TWI628239B - Compound,colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

This specification relates to a novel compound, a coloring material composition containing the same, and a resin composition containing the same.

Description

Compound, coloring material composition containing the same, and resin composition containing the same

This specification relates to a novel compound, a coloring material composition containing the same, and a resin composition containing the same.

In recent years, as a light source of a liquid crystal display (LCD), a light emitting diode (Light Emitting Diode, LED), an organic light emitting diode (Organic Light Emitting Diode, OLED), and a quantum dot (Quantum Dot, QD) and other components to replace the existing Cold Cathode Fluorescent Lamp (CCFL). However, display products in which a color filter is removed in order to produce a thin film display, a flexible display, and the like, that is, display products using self-luminous light such as LEDs, OLEDs, and QDs as unit pixels are being developed and produced.

However, in the case of using LED, OLED, QD, etc. as a display unit pixel, it is difficult to increase the area. In the case of using LED, OLED, QD, etc., in order to develop these elements as light sources and color Filter displays, while many efforts are underway.

In order to achieve a desired color, a color filter suitable for a light source is required. Currently, a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion liquid, not only the pigment exists in the state of particles to scatter light, but also the surface area of the pigment sharply increases due to the miniaturization of the pigment. As a result, the dispersion stability is deteriorated and unevenness is generated Pigment particles.

Therefore, it is considered that it is difficult to meet the requirements of high-quality requirements such as high brightness, high contrast, and high definition that have recently reached the limit.

In order to solve the problems and achieve high brightness, high contrast, and high resolution, research into using dyes as pigments instead of pigments has recently been conducted. Among them, many attempts have been made to use triarylmethane dyes as blue colorants. Generally, triarylmethane dyes have high light transmittance at 420nm to 450m and have effective color characteristics. However, chemical resistance is reduced due to higher solubility than pigments, and they are found in color filters due to lower heat resistance than pigments. Restricted use.

[Prior Art Literature]

[Patent Literature]

Korean Published Patent No. 2001-0009058

Korean Public Patent No. 2013-0130976

This specification provides a novel compound, a coloring material composition containing the same, and a resin composition containing the same.

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

In the chemical formula 1, A is represented by the following chemical formula A-1 or A-2,

At least one of R1 to R6 is a structure represented by the following chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -R (C = O) R ', -RO (C = O) R',- ROR ', , Substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or crosslinkable group; or Said that at least one of R1 and R2, R3 and R4, and R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring, R7 to R22 are the same or different from each other, and are each independently hydrogen, halogen, hydroxyl, A substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group, R and R "are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group, Or substituted or unsubstituted arylene, R 'and R''' are the same or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, Or a substituted or unsubstituted aryl group, Z ^- is an anionic group, In the chemical formula a, Q is -R101C (= O) R102-, -R103OC (= O) R104-, -R105C (= O) OR106-, -R107OC (= O) OR108-, ; , -SOOR115-, -SOR116-, -SR117-, substituted or unsubstituted alkylene, or substituted or unsubstituted alkylene, and X is hydroxyl, amine, -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 from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group, A substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted alkylene group, R110, R113, and R118 to R122 are the same as or different from each other, and are each independently hydrogen, or substituted or unsubstituted Alkyl, p and q are integers from 1 to 4, 2 ≦ p + q ≦ 5, and when p and q are 2 or more, the structures in two or more parentheses are the same or different from each other, and * is the same as The N-linked site of Chemical Formula 1, It is a site | part connected with said chemical formula 1.

According to another aspect of the present specification, a coloring material composition including the compound represented by the chemical formula 1 is provided.

According to another aspect of the present specification, a resin composition including the coloring material composition is provided.

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

In addition, according to an aspect of the present specification, a display device including the color filter is provided.

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

In addition, according to an embodiment of the present specification, the coloring material composition including the compound represented by the chemical formula 1 exhibits higher brightness than when a conventional pigment is used, and a crosslinkable group can be introduced to improve triarylmethane. The fragile chemical resistance of dyes. Furthermore, a coloring resin composition using the same can be used to produce a color filter excellent in chemical resistance.

