KR101696182B1 - Resin composition for color filter comprising pyridone azo compounds - Google Patents

Abstract

[화학식 2]

[화학식 3]

[화학식 4]

상기 화학식에서 치환기는 명세서에 정의된 바와 같다.The present invention relates to a resin composition for a color filter comprising a pyridone azo compound, wherein the composition according to the present invention uses a compound represented by the following formulas (1) to (4) as a colorant and has heat resistance and chemical resistance It is possible to manufacture excellent color filters.
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

The substituents in the above formulas are as defined in the specification.

Description

[0001] The present invention relates to a resin composition for a color filter comprising a pyridone azo compound,

The present invention relates to a resin composition for a color filter comprising a pyridone azo compound, and more specifically to a resin composition for a color filter excellent in heat resistance and chemical resistance.

A liquid crystal display displays an image using the optical and electrical properties of a liquid crystal material. The liquid crystal display device has advantages such as light weight, low power, low driving voltage and the like as compared with a CRT, a plasma display panel and the like. A liquid crystal display device includes a liquid crystal layer disposed between glass substrates. Light generated from the light source passes through the liquid crystal layer, and the liquid crystal layer controls the transmittance of light. The light passing through the liquid crystal passes through the color filter layer, and a full color image is realized by adding color mixture using light passing through the color filter layer.

Generally, in order to manufacture a color filter, a photoresist-type resin composition is manufactured, and a photolithography technique in which various processes such as coating, photo-curing, post-baking, and development are repeatedly performed on a glass plate for each color of R, To form an RGB pattern to produce a color filter.

At this time, since the steps such as exposure, post-baking and development are repeatedly carried out for pattern formation, heat resistance and chemical resistance of the colorant are very important.

Recently, there is a growing demand for color filters having high brightness, high color reproducibility, and high contrast ratio, and it is inevitable to develop a colored resin composition for a color filter having excellent heat resistance and chemical resistance.

SUMMARY OF THE INVENTION The present invention is directed to provide a colored resin composition for a color filter comprising a pyridone azo compound excellent in heat resistance and chemical resistance in order to solve the above-described problems.

In order to solve the above problems, the present invention provides a resin composition for a color filter comprising a pyridone azo compound represented by any one of the following formulas (1) to (4).

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

R ₁ , R ₃ and R ₅ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group;

R ₂ , R ₄ and R ₆ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, an alkyl group having 2 to 18 carbon atoms containing an ether group, a cycloalkyl group having 3 to 10 carbon atoms, A substituted phenyl group, or a substituted or unsubstituted heterocyclic group;

Y ₁ , Y ₂ and Y ₃ are each independently hydrogen, cyano group, or substituted or unsubstituted carbamoyl group;

X and Z are each independently selected from the group consisting of nitro, hydroxy, halogen atom, sulfonic acid group, amino group, alkoxy of 1 to 18 carbon atoms, alkylamino group of 1 to 10 carbon atoms, allyl amino group, arylamino group of 6 to 10 carbon atoms, An alkylsulfonyl group having 1 to 10 carbon atoms, or an alkylsulfonyl group having 1 to 10 carbon atoms;

a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X and Z are the same or different from each other.

The composition may further include at least one selected from a reactive unsaturated compound, a polymerization initiator, an organic solvent, and an additive.

In addition, the composition may further include at least one selected from the group consisting of pigments or dyes in consideration of color coordinates and color correction of the color filter.

The reactive unsaturated compound may be at least one selected from the group consisting of thermosetting monomers and oligomers, photocurable monomers and oligomers, and combinations thereof.

The polymerization initiator may be at least one selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof.

Further, according to a preferred embodiment, in the formulas (1) to (4)

The R ₁ , R ₃ and R ₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;

R ₂ , R ₄ and R ₆ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;

Y ₁ , Y ₂ and Y ₃ are each independently a hydrogen atom or a cyano group;

X and Z are, independently of each other, a hydroxy or halogen atom,

a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X and Z may be the same or different from each other.

The present invention also provides a color filter manufactured using the resin composition for a color filter described above.

