KR20170094658A - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present invention relates to a new compound, a coloring composite including the same, and a resin composite including the same. According to an embodiment of the present invention, the compound, indicated in the chemical formula 1, is capable of having excellent solubility to a solvent and excellent chemical resistance. As to the chemical formula 1, Y1 is N or CR9, Y2 is N or CR10, Y3 is N or CR11, Y4 is N or CR12, Y5 is N or CR13, Y6 is N or CR14, and at least one among the Y1 to the Y6 is N.

Description

TECHNICAL FIELD [0001] The present invention relates to a coloring material composition, a coloring material composition containing the same, and a resin composition containing the same. BACKGROUND ART [0002]

The present invention relates to a novel compound, a colorant composition containing the same, and a resin composition containing the same.

BACKGROUND ART [0002] In recent years, LEDs or OLED devices which do not drive liquid crystal but perform self-luminescence instead of conventional CCFL have been widely used as a light source of a liquid crystal display (LCD). When an LED or an OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required.

However, it is generally not easy to adjust or adjust the required color coordinates using light emitted from an LED or OLED light source. In addition, the method of improving the color purity, luminance and contrast ratio in the production of a color filter using a pigment dispersion method using already developed color materials, in particular, a pigment has reached a limit.

Recently, in order to solve such problems and achieve high brightness, high contrast ratio and high resolution, it has been studied to use dyes instead of pigments as colorants. Many attempts have been made with triarylmethane dyes as blue coloring agents. In general, triarylmethane dyes are effective for color characteristics because of their high transparency at 420 to 450 nm, but they have been limitedly used in color filters because of their lower chemical resistance and lower heat resistance than pigments due to their higher solubility than pigments.

Korean Patent Publication No. 2001-0009058 Korean Patent Publication No. 2013-0130976

The present invention provides a novel compound, a colorant composition containing the same, and a resin composition containing the same.

According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

Y1 is N or CR9, Y2 is N or CR10, Y3 is N or CR11, Y4 is N or CR12, Y5 is N or CR13, Y6 is N or CR14,

At least one of Y1 to Y6 is N,

; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 가교성기이거나, 상기 R1과 R2; R3와 R4; 및 R5와 R6 중 적어도 하나는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며, At least one of R 1 to R 6 is a structure represented by the following formula (a), and the others are the same or different and each independently hydrogen; -R (C-O) R '; -R (C = O) R '; -OR ';

; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a bridging group, or R1 and R2; R3 and R4; And at least one of R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring,

R9 to R14 and G1 to G8 are the same or different from each other and each independently hydrogen; A halogen group; A hydroxy group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,

R and R "are the same or different and each independently represents a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,

R 'and R "' are the same or different and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group,

Z ^- is an anionic group,

(A)

In the above formula (a)

;

; -SOOR115-; -SOR116-; -SR117-; 치환 또는 비치환된 알킬렌기; 또는 치환 또는 비치환된 알케닐렌기이고,Q is - R101C (= O) R102-; -R103OC (-O) R104-; -R105C (-O) OR106-; -R107OC (-O) OR108-;

;

; -SOOR115-; -SOR116-; -SR117-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,

X is a hydroxy group; An amine group; -OCOOR118; -CONR119R120; Or -NR121COOR122,

T is a substituted or unsubstituted alkyl group,

R101 to R109, R111, R112, and R114 to R117 are the same or different, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted alkenylene group,

R110, R113 and R118 to R122 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

p and q are each an integer of 1 to 4,

2? N + m? 5,

When p and q are each 2 or more, the structures in parentheses of 2 or more are the same or different,

* Is a moiety connected to N in formula (1).

According to another embodiment of the present invention, there is provided a polymer compound comprising a monomer liberated from a compound represented by the general formula (1).

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

According to another embodiment of the present invention, there is provided a color material composition comprising the polymer compound.

According to another embodiment of the present invention, there is provided a resin composition comprising the color material composition.

According to one embodiment of the present invention, there is provided a color filter comprising the above-mentioned resin composition.

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

The compound represented by Chemical Formula 1 according to one embodiment of the present invention is excellent in solubility in a solvent and has excellent chemical resistance.

