KR102162610B1 - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by Chemical Formula 1, a colorant composition including the same, and a resin composition including the same.

Description

A compound, a colorant composition containing the same, and a resin composition containing the same {COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}

The present specification relates to a novel compound, a colorant composition comprising the same, and a resin composition comprising the same.

Recently, as a light source of a liquid crystal display (LCD), instead of the conventional CCFL, LEDs or OLED devices that emit light without being driven or liquid crystal have been widely used. When LED or OLED is used as a light source, red, green, and blue light is emitted by itself, so a separate color filter is not required.

However, in general, it is not easy to adjust or adjust the color coordinates required by using light from an LED or OLED light source. In addition, a method of improving color purity, luminance, and contrast ratio when manufacturing a color filter using a pigment dispersion method using a pigment dispersion method, which has already been developed, has reached its limit. In addition, in order to thin the color filter, it is necessary to reduce the amount of color material used.

In order to overcome these problems and satisfy the requirements, development of a new color material is required.

Korean Patent Publication No. 2001-0009058

The present specification provides a novel compound, a colorant composition comprising the same, and a resin composition comprising the same.

According to an exemplary embodiment of the present specification, a compound represented by the following Formula 1 is provided.

[Formula 1]

In Formula 1,

; 또는

이며, 나머지는 직접결합이고,At least one of L1 and L2 is

; or

And the rest are direct bonds,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; An aryl group substituted with at least one carboxyl group; Or an aryl group condensed with a cyclic anhydride,

; 또는

인 경우, Ar1은 적어도 하나의 카르복시기로 치환된 아릴기; 또는 고리형 무수물로 축합된 아릴기이고,L1 is

; or

In the case of, Ar1 is an aryl group substituted with at least one carboxyl group; Or an aryl group condensed with a cyclic anhydride,

; 또는

인 경우, Ar2는 적어도 하나의 카르복시기로 치환된 아릴기; 또는 고리형 무수물로 축합된 아릴기이며,L2 is

; or

In the case of, Ar2 is an aryl group substituted with at least one carboxyl group; Or an aryl group condensed with a cyclic anhydride,

R1 to R5 and R105 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; Sulfonate group; Sulfonamide group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,

R101 to R104 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group,

r1 and r2 are each an integer of 1 to 5,

r3 and r4 are each an integer of 1 to 3,

r5 is an integer from 1 to 4,

When r1 to r5 are each 2 or more, the structures in the two or more parentheses are the same or different from each other,

는 상기 화학식 1의 N 및 Ar1; 또는 N 및 Ar2를 연결하는 부위이다.

Is N and Ar1 of Formula 1; Or a site connecting N and Ar2.

According to another exemplary embodiment of the present specification, a colorant composition comprising the compound represented by Formula 1 is provided.

According to another exemplary embodiment of the present specification, a resin composition including the colorant composition is provided.

According to an exemplary embodiment of the present specification, a color filter including the resin composition described above is provided.

Further, according to an exemplary embodiment of the present specification, a display device including the above-described color filter is provided.

The compound represented by Formula 1 according to the exemplary embodiment of the present specification has excellent solubility in a solvent, and excellent heat resistance and chemical resistance.

In addition, according to an exemplary embodiment of the present specification, the color material composition including the compound represented by Formula 1 may exhibit higher brightness and improve heat resistance and chemical resistance than when using a conventional pigment. By using the used colored resin composition, it is possible to manufacture a color filter excellent in heat resistance and chemical resistance.

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

According to an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.

Examples of the substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxy group; Sulfonate group; Sulfonamide group; Carboxyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or does not have any substituents.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In this specification,

Means a site bonded to another substituent or a bonding portion.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight-chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the nitrogen of the sulfonic acid amide may be substituted with hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

In the present specification, the sulfonate group may be expressed as -SO ₃ X, and X may be hydrogen or a Group 1 element. For example, the sulfonate group is -SO ₃ Na.

In the present specification, a carboxyl group means -COOH.

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ (amino group); Alkylamine group; N-arylalkylamine group; Arylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, and the like, but are not limited thereto.

In the present specification, the N-alkylarylamine amine group means an amine group in which an alkyl group and an aryl group are substituted with N of the amine group.

In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

In the present specification, the N-alkylheteroarylamine group refers to an amine group in which an alkyl group and a heteroarylamine group are substituted with N of the amine group.

