KR20170024840A

KR20170024840A - Photosensitive resin composition and color fliter

Info

Publication number: KR20170024840A
Application number: KR1020150120370A
Authority: KR
Inventors: 박세희; 이영기; 정민결; 형경희; 황지현
Original assignee: 삼성에스디아이 주식회사
Priority date: 2015-08-26
Filing date: 2015-08-26
Publication date: 2017-03-08

Abstract

(A) a dye comprising a compound represented by the following formula (1); (B) a binder resin; (C) a photopolymerization initiator; (D) a photopolymerizable monomer; And (E) a solvent, wherein a compound represented by the following general formula (1) is contained in an amount of 0.1 to 5 wt% based on the total amount of the photosensitive resin composition, and a color filter.
[Chemical Formula 1]

(Wherein each substituent is as defined in the specification).

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a photosensitive resin composition,

The present invention relates to a photosensitive resin composition and a color filter.

In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.

Therefore, it is necessary to study a compound suitable as a dye used in the production of a photosensitive resin composition.

One embodiment of the present invention is to provide a photosensitive resin composition.

Another embodiment of the present invention is to provide a color filter manufactured using the photosensitive resin composition.

One embodiment of the present invention is a dye-sensitized solar cell comprising (A) a dye comprising a compound represented by the following formula (1); (B) a binder resin; (C) a photopolymerization initiator; (D) a photopolymerizable monomer; And (E) a solvent, wherein the compound represented by the following general formula (1) is contained in an amount of 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition.

[Chemical Formula 1]

In Formula 1,

M is Cu, Zn, Co or Mo,

R ¹ to R ¹⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted C3 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 C20 < / RTI >

At least one of R ¹ to R ¹⁶ is a substituted C3 to C20 alkoxy group,

The substituted C3 to C20 alkoxy group -OR * ¹⁸ is represented by (wherein R ¹⁸ is a substituted C3 to C20 alkyl group).

The substituted C3 to C20 alkoxy group may include an isopropyl group or a t-butyl group at the terminal.

The substituted C3 to C20 alkoxy group may be represented by the following general formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

L ¹ and L ² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The compound represented by the formula (1) may be represented by any one selected from the group consisting of a compound represented by the following formula (4) and a compound represented by the following formula (13).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Chemical Formulas 4 to 13,

At least one of R ¹ to R ¹⁶ is a substituted C 3 to C 20 alkoxy group, and at least one of R ¹ to R ¹⁶ may be a substituted or unsubstituted C6 to C20 aryloxy group.

The substituted or unsubstituted C6 to C20 aryloxy group may be represented by the following general formula (14).

[Chemical Formula 14]

In Formula 14,

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

The compound represented by Formula 1 may be a compound represented by Formula 15 or a compound represented by Formula 22 below.

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

In the above Chemical Formulas 15 to 22,

The dye may be a green dye.

The green dye may have a maximum transmittance in a wavelength range of 445 nm to 560 nm.

The photosensitive resin composition may further comprise a pigment.

The pigment may comprise a yellow pigment, a green pigment or a combination thereof.

The photosensitive resin composition may contain 0.1% by weight to 5% by weight of the dye relative to the total amount of the photosensitive resin composition; 5% to 40% by weight of a pigment dispersion comprising the pigment; 0.5 to 15% by weight of the binder resin; 0.1% by weight to 10% by weight of the photopolymerization initiator; 0.5% to 15% by weight of the photopolymerizable monomer and the balance of the solvent.

The binder resin may be an acrylic binder resin.

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

Another embodiment of the present invention provides a color filter manufactured using the photosensitive resin composition.

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

The photosensitive resin composition according to one embodiment of the present invention can provide a color filter having excellent brightness, contrast ratio, and heat resistance, including a green dye having an excellent green spectroscopic characteristic and a high molar extinction coefficient.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

Means that at least one hydrogen atom of the functional group of the present invention is substituted with 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, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted alicyclic alkyl group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.

Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.