In addition, according to one embodiment of the present invention, the colorant composition containing the compound represented by Formula 1 exhibits a higher luminance than the conventional pigment, introduces a crosslinkable group, It is possible to improve the chemical resistance, and it is also possible to manufacture a color filter excellent in chemical resistance by using the colored resin composition using the colored resin composition.

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

According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).

Examples of 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 substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy 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 alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or does not have any substituent (s).

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

Quot; refers to a moiety bonded to another substituent or bond.

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

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but 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 amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 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 carbon number of the carbonyl group is not particularly limited, but 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 an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 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 alkyl group may be linear or branched, 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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, 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.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, 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 is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-arylalkylamine groups; An arylamine group; An N-arylheteroarylamine group; 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, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , A diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, and a triphenylamine group, but are not limited thereto.

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

In the present specification, the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroarylamine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

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 is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group, and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- 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 phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention 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 having at least two aryl groups may contain 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 this specification, the heteroaryl group in the present specification includes one or more non-carbon atoms and hetero atoms, and specifically, the hetero atom may be an atom selected from the group consisting of O, N, Se and S, . 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 a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, But are not limited to, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl and dibenzofuranyl groups.

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 having 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 above-mentioned heteroaryl group.

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

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and examples thereof may be selected from the above heteroaryl groups.

In the present specification, an alkylene group means that the alkyl group has two bonding positions, i.e., divalent. The description of the above-mentioned alkyl groups can be applied, except that they are each 2 groups.

In the present specification, the cycloalkylene group means a cycloalkylene group having two bonding positions, i.e., divalent. The description of the above-mentioned cycloalkyl group can be applied except that each of them is 2 groups.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

According to one embodiment of the present invention, in Formula 1, one of Y 1 to Y 6 is N.

According to one embodiment of the present invention, the 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]

[Chemical Formula 1-6]

In Formulas 1-1 to 1-6,

The definitions of R 1 to R 6, R 9 to R 14, G 1 to G 8 and Z ^- are the same as those of the above formula (1).

According to one embodiment of the present invention, at least one of R 1 to R 6 in the general formula (1) is a structure represented by the general formula (a), and the others are the same or different, and each independently hydrogen; -OR '; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a crosslinkable group.

According to one embodiment of the present invention, at least one of R 1 to R 6 in the general formula (1) is a structure represented by the general formula (a), and the others are the same or different, and each independently hydrogen; -OR '; An alkyl group substituted or unsubstituted with a hydroxy group; An alkenyl group; An aryl group substituted or unsubstituted with an alkyl group; Or a crosslinkable group.

According to one embodiment of the present invention, at least one of R 1 to R 6 in the general formula (1) is a structure represented by the general formula (a), and the others are the same or different, and each independently hydrogen; -OR '; An ethyl group substituted or unsubstituted with a hydroxy group; Vinyl group; A phenyl group substituted or unsubstituted with an alkyl group; Or a crosslinkable group.

According to one embodiment of the present invention, at least one of R 1 to R 6 in the general formula (1) is a structure represented by the general formula (a), and the others are the same or different, and each independently hydrogen; -OR '; An ethyl group substituted or unsubstituted with a hydroxy group; Vinyl group; A phenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of a methyl group and an ethyl group; Or a crosslinkable group.

According to another embodiment of the present invention, R is a substituted or unsubstituted alkylene group.

According to another embodiment of the present invention, R is an alkylene group.

According to another embodiment of the present disclosure, R is an ethylene group.

According to another embodiment of the present disclosure, R is a substituted or unsubstituted alkyl group.

According to another embodiment of the present disclosure, R is an alkyl group.

According to another embodiment of the present disclosure, R is a vinyl group.

According to one embodiment of the present invention, the crosslinkable group is a structure represented by any one of the following formulas (2) to (5).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

R201 to R203 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

R204 to R207 are the same or different and are each independently a direct bond; O; NR208; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group,

R208 is hydrogen; Or a substituted or unsubstituted alkyl group,

r, s, t and u are each 1 or 2,

When r, s, t, and u are each 2, the structures in the two brackets are the same or different.