FIG. 1 is a view showing the results of chemical resistance evaluation of Examples 1 to 3 and Comparative Example 1 as one embodiment of the present specification.

Hereinafter, this specification will be described in more detail.

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

In the present specification, examples of the substituent are described below, but the invention is not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and if the substituted position is a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, then Without limitation, when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

The term "substituted or unsubstituted" in this specification means substituted or not having any substituent selected from the group consisting of: deuterium, halo, nitrile, nitro,醯 imino, 醯 amino, carbonyl, ester, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted Or unsubstituted aryloxy, substituted or unsubstituted alkylthiooxy, substituted or unsubstituted arylthiooxy, substituted or unsubstituted alkylsulfonyloxy, Substituted or unsubstituted arylsulfonyloxy, substituted or unsubstituted alkenyl, substituted or unsubstituted amine, substituted or unsubstituted aryl, and substituted or unsubstituted One or two or more substituents in the group consisting of substituted heterocyclic groups.

In this manual, It is a site | part bonded with another substituent or a bond part.

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

In this specification, the carbon number of the fluorene imino group is not particularly limited, but is preferably 1 to 30 carbon numbers. Specifically, the compound may be a compound having a structure described below, but is not limited thereto.

In the present specification, in the amidino group, the nitrogen of the amidino group may be substituted by hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, although it may be a compound of the following structural formula, it is not limited to this.

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

In the present specification, in the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. in particular, It may be a compound of the following structural formula, but it is not limited thereto.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, but is preferably 1 to 30. Specific examples are: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, third butyl, second butyl, 1-methyl-butyl, 1-ethyl-butyl Base, n-pentyl, isopentyl, neopentyl, third pentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3- Dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, n-octyl, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4 -Methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In this specification, the cycloalkyl group is not particularly limited, but preferably has a carbon number of 3 to 30. Specifically, there are: cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3- Dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-third Butylcyclohexyl, cycloheptyl, cyclooctyl and the like are not limited thereto.

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. Specifically: Methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, third butoxy, second butoxy, n-pentyloxy, neopentyloxy Methyl, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy Group, benzyloxy group, p-methylbenzyloxy group, and the like, but are not limited thereto.

In the present specification, the amine group may be selected from the group consisting of -NH ₂ , alkylamino, N-arylalkylamino, arylamino, N-arylheteroarylamine, and N-alkylheteroarylamine. The number of carbon atoms in the group consisting of a group and a heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methyl-anthrylamido, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, etc., but not Limited to this.

In the present specification, the N-alkylarylamino group refers to an amine group in which an alkyl group and an aryl group are substituted on N of the amine group.

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

In the present specification, the N-alkylheteroarylamino group refers to an amino group in which an alkyl group and a heteroarylamino group are substituted on N of the amine group.

In this specification, an alkyl group in an alkylamino group, an N-arylalkylamino group, an alkylthiooxy group, an alkylsulfonic acidoxy group, or an N-alkylheteroarylamino group is an alkyl group as described above. The example is described. Specifically, the alkylthiooxy group includes methylthiooxy group, ethylthiooxy group, third butylthiooxy group, hexylthiooxy group, and octylthiooxy group. base, Ethylsulfonic acidoxy group, propylsulfonic acidoxy group, butylsulfonic acidoxy group, and the like are not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, but is preferably 2 to 30. Specific examples are: vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentene Group, 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, distyryl, styryl, and the like are not limited thereto.

In this specification, an aryl group may be monocyclic or polycyclic.

In the case where the aryl group is a monocyclic aryl group, the number of carbons is not particularly limited, and preferably 6 to 30 carbons. Specific examples of the monocyclic aryl group include, but are not limited to, phenyl, biphenyl, and bitriphenyl.

In the case where 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, fluorenyl, fluorenyl, But not limited thereto.