Unless otherwise specified in the present specification, the term "aliphatic organic group" means a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C1 to C20 alkylene group, a C2 to C20 alkenylene group, Means a C1 to C15 alkyl group, a C2 to C15 alkenyl group, a C2 to C15 alkynyl group, a C1 to C15 alkylene group, a C2 to C15 alkenylene group or a C2 to C15 alkynylene group, Means a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C3 to C20 cycloalkylene group, a C3 to C20 cycloalkenylene group or a C3 to C20 cycloalkynylene group, Include a C3 to C15 cycloalkyl group, a C3 to C15 cycloalkenyl group, a C3 to C15 cycloalkynyl group, a C3 to C15 cycloalkylene group, a C3 to C15 cycloalkenylene group, Means a C6 to C20 aryl group or a C6 to C20 arylene group, specifically, a C6 to C16 aryl group or a C6 to C16 arylene group, and the term " aromatic hydrocarbon group " means a C3 to C15 cycloalkynylene group, The "heterocyclic group" means a C2 to C20 cycloalkyl group containing 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si and combinations thereof in one ring, C2 to C20 cycloalkyl Means a C2 to C20 cycloalkenyl group, a C2 to C20 cycloalkenylene group, a C2 to C20 cycloalkynyl group, a C2 to C20 cycloalkynylene group, a C2 to C20 heteroaryl group or a C2 to C20 heteroarylene group, Include C 2 to C 15 cycloalkyl groups containing 1 to 3 hetero atoms selected from the group consisting of O, S, N, P, Si and combinations thereof in one ring, C 2 to C 15 C2 to C15 cycloalkenyl group, C2 to C15 cycloalkenyl group, C2 to C15 cycloalkynylene group, C2 to C15 cycloalkynylene group, C2 to C15 heteroaryl group or C2 to C15 heteroarylene group .

As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.

Also, unless otherwise specified herein, "hetero" means that at least one heteroatom of N, O, S, and P is included in the formula.

&Quot; (Meth) acrylic acid "refers to both" acrylic acid "and" methacrylic acid " "It means both are possible.

Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.

In the present specification, "*" means the same or different atom or part connected to a chemical formula.

One embodiment includes (A) a dye comprising a compound represented by Formula 1 below; (B) a binder resin; (C) a photopolymerization initiator; (D) a photopolymerizable monomer; And (E) a solvent, wherein the compound represented by the following general formula (1) is contained in an amount of 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition.

[Chemical Formula 1]

In Formula 1,

M is Cu, Zn, Co or Mo,

At least one of R ¹ to R ¹⁶ is a substituted C3 to C20 alkoxy group,

The compound represented by Formula 1 has excellent green spectroscopic characteristics and molar extinction coefficient, and is capable of expressing vivid colors even in a small amount. Furthermore, the color filter prepared from the photosensitive resin composition containing the compound represented by the formula (1) in an amount of 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition has not only excellent brightness and contrast ratio but also excellent heat resistance.

Each component will be described in detail below.

(A) Dye

The photosensitive resin composition according to one embodiment includes a dye, and the dye includes the compound represented by the above formula (1).

In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, since the compound represented by the above formula (1) can achieve excellent color characteristics such as high brightness and high contrast ratio even in a small amount, the production cost can be reduced.

In addition, although the solubility of the pigment in the organic solvent is very low, there is a problem that the stability is poor. However, the compound represented by the formula (1) has higher solubility in the organic solvent than the pigment, and the brightness and the contrast ratio can be improved.

For example, in Formula 1, at least one of R ¹ to R ¹⁶ is a substituted C 3 to C 20 alkoxy group, and the substituted C 3 to C 20 alkoxy group is * -OR ¹⁸ (wherein R ¹⁸ is a substituted C 3 to C 20 alkyl group) And the substituted C3 to C20 alkoxy group may include an isopropyl group or a t-butyl group at the terminal.

For example, the substituted C3 to C20 alkoxy group may be represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

The compound represented by Formula 1 may be a compound represented by Formula 4 or a compound represented by Formula 13 below.

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Chemical Formulas 4 to 13,

For example, L ¹ and L ² each independently represent a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, a substituted or unsubstituted butylene group, a substituted or unsubstituted pentyl A substituted or unsubstituted heptylene group, a substituted or unsubstituted octylene group, a substituted or unsubstituted nonylene group, or a substituted or unsubstituted decylene group.

In Formula 1, at least one of R ¹ to R ¹⁶ is a substituted C 3 to C 20 alkoxy group, and at least one of R ¹ to R ¹⁶ may be a substituted or unsubstituted C6 to C20 aryloxy group. For example, in Formula 1, R ¹ to R ¹⁶ may include the substituted C3 to C20 alkoxy group and the substituted or unsubstituted C6 to C20 aryloxy group.

[Chemical Formula 14]

In Formula 14,

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

In the above Chemical Formulas 15 to 22,

Since the compound represented by Formula 1 includes a substituted alkoxy group such as an alkoxy group including an isopropyl group or a t-butyl group at the terminal thereof, it is possible to express a clearer color in a small amount, and when used as a colorant, It is possible to manufacture a display device having excellent color characteristics such as contrast ratio. For example, the compound represented by Formula 1 may be a coloring agent such as a dye, for example, a green dye, for example, a dye having a maximum transmittance in a wavelength range of 445 nm to 560 nm.

