopolymerizable compound

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

Since the photopolymerizable compound 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 upon exposure in the pattern forming process.

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, pentaerythritol tetra(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylic rate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethyl ether (meth) acrylate, trimethylol propane tri (meth) ) acrylate, tris (meth) acryloyloxyethyl phosphate, and novolac epoxy (meth) acrylate.

Examples of commercially available products of the photopolymerizable compound are as follows. Examples of the monofunctional ester of (meth)acrylic acid include Aronix M-101 ^® , M-111 ^® , M-114 ^® by Toagosei Chemical Co., Ltd.; Nihon Kayaku Co., Ltd.'s KAYARAD TC-110S ^® , Copper TC-120S ^®, etc.; ^{V-158 ®} , V-2311 ^®, etc. of Osaka Yuki Chemical High School Co., Ltd. are mentioned. Examples of the bifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-210 ^® , M-240 ^® , M-6200 ^® and the like; Nihon Kayaku Co., Ltd.'s KAYARAD HDDA ^® , Copper HX-220 ^® , Copper R-604 ^®, etc.; ^{and V-260 ®} , V-312 ^® , V-335 HP ^{® of} Osaka Yuki Chemical High School Co., Ltd. and the like. Examples of the trifunctional ester of (meth)acrylic acid, Toagosei Chemical Co., Ltd. Aronix M-309 ^® , Copper M-400 ^® , Copper M-405 ^® , Copper M-450 ^® , Copper M -710 ^® , copper M-8030 ^® , copper M-8060 ^® etc; Nihon Kayaku Co., Ltd.'s KAYARAD TMPTA ^® , Copper DPCA-20 ^® , Copper-30 ^® , Copper-60 ^® , Copper-120 ^® etc.; ^{V-295 ®} , Dong-300 ^® , Dong-360 ^® , Dong-GPT ^® , Dong-3PA ^® , Dong-400 ^® etc. from Osaka Yuki Kayaku High School Co., Ltd. are mentioned. These products may be used alone or in combination of two or more.

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

The photopolymerizable compound may be included in an amount of 1 wt% to 10 wt%, for example 3 wt% to 8 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, curing occurs sufficiently during exposure in the pattern forming process, thereby providing excellent reliability and excellent developability in an alkaline developer.

(D) photopolymerization initiator

The photopolymerization initiator is an initiator generally used in the photosensitive resin composition, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, a triazine-based compound, an oxime-based 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-butyltrichloroacetophenone, pt -Butyldichloro acetophenone, 4-chloro acetophenone, 2,2'-dichloro-4-phenoxy acetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholino propane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one, etc. are mentioned.

Examples of the benzophenone-based compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenyl benzophenone, hydroxy benzophenone, acrylated benzophenone, 4,4'-bis (dimethyl amino) benzophenone, 4,4 '-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc. are mentioned.

Examples of the thioxanthone-based compound include thioxanthone, 2-methylthioxanthone, isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, 2- Chlorothioxanthone etc. are mentioned.

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

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 an O-acyloxime-based compound, 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, and 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-dione2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1,2-dione2 -oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octane-1-oneoxime-O-acetate, 1-(4-phenylsulfanylphenyl)-butan-1-oneoxime-O- Acetate etc. are mentioned.

As the photopolymerization initiator, a carbazole-based compound, a diketone-based compound, a sulfonium borate-based compound, a diazo-based compound, an imidazole-based compound, a biimidazole-based compound, or a fluorene-based compound may be used in addition to the above compound.

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

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

The photopolymerization initiator may be included in an amount of 0.1 wt% to 5 wt%, for example 0.1 wt% to 3 wt%, based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, curing occurs sufficiently during exposure in the pattern forming process to obtain excellent reliability, and the pattern has excellent heat resistance, light resistance and chemical resistance, and excellent resolution and adhesion, and A decrease in transmittance can be prevented.

(E) solvent

As the solvent, materials having compatibility with but not reacting with the colorant, the binder resin, the photopolymerizable compound and the photoinitiator may 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; 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 methylethyl 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 methyl 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; lactic acid esters such as methyl lactate and ethyl lactate; alkyl oxyacetic acid esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetate alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl 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 methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; 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 propionate, 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl propionate, 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl propionate alkyls such as ethyl methyl propionate; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methyl ethyl propionate, ethyl hydroxyacetate, and 2-hydroxy-3-methyl methyl butanoate; Ketonic acid esters such as ethyl pyruvate, and the like, and N-methylformamide, N,N-dimethylformamide, N-methylformanilad, N-methylacetamide, and N,N-dimethylacetamide. , N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, benzoic acid and high boiling point solvents such as ethyl, 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; 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 can be used.