In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the example of the aforementioned alkyl group. Specifically, the alkyl thioxy group includes methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group, and the like. And the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group among the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the example of the aryl group described above. Specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group, and the arylthioxy group includes a phenylthioxy group, 2- There are a methylphenyl thioxy group, a 4-tert-butylphenyl thioxy group, and the like, and the aryl sulfoxy group includes a benzene sulfoxy group and a p-toluene sulfoxy group, but is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, in the present specification, the heteroaryl group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatom is one or more atoms selected from the group consisting of O, N, Se and S Can include. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Zolyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, p Nanthrolinyl group (phenanthroline), thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as those of the aforementioned heteroaryl group.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic, or condensed rings of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

In the present specification, an alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the alkyl group described above can be applied.

In the present specification, the cyclic anhydride includes maleic anhydride, fumaric anhydride, glutalic anhydride, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-6.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,

Definitions of R1 to R5, r1 to r5, R101 to R105, Ar1 and Ar2 are the same as in Formula 1,

R205 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; Sulfonate group; Sulfonamide group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,

R201 to R204 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group.

According to an exemplary embodiment of the present specification, in Formulas 1-3 and 1-4, Ar1 is a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in Formulas 1-3 and 1-4, Ar1 is an alkyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formulas 1-3 and 1-4, Ar1 is an n-propyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formulas 1-3 and 1-4, Ar1 is an n-propyl group substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formulas 1-5 and 1-6, Ar2 is a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in Formulas 1-5 and 1-6, Ar2 is an alkyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formulas 1-5 and 1-6, Ar2 is an n-propyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formulas 1-5 and 1-6, Ar2 is an n-propyl group substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L1 is a direct bond, Ar1 is a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, when L1 is a direct bond, Ar1 is an alkyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L1 is a direct bond, Ar1 is an n-propyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L1 is a direct bond, Ar1 is an n-propyl group substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L2 is a direct bond, Ar2 is a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in Formula 1, when L2 is a direct bond, Ar2 is an alkyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L2 is a direct bond, Ar2 is an n-propyl group unsubstituted or substituted with an amino group, a carboxyl group, or a hydroxy group.

According to an exemplary embodiment of the present specification, in Formula 1, when L2 is a direct bond, Ar2 is an n-propyl group substituted with an amino group, a carboxyl group or a hydroxy group.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Sulfonate group; Sulfonamide group; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; -SO ₃ Na; Alkylsulfonamide group; Or an alkyl group.

According to an exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; -SO ₃ Na; 2-ethylhexyl sulfonamide group; Methyl group; Ethyl group; n-propyl group; Or isopropyl group.

According to an exemplary embodiment of the present specification, R105 is hydrogen.

According to an exemplary embodiment of the present specification, R101 to R104 are the same as or different from each other, and each independently a direct bond; Or an alkylene group.

According to an exemplary embodiment of the present specification, R101 to R104 are the same as or different from each other, and each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R101 to R104 are the same as or different from each other, and each independently a direct bond; Or n-propylene group.

; 또는

인 경우, Ar1은 적어도 하나의 카르복시기로 치환된 아릴기; 또는 고리형 무수물로 축합된 아릴기이고,According to an exemplary embodiment of the present specification, in Formula 1, L1 is

; or

In the case of, Ar1 is an aryl group substituted with at least one carboxyl group; Or an aryl group condensed with a cyclic anhydride,

; 또는

인 경우, Ar2는 적어도 하나의 카르복시기로 치환된 아릴기; 또는 고리형 무수물로 축합된 아릴기이다.L2 is

; or

In the case of, Ar2 is an aryl group substituted with at least one carboxyl group; Or it is an aryl group condensed with a cyclic anhydride.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently represented by the following Formula 1-A.

[Formula 1-A]

In Formula 1-A,

At least one of G1 to G5 is a carboxyl group, and the remainder is hydrogen, or adjacent rings are bonded to each other to form maleic anhydride,

는 상기 화학식 1의 L1 또는 L2에 결합되는 부위이다.

Is a site bonded to L1 or L2 of Formula 1 above.

According to an exemplary embodiment of the present specification, in Formula 1-A, any one of G1 to G5 is a carboxyl group, and the rest is hydrogen.