Further, the compound represented by Formula 1 may further include an aryloxy group substituted in addition to the substituted alkoxy group. In this case, the solubility and luminance of the organic solvent may be further improved.

Meanwhile, the compound represented by the formula (1), for example, the dye comprising the compound represented by the formula (1) may be contained in an amount of 0.1 to 5 wt%, for example, 0.5 to 5 wt% based on the total amount of the photosensitive resin composition . When the compound represented by the above formula (1) is contained in the above content range, the color characteristic is excellent without lowering the heat resistance. Specifically, when the dye represented by the formula (1), for example, the dye containing the compound represented by the formula (1) is contained in an amount of less than 0.1% by weight based on the total amount of the photosensitive resin composition, the coloring property such as brightness and contrast ratio And the dye represented by the formula (1), for example, the compound represented by the formula (1), is contained in an amount of more than 5% by weight based on the total amount of the photosensitive resin composition, the color characteristic is excellent but the heat resistance is lowered .

(A ') pigment

The photosensitive resin composition according to one embodiment may further include a pigment.

The pigment is used in the form of a pigment dispersion, and the pigment dispersion may include a solid pigment, a dispersant, a solvent, and the like. In this case, the pigment of solid content relative to the total amount of the pigment dispersion may be 8 wt% to 30 wt%, for example 8 wt% to 15 wt%, for example 8 wt% to 12 wt%. In this case, the pigment can be effectively dispersed, dispersion stability can be ensured, and color characteristics such as luminance can be improved.

The yellow pigments have a C.I. Pigment yellow 139, C.I. Pigment yellow 138, C.I. Pigment yellow 150, etc. These may be used alone or in combination of two or more.

The green pigment may be a halogenated phthalocyanine-based green pigment, for example, a compound classified as a pigment in the color index. Green pigment (Color Index Pigment Green) 7, 36, 58 and the like.

The primary particle diameter of the pigment may be from 10 nm to 80 nm, for example from 10 nm to 70 nm. When the primary particle diameter is within the above-mentioned particle diameter range, the stability in the pigment dispersion is excellent and there is no fear of deterioration of the resolution of the pixel, which is preferable.

As the solvent in the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether or 3-methoxy-1-butanol can be used Among them, propylene glycol monomethyl ether acetate can be preferably used. At this time, the content of the solvent is preferably adjusted so that the solid content of the pigment dispersion is 5 wt% to 30 wt%, but is not limited thereto.

The solvent may be present in an amount of from 30% by weight to 90% by weight, such as from 40% by weight to 90% by weight, such as from 50% by weight to 90% by weight, such as from 60% by weight to 90% 70% to 90% by weight, such as 80% to 90% by weight.

In addition, the pigment dispersion may further include a dispersant. As the dispersing agent, nonionic, anionic or cationic dispersing agents can be used. Examples thereof include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts , A sulfonic acid ester, a sulfonic acid salt, a carboxylic acid ester, a carboxylate, an alkylamide alkylene oxide adduct, and an alkylamine. These dispersants may be used singly or in combination of two or more.

The dispersing agent may be contained in an amount of 0.01 to 15% by weight based on the total amount of the photosensitive resin composition. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition is excellent, so that excellent stability, developability and patternability can be obtained.

The amount of the pigment dispersion containing the pigment is preferably 5 wt% to 40 wt%, for example, 5 wt% to 30 wt% with respect to the total amount of the photosensitive resin composition. When the content of the pigment dispersion is within the above range, reliability and developability such as color characteristics such as luminance and chemical resistance can be improved.

The photosensitive resin composition may be prepared by mixing a dye and a pigment in a weight ratio of 1: 99 to 99: 1, and mixing the mixture at a weight ratio of, for example, 1: 5 to 1:60, . When they are mixed in the above-mentioned weight ratio range, they can have a high contrast ratio while maintaining color characteristics, and can have excellent heat resistance.

(B) binder resin

The photosensitive resin composition according to one embodiment includes a binder resin, for example, an acrylic binder resin.

The acrylic binder resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and may be a resin containing at least one acrylic repeating unit.

The acrylic binder resin may be a copolymer of the second ethylenically unsaturated monomer.

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% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.

The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (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 aminoalkyl 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; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly 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- Acrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and a benzyl methacrylate copolymer. However, it is not limited to these, More than two species may be used in combination.