The present invention also provides a pyridone azo compound represented by any one of the following Chemical Formulas 1 to 4:

[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,

R ₁ , R ₃ and R ₅ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group;

R ₂ , R ₄ and R ₆ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, an alkyl group having 2 to 18 carbon atoms containing an ether group, a cycloalkyl group having 3 to 10 carbon atoms, A substituted phenyl group, or a substituted or unsubstituted heterocyclic group;

Y ₁ , Y ₂ and Y ₃ are each independently hydrogen, cyano group, or substituted or unsubstituted carbamoyl group;

X and Z are each independently selected from the group consisting of nitro, hydroxy, halogen atom, sulfonic acid group, amino group, alkoxy of 1 to 18 carbon atoms, alkylamino group of 1 to 10 carbon atoms, allyl amino group, arylamino group of 6 to 10 carbon atoms, An alkylsulfonyl group having 1 to 10 carbon atoms, or an alkylsulfonyl group having 1 to 10 carbon atoms;

a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X and Z are the same or different from each other.

The inventors of the present invention have conducted various experiments on a colored resin composition for a color filter and found that when a pyridone azo compound having a specific structure is used, the composition is excellent in heat resistance and chemical resistance. The colored resin composition for a color filter according to the present invention can realize a color filter excellent in heat resistance and chemical resistance.

Unless otherwise defined herein, the meaning of "substituted" means a halogen atom, an alkyl group having 1 to 15 carbon atoms, a haloalkyl group having 1 to 15 carbon atoms, a hydroxy group, a nitro group, a cyano group, Group and an alkylamino group having 1 to 10 carbon atoms.

Unless defined otherwise herein, the term "heterocyclic" means an alicyclic or aromatic group containing from 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si.

Hereinafter, the present invention will be described in more detail.

The present invention relates to a resin composition for a color filter having excellent heat resistance and chemical resistance, and is characterized by containing a compound represented by any one of the following formulas (1) to (4) as a coloring agent.

First, the compound of formula (1) is described.

[Chemical Formula 1]

In the above formula (1)

R ₁ represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted alkyl group having 2 to 18 carbon atoms including an ether group, An unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group,

R ₂ represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, an alkyl group having 2 to 18 carbon atoms including an ether group, a cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, Is a heterocyclic group,

Y ₁ is a hydrogen atom, a cyano group, or a substituted or unsubstituted carbamoyl group,

X and Z each independently represent a hydrogen atom, a nitro group, a hydroxy group, a halogen atom, a sulfonic acid group, an amino group, an alkoxy group having 1 to 18 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an allyl amino group, an arylamino group having 6 to 10 carbon atoms, An acylamino group having 1 to 10 carbon atoms, an alkylsulfonate group having 1 to 10 carbon atoms, or an alkylsulfonamide group having 1 to 10 carbon atoms,

a is an integer of 0 to 4, b is an integer of 0 to 3, and when a or b is 2 or more, plural X and Z are the same or different from each other.

According to one embodiment, in Formula 1, R ₁ Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;

R ₂ is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;

Y ₁ is a hydrogen atom or a cyano group;

X and Z are, independently of each other, a hydroxy or halogen atom;

a is an integer of 0 to 4, b is an integer of 0 to 3, and when a or b is 2 or more, a plurality of X and Z may be the same or different from each other.

According to another embodiment, R ₁ may be a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group.

The compound according to the formula 1 may be specifically exemplified by the following compounds [1] to [12], but the range of the compound represented by the formula 1 according to the present invention is not limited.

Next, the compound of formula (2) is described.

(2)

In the above formula (2)

R ₁ , R ₂ , Y ₁ , X and Z are each, independently of one another, the same as defined in the above formula (1)

c and d are each independently an integer of 0 to 3, and when c or d is 2 or more, plural X and Z are the same or different from each other.

According to one embodiment, in Formula 2, R < _{1 >} Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;

R ₂ is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;

Y ₁ is a hydrogen atom or a cyano group;

X and Z are, independently of each other, a hydroxy or halogen atom;

c and d are each independently an integer of 0 to 3, and when c or d is 2 or more, a plurality of X and Z may be the same or different from each other.

The compound according to the above formula 2 may be specifically exemplified by the following compounds [1] to [8], but the range of the formula 2 according to the present invention is not limited thereto.