According to one embodiment of the present disclosure, in Formula 2, R201 represents hydrogen; Or an alkyl group.

According to one embodiment of the present disclosure, in Formula 2, R201 represents hydrogen; Or a methyl group.

According to one embodiment of the present invention, in Formula 2, R204 is a direct bond; O; NR208; An alkylene group; Or a cycloalkylene group.

According to one embodiment of the present invention, in Formula 2, R204 is a direct bond; O; NR208; An ethylene group; Or a cyclohexylene group.

According to one embodiment of the present invention, in Formula 3, R205 represents a direct bond; Or an alkylene group.

According to one embodiment of the present invention, in Formula 3, R205 represents a direct bond; Or a methylene group.

According to one embodiment of the present invention, in Formula 4, R202 is hydrogen.

According to one embodiment of the present invention, in Formula 4, R206 is a direct bond; Or an alkylene group.

According to one embodiment of the present invention, in Formula 4, R206 is a direct bond; Or a methylene group.

According to one embodiment of the present disclosure, in Formula 5, R203 represents hydrogen; And is an alkyl group having 1 to 4 carbon atoms.

According to one embodiment of the present invention, in Formula 5, R207 is a direct bond; Or an alkylene group.

According to one embodiment of the present invention, in Formula 5, R207 is a direct bond; Or a methylene group.

According to one embodiment of the present disclosure, R208 is hydrogen; Or an alkyl group having 1 to 4 carbon atoms.

According to one embodiment of the present disclosure, in Formula (a), X is bonded at an ortho position with respect to the bonded position of the phenyl group of Formula (a).

According to one embodiment of the present invention, in the above formula (1), Z ^- is an anionic group, and the anionic group is not particularly limited and includes, for example, those described in U.S. Patent No. 7,939,644, Japanese Patent Publication No. 2006-003080, -01917, Japanese Patent Publication No. 2005-159926, Japanese Patent Publication No. 2007-7028897, Japanese Patent Publication No. 2005-071680, Korean Patent Application Publication No. 2007-7000693, Japanese Patent Publication No. 2005-111696, Japanese Patent Publication No. 2008- The anions described in U.S. Patent No. 249663 can be applied.

Specific examples of the anion include a trifluoromethanesulfonic acid anion, a bis (trifluoromethylsulfonyl) amide anion, a bistrifluoromethanesulfonimide anion, a bisperfluoroethylsulfonimide anion, a tetraphenylborate anion, a tetra (Pentafluorophenyl) borate, tris (trifluoromethanesulfonyl) methide, phosphate ion, nitrate ion, carbonate ion, sulfite ion, halogen group such as bromine group, fluorine group , An iodine group, and a chlorine group.

Also, Z ^- represents boron; Anions including aluminum; Tungsten, molybdenum, silicon and phosphorus, and an oxygen-containing anion. In particular, Z ^- may include an anion of tungstophosphoric acid, an anion of tungstosilicic acid, or an anion of tungsten-based isopoly acid.

According to one embodiment of the present invention, in the general formula (1), Z ^- represents a sulfonimidic acid containing a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen.

According to an exemplary embodiment of the present specification, in the general formula a, Q is - R101C (= O) R102-; Or -R103OC (= O) R104-.

According to another embodiment of the present invention, R101 to R104 are the same or different and are each independently a direct bond; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group.

According to another embodiment of the present invention, R101 to R104 are the same or different and are each independently a direct bond; An alkylene group; Or a cycloalkylene group.

According to another embodiment of the present invention, R101 to R104 are the same or different and are each independently a direct bond; A methylene group; An ethylene group; Or a cyclohexylene group.

According to one embodiment of the present invention, in the formula (a), X is a hydroxyl group; -OCOOR118.

According to another embodiment of the disclosure, R118 is hydrogen; Or a substituted or unsubstituted alkyl group.

According to another embodiment of the disclosure, R118 is hydrogen; Or an alkyl group.

According to another embodiment of the disclosure, R118 is hydrogen; Or a t-butyl group.

According to one embodiment of the present invention, in Formula (a), T is a substituted or unsubstituted alkyl group.