The weight average molecular weight of the binder resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 6,000 g / mol to 10,000 g / mol. When the weight average molecular weight of the binder resin is within the above range, the photosensitive resin composition is excellent in physical and chemical properties, has an appropriate viscosity, and is excellent in adhesion with a substrate in the production of a color filter.

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

The binder resin may be a form in which a solid binder resin is dissolved in a solvent described later. The solid binder resin may be contained in an amount of 15% by weight to 40% by weight based on the total amount of the binder resin in which the solid binder resin is dissolved.

The binder resin may be contained in an amount of 0.5% by weight to 15% by weight, for example, 1% by weight to 10% by weight based on the total amount of the photosensitive resin composition. When the binder resin is contained within the above range, the color filter is excellent in developing property and the crosslinkability is improved, so that excellent surface smoothness can be obtained.

(C) Light curing Initiator

The photopolymerization initiator may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, an oxime-based compound or a combination thereof as an initiator generally used in a photosensitive resin composition.

Examples of the acetophenone compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt Dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropane-1 2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one.

Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

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

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

Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -Dimethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) (Trichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) - 4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol-1-yl) -Bis (trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like. .

Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- - On can be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O- Acetate and the like.

For example, the photopolymerization initiator may include an oxime-based compound and an acetophenone-based compound, and the oxime-based compound may include more of the acetophenone-based compound. For example, the oxime compound and the acetophenone compound may be contained in a weight ratio of 7: 3 to 5: 5.

The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.

The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.

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

The photopolymerization initiator may be included in an amount of 0.1% by weight to 10% by weight, for example, 0.1% by weight to 5% by weight based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, it is possible to obtain sufficient reliability due to sufficient curing during exposure in the pattern formation step, to have excellent heat resistance, light resistance and chemical resistance, excellent resolution and adhesion, It is possible to prevent the transmittance from being lowered.

(D) Photopolymerization Monomer

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

By having the ethylenically unsaturated double bond, the photopolymerizable monomer can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.

Specific examples of the photopolymerizable monomer 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, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.

Examples of 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 ^® and TC-120S ^{® from} Nihon Kayaku Co., Ltd.; 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 ^® and R-604 ^{® from} Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of ^{社V-260 ®, V-} 312 ®, V-335 HP ®. 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 -7100 ^® , copper M-8030 ^® , copper M-8060 ^® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ^®, copper DPCA-20 ^®, ^® copper -30, -60 ^® copper, copper ^® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ^®, copper ^® -300, -360 ^® copper, copper -GPT ^®, copper -3PA ^®, and the like copper -400 ^®. These products may be used alone or in combination of two or more.

The photopolymerizable monomer may be treated with an acid anhydride to give better developing properties.

The photopolymerizable monomer may be contained in an amount of 0.5% by weight to 15% by weight, for example, 1% by weight to 10% by weight based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is contained within the above range, the photopolymerizable monomer sufficiently cures upon exposure in the pattern forming step, and therefore, the photopolymerizable monomer is excellent in reliability and developability in an alkaline developer.

(E) Solvent

The solvent may be a material which has compatibility with the dye, the pigment, the binder resin, the photopolymerization initiator, the photopolymerizable monomer, and the like but does not react.

Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl 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 methylethylcarbitol, diethylcarbitol, 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- ; 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; Oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; 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 contained in a residual amount, for example, 20% by weight to 90% by weight based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, and thus the processability in the production of the color filter is excellent.

(F) Other additives

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

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

Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.

The epoxy compound may be contained 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 contained within the above range, the adhesiveness and storage stability are excellent.

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 or an epoxy group in order to improve the adhesion with the substrate.

Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatepropyltriethoxysilane,? -Glycidoxine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.

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 contained within the above range, the adhesion and storage stability are excellent.

The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.

Examples of the surfactants include, BM Chemie BM-1000 ^® of社, BM-1100 ^®, and the like; Mechacup F 142D ^® , copper F 172 ^® , copper F 173 ^® , copper F 183 ^® and the like manufactured by Dainippon Ink & Chemicals Incorporated; Sumitomo M. (Note)社Pro rod FC-135 ^®, the same FC-170C ^®, copper FC-430 ^®, the same FC-431 ^®, and the like; Asahi Grass Co., Saffron S-112 ^® of社, such S-113 ^®, the same S-131 ^®, the same S-141 ^®, the same S-145 ^®, and the like; 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 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, coating uniformity is ensured, no staining occurs, and wetting of the glass substrate is excellent.

The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.