Next, the compound of formula (3) is described.

(3)

In the above formula 3,

R ₁ , R ₂ , Y ₁ , X and Z are each, independently of one another, the same as defined in the above formula (1)

a is an integer of 0 to 4, e is an integer of 0 to 2, and when a or e is 2 or more, plural X and Z are the same or different from each other.

According to one embodiment, in Formula 3, R < _{1 >} Is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;

R ₂ is a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;

Y ₁ is a hydrogen atom or a cyano group;

X and Z are, independently of each other, a hydroxy or halogen atom;

a is an integer of 0 to 4, e is an integer of 0 to 2, and when a or e is 2 or more, plural X and Z are the same or different from each other.

The compound according to the above formula 3 may be specifically exemplified by the following compounds [1] to [8], but the range of the formula 3 according to the present invention is not limited thereto.

Next, the compound of formula (4) is described.

In the above formula (4)

R ₃ and R ₅ are each, independently of one another, the same as R ₁ in the above formula (1)

R ₄ and R ₆ are each, independently of one another, the same as R ₂ in the above formula (1)

Y ₂ and Y ₃ are each independently the same as Y ₁ in the above-mentioned formula (1)

X and Z are, independently of each other, the same as defined in the above formula (1)

c and d are each independently the same as defined in the above formula (2).

According to one embodiment, in Formula 4, R ₃ And R ₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;

R ₄ and R ₆ are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;

Y ₂ and Y ₃ are each independently a hydrogen atom or a cyano group;

X and Z are, independently of each other, a hydroxy or halogen atom;

c and d are each independently an integer of 0 to 3, and when c or d is 2 or more, a plurality of X and Z may be the same or different from each other.

The compound according to the above formula 4 may be specifically exemplified by the following compounds [1] to [10], but the range of the formula 4 according to the present invention is not limited thereto.

 The resin composition for a color filter according to the present invention can be obtained by using the pyridonazo compound represented by the above-mentioned formulas (1) to (4) according to the present invention as a colorant and by using a binder resin, a reactive unsaturated compound, Additives, and the like.

The colorant may be contained in an amount of 0.01% to 50% by weight based on the total weight of the resin composition.

The remaining components to be added together may be added within the range of contents commonly used in the production of the color filter composition and are not particularly limited.

Further, in consideration of the color coordinates and color correction of the color filter, the coloring agent selected from the pyridone azo compounds of the formulas (1) to (4) according to the present invention may further optionally contain a dye compound or a pigment compound .

Examples of the dye compounds include methine dyes, cyanine dyes, phthalocyanine dyes, and the like. The pigment compounds may be used without any particular limitation as long as they are yellow pigments and green pigments. For example, the color indexes (The Society of Dyers and Colourists Published as CI Pigment) Color Index Pigment Yellow 138, 139, 150, 185 and CI Color Index Pigment Green 7, 36,

The binder resin is not particularly limited as long as it is a resin capable of exhibiting binding force, and may be a known film-forming resin.

For example, cellulose resins such as carboxymethylhydroxyethylcellulose and hydroxyethylcellulose, acrylic acid resin, alkyd resin, melamine resin, epoxy resin, polyvinyl alcohol, polyvinylpyrrolidone, polyamide, polyamide- Polyimide and the like. More preferably, a resin having a photopolymerizable unsaturated bond is included, and for example, it may be an acrylic acid resin. In particular, homopolymers and copolymers of polymerizable monomers such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, styrene and styrene derivatives, methacrylic acid, itaconic acid, maleic acid, Copolymers between polymerizable monomers containing carboxyl groups such as acid anhydrides, monoalkyl maleates, and polymeric monomers such as methacrylic acid, styrene and styrene derivatives are useful.

Further, it is also possible to use a compound containing an oxirane ring and an ethylenically unsaturated compound such as glycidyl (meth) acrylate, acryloylglycidyl ether, monoalkylglycidyl itaconate, etc., A reaction product of a compound and a compound each containing a hydroxyl group and an ethylenically unsaturated compound (unsaturated alcohol) such as allyl alcohol, 2-buten-4-ol, oleyl alcohol, 2- ) Acrylate, N-methylol acrylamide, and the like, and a reaction product of a carboxyl group-containing polymer compound and such a binder may contain an unsaturated compound having no isocyanate group.