According to one embodiment of the present invention, in Formula (a), T is an alkyl group.

According to one embodiment of the present invention, in the above formula (a), T is a t-butyl group.

According to one embodiment of the present invention, the formula (1) may be selected from the following compounds, but is not limited thereto.

The compound represented by the formula (1) can be prepared by referring to the following Production Examples.

According to one embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.

According to one embodiment of the present invention, there is provided a polymer compound comprising a monomer derived from the compound represented by the formula (1).

As used herein, the term "monomer" means a structure in which a compound is contained in the polymer in a form of two or more groups by polymerization reaction.

According to one embodiment of the present invention, there is provided a color material composition comprising the polymer compound.

The colorant composition may further include at least one of a dye and a pigment in addition to the compound represented by Formula 1 or the polymer compound. For example, the colorant composition may include only the compound represented by the formula (1), but may include the compound represented by the formula (1) and one or more dyes, or the compound represented by the formula (1) , A compound represented by the formula (1), at least one dye, and at least one pigment.

In one embodiment of the present invention, there is provided a resin composition comprising the color material composition.

In one embodiment of the present invention, the resin composition comprises a binder resin; Multifunctional monomers; Antioxidants; Photoinitiators; And a solvent.

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 monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility. The binder resin may further include a binder generally used in the art.

The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include 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 Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the unsaturated imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.

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

The alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.

According to one embodiment of the present invention, 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 multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include 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, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate. Species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator is selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound Or more.

The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.

Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.

The triazine-based compound may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] Methyl) -6- p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like .

The oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.

The solvent is selected from the group consisting of 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 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one selected from the group consisting of citrate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.

According to one embodiment of the present invention, the content of the colorant composition is 5 wt% to 90 wt%, the content of the binder resin is 1 wt% to 30 wt% based on the total weight of the solid content in the resin composition , The content of the antioxidant is 0.001 to 20 wt%, the content of the photoinitiator is 0.1 to 20 wt%, and the content of the polyfunctional monomer is 0.1 to 50 wt%.

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

According to one embodiment of the present invention, the resin composition is one or more than one 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, Further comprising an additive.

According to one embodiment of the present invention, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of the solid content in the resin composition.

The photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone 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-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide; Benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.

As the curing accelerator, curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.

Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.

Specifically, the silicone surfactant is 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-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F- TF-1116SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1025SF, TF- , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.

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 type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -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 and alkoxybenzophenone may be used. Anything that is commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.

The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.

According to one embodiment of the present invention, there is provided a photosensitive material produced using the resin composition.

More specifically, the resin composition of the present invention is applied onto a substrate by a suitable method to form a photosensitive material in the form of a thin film or a pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.

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

The resin composition according to the present invention can be used as a pigment dispersing 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 an organic light emitting diode or a thin film transistor liquid crystal display (TFT LCD) And can be used for a photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board and a photosensitive material for a plasma display panel (PDP) Is not specifically set.

According to an embodiment of the present invention, there is provided a color filter including the photosensitive material.

The color filter can be produced by using the resin composition containing the color material composition. The resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

The resin composition according to one embodiment of the present invention can provide a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance, have.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the kind 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 embodiment, the color filter may further include an overcoat layer.

Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectivity of chrome, and environmental pollution caused by a chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.

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

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD) A liquid crystal display (LCD), and a cathode ray tube (CRT).

Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.

Production Example 1. Preparation of Compound A

5 ml of acetic acid, 5 ml of methylene chloride and 1.64 g (1.2 eq) of cyclohexanone were added to 2 g (8 eq) of 8-aminoquinoline, and the mixture was stirred for 30 minutes. Add 3.5 g of NaBH (OAC) ₃ slowly. After 16 hours of reaction at room temperature, it is washed several times with distilled water and extracted with MC. After drying under reduced pressure, the residue was purified by column chromatography (ethyl acetate: hexane = 1:10) to obtain 2.48 g (yield: 85.4%) of an off-white oil compound A.