The solvent may be included in a balance, for example, 25 wt% to 80 wt%, based on the total amount of the photosensitive resin composition. When the solvent is included within the above range, since the photosensitive resin composition has an appropriate viscosity, processability in manufacturing the color filter is excellent.

(F) other additives

The photosensitive resin composition according to an embodiment 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 silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group, and an epoxy group to improve adhesion to the substrate.

Examples of the silane coupling agent include trimethoxysilyl benzoic acid, γ methacryl oxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, γ isocyanate propyl triethoxysilane, γ glycidoxy propyl tri Methoxysilane, β-epoxycyclohexyl)ethyltrimethoxysilane, etc. are mentioned, and these can be used individually or in mixture of 2 or more types.

The silane coupling agent may be included in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent 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 the formation of defects, if necessary.

Examples of the surfactant include BM-1000 ^® , BM-1100 ^® and the like by BM Chemie; Dai Nippon Inky Chemical Co., Ltd. Mecha Pack F 142D ^® , F 172 ^® , F 173 ^® , F 183 ^® , F 554 ^® and the like; Sumitomo 3M Co., Ltd.'s Prorad FC-135 ^® , copper FC-170C ^® , copper FC-430 ^® , copper FC-431 ^®, etc.; Asahi Grass Co., Ltd.'s Saffron S-112 ^® , Copper S-113 ^® , S-131 ^® , S-141 ^® , S-145 ^{® and} others; Toray silicone (Note)社SH-28PA ^®, copper -190 ^®, may be used copper ^® -193, fluorine-based surfactants and commercially available under the name, such as ^{SZ-6032 ®, SF-8428} ®.

The surfactant may be used in an amount of 0.001 parts by weight 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 secured, staining does not occur, and wettability to a glass substrate is excellent.

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, there is provided a photosensitive resin film prepared using the photosensitive resin composition according to the embodiment.

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

applying the photosensitive resin composition onto a support 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; developing the exposed photosensitive resin composition film with an aqueous alkali solution to prepare a photosensitive resin film; and heat-treating the photosensitive resin film. Since the conditions and the like in the process are well known in the art, a detailed description thereof will be omitted herein.

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

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 yellow dye)

Synthesis Example 1: Synthesis of yellow dye

Add hydrochloric acid (2.5 mL) and sodium nitrate (2 mL of 1.25M aqueous solution) to 4-Aminophthalonitrile (2.5 mmol) to make azonium ions, and then put it in a weakly basic aqueous solution of barbituric acid (2.5 mmol) in NaOH aqueous solution. Azo compounds were made. At this time, the obtained solid was filtered, purified and vacuum dried, 1-iodobutane (5.5 mmol) and potassium carbonate (7.5 mmol) were added, and the reaction was performed in a DMF solvent, followed by purification and vacuum drying to obtain yellow dye 1.

(Synthesis of Violet Dye)

Synthesis Example 2

(1) Synthesis of the compound represented by the formula (A)

2-Bromoacetophenone (1 mol) was added to DMF (dimethylformamide, 250 ml) and stirred at room temperature. Potassium phthalimide (0.95 mol) was added to the reaction solution, followed by stirring for 3 hours. After completion of the reaction, the mixture was precipitated using 2500 ml of water, filtered and dried to obtain a compound represented by Formula A. (Yield: 78%)

(2) Synthesis of the compound represented by the formula (B)

Cyanoacetic acid (1.46 mol) and 2,6-di-tert-butyl-4-methylcyclohexanol (1.33 mol) were added to toluene (500 ml) and stirred at room temperature. Pyridine (1.59 mol) was added to the reaction solution and stirred. Acetic anhydride (2.65 mol) was added to this solution and stirred for 6 hours to complete the reaction. The reaction solution was washed twice with a 10% aqueous hydrochloric acid solution (500 g), and then washed twice with an aqueous sodium chloride solution (500 g). After removing water with magnesium sulfate, filtration and drying were performed to obtain a compound represented by the above formula (B). (Yield: 62.5%)

(3) Synthesis of the compound represented by the formula (C)

The compound represented by Formula A (3.8 mol) and the compound represented by Formula B (4.15 mol) were added to a mixture of methanol (10 ml) and water (10 ml), followed by stirring. After adding dropwise a 48% sodium hydroxide aqueous solution (8.36 mol) to the reaction solution, the temperature was raised to 70° C. and stirred for 3 hours. After monitoring the reaction by TLC, the reaction was completed. After cooling to room temperature, the mixture was filtered, washed with water and hexane, and dried to obtain a compound represented by the above formula (C). (Yield: 69%)