In this specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to the atom to which the substituent is substituted, a substituent closest to the position of the substituent in the stereostructure, or Other substituents substituted on a substituted atom. For example, two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon on the aliphatic ring can be interpreted as "adjacent" groups to each other.

In this specification, the aryl group in the aryloxy group, arylthiooxy group, arylsulfonic acid group, N-arylalkylamino group, N-arylheteroarylamino group, and arylphosphine group is As described for the exemplification of the aryl group. Specifically, aryloxy includes: phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy P-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthyloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9 -Phenanthryloxy, etc., arylthiooxy is: phenylthio, 2-methylphenylthio, 4-tert-butylphenylthio, etc., and arylsulfoxy is : Benzenesulfonic acid oxy group, p-toluenesulfonic acid oxy group, and the like, but are not limited thereto.

Examples of arylamino groups in this specification are: substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, or substituted or unsubstituted triarylamino groups . The aryl group in the arylamino group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more of the aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamino group may be selected from the exemplification of the aryl group.

In this specification, a heteroaryl group includes one or more atoms other than carbon and heterogeneous atoms. Specifically, the heteroaryl group may include one or more atoms selected from the group consisting of O, N, Se, S, and the like. Atoms in the group. The number of carbons is not particularly limited, but preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclyl are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acryl Pyridine Base, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxaline, phthalazinyl, pyrazolopyrimidyl, pyrazolopyrazinyl, pyrazinopyrazinyl, isoquine Phenyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, brown Phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazyl, and dibenzofuranyl are not limited to these.

Examples of heteroarylamino groups in this specification are: substituted or unsubstituted monoheteroarylamine groups, substituted or unsubstituted diheteroarylamino groups, or substituted or unsubstituted triarylamino groups Heteroarylamino. The heteroarylamine group containing two or more of the heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamino group may be selected from the illustrations of the heteroaryl group.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group are as described above.

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 may be selected from the examples of the heteroaryl group.

In this specification, an alkylene group means that there are two bonding positions on an alkyl group, that is, a divalent group. Except that these are each a divalent group, the description of the alkyl group can be applied.

In this specification, a cycloalkyl group means a divalent group having two bonding positions on the cycloalkyl group. In addition to these being divalent groups, the description of the cycloalkyl group can be applied.

In the present specification, the arylene group means that there are two bonding positions on the aryl group, that is, a divalent group. In addition to these being divalent groups, the description of the aryl group can be applied.

In the present specification, a heteroaryl group means that there are two bonding positions on a heteroaryl group, that is, a divalent group. In addition to these being divalent groups, the description of the heteroaryl group can be applied.

According to an aspect of the present specification, the chemical formula 1 is represented by the following chemical formulas 1-1 or 1-2.

In Chemical Formula 1-1 and 1-2, R1 to R4, R7 to R14 and Z ^- is the same as defined in Chemical Formula 1, R5, definition of R6, R15 to R22 and the chemical formulas A-1 and A- 2 are the same.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -ROR ', substituted or unsubstituted. Alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or crosslinkable group.

According to an embodiment of the present specification, in the chemical formula 1, at least one of R1 to R6 is a structure represented by the chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -ROR ', substituted Or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or crosslinkable group.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -ROR ', substituted or unsubstituted by a hydroxyl group. A substituted alkyl group, an alkenyl group, an aryl group substituted or unsubstituted, or a crosslinkable group.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -ROR ', substituted or unsubstituted by a hydroxyl group. A substituted ethyl, vinyl, alkyl, substituted or unsubstituted phenyl, or crosslinkable group.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the rest are the same or different from each other, and are each independently hydrogen, -ROR ', substituted or unsubstituted by a hydroxyl group. Substituted ethyl, vinyl, unsubstituted or substituted with one or more substituents selected from the group consisting of methyl and ethyl A substituted phenyl group or a crosslinkable group.

According to another aspect of the present specification, the R is a substituted or unsubstituted alkylene group, or a substituted or unsubstituted cycloalkylene group.

According to another aspect of the present specification, R is an alkylene group or a cycloalkylene group.