The equivalent of the unsaturation of the binder (molecular weight of the binder per unsaturated compound) may generally range from 200 to 3,000, in particular from 230 to 1,000, in order to provide adequate photopolymerization as well as film hardness. In order to provide sufficient alkali developability after film exposure, the acid number may generally be from 20 to 300, in particular from 40 to 200. The average molecular weight of the binder is preferably 1,500 to 200,000, particularly 10,000 to 50,000 g / mol.

The reactive unsaturated compound may be selected from the group consisting of thermosetting monomers or oligomers, photocurable monomers or oligomers, and combinations thereof. Preferably, the reactive unsaturated compounds may be the photocurable monomers and include at least one reactive double bond and a further reactive group ≪ / RTI >

Useful photocurable monomers in this connection are in particular reactive solvents or reactive diluents, for example mono-, di-, tri- and multifunctional acrylates and methacrylates, vinyl ethers, glycidyl ethers and the like. Additional reactive groups include aryl, hydroxyl, phosphate, urethane, secondary amines, N-alkoxymethyl groups and the like.

Monomers of this type are known in the art and are described, for example, in Roempp, Lexikon, Lacke und Druckfarben, et al. Ulrich Zorll, Thime Verlag Stuttgart-New York, 1998, p 491/492. The choice of monomers will depend, inter alia, on the type and intensity of the irradiation used, the desired reaction by the photoinitiator and the film properties. These photocurable monomers may be used alone or in combination of monomers.

The polymerization initiator may be a thermosetting initiator, a photo-curing initiator, or a combination thereof, and may preferably be a photo-curing initiator. Such a photo-curing initiator may be, for example, as a result of absorption of visible light or ultraviolet light, To form a reaction intermediate capable of inducing polymerization reaction. Photoinitiators or are known in the art, see for example Roempp, Lexikon, Lacke und Druckfarben, et al. Ulrich Zorll, Thime Verlag Stuttgart-New York, 1998, p 445/446.

The organic solvents may be, for example, ketones, alkylene glycol ethers, alcohols and aromatic compounds. But are not limited to, ketone groups such as acetone, methyl ethyl ketone, cyclohexanone and the like;

Examples of the alkylene glycol ether group include methyl cellosolve (ethylene glycol monomethyl ether), butyl cellosolve (ethylene glycol monobutyl ether), methyl cellosolve acetate, ethyl cellosolve acetate, butyl cellosolve acetate, ethylene glycol Monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether Acetate, diethylene glycol methyl ether acetate, diethylene glycol ethyl ether acetate, diethylene glycol propyl ether acetate, diethylene glycol isopropyl ether acetate, diethylene glycol butyl ether acetate, Diethylene glycol t-butyl ether acetate, triethylene glycol methyl ether acetate, triethylene glycol ethyl ether acetate, triethylene glycol propyl ether acetate, triethylene glycol isopropyl ether acetate, triethylene glycol, triethylene glycol butyl ether acetate, tri Ethylene glycol t-butyl ether acetate and the like;

Examples of the alcohol group include methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, 3-methyl-3-methoxybutanol and the like;

Examples of aromatic solvents include benzene, toluene, and xylene.

Further other solvents include N-methyl-2-pyrrolidone, ethyl N-hydroxymethylpyrrolidone-2 acetate, 1,2-propanediol diacetate, 3-methyl- Acetate, ethyl acetate, tetrahydrofuran and the like.

The above-mentioned solvents may be used singly or as a mixture.

Additional additives may be used without limitation as long as they meet the respective purposes. As a preferable example, a fatty acid, a fatty amine, an alcohol, an oil, a wax, a rosin, a resin, a benzotriazole derivative and the like may be used for improving the surface texture. Stearic acid or behenic acid may be used as the fatty acid, and stearylamine may be used as the fatty amine. Examples of the fatty acid include soybean oil (bean oil) ).

Hereinafter, the present invention will be described in detail with reference to the preferred embodiments, which will be readily apparent to those skilled in the art to which the present invention pertains. The present invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.