Another embodiment provides a color filter manufactured using the photosensitive resin composition.

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

Applying the photosensitive resin composition on 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 produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.

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

(Synthesis of Compound)

Synthetic example 1: Synthesis of Compound Represented by Formula 8-1

(1) 3,4,5,6-Tetrachlorophthalonitrile (10 g), Diazabicycloundec-7-ene (6.2 g), 3-methyl-1-butanol (3.3 g) and Tetrahydrofuran (50 ml) The reaction was carried out at room temperature for 6 hours. After completion of the reaction, the reaction solution was filtered and vacuum distilled, and then ethyl acetate (10 mL) and hexane (100 mL) were added to purify and filtrate to obtain 10 g of the precursor compound 1 (substituted phthalonitrile) represented by the following formula .

(A)

(2) Into a 100 mL flask, the precursor compound 1 (4.2 g) and benzonitrile (40 mL) represented by the above formula (A) are added and heated. After the solid is dissolved, Zinc Iodide (1.0 g) is added and the mixture is refluxed while heating. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (8-1).

[Formula 8-1]

MALDI-TOF MS, m / z Calcd . for C ₅₂ H ₄₄ Cl ₁₂ N ₈ O ₄ Zn, [M + H] + 1336.90; found 1335.80

Synthetic example 2: Synthesis of Compound Represented by Formula 7-1

The precursor compound 1 (3.6 g), 3,4,5,6-tetrachlorophthalonitrile (1 g) and benzonitrile (40 mL) represented by the above formula (A) were placed in a 100 mL flask and heated. After solving the solid, Zinc Iodide And reflux while heating. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (7-1).

[Formula 7-1]

MALDI-TOF MS, m / z Calcd . for C ₄₇ H ₃₃ Cl ₁₃ N ₈ O ₃ Zn, [M + H] + 1284.78; found 1283.11

Synthetic example 3: Synthesis of Compound Represented by Formula 5-1

The precursor compound 1 (2.4 g), 3,4,5,6-tetrachlorophthalonitrile (2 g) and benzonitrile (40 mL) represented by the above formula (A) was added to a 100 mL flask and the mixture was heated. Zinc Iodide And reflux while heating. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (5-1).

[Formula 5-1]

MALDI-TOF MS, m / z Calcd . for C ₄₂ H ₂₂ Cl ₁₄ N ₈ O ₂ Zn, [M + H] + 1232.67; found 1231.48

Synthetic example 4: Synthesis of Compound Represented by Formula 4-1

(1.2 g), 3,4,5,6-Tetrachlorophthalonitrile (3 g) and benzonitrile (40 mL) were added to a 100 mL flask and heated to dissolve the solid. Then, Zinc Iodide (1.0 g) And reflux while heating. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula 4-1.

[Formula 4-1]

MALDI-TOF MS, m / z Calcd . for C ₃₇ H ₁₁ Cl ₁₅ N ₈ OZn, [M + H] + 1180.56; found 1179.74

Synthetic example 5: Synthesis of the compound represented by the formula (15-1)

(1) To a 500 ml flask was added 3-nitro phthalonitrile (5.0 g), 4-hydroxy benzoinic acid isopropyl ester (3.0 g), Tetrahydrofuran (30 ml) and Potassium Carbonate (5.8 g) Respectively. After the completion of the reaction, the reaction mixture was filtered and vacuum distilled. Ethyl acetate (10 mL) and hexane (100 mL) were added and purified by column chromatography to obtain 3.6 g of precursor compound 2 (substituted phthalonitrile).

(2) A precursor compound 1 (3.6 g) represented by the above formula (A), 1.2 g of the precursor compound 2 and 40 mL of benzonitrile were placed in a 100 mL flask, and after the solid was dissolved, Zinc Iodide Continue heating while refluxing. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (15-1).

[Formula 15-1]

MALDI-TOF MS, m / z Calcd . for C ₅₇ H ₄₇ Cl ₉ N ₈ O ₆ Zn, [M + H] + 1325.00; found 1324.51

Synthetic example 6: Synthesis of the compound represented by the formula (16-1)

2.4 g of the precursor compound 1 (2.4 g), the precursor compound 2 (2.4 g) and benzonitrile (40 ml) were added to a 100 ml flask and heated to dissolve the solid. Zinc Iodide (1.0 g) Reflux. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (16-1).