Production Example 2. Preparation of Compound B

(0.026 mol, 1 eq) of 8-aminoquinoline was added 50 mL of dimethylformamide (DMF), 17.97 g (0.13 mol, 5 eq) was slowly added at room temperature, and the mixture was stirred for 30 minutes. Then, 7.86 g (0.065 mol, 2.5 eq) of aryl bromide was added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, distilled water was added and extracted with ether. The organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by column (ethyl acetate: hexane = 1: 100 ~ 1: 80) to obtain 1.2 g of Compound B at a yield of 27%.

Production Example 3. Preparation of Compound C

(0.021 mol, 1 eq) of 8-aminoquinoline was added 30 mL of methylene chloride, and 2.73 g (0.027 mol, 1.3 eq) of triethylamine was added slowly at room temperature. Then, 4.8 g (0.056 mol, 2.7 eq) of methacrylic acid was added and stirred at room temperature for 16 hours.

After completion of the reaction, distilled water was added, and the mixture was extracted with methylene chloride. The organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by column (ethyl acetate: hexane = 1:10 to 1:15) to obtain Compound C (0.5 g, 11%).

Production Example 4. Preparation of Compound (D)

5 ml of acetic acid, 5 ml of methylene chloride and 1.64 g (1.2 eq) of cyclohexanone were added to 2 g (1 eq) of 5-amino-isoquinoline and stirred for 30 minutes. Add 3.5 g of NaBH (OAC) ₃ slowly. After 16 hours of reaction at room temperature, it is washed several times with distilled water and extracted with MC. After drying under reduced pressure, the residue was purified by column chromatography (ethyl acetate: hexane = 1: 10) to obtain an off-white oil D (2.25 g, 71.7%).

Production Example 5. Preparation of Compound E

15 g (0.069 mol, 1 eq) of 4,4-difluorobenzophenone and 31.1 g (0.35 mol, 5 eq) of 2-ethylamino ethanol were placed in a nitrogen atmosphere and the temperature was raised to 160 ° C with stirring. The reaction was carried out at 160 DEG C for 48 hours and then cooled to room temperature. Distilled water was added, and methylene chloride was extracted and dried under reduced pressure. The residue was recrystallized from ethyl acetate at room temperature to obtain Compound E (20 g, 82%).

Production Example 6. Preparation of Compound F

9.6 g (0.035 mol, 3 eq) of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid was dissolved in 70 mL of tetrahydrofuran under an atmosphere of nitrogen, and then an ice bath was provided . After 4.28 g (0.028 mol, 2.4 eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added to the reactor, the mixture was stirred for about 15 minutes and then 0.56 g of 4-dimethylaminopyridine (0.005 mol , 0.4 eq). After 15 minutes, 4.10 g (0.011 mol, 1 eq) of Compound E was dissolved in 30 mL of tetrahydrofuran and added slowly. After stirring for 24 hours, the mixture was extracted with methylene chloride and dried under reduced pressure. The residue was purified by column chromatography (ethyl acetate: hexane = 1: 3) to obtain Compound F (4.31 g) in a yield of 43%. When 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid was left after the column, , Washed with NaHCO ₃ (pH 10) solution, extracted with methylene chloride, and dried under reduced pressure.

Preparation 7. Compounds G and H

The title compound was prepared in the same manner as Compound F and purified by column (ethyl acetate: hexane = 1: 3 ratio) to obtain 2.5 g of Compound G (yield: 31.7%). To 2.5 g (0.004 mol, 1 eq) of compound G is added 30 mL of methylene chloride. 0.53 g (0.0053 mol, 1.3 eq) of triethylamine is slowly added at room temperature. Then, 0.77 g (0.009 mol, 2.2 eq) of methacrylic acid was added and stirred at room temperature for 16 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with methylene chloride. The organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by column (ethyl acetate: hexane = 1: 5 ratio) to obtain Compound H (1.9 g, 68%).

Production Example 8. Preparation of Compound (I)

4.31 g (0.005 mol, 1 eq) of Compound F was dissolved in 40 mL of pyridine and then 2.68 g (0.012 mol, 2.5 eq) of di-tert-butyl dicarbonate was slowly added. After 15 minutes, 1.20 g (0.01 mol, 2 eq) of 4-dimethylaminopyridine was added. After the reaction at 60 ° C for 3 hours, distilled water was added and extracted with methylene chloride and the solvent was removed under reduced pressure. The residue was purified by column chromatography (methylene chloride: ethyl acetate = 10: 1) to obtain Compound I (3.87 g, 73%).