According to another embodiment of the present specification, the R is an ethylidene group or a cyclohexyl group.

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

According to another aspect of the present specification, R ′ is an alkyl group.

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

According to an embodiment of the present specification, the crosslinkable group has a structure represented by any one of the following chemical formulas 2 to 5.

[Chemical Formula 5]

In the chemical formulas 2 to 5, the R201 to R203 are the same or different from each other, and are independently hydrogen or a substituted or unsubstituted alkyl group, and the R204 to R207 are the same or different from each other, and are each independently directly bonded. , O, NR208, substituted or unsubstituted alkylene, or substituted or unsubstituted cycloalkyl, R208 is hydrogen, or substituted or unsubstituted alkyl, r, s, t and u is 1 or 2, respectively, and in the case where r, s, t, and u are 2, the structures in the two parentheses may be the same or different.

According to an embodiment of the present specification, in the chemical formula 2, R201 is hydrogen or an alkyl group.

According to an embodiment of the present specification, in the chemical formula 2, R201 is hydrogen or methyl.

According to an embodiment of the present specification, in the chemical formula 2, R204 is a direct bond, O, NR208, an alkylene group, or a cycloalkylene group.

According to an embodiment of the present specification, in the chemical formula 2, R204 is a direct bond, O, NR208, ethylene, or cyclohexyl.

According to an embodiment of the present specification, in the chemical formula 3, R205 is a direct bond or an alkylene group.

According to an embodiment of the present specification, in the chemical formula 3, R205 is a direct bond or a methylene group.

According to an embodiment of the present specification, in the chemical formula 4, R202 is hydrogen.

According to an embodiment of the present specification, in the chemical formula 4, R206 is a direct bond or an alkylene group.

According to an embodiment of the present specification, in the chemical formula 4, R206 is a direct bond or a methylene group.

According to an embodiment of the present specification, in the chemical formula 5, R203 is hydrogen and an alkyl group having 1 to 4 carbon atoms.

According to an embodiment of the present specification, in the chemical formula 5, R207 is a direct bond or an alkylene group.

According to an embodiment of the present specification, in the chemical formula 5, R207 is a direct bond or a methylene group.

According to an embodiment of the present specification, the R208 is hydrogen or an alkyl group having 1 to 4 carbon atoms.

According to an embodiment of the present specification, in the chemical formula a, X is bonded to an ortho position with respect to the position where T is bonded to the phenyl group of the chemical formula a.

According to an embodiment of the present specification, in the chemical formula 1, Z ^- is an anionic group, and the anionic group is not particularly limited. For example, it can be applied: US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080 , Japanese Patent Laid-Open No. 2006-001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. 2007-7028897, Japanese Patent Laid-Open No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Laid-Open Anions described in 2005-111696 and Japanese Patent Laid-Open No. 2008-249663.

Specific examples of the anion include trifluoromethanesulfonate anion, bis (trifluoromethylsulfonyl) fluorenimide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, Phenylborate anion, tetra (4-fluorophenyl) borate, tetra (pentafluorophenyl) borate, tris-trifluoromethanesulfonylmethylate, phosphate ion, nitrate ion, carbonate ion , Sulfite ion, halogen group, such as bromo, fluoro, iodo, chloro and the like.

Further, the Z ^- anion comprises means boron, aluminum; selected from the group comprising tungsten, molybdenum, the group, consisting of silicon and phosphorus and one or more elements of oxygen and anions. In particular, the Z ^- anion may include tungsten acid, tungsten silicate anions, isopoly or tungsten anion of an acid.

According to an embodiment aspect of the present specification, the Chemical Formula 1, Z ^- is: sulfonylureas imidate containing a halogenated hydrocarbon group; containing sulphonic acid; halogen-containing, boron, aluminum anions; comprising or selected from the group consisting of tungsten, An anion of one or more elements and oxygen in a group consisting of molybdenum, silicon, and phosphorus.

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

According to another embodiment of the present specification, the R101 to R104 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene, or a substituted or unsubstituted cycloalkane base.