(4) Synthesis of the compound represented by the formula (D)

The compound represented by Formula C (0.38 mol) was added to acetic acid (800 g) and stirred at room temperature. Triethyl orthoformate (0.23 mol) was added to the reaction solution, the temperature was raised to 130° C., and the mixture was stirred for 10 hours. After completion of the reaction, acetonitrile (100 g) was used to filter, and acetonitrile (100 g) was added and stirred. After filtration, the solution was washed with acetonitrile (100 g) and dried to obtain a compound represented by the above formula (D). (Yield: 68.7%)

(5) Synthesis of the compound represented by the formula (E)

The compound represented by Formula D was added to toluene (17 ml) and stirred. Sodium hydroxide (40% aqueous solution, 0.036 mmol) was added dropwise to this solution. Then, TBAB (tetrabutylammonium bromide, 0.0012 mmol) was added at room temperature and stirred for 30 minutes, and the temperature of the reaction solution was lowered to 0° C. using an ice bath. To the reaction solution was added 1-adamantanecarbonyl chloride (0.072. mmol). After removing the ice bath, the reaction was completed after stirring for 2 hours while raising the temperature to room temperature. It was washed with 100 ml of water and 100 ml of ethyl acetate and dried to obtain a compound represented by Formula E. (Yield: 72.5%)

(6) Synthesis of a compound represented by Formula F

4-tert-butylbenzoic acid (0.14 mol) and sodium methoxide (30% methanol solution, 0.14 mol) were added to a water (60 ml)/methanol (90 ml) mixture and stirred. Zinc sulfate heptahydrate (0.06 mol) was added to this solution. The reaction was completed by stirring at room temperature for 1 hour. After the reaction, the mixture was filtered and washed with 1000 ml of water and 1000 ml of methanol to obtain a compound represented by the above formula (F). (Yield: 90.1%)

(7) Synthesis of the compound (dye) represented by the formula G

The compound represented by the formula E (0.642 mmol) and the compound represented by the formula F (0.835 mmol) were added to 10 ml of ethanol and stirred at room temperature. The reaction was confirmed by TCL and completed. The ethanol of the reaction solution was dried, washed with 100 ml of methylene chloride and 100 ml of water, and dried to obtain a compound (dye) represented by the above formula (G). (Yield: 81.7%, Maldi tof Mass: 1454.8)

(Synthesis of photosensitive resin composition)

Examples 1, 2 and Comparative Examples 1 to 4

The photosensitive resin compositions according to Examples 1, 2 and Comparative Examples 1 to 4 were prepared by mixing the components mentioned below in the composition shown in Table 1 below.

Specifically, a photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours, and then a binder resin and a photopolymerizable compound were added thereto and stirred at room temperature for 2 hours. Then, a blue pigment dispersion, a yellow dye, a violet dye, and other additives were added to the obtained reactant as a colorant, and the mixture was stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: % by weight) Example 1 Example 2 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 (a-1) blue pigment dispersion 26.0 36.0 52.0 45.0 19.0 30.0 (a-2) yellow dye 0.15 0.1 0.1 - - - (a-3) violet dye (a-3-1) 0.35 - - - 0.3 - (a-3-2) - 0.4 - - - 0.4 (B) binder resin 12.7 10.5 9.1 10.9 15.0 12.2 (C) photopolymerizable compound 7.2 6.1 5.4 6.4 8.3 7.1 (D) photoinitiator 0.6 0.5 0.4 0.5 0.6 0.6 (E) solvent 52.8 46.2 32.8 37.0 56.6 49.5 (F) other additives 0.2 0.2 0.2 0.2 0.2 0.2

(A) Colorant

(a-1) C.I. Pigment Blue 15:6 dispersion (SANYO company; pigment solids 10%)

(a-2) Yellow dye: the compound of Synthesis Example 1

(a-3) violet dye

(a-3-1) Violet 2B (Kyungin Corporation)

(a-3-2) Compound of Synthesis Example 2 (Compound represented by Formula G)

(B) binder resin

Acrylic binder resin (SP-RY-25, Showadenko)

(C) photopolymerizable compound

Dipentaerythritol hexaacrylate (DPHA) (Nippon Kayaku Co.)