[Formula 16-1]

MALDI-TOF MS, m / z Calcd . for C ₆₂ H ₅₀ Cl ₆ N ₈ O ₈ Zn, [M + H] + 1313.11; found 1312.23

Synthetic example 7: Synthesis of the compound represented by the formula (17-1)

The precursor compound 1 (2.4 g), the precursor compound 2 (2.4 g) and benzonitrile (40 mL) were added to a 100 mL flask and heated to dissolve the solid. Zinc Iodide (1.0 g) Reflux. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (17-1).

[Formula 17-1]

Synthetic example 8: Synthesis of the compound represented by the formula (18-1)

1.2 g of the precursor compound 1 represented by the above formula A, 3.6 g of the precursor compound 2 (3.6 g) and benzonitrile (40 mL) were added to a 100 mL flask, and after the solid was dissolved, Zinc Iodide (1.0 g) Reflux. After completion of the reaction, the solvent is removed, and the residue is purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, followed by addition of methanol to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (18-1).

[Formula 18-1]

MALDI-TOF MS, m / z Calcd . for C ₆₇ H ₅₃ Cl ₃ N ₈ O ₁₀ Zn, [M + H] + 1301.22; found 1300.95

compare Synthetic example 1: Synthesis of compound represented by formula (23)

(Biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile (1.0 g), 1,8-Diazabicycloundec-7-ene (0.7 g) and 1-pentanol , And 4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile. After that, zinc acetate (0.115 g) was added and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, and hexane was added to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following formula (23).

(23)

Maldi-tof MS 1664.80 m / z

compare Synthetic example 2: Synthesis of Compound Represented by Formula 24

1,6-trichloro-5- (pentyloxy) phthalonitrile (1.0 g), 1,8-Diazabicycloundec-7-ene (0.96 g) and 1-pentanol (20 mL) were placed in a 100 mL flask, (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile. Then, zinc acetate (0.14 g) was added and refluxed while heating. After completion of the reaction, the solvent was removed, and the residue was purified by column chromatography. Dichloromethane was appropriately added to the obtained solid to dissolve the solid, and hexane was added to crystallize it. At this time, the obtained solid was filtered and dried under vacuum to obtain a compound represented by the following chemical formula (24).

&Lt; EMI ID =

Maldi-tof MS 1335.70 m / z

(Synthesis of photosensitive resin composition)

Example 1 to Example 9

The photosensitive resin compositions according to Examples 1 to 9 were prepared by mixing the following components in the compositions shown in Table 1 below.

Specifically, a photopolymerization initiator was dissolved in a solvent, and the mixture was stirred at room temperature for 2 hours. Then, a binder resin and a photopolymerizable monomer were added thereto, followed by stirring at room temperature for 2 hours. Then, a dye (any one of the compounds prepared in Synthesis Examples 1 to 8) and a pigment (in the form of a pigment dispersion) as a colorant were added to the obtained reaction product and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.

(Unit: wt%) Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 dyes A 0.1 - - - - - - - - B - 0.3 - - - - - - - C - - 1.0 - - - - - - D - - - 2.0 - - - - - E - - - - 3.0 - - - - F - - - - - 0.5 4.0 - - G - - - - - - - 4.5 - H - - - - - - - - 5.0 Pigment dispersion A 12.11 12.11 12.11 12.11 12.11 12.11 12.11 12.11 12.11 B 13.4 13.2 12.5 11.5 10.5 13 9.5 9.0 8.5 Binder resin 8.5 8.5 8.5 8.5 8.5 8.5 8.5 8.5 8.5 Photopolymerization initiator A 0.52 0.52 0.52 0.52 0.52 0.52 0.52 0.52 0.52 B 0.46 0.46 0.46 0.46 0.46 0.46 0.46 0.46 0.46 Photopolymerizable monomer 6 6 6 6 6 6 6 6 6 menstruum 58.71 58.71 58.71 58.71 58.71 58.71 58.71 58.71 58.71 Other additives 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Total 100 100 100 100 100 100 100 100 100

(In Table 1, the solid content (pigment) content in the pigment dispersion is 10% by weight based on the total amount of the pigment dispersion, and the solid content in the binder resin is 30% by weight based on the total amount of the binder resin. Means a solution state in which the binder resin is dissolved.)

In Table 1, the components used in the synthesis of the photosensitive resin composition are as follows.