According to an exemplary embodiment of the present specification, in Formula 1-A, two of G1 to G5 are carboxyl groups, and the rest are hydrogen.

According to an exemplary embodiment of the present specification, in Formula 1-A, any three of G1 to G5 are carboxyl groups, and the rest are hydrogen.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group substituted with 1 to 3 carboxyl groups.

According to an exemplary embodiment of the present specification, Formula 1-A is selected from the following structural formulas.

In the above structural formula,

는 상기 화학식 1의 L1 또는 L2에 결합되는 부위이다.

Is a site bonded to L1 or L2 of Formula 1 above.

According to an exemplary embodiment of the present specification, Formula 1 is selected from the following compounds.

In the above compound, X is -SO ₃ Na or -SO ₂ NHR',

R'is a C 1 to C 20 linear or branched alkyl group.

The compound represented by Formula 1 may be prepared by referring to Preparation Examples described later.

According to an exemplary embodiment of the present specification, a colorant composition comprising the compound represented by Formula 1 is provided.

The color material composition may further include at least one of a dye and a pigment in addition to the compound represented by Formula 1 above. For example, the color material composition may include only the compound represented by Formula 1, but may include the compound represented by Formula 1 and at least one dye, or include the compound represented by Formula 1 and at least one pigment. , It may include a compound represented by Formula 1, at least one dye, and at least one pigment. In an exemplary embodiment of the present specification, a resin composition comprising the colorant composition is provided.

According to an exemplary embodiment of the present specification, the dye is at least one dye selected from a xanthene dye, a cyanine dye, and an azaporphyrin dye, and the pigment is a blue pigment or a purple pigment.

The xanthene dye, cyanine dye, and azaporphyrin dye are not particularly limited as long as they are used in the art.

The blue pigment is not limited as long as it is used in the art, and may include a copper phthalocyanine-based blue pigment among them. Examples of the copper phthalocyanine-based blue pigment include compounds classified as pigments in the color index (published by The Society of Dyers and Colorists). For a specific example, C.I. Blue pigment (Color Index Pigment Blue) 1, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc. are mentioned.

The purple pigment is not limited as long as it is used in the art, and is classified as a pigment in the color index (published by The Society of Dyers and Colourists). Purple pigment (Color Index Pigment Violet) 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc. are mentioned.

In one embodiment of the present specification, the resin composition is a binder resin; Polyfunctional monomers; Antioxidants; Photoinitiators; And a solvent may be further included.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of a resin composition.

The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.

Polyfunctional monomers that impart mechanical strength of the film include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And it may be any one or more of an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters are benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl ( Meth)acrylate, t-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetra Hydrofurpril (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl ( Meth)acrylate, acyloctyloxy-2-hydroxypropyl (meth)acrylate, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxy Cydiethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, phenoxydiethylene glycol (meth) )Acrylate, p-nonylphenoxypolyethylene glycol (meth)acrylate, p-nonylphenoxypolypropylene glycol (meth)acrylate, glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoropentyl (meth)acrylate, heptadecafluorodecyl (meth)acrylate, tribromophenyl (meth) ) Acrylate, methyl ?-hydroxymethyl acrylate, ethyl ?-hydroxymethyl acrylate, propyl ?-hydroxymethyl acrylate and butyl ?-hydroxymethyl acrylate may be selected from the group consisting of, but only these It is not limited.

Specific examples of the aromatic vinyl monomers include styrene, ?-methylstyrene, (o,m,p)-vinyl toluene, (o,m,p)-methoxy styrene, and (o,m,p)-chloro It may be selected from the group consisting of styrene, but is not limited thereto.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether, but are not limited thereto.

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.

Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.

The monomer imparting alkali solubility is not particularly limited as long as it includes an acid group, and examples include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono -2-((meth)acryloyloxy)ethyl phthalate, mono-2-((meth)acryloyloxy)ethyl succinate, ?-carboxy polycaprolactone mono(meth)acrylate selected from the group consisting of It is preferable to use one or more, but is not limited to these.

According to an exemplary embodiment of the present specification, the acid value of the binder resin is 50 to 130 KOH mg/g, and the weight average molecular weight is 1,000 to 50,000.

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di. Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more.

The photoinitiator is not particularly limited as long as it is an initiator that generates a radical by light to trigger crosslinking, but is, for example, selected from the group consisting of an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more.