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

According to another embodiment of the present specification, the R101 to R104 are the same as or different from each other, and are each independently a direct bond, a methylene group, an ethylene group, or a cyclohexyl group.

According to an embodiment of the present specification, in the chemical formula a, X is a hydroxyl group and -OCOOR118.

According to another aspect of the present specification, R118 is hydrogen, or a substituted or unsubstituted alkyl group.

According to another aspect of the present specification, R118 is hydrogen or alkyl.

According to another embodiment of the present specification, R118 is hydrogen or a third butyl group.

According to an embodiment of the present specification, in the chemical formula a, T is a substituted or unsubstituted alkyl group.

According to an embodiment of the present specification, in the chemical formula a, T is an alkyl group.

According to an embodiment of the present specification, in the chemical formula a, T is a third butyl group.

According to an embodiment of the present specification, the chemical formula 1 may be selected from the following compounds, but is not limited thereto.

The compound represented by the said Chemical Formula 1 can be manufactured with reference to the manufacturing example mentioned later as a reference.

According to an aspect of the present specification, a coloring material composition including the compound represented by the chemical formula 1 is provided.

The coloring material composition may include at least one of a dye and a pigment in addition to the compound represented by the chemical formula 1. For example, the coloring material composition may include only the compound represented by the chemical formula 1, or the compound represented by the chemical formula 1 and one or more dyes, or the compound represented by the chemical formula 1 and one kind. The above pigments may include the compound represented by Chemical Formula 1, one or more dyes, and one or more pigments. this In one aspect of the specification, a resin composition including the coloring material composition is provided.

In an embodiment of the present specification, the resin composition may further include a binder resin, a polyfunctional monomer, an antioxidant, a photoinitiator, and a solvent.

The binder resin is not particularly limited as long as it exhibits physical properties such as strength and developability of a film produced from a resin composition.

The binder resin may be a copolymerized resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further include a binder commonly used in the technical field.

The polyfunctional monomer that imparts mechanical strength to the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated sulfonimines, and acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters can be selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, (methyl) ) Butyl acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, tertiary butyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) Isobornyl acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, (methyl) ) 2-hydroxypropyl acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, fluorenyl octyloxy-2-hydroxypropyl (meth) acrylate Ester, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate Esters, methoxytriethylene glycol (methyl Base) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylbenzene Oxypolyethylene glycol (meth) acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, (meth) ) Hexafluoroisopropyl 1,1,1,3,3,3-acrylic acid, octafluoropentyl (meth) acrylate, heptafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate Α-hydroxymethyl methacrylate, α-hydroxymethacrylate, α-hydroxymethacrylate, and α-hydroxymethacrylate, but it is not limited to these.

Specific examples of the aromatic vinyl monomers include free styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxystyrene And (ortho, meta, para) -chlorostyrene, but not limited to these.

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

Specific examples of the unsaturated fluorene imines can be selected from N-phenylcis butylene diimide, N- (4-chlorophenyl) cis butylene diimide, and N- (4-hydroxybenzene Group), but is not limited to this group consisting of maleimide diimide and N-cyclohexylmaleimide.

The acid anhydride includes maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, and the like, but is not limited to these.

If the monomer which provides the said alkali solubility is an acid group, it does not have a special thing. The limitation is, for example, preferably selected from (meth) acrylic acid, butenoic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- 2-carboxylic acid, mono-2-(((meth) acryloxy) ethyl) phthalate, mono-2-(((meth) acryl) oxy) ethyl succinate, ω-carboxy poly One or more of the group consisting of caprolactone mono (meth) acrylate is not limited to these.

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

The polyfunctional monomer is a monomer having a function of forming a photoresist image by light, and specifically may be selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl Alcohol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanurate A group of trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate One or a mixture of two or more of them.

The photoinitiator is not particularly limited as long as it is an initiator that generates free radicals by light to trigger cross-linking. And one or more of the group consisting of oxime-based compounds.