Production Example 9. Preparation of Compound J and J-1

1.5 g (0.002 mol, 1 eq) of compound H was dissolved in chloroform. 0.44 g (0.003 mol, 1.3 eq) of phosphorus chloride was added in a nitrogen atmosphere and stirred for about 30 minutes. Then, 0.59 g (0.0026 mol, 1.3 eq) of Compound A was dissolved in chloroform and slowly added. After reacting at 60 ° C for 2 hours, the reaction was terminated with distilled water and extracted with methylene chloride. The solvent was removed under reduced pressure, and the solvent was removed. The solvent was removed and the residue was purified by column chromatography with methylene chloride: ethyl acetate = 1: 1 to remove the precursor and then purified by changing the composition to methylene chloride: methanol: ethyl acetate = 6: ≪ / RTI > Thereafter, 1.0 g (0.001 mol, 1 eq) of Compound J was dissolved in 30 mL of methanol, 0.46 g (0.0016 mol, 1.5 eq) of bistrifluoromethanesulfonimide (BMI) was added, and the mixture was stirred at room temperature. Distilled water was added and the precipitated blue powder was filtered to obtain 1.1 g of the compound J-1 in a yield of 87%.

Production Example 10. Preparation of Compound K and K-1

Compound K was prepared in the same manner as in Production Example 9, except that Compound F was used instead of Compound H and Compound B was used instead of Compound A to obtain 0.52 g of Compound K in a yield of 28% 87% yield.

Production Example 11. Preparation of Compound L and L-1

In the same manner as in Production Example 9 except that Compound F was used instead of Compound H and Compound C was used instead of Compound A, 0.8 g of Compound L was obtained in a yield of 42%, and 0.82 g of Compound L- 83% yield.

Preparation 12. Preparation of compounds M and M-1

In the same manner as in Production Example 9 except that Compound I was used instead of Compound H and Compound C was used instead of Compound A, 0.61 g of Compound M was obtained in a yield of 33%, and 0.62 g of Compound M- 85% yield.

Production Example 13. Preparation of Compound N and N-1

In the same manner as in Production Example 9, except that Compound F was used instead of Compound H and Compound D was used instead of Compound A, 0.45 g of Compound N was obtained in a yield of 22%, and 0.50 g of Compound N- 88% yield.

Production Example 14: Preparation of compound O

The anion was prepared in the same manner as in Synthesis Example 1 of the domestic patent publication No. 2015-0009447. 0.5 g (0.0005 mol, 1 eq) of the compound J-1 is dissolved in 10 g of dimethylformamide. 0.27 g (0.0008 mol, 1.5 eq) of an anion is added. Stir at 55 ° C for 3 hours and cool to room temperature. And the mixture was dropwise added to 1000 g of distilled water with stirring for 1 hour, followed by vacuum filtration to obtain 0.45 g of Compound O in a yield of 69%.

Production Example 15. Preparation of Comparative Example Compound 1

Except that bistrifluoromethanesulfonimide was used as the anion in Example 7 of the domestic patent application publication No. 2012-0014111, 0.8 g of the compound of the comparative example 1 was obtained in a yield of 80%.

[Preparation and evaluation of coloring composition]

Comparative Example 1

A photosensitive blue resin composition was prepared in the following composition.

0.85% by weight of the comparative compound prepared in Preparation Example 15 as a blue dye compound, 0.5% by weight of a binder resin (benzylmethacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: (TF-1740) and 20.58% by weight of a photopolymerization initiator (PBG-3142), 20.46% by weight of dipentaerythritol hexaacrylate as an acrylic monomer, 56.57% by weight of propylene glycol monomethyl ether acetate, 0.68% And 0.66% by weight of the auxiliary (KRM-503) were mixed so as to be uniformly mixed to prepare a photosensitive blue resin composition.