The acetophenone compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1-(4-morpholinophenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, and the like, but is not limited thereto.

The biimidazole-based compound is 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4 ,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)-4, 4',5,5'-tetraphenyl biimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , Is not limited thereto.

The triazine compound is 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionate, ethyl-2-{4-[2,4 -Bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, benzyl-2-{4-[ 2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazine-6 -Yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazine-6-yl]phenylthio}propionamide, 2,4-bis(trichloro Methyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s -Triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.

The oxime compound is 1,2-octadione,-1-(4-phenylthio)phenyl,-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii124), ethanol,-1-(9 -Ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime)(CGI 242), N-1919 (Adeca), and the like, but are not limited thereto.

The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 ,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 -Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.

According to an exemplary embodiment of the present specification, based on the total weight of the solid content in the resin composition, the content of the color material composition is 5% by weight to 90% by weight, the content of the binder resin is 1% by weight to 30% by weight, , The content of the antioxidant is 0.001% by weight to 20% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight to 50% by weight.

The total weight of the solid content means the sum of the total weight of components excluding the solvent in the resin composition. The basis of the solid content and the weight percent based on the solid content of each component can be measured by a general analysis means used in the art such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the resin composition is one or two or more selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent. It further contains an additive.

According to an exemplary embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the resin composition.

The photocrosslinking sensitizer is benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone, and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone, and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane, etc. Acridine compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, and 2-n-butoxyethyl-4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzal)cyclopentanone, 2,6-bis(4-diethylaminobenzal)cyclohexanone, 2,6-bis(4-diethylaminobenzal)-4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzoyl-7-(diethylamino)coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzo Coumarin compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

The curing accelerator is used to increase curing and mechanical strength, and specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 2,5-dimercapto-1,3 ,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio) Nate) can be used one or more selected from the group consisting of.

The adhesion promoter used in this specification is methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents such as may be selected and used, and as an alkyl trimethoxy silane, one or more types of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. You can choose and use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK -354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. can be used, and as a fluorine-based surfactant, DIC (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like may be used, but are not limited thereto.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethylphosphate, or triethylphosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetrabis[methylene-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxy Benzyl)benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethylester, 2,2-thiobis(4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis(3-methyl-6-t-butylphenol), 4,4'-thiobis(3-methyl-6-t-butylphenol) or bis[3 ,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid]glycol Hindered phenol-based primary antioxidants such as ester); Amines such as phenyl-?-naphthylamine, phenyl-?-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-?-naphthyl-p-phenylenediamine Secondary antioxidants; Thio such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane Secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl)-4,4'-diylbisphosphonoic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester ((1,1'-Biphenyl)-4,4' -Phosphite-based secondary antioxidants such as -Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester).

As the ultraviolet absorber, 2-(3-t-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but the present invention is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxy. Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology It may include those generally known in the field.

The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. Compound type, nonionic, anionic or cationic dispersants can be used as the dispersant, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants and the like can be used. These may be used individually or in combination of two or more.

Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylate, There may be at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but is not limited thereto, all those generally used in the art may be used.

According to an exemplary embodiment of the present specification, a color filter including the resin composition is provided.

The color filter may be manufactured by using a resin composition including the color material composition. A color filter may be formed by applying the resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. Further, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

Examples of the light source for curing the resin composition according to the present specification include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm.

The resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, It can be used for overcoat layer formation photosensitive material, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), and limited to its use. Is not specifically placed.

The resin composition according to the exemplary embodiment of the present specification has excellent heat resistance, and has little change in color due to heat treatment, so that a color filter having high color reproducibility and high luminance and contrast ratio can be provided even by a curing process when manufacturing a color filter. have.

The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited.

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

According to another exemplary embodiment, the color filter may further include an overcoat layer.

A grid-like black pattern called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving the contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching treatment may be used. However, in consideration of the high process cost, high reflectance of chromium, and environmental pollution due to chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing may be used.

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material increases. There is an advantage that does not work.

A display device including the color filter according to the present specification is provided.

The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be any one of a liquid crystal display (Thin Film Transistor- Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, the present specification will be described in detail with reference to examples. The following examples are for explaining the present specification, and the scope of the present specification includes the ranges described in the following claims and substitutions and modifications thereof, and is not limited to the scope of the examples.