The acetophenone compounds are: 2-hydroxy-2-methyl-1-phenylpropane-1- Ketone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propane 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-morpholinyl-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl)- Butane-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butane-1-one, or 2-methyl-1 -[4- (methylthio) phenyl)]-2-morpholinylpropane-1-one and the like are not limited thereto.

The biimidazole-based compounds include: 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl)- 4,4 ', 5,5'-tetra (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl)- 4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. Is not limited to this.

The triazine-based compound includes: 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propanoic acid, 3- {4- [2,4 -Bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanoic acid 1,1,1,3,3,3-hexafluoroisopropyl ester, 2- {4- [2,4 -Bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} ethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl ] Phenylthio} 2-epoxyethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -trisazine-6-yl] phenylthio} cyclohexyl acetate, 2 -{4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} benzyl acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) ) -Mesytriazine-6-yl] phenylthio} propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanyl Amine, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylamine Phenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc. are not limited thereto .

The oxime-based compounds include: 1,2-octanedione-1- (4-phenylthio) phenyl-2- (o-benzoyl oxime) (Ciba-Geigy), CGI124), ethyl ketone-1- (9-ethyl) -6- (2-methylbenzylidene-3-yl) -1- (O-acetamidooxime) (CGI242), N-1919 ( ADEKA, etc.) is not limited to this.

The solvent may be one or more 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 ether , Chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane , Heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tertiary butanol, 2-ethoxypropanol, 2-methoxy Propanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ether acetate, 3-methoxybutyl acetate, 3-ethoxypropionic acid Ethyl ester, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether are not limited thereto.

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

The total weight of the solid content refers to the total of the total weight of components other than the solvent in the resin composition. The solid content and the basis weight percentage of each component based on the solid content can be measured by a general analysis method used in the art such as liquid chromatography or gas chromatography.

According to an embodiment of the present specification, the resin composition additionally includes a member selected from the group consisting of a photocrosslinking sensitizer, a hardening accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, One or two or more additives in a group consisting of a dispersant and a leveling agent.

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

As the photocrosslinking sensitizer, one or more members selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4- Bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl benzoate, 3,3-dimethyl- Benzophenone compounds such as 4-methoxybenzophenone, 3,3,4,4-tetrakis (third butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9 -Fluorenone compounds such as fluorenone, 2-methyl-9-fluorenone; thioanthrone, 2,4-diethylthioxanthone, 2-chlorothiaxanthone, 1-chloro-4- Thioxanthone-based compounds such as propyloxythioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthracenes such as xanthone and 2-methylxanthone Ketone compounds; anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, third butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone and other anthraquinone compounds; 9-benzene Acridine, Acridine compounds such as 1,7-bis (9-acridyl) heptane, 1,5-bis (9-acridylpentane), 1,3-bis (9-acridyl) propane; benzyl Dicarbonyl compounds such as 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; 2,4,6-trimethyl Phosphine oxide compounds such as benzamyl diphenylphosphine oxide, bis (2,6-dimethoxybenzyl) -2,4,4-trimethylpentyl phosphine oxide; methyl-4- (Dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoic acid Benzoate compounds such as esters; 2,5-bis (4-diethylaminobenzylidene) cyclopentanone, 2,6-bis (4-diethylaminobenzylidene) cyclohexanone Amine synergists such as 2,6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino ) Coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzylidene-7- (diethylamino) coumarin, 3 -Benzylidene-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, Coumarin compounds such as 11H-C1] -benzopyrano [6,7,8-ij] -quinazin-11-one; 4-diethyl Chalcone group, 4-azido benzylidene acetophenone chalcone compound; 2- benzoyl methylene, 3-methyl-naphtho -b- thiazoline.

The hardening accelerator is used for improving hardening and mechanical strength. Specifically, one or more members selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2- Mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), Pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetra (2-mercaptoacetate), pentaerythritol-tri (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate) ), And trimethylolpropane-tris (3-mercaptopropionate).