(dyes)

Dye A: Compound of Synthesis Example 1 (compound represented by Formula 8-1)

Dye B: Compound of Synthesis Example 2 (compound represented by Formula 7-1)

Dye C: Compound of Synthesis Example 3 (compound represented by Formula 5-1)

Dye D: Compound of Synthesis Example 4 (compound represented by Formula 4-1)

Dye E: Compound of Synthesis Example 5 (compound represented by Formula 15-1)

Dye F: Compound of Synthesis Example 6 (compound represented by Formula 16-1)

Dye G: Compound of Synthesis Example 7 (compound represented by Formula 17-1)

Dye H: Compound of Synthesis Example 8 (compound represented by Formula 18-1)

(Pigment dispersion)

Pigment dispersion A: Yellow pigment 138 (Sanyo, Y138) Pigment dispersion

Pigment dispersion B: Green pigment 58 (SKC HASS, G58) Pigment dispersion

(Binder resin)

Methacrylic acid / benzyl methacrylate (30/70 weight ratio) copolymer having a weight average molecular weight of 8,000 g / mol (available from Mitsunobu Co., Ltd., NPR1520)

(Photopolymerizable monomer)

Dipentaerythritol hexaacrylate (DPHA)

(Photopolymerization initiator)

Photopolymerization initiator A: Oxime photopolymerization initiator (1,2-octanedione)

Photopolymerization initiator B: Acetophenone photopolymerization initiator (2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-

(menstruum)

Propylene glycol monomethyl ether acetate (Shiny)

(Other additives)

Surfactants (DIC, F-554)

Comparative Example 1 to Comparative Example 4

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

(Unit: wt%) Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 dyes F - 6 - - I - - 4 - J - - - 4 Pigment dispersion A 12.11 12.11 12.11 12.11 B 13.5 7.5 9.5 9.5 Binder resin 8.5 8.5 8.5 8.5 Photopolymerization initiator A 0.52 0.52 0.52 0.52 B 0.46 0.46 0.46 0.46 Photopolymerizable monomer 6 6 6 6 menstruum 58.71 58.71 58.71 58.71 Other additives 0.2 0.2 0.2 0.2 Total 100 100 100 100

(In Table 2, the solid content (pigment) content in the pigment dispersion is 10% by weight based on the total amount of the pigment dispersion, and the solid content in the binder resin is 30% by weight based on the total amount of the binder resin. Means a solution state in which the binder resin is dissolved.)

In Table 2, the respective components used in the synthesis of the photosensitive resin composition are as follows.

(dyes)

Dye F: Compound of Synthesis Example 6 (compound represented by Formula 16-1)

Dye I: Compound of Comparative Synthesis Example 1 (compound represented by Formula 23)

Dye J: Compound of Comparative Synthesis Example 2 (compound represented by Formula 24)

(Pigment dispersion)

Pigment dispersion A: Yellow pigment 138 (Sanyo, Y138) Pigment dispersion

Pigment dispersion B: Green pigment 58 (SKC HASS, G58) Pigment dispersion

(Binder resin)

(Photopolymerizable monomer)

Dipentaerythritol hexaacrylate (DPHA)

(Photopolymerization initiator)

(menstruum)

Propylene glycol monomethyl ether acetate (Shiny)

(Other additives)

Surfactants (DIC, F-554)

(evaluation)

Rating 1: Color coordinates , Luminance, contrast ratio measurement

The photosensitive resin composition prepared in Examples 1 to 9 and Comparative Examples 1 to 4 was coated on a glass substrate having a thickness of 1 mm and a thickness of 2.5 m to 3.5 m, Sec to obtain a coating film. Subsequently, the entire surface of the coating film is exposed with an exposure condition of 50 mJ. Thereafter, it is dried in an oven at 230 DEG C for 28 minutes. The color coordinates (x, y) and the luminance (Y) of the dried coating film were measured using a colorimeter (MCPD3000, Otsuka), and the contrast ratio was measured using a contrast ratio meter (Tsubosaka electronic Co., 1), and the results are shown in Table 3 below.

Evaluation 2: Heat resistance measurement

The photosensitive resin composition prepared in Examples 1 to 9 and Comparative Examples 1 to 4 was coated on a glass substrate having a thickness of 1 mm and a thickness of 2.5 m to 3.5 m, Sec to obtain a coating film. Subsequently, the entire surface of the coating film is exposed with an exposure condition of 50 mJ. Thereafter, the heat resistance was measured by converting the color difference into del (E *) before and after oven drying using a colorimeter while repeating the operation three times for 1 hour in an oven at 230 DEG C, The standard method is shown in Table 3 below.