(D) photopolymerization initiator

OXE01 (Basf)

(E) solvent

PGMEA (Kyohwa)

(F) additives

Fluorine surfactant (F-554, DIC)

(Evaluation) Color coordinates and luminance

The photosensitive resin composition prepared in Examples 1 and 2 and Comparative Examples 1 to 4 was applied to a thickness of 1 μm to 3 μm on a degreasing-washed glass substrate having a thickness of 1 mm at a condition of 250 rpm to 350 rpm, and , and dried for 2 minutes on a hot plate at 90° C. to obtain a coating film. Then, under the condition of 50 mJ/cm ² , the entire surface was exposed using a high-pressure mercury lamp with a dominant wavelength of 365 nm under the condition of 50 mJ/cm 2 . The development history was given by developing for 60 seconds under the condition of After that, it was dried for 20 minutes in a hot air circulation drying furnace at 230° C. to obtain a color chip.

The prepared color specimen was evaluated for color characteristics based on C light source using a spectrophotometer (MCPD3000, Otsuka electronic), and the luminance (Y) was calculated based on the CIE color coordinate (By 0.0510), and the results are shown in Table 2 below. indicated.

CIE color coordinates Luminance (%) Bx By Example 1 0.1473 0.0510 7.99 Example 2 0.1473 0.0510 8.21 Comparative Example 1 0.1473 0.0510 7.97 Comparative Example 2 0.1500 0.0510 10.16 Comparative Example 3 0.1517 0.0510 11.12 Comparative Example 4 0.1503 0.0510 10.78

From Table 2, when a blue colorant, a yellow dye having a maximum absorption wavelength in a wavelength region of 360 nm to 390 nm and a transmittance of 95% or more in a wavelength region of 450 nm to 900 nm, and a violet dye are used together, high color coordinates are implemented and at the same time It can be confirmed that excellent luminance is exhibited. Specifically, from Example 1, Example 2 and Comparative Example 1, when the blue colorant, yellow dye, and violet dye are used together, it can be confirmed that high color coordinates can be realized and luminance deterioration can be prevented at the same time by reducing the total amount of colorant used. have. In addition, through Comparative Examples 2 to 4, when the colorant composition according to the embodiment is not present, it can be confirmed that even if the luminance is excellent, it is impossible to implement high color coordinates.

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

Claims (14)

(A) a colorant comprising the following (a-1) to (a-3);
(a-1) a blue dye, a blue pigment, or a mixture thereof;
(a-2) having a maximum absorption wavelength in a wavelength range of 360 nm to 390 nm, and a wavelength of 450 nm to 900 nm
a yellow dye having a transmittance of 95% or more in the area; and
(a-3) a violet dye represented by the following Chemical Formula 1-1 or 1-2;
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 and 1-2,
R ¹⁰¹ to R ¹⁰⁵ 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,
R ¹⁰⁶ is a hydrogen atom,
R ¹⁰⁷ is a substituted or unsubstituted adamantyl group,
R ¹⁰⁸ to R ¹¹⁰ are each independently a substituted or unsubstituted C1 to C20 alkyl group,
n is an integer from 1 to 5;
L is represented by the following formula 1-3-1,
[Formula 1-3-1]

In Formula 1-3-1,
R ¹¹¹ is a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted amino group, or a substituted or unsubstituted acyl group,
(B) binder resin;
(C) a photopolymerizable compound;
(D) a photoinitiator; and
(E) solvent
A photosensitive resin composition comprising a.
According to claim 1,
The violet dye is contained in an amount of 0.1 wt% to 2 wt% based on the total amount of the photosensitive resin composition.
delete delete delete According to claim 1,
The yellow dye is an azo dye photosensitive resin composition.
According to claim 1,
The yellow dye is included in an amount of 0.01 wt% to 1 wt% based on the total amount of the photosensitive resin composition.
According to claim 1,
The yellow dye is included in an amount less than that of the violet dye, and the violet dye is included in an amount less than that of the blue dye.
According to claim 1,
The binder resin is an acrylic binder resin, a cardo-based binder resin, or a photosensitive resin composition comprising a combination thereof.
According to claim 1,
The photosensitive resin composition is based on the total amount of the photosensitive resin composition,
2% to 40% by weight of the colorant;
3 wt% to 20 wt% of the binder resin;
1 wt% to 10 wt% of the photopolymerizable compound;
0.1 wt% to 5 wt% of the photopolymerization initiator and
the remaining amount of the solvent
A photosensitive resin composition comprising a.
According to claim 1,
The photosensitive resin composition further comprises an epoxy compound, a silane coupling agent, a surfactant, or a combination thereof.
delete The photosensitive resin film produced using the photosensitive resin composition of any one of Claims 1, 2, and 6-11.
A color filter comprising the photosensitive resin film of claim 13 .