The adhesion promoter used in this specification can be selected from methacrylic acid Methyl groups such as methyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropyldimethoxysilane, etc. One or more acrylic silane coupling agents are selected and used. As the alkyltrimethoxysilane, it can be selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc. Use more than one.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant can be used: BYK-077, BYK-085, BYK-Chemie, 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., fluorine-based surfactants can be used: F-114, F-177, F-410, F-411, F-411 of Dai Nippon Ink & Chemicals 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, etc. are not limited to this.

The antioxidant may be selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a sulfur antioxidant, and a phosphine antioxidant. One or more of the groups formed are not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; 2,6-di-third-butyl-p-cresol, and octadecane 3- (4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-tert-butyl-4-hydroxy) Phenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-third-butyl-4-hydroxybenzyl) benzene, 3,5- Diethyl tertiary butyl-4-hydroxybenzyl phosphite, 2,2-thiobis (4-methyl-6-third butylphenol), 2,6-g, t-butyl Phenol 4,4'-butylene-bis (3-methyl-6-third butylphenol), 4,4'-thiobis (3-methyl-6-third butylphenol) or bis [ 3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) Hindered phenol such as butanoicacid] glycol ester) is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine Or amine secondary antioxidants such as N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilaurylthiopropionate, distearylsulfide Thio-based secondary antioxidants such as propionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or Triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4- ditbutylphenyl) Pentaerythritol Diphosphite) or (1,1'-biphenyl) -4,4'-diylbisphosphinic acid tetra [2,4-bis (1,1-dimethylethyl) phenyl] ester Phosphite-based secondary antioxidants such as ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

The ultraviolet absorber can be used: 2- (3-third butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, etc., but It is not limited to this, and generally any user can use either of them in the art.

The thermal polymerization inhibitor may include, for example, one or more members selected from the group consisting of p-anisole, hydroquinone, pyrocatechol, and tert-butylcatechol. (tert-butyl catechol), N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-third-butyl-p-cresol, o-benzene Triphenol, benzoquinone, 4,4-thiobis (3-methyl-6-third butylphenol), 2,2-methylenebis (4-methyl-6-third butylphenol) , 2-mercaptoimidazole, and phenothiazine, but are not limited to these, and may include those generally known in the technical field.

The dispersant may be used in a method of internally adding to the pigment or a method of externally adding to the pigment in a state where the pigment is surface-treated in advance. The dispersant may be a compound type, nonionic, anionic or cationic dispersant, and examples thereof include fluorine-based, ester-based, cationic, anionic, non-ionic, and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant is selected from the group consisting of polyalkylene glycols and their esters, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonate esters, and sulfonate salts. Or more, but is not limited to the group consisting of carboxylic acid esters, carboxylic acid salts, alkylamidoalkylene oxide adducts, and alkylamines.

The leveling agent may be polymeric or non-polymeric. Polymeric Specific examples of the leveling agent include polyethyleneimine, polyamidoamine, a reaction product of an amine and an epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur compounds and non-polymer compounds The nitrogen compound is not limited to this, and any one of ordinary users in the art can use either one.

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

The color filter can be manufactured using a resin composition containing the coloring 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 coating method is not particularly limited, and a spray method, a roll coating method, a spin coating method, or the like can be used, and a spin coating method is generally widely used. In addition, after forming the coating film, a part of the residual solvent can be removed under reduced pressure as appropriate.

The light source for hardening the resin composition of the present specification includes, for example, mercury vapor arc (arc), carbon arc, Xe arc, and the like, which emit light having a wavelength of 250 nm to 450 nm, but is not necessarily limited thereto.

The resin composition of this specification can be used for: pigment-dispersed photosensitive materials for manufacturing thin-film transistor liquid crystal display devices (TFT LCD), color filters, thin-film transistor liquid-crystal display devices (TFT LCD), or black matrices of organic light-emitting diodes. Photosensitive material for formation, Photosensitive material for overcoat layer formation, Columnar spacer photosensitive material, Photocurable paint, Photocurable ink, Photocurable adhesive, Printing plate, Photosensitive material for printed wiring board, Plasma display The use of the photosensitive material for a panel (Plasma Diasplay Panel, PDP) is not particularly limited.