Manufacturing example

Preparation Example 1. Preparation of compound 1

B-1 11.59 (15.23 mmol) and A-1 2.5 g (15.23 mmol) were added to 700 g of pyridine, and stirred at room temperature for 24 hours. The reaction was put in DI-Water and stirred for 1 hour. The precipitate was filtered and washed with water under reduced pressure, and dried at 80 DEG C for 12 hours. Thereafter, the dried precipitate was subjected to column chromatography to obtain compound 1.

Ionization mode =: APCI +: m/z=928[M+H]+, Exact Mass: 927

Preparation Example 2. Preparation of Compound 2

In Preparation Example 1, except for using C-1 instead of B-1, it was prepared in the same manner to obtain compound 2.

Ionization mode =: APCI +: m/z = 984[M+H]+, Exact Mass: 983

Preparation Example 3. Preparation of compound 3

In Preparation Example 1, except for using D-1 instead of B-1, it was prepared in the same manner to obtain compound 3.

Ionization mode =: APCI +: m/z=1040[M+H]+, Exact Mass: 1039

Preparation Example 4. Preparation of compound 4

In Preparation Example 1, except for using E-1 instead of B-1, it was prepared in the same manner to obtain compound 4.

Ionization mode =: APCI +: m/z=1012[M+H]+, Exact Mass: 1011

Preparation Example 5. Preparation of compound 5

In Preparation Example 1, except for using F-1 instead of B-1, it was prepared in the same manner to obtain compound 5.

Ionization mode=: APCI +: m/z=1096[M+H]+, Exact Mass: 1095

Preparation Example 6. Preparation of compound 6

In Preparation Example 1, except for using G-1 instead of B-1, it was prepared in the same manner to obtain compound 6.

Ionization mode=: APCI +: m/z=1096[M+H]+, Exact Mass: 1095

Preparation Example 7. Preparation of compound 7

)를 사용한 것을 제외하고는 동일하게 제조하여,

(화합물 7)을 제조하였다.Instead of A-1 in Preparation Example 1, A-2 (

), except that it was manufactured in the same way,

(Compound 7) was prepared.

Preparation Example 8. Preparation of compound 8

)를 사용한 것을 제외하고는 동일하게 제조하여,

(화합물 8) 을 제조하였다.Instead of A-1 in Preparation Example 2, A-2 (

), except that it was manufactured in the same way,

(Compound 8) was prepared.

Preparation Example 9. Preparation of compound 9

) 를 사용한 것을 제외하고는 동일하게 제조하여,

(화합물 9)를 제조하였다.Instead of A-1 in Preparation Example 3, A-2 (

), except that it was prepared in the same way,

(Compound 9) was prepared.

Preparation Example 10 Preparation of Compound 10

)를 사용한 것을 제외하고는 동일하게 제조하여

(화합물 10)을 제조하였다.Instead of A-1 in Preparation Example 4, A-2 (

Except for using ),

(Compound 10) was prepared.

Preparation Example 11. Preparation of compound 11

)를 사용한 것을 제외하고는 동일하게 제조하여

(화합물 11)을 제조하였다.Instead of A-1 in Preparation Example 5, A-2 (

Except for using ),

(Compound 11) was prepared.

Preparation Example 12. Preparation of compound 12

)를 사용한 것을 제외하고는 동일하게 제조하여,

(화합물 12)를 제조하였다.In Preparation Example 6, A-2 instead of A-1 (

), except that it was manufactured in the same way,

(Compound 12) was prepared.

Comparative compound 1

Comparative compound 2

The comparative compound 1 is Basic blue7, and the comparative compound 2 is rhodamine 6G.

Example

To prepare a colorant composition in the same ratio as in Table 1 below. The dosage unit of the compound is grams (g).