Example

Synthesis of pyridone azo compounds and resin composition production

The compound represented by the following formulas (1) to (4) according to the present invention was synthesized as a pyridone azo compound represented by the following [compounds 1] to [compound 18].

Hereinafter, the synthesis method for the above compound will be described in detail.

(1) Synthesis Example 1: Synthesis of [Compound 1]

After adding 0.210 mol of 40% nitrosylsulfuric acid to 1.800 mol of 96% H ₂ SO ₄ , the mixture was stirred. After keeping the temperature at 18 to 20 ° C, 0.200 mol of [structural formula 1_a] was slowly added to the solution. 0.200 mol of [structural formula 2_a] is dissolved in 400 mL of methanol, and then cooled to 0 ° C or lower. [Structural Formula 1_a] The sulfuric acid solution was slowly added dropwise, and after completion of the reaction, the solution was filtered, washed with water and purified to obtain 0.111 mol of [Compound 1]. The molecular weight of the obtained compound was confirmed by LC / MS analysis.

(2) Synthetic example  2 to 18: Synthesis of [Compound 2] to [Compound 18]

The synthesis was carried out in the same manner as in Synthesis Example 1 by selecting reactants as shown in [Table 1] below to obtain [Compounds 2] to [Compound 18]. The molecular weight of the obtained compound was confirmed by LC / MS analysis.

Example  1: Preparation of resin composition

The mixture was mixed with the following composition and stirred at room temperature for 2 hours to prepare a resin composition.

1.4 g of a copolymer (Mw = 20,000) of benzyl methacrylate / methacrylic acid (weight ratio 60:40) as a binder resin,

5 g of dipentaerythritol hexaacrylate as an acrylic monomer,

1.5 g of [Compound 1] as a coloring agent,

1 g of Irgacure OXE-01 available from BASF as a photopolymerization initiator,

41.1 g of propylene glycol monomethyl ether as a solvent.

Examples 2 to 18: Preparation of resin composition

A resin composition was prepared in the same manner as in Example 1 except that [Compound 2] to [Compound 18] were used in place of [Compound 1] as a colorant.

Comparative Example 1: Production of resin composition

A resin composition was prepared in the same manner as in Example 1 except that Disperse Yellow 114 was used instead of [Compound 1] as a colorant.

Comparative Example 2: Production of resin composition

A resin composition was prepared in the same manner as in Example 1 except that Disperse Yellow 119 was used instead of [Compound 1] as a colorant.

Experimental Example 1. Heat resistance measurement

Each of the resin compositions prepared in the above Examples and Comparative Examples was spin-coated on a glass substrate having a size of 10 cm x 10 cm to a thickness of 2 占 퐉, pre-baked on a hot plate at 90 占 폚 for 3 minutes, And then cooled at room temperature for 1 minute. This was exposed using an exposure machine at an exposure amount of 100 mJ / cm 2 (based on 365 nm).

Thereafter, post-baking was carried out in a convection oven at 230 ° C for 30 minutes, color characteristics were confirmed using a spectrophotometer MCPD3700 from Otsuka electronic Co., After the heat treatment, ΔEab * was measured again with a color difference meter. The results of the heat resistance evaluation are shown in Table 2 below.

Experimental Example 2: Measurement of chemical resistance

After the spin coating, exposure and post-baking were carried out in the same manner as in the measurement of heat resistance, color characteristics were confirmed using a spectrophotometer, MCPD3700 manufactured by Otsuka electronic Co., Ltd., and immersed in propylene glycol monomethyl ether acetate (PGMEA) . Changes in the color characteristics of the specimens before and after immersion in the solvent were confirmed. The results are shown in Table 2 below.

division Heat resistance
(? Eab *) Chemical resistance
(? Eab *) Example 1 1.81 1.78 Example 2 1.94 1.84 Example 3 2.46 2.55 Example 4 2.84 2.68 Example 5 3.14 3.07 Example 6 2.95 3.02 Example 7 3.18 3.20 Example 8 3.84 3.66 Example 9 1.75 1.52 Example 10 2.07 1.87 Example 11 3.48 3.34 Example 12 2.43 2.64 Example 13 4.15 4.09 Example 14 3.74 3.65 Example 15 3.61 3.45 Example 16 2.57 2.68 Example 17 3.81 3.97 Example 18 2.42 2.15 Comparative Example 1 25.44 15.49 Comparative Example 2 33.16 10.88

As can be seen from the above Table 2, Examples 1 to 18 according to the present invention show excellent heat resistance and chemical resistance as compared with Comparative Example 1 and Comparative Example 2 using a colorant used for fiber dyeing And thus it can be applied to a color filter.