○: Excellent heat resistance (del (E *) <2.5)

?: Good heat resistance (2.5? Del (E *) <3.5)

Ⅹ: poor heat resistance (del (E *) ≥≥ 3.5)

The color coordinates (x, y) Luminance (Y) Contrast ratio Heat resistance Example 1 (0.2739, 0.560) 61.69 15791 ○ Example 2 (0.2739, 0.560) 61.65 15964 ○ Example 3 (0.2735, 0.560) 61.84 16128 ○ Example 4 (0.2731, 0.560) 62.12 16303 ○ Example 5 (0.2728, 0.560) 62.37 16485 ○ Example 6 (0.2735, 0.560) 61.75 16069 ○ Example 7 (0.2724, 0.560) 62.82 16580 ○ Example 8 (0.2722, 0.560) 62.91 16601 ○ Example 9 (0.2720, 0.560) 63.05 16618 ○ Comparative Example 1 (0.2741, 0.560) 61.09 15762 ○ Comparative Example 2 (0.2715, 0.560) 63.25 16624 X Comparative Example 3 (0.2721, 0.560) 61.56 15911 ○ Comparative Example 4 (0.2726, 0.560) 62.61 16503 X

From Table 3, it can be confirmed that the photosensitive resin composition (Examples 1 to 9) according to one embodiment exhibits better color characteristics and heat resistance than the photosensitive resin compositions of Comparative Examples 1 to 4.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.

Claims

(A) a dye comprising a compound represented by the following formula (1);
(B) a binder resin;
(C) a photopolymerization initiator;
(D) a photopolymerizable monomer; And
(E) Solvent
Lt; / RTI >
Wherein the compound represented by the following formula (1) is contained in an amount of 0.1% by weight to 5% by weight based on the total amount of the photosensitive resin composition:
[Chemical Formula 1]

In Formula 1,
M is Cu, Zn, Co or Mo,
R ¹ to R ¹⁶ are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted C3 to C20 alkoxy group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C6 C20 < / RTI >
At least one of R ¹ to R ¹⁶ is a substituted C3 to C20 alkoxy group,
The substituted C3 to C20 alkoxy group -OR * ¹⁸ is represented by (wherein R ¹⁸ is a substituted C3 to C20 alkyl group).

The method according to claim 1,
The substituted C3 to C20 alkoxy group comprises an isopropyl group or a t-butyl group at the terminal.

The method according to claim 1,
The substituted C3 to C20 alkoxy group is represented by the following general formula (2) or (3)
(2)

(3)

In the general formulas (2) and (3)
L ¹ and L ² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The method according to claim 1,
Wherein the compound represented by Formula 1 is any one selected from the group consisting of a compound represented by Formula 4 and a compound represented by Formula 13:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

In the above Chemical Formulas 4 to 13,
L ¹ and L ² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The method according to claim 1,
At least one of R ¹ to R ¹⁶ is a substituted C3 to C20 alkoxy group,
Wherein at least one of R ¹ to R ¹⁶ is a substituted or unsubstituted C6 to C20 aryloxy group.

6. The method of claim 5,
The substituted or unsubstituted C6 to C20 aryloxy group is represented by the following general formula (14)
[Chemical Formula 14]

In Formula 14,
R ¹⁹ is a hydrogen atom, a halogen atom or a substituted or unsubstituted C1 to C10 alkyl group.

6. The method of claim 5,
Wherein the compound represented by Formula 1 is a compound represented by any one selected from the group consisting of a compound represented by Formula 15 and a compound represented by Formula 22:
[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

[Chemical Formula 20]

[Chemical Formula 21]

[Chemical Formula 22]

In the above Chemical Formulas 15 to 22,
L ¹ and L ² are each independently a substituted or unsubstituted C1 to C10 alkylene group.

The method according to claim 1,
Wherein the dye is a green dye.

9. The method of claim 8,
Wherein the green dye has a maximum transmittance in a wavelength range of 445 nm to 560 nm.

The method according to claim 1,
Wherein the photosensitive resin composition further comprises a pigment.

11. The method of claim 10,
Wherein the pigment comprises a yellow pigment, a green pigment or a combination thereof.

11. The method of claim 10,
The above-mentioned photosensitive resin composition is preferably used in an amount of
0.1% to 5% by weight of said dye;
5% to 40% by weight of a pigment dispersion comprising the pigment;
0.5 to 15% by weight of the binder resin;
0.1% by weight to 10% by weight of the photopolymerization initiator;
0.5% to 15% by weight of the photopolymerizable monomer and
The solvent balance
.

The method according to claim 1,
Wherein the binder resin is an acrylic binder resin.

The method according to claim 1,
Wherein the photosensitive resin composition further comprises an epoxy compound, a silane coupling agent, a surfactant, or a combination thereof.

A color filter produced by using the photosensitive resin composition according to any one of claims 1 to 14.