Example 1

A blue resin composition was prepared in the same composition as in Comparative Example 1, except that Compound J-1 was used in place of Comparative Example Compound 1 as a blue dye compound.

Example 2

A blue resin composition was prepared in the same composition as in Comparative Example 1, except that Compound N-1 was used in place of Comparative Example Compound 1 as a blue dye compound.

Substrate manufacturing method

The photosensitive resin composition was spin-coated on glass (5 x 5 cm) and pre-baked at 100 ° C for 100 seconds to form a film. The entire surface of the substrate on which the film was formed was irradiated with an exposure dose of 40 mJ / cm ² using an exposure machine.

The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and post baked at 230 캜 for 20 minutes to obtain a color pattern.

Chemical resistance evaluation

Subsequently, the substrate was cut into 1 × 5 cm, and 16 g of N-methyl-2-pyrrolidone solvent was dipped into 2 × 5 cm pieces. Subsequently baking was carried out in a convection oven at 80 ° C. for 40 minutes . The absorbance of the solvent from which the substrate pieces were taken out was measured and is shown in Table 1 below.

division Absorbance Improvement rate (%) Comparative Example 1 0.761 - Example 1 0.054 92.95% Example 2 0.072 90.61%

From the above, it becomes possible to obtain a coloring composition for a color filter and a color filter excellent in chemical resistance by using the coloring material composition containing the compound represented by the general formula (1) according to one embodiment of the present specification.

Claims (10)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
Y1 is N or CR9, Y2 is N or CR10, Y3 is N or CR11, Y4 is N or CR12, Y5 is N or CR13, Y6 is N or CR14,
At least one of Y1 to Y6 is N,
At least one of R 1 to R 6 is a structure represented by the following formula (a), and the others are the same or different and each independently hydrogen; -R (C-O) R '; -R (C = O) R '; -OR ';

; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a bridging group, or R1 and R2; R3 and R4; And at least one of R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring,
R9 to R14 and G1 to G8 are the same or different from each other and each independently hydrogen; A halogen group; A hydroxy group; A substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,
R and R "are the same or different and each independently represents a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group,
R 'and R "' are the same or different and each independently represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted aryl group,
Z ^- is an anionic group,
(A)

In the above formula (a)
Q is - R101C (= O) R102-; -R103OC (-O) R104-; -R105C (-O) OR106-; -R107OC (-O) OR108-;

;

; -SOOR115-; -SOR116-; -SR117-; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; An amine group; -OCOOR118; -CONR119R120; Or -NR121COOR122,
T is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112, and R114 to R117 are the same or different, and are each independently a direct bond; A substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted alkenylene group,
R110, R113 and R118 to R122 are the same or different and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
p and q are each an integer of 1 to 4,
2? N + m? 5,
When p and q are each 2 or more, the structures in parentheses of 2 or more are the same or different,
* Is a moiety connected to N in formula (1). The compound according to claim 1, wherein the crosslinkable group is a structure represented by any one of the following formulas (2) to (5):
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
R201 to R203 are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
R204 to R207 are the same or different and are each independently a direct bond; O; NR208; A substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group,
R208 is hydrogen; Or a substituted or unsubstituted alkyl group,
r, s, t and u are each 1 or 2,
When r, s, t, and u are each 2, the structures in the two brackets are the same or different. 2. The compound according to claim 1, wherein X is attached to an ortho position with respect to the bonded position of the phenyl group of formula (a). 2. The compound of claim 1, wherein Z ^- is a sulfonimidic acid comprising a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen. The compound according to claim 1, wherein the compound of formula (1) is selected from the following compounds:

A colorant composition comprising a compound according to any one of claims 1 to 5. The colorant composition according to claim 6, further comprising at least one of a dye and a pigment. [Claim 9] The method according to claim 7, wherein the dye is at least one dye selected from xanthene dyes, cyanine dyes and azapphyrin dyes,
Wherein the pigment is a blue pigment or a purple pigment. A compound represented by formula (1) according to claim 1; Binder resin; Multifunctional monomers; Photoinitiators; Antioxidants; And a solvent. A color filter comprising the resin composition according to claim 9.