Claims (8)

A resin composition for a color filter, which comprises a pyridone azo compound represented by any one of structural formulas (1) to (4) as a coloring agent:
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,
R ₁ , R ₃ and R ₅ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group;
R ₂ , R ₄ and R ₆ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, an alkyl group having 2 to 18 carbon atoms containing an ether group, a cycloalkyl group having 3 to 10 carbon atoms, A substituted phenyl group, or a substituted or unsubstituted heterocyclic group;
Y ₁ , Y ₂ and Y ₃ are each independently a hydrogen atom, a cyano group, or a substituted or unsubstituted carbamoyl group;
X 'represents a nitro group, a hydroxy group, a halogen atom, a sulfonic acid group, an alkoxy group having 1 to 18 carbon atoms, an alkyl sulfonate group having 1 to 10 carbon atoms, or an alkyl sulfonamide group having 1 to 10 carbon atoms, An alkoxy group having 1 to 18 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an allyl amino group, an arylamino group having 6 to 10 carbon atoms, an acylamino group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, An alkylsulfone group having 1 to 10 carbon atoms, or an alkylsulfonamide group having 1 to 10 carbon atoms;
a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X 'or X and Z are the same or different from each other.
The method according to claim 1,
Wherein the resin composition further comprises at least one selected from a binder resin, a reactive unsaturated compound, a polymerization initiator, an organic solvent, and an additive.
The method according to claim 1,
Wherein the resin composition further comprises a pigment compound or a dye compound.
3. The method of claim 2,
Wherein the reactive unsaturated compound is selected from the group consisting of thermosetting monomers and oligomers, photocurable monomers and oligomers, and combinations thereof.
3. The method of claim 2,
Wherein the polymerization initiator is selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator, and a combination thereof.
The method according to claim 1,
The R ₁ , R ₃ and R ₅ are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted phenyl group;
R ₂ , R ₄ and R ₆ are each independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms;
Y ₁ , Y _2, and Y ₃ are each independently hydrogen or cyano group;
X 'or X and Z are, independently of each other, a hydroxy or halogen atom,
a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X 'or X and Z are the same as or different from each other.
A color filter produced by using the resin composition for a color filter according to claim 1.
A pyridone azo compound represented by any one of the following Chemical Formulas 1 to 4:
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

In the above Chemical Formulas 1 to 4,
R ₁ , R ₃ and R ₅ are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted C2- A substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted heterocyclic group;
R ₂ , R ₄ and R ₆ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, an alkyl group having 2 to 18 carbon atoms containing an ether group, a cycloalkyl group having 3 to 10 carbon atoms, A substituted phenyl group, or a substituted or unsubstituted heterocyclic group;
Y ₁ , Y ₂ and Y ₃ are each independently a hydrogen atom, a cyano group, or a substituted or unsubstituted carbamoyl group;
X 'represents a nitro group, a hydroxy group, a halogen atom, a sulfonic acid group, an alkoxy group having 1 to 18 carbon atoms, an alkyl sulfonate group having 1 to 10 carbon atoms, or an alkyl sulfonamide group having 1 to 10 carbon atoms, An alkoxy group having 1 to 18 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an allyl amino group, an arylamino group having 6 to 10 carbon atoms, an acylamino group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, An alkylsulfone group having 1 to 10 carbon atoms, or an alkylsulfonamide group having 1 to 10 carbon atoms;
a is an integer of 0 to 4, b, c and d are each independently an integer of 0 to 3, e is an integer of 0 to 2, and when a, b, c, d or e is 2 or more, X 'or X and Z are the same or different from each other.