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Comparative Example 1 Comparative Example 2 Compound 1 5.554 - - - - - - - Compound 2 - 5.554 - - - - - - Compound 3 - - 5.554 - - - - - Compound 4 - - - 5.554 - - - - Compound 5 - - - - 5.554 - - - Compound 6 - - - - - 5.554 - - Comparative compound 1 - - - - - - 5.554 - Comparative compound 2 - - - - - - - 5.554 Binder resin (g) 10.376 Photoinitiator (g) 2.018 Additive (g) 1.016 Polyfunctional monomer (g) 12.443 Solvent (g) 68.593 Total content (g) 100 Binder resin: A copolymer of benzyl methacrylate and methacrylic acid (molar ratio of 70:30, acid value is 113
KOH mg/g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI) 2.0,
Solid content (SC) 25%, including solvent PGMEA)
Photoinitiator: I-369 (BASF)
Polyfunctional monomer: DPHA (Japanese Explosives)
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Additive: DIC F-475
* Evaluation after filtering insoluble components

Board fabrication

The compound prepared by the above synthesis was spin-coated on glass (5×5 cm) and pre-heated at 100° C. for 100 seconds to form a film. The distance between the substrate on which the film was formed and a photo mask was set to 250 μm, and an exposure amount of 40 mJ/cm ² was irradiated on the entire surface of the substrate using an exposure machine.

Then, the exposed substrate was developed in a developer (KOH, 0.05%) for 60 seconds, and post bake was performed at 230° C. for 20 minutes to prepare a substrate.

Heat resistance evaluation

The transmittance spectrum of the visible light region in the range of 380 nm to 780 nm was obtained from the prebake substrate prepared under the above conditions using a spectrometer (MCPD-Otsuka Corporation). In addition, a prebake substrate was additionally subjected to post bake at 230° C. for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, Δ Eab was calculated using the obtained value E (L*, a*, b*), and is shown in Table 2 below.

ΔE(L*, a*, b*) ={(ΔL*) ² +(Δa*) ² +(Δb*) ² } ^1/2

A small ΔE value indicates excellent color heat resistance.

Table 2 shows the heat resistance measurement results for the substrates prepared according to Examples 1 to 6 and the substrates prepared according to Comparative Examples 1 and 2. As shown in Table 2, it was confirmed that the color change (Δ Eab) of the substrates prepared according to Examples 1 to 6 was smaller than that of Comparative Examples 1 and 2.

△Eab(PB-PrB) Example 1 3.21 Example 2 2.68 Example 3 3.03 Example 4 2.98 Example 5 2.87 Example 6 3.68 Comparative Example 1 27.48 Comparative Example 2 24.54

Claims (11)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
At least one of L1 and L2 is

; or

And the rest are direct bonds,
Ar1 and Ar2 are the same as or different from each other, and each independently represented by the following formula 1-A,
R1 to R5 are the same as or different from each other, and each independently hydrogen; -SO ₃ Na; An alkylsulfonamide group having 1 to 10 carbon atoms; Or an alkyl group having 1 to 10 carbon atoms,
R101 to R104 are the same as or different from each other, and each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms,
R105 is hydrogen,
r1 and r2 are each an integer of 1 to 5,
r3 and r4 are each an integer of 1 to 3,
r5 is an integer from 1 to 4,
When r1 to r5 are each 2 or more, the structures in the two or more parentheses are the same or different from each other,

Is N and Ar1 of Formula 1; Or a site connecting N and Ar2,
[Formula 1-A]

In Formula 1-A,
At least one of G1 to G5 is a carboxyl group, and the remainder is hydrogen, or adjacent rings are bonded to each other to form maleic anhydride,

Is a site bonded to L1 or L2 of Formula 1 above. The compound of claim 1, wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-6:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Formulas 1-1 to 1-6,
Definitions of R1 to R5, r1 to r5, R101 to R105, Ar1 and Ar2 are the same as in Formula 1,
R205 is hydrogen,
R201 to R204 are the same as or different from each other, and each independently a direct bond; Or an alkylene group having 1 to 10 carbon atoms. delete The compound of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group substituted with 1 to 3 carboxyl groups. The compound of claim 1, wherein Formula 1 is selected from the following compounds:

In the above compound, X is -SO ₃ Na or -SO ₂ NHR',
R'is a C 1 to C 20 linear or branched alkyl group. A color material composition comprising the compound according to any one of claims 1, 2, 4 and 5. The colorant composition according to claim 6, further comprising at least one of a dye and a pigment. The method of claim 7, wherein the dye is at least one dye selected from xanthene dyes, cyanine dyes and azaporphyrin dyes,
The pigment is a color material composition that is a blue pigment or a purple pigment. A compound represented by Formula 1 according to claim 1; Binder resin; Polyfunctional monomers; Photoinitiators; Antioxidants; And a resin composition containing a solvent. A color filter comprising the resin composition according to claim 9. A display device comprising the color filter according to claim 10.