The resin composition according to an embodiment of the present specification is excellent in heat resistance, and has little color change due to heat treatment. The color reproduction rate is high even through a hardening process during the manufacture of a color filter, and high brightness and contrast can be provided. Color filters.

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

Between the color pixels of the color filter, a grid-like black pattern called a black matrix may be arranged for the purpose of improving the contrast. The material of the black matrix can use chromium. In this case, a method can be used in which chromium is deposited on the entire glass substrate and a pattern is formed by an etching process. However, in consideration of the high cost of the steps, the high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing can be used.

The black matrix according to an embodiment of the present specification may use a black pigment or a black dye as a coloring material. For example, carbon black can be used alone, or carbon black can be used in combination with colored pigments. At this time, because colored pigments with insufficient light-shielding properties are mixed, it has the following advantages: even if the amount of coloring material increases, the strength of the film or the substrate The adhesion will not decrease.

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

The display device may be a plasma display panel (Plasma Display Panel (PDP), Light Emitting Diode (LED), Organic Light Emitting Diode (OLED), Liquid Crystal Display (LCD), Thin Film Transistor (Thin Film Transistor) -Liquid Crystal Display (LCD-TFT) and Cathode Ray Tube (CRT).

Hereinafter, the present specification will be described in detail with examples. The following examples are intended to explain the present specification, and the scope of the present specification includes the scope described in the scope of the following patent application and its substitutions and changes, and is not limited to the scope of the embodiments.

[Production Example 1] Production of Compound A

To 0.55 g (0.38 mmol, 1.2 eq) of naphthalene-1-amine were added 1 mL of acetic acid (AcOH), 0.3 g (0.31 mmol, 1 eq) of cyclohexanone, and 1 mL of dichloromethane (MC), and stirred for 30 minutes. about. Then, 1.0 g (4.7 mmol, 1.5 eq) of sodium triacetoxyborohydride (NaBH (OAc) ₃ ) was slowly added. After stirring at room temperature for about 16 hours, distilled water was added, extraction was performed with dichloromethane, and the organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (at a ratio of ethyl acetate: hexane = 1: 9) to obtain 0.74 g of compound A. (Yield 86%)

[Production Example 2] Production of Compound B

50 ml of dimethylformamide (DMF) was added to 3.7 g (0.026 mol, 1 eq) of naphthalene-1-amine, and 17.85 g (0.13 mol, 5 eq) of potassium carbonate was slowly added at room temperature, followed by stirring 30 minutes. Then, 7.8 g (0.065 mol, 2.5 eq) of bromopropene was added, and it stirred at room temperature for 4 hours. After the reaction was completed, distilled water was added, extraction was performed with ether, and the organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate: hexane = 1: 100 to 1:80) to obtain 1.5 g of Compound B in a yield of 34%.

[Production Example 3] Production of Compound C

30 mL of dichloromethane was added to 3.0 g (0.021 mol, 1 eq) of naphthalene-1-amine, and 2.75 g (0.027 mol, 1.3 eq) of triethylamine (TEA) was slowly added at room temperature. Then, 4.8 g (0.056 mol, 2.7 eq) of methacrylic acid was added and stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate: hexane = 1: 10 to 1:15), and 0.9 g of compound C was obtained in a yield of 20%.

[Production Example 4] Production of Compound D

25 mL of dichloromethane was added to 2.41 g (0.01 mol, 1 eq) of 4- (naphthalene-1-ylamino) cyclohex-1-ol, and 1.32 g (0.013 mol, 1.3 eq) was slowly added at room temperature. ) Triethylamine. Then, 2.3 g (0.022 mol, 2.2 eq) of methacrylic acid was added and stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate: hexane = 1: 5) to obtain 2.3 g of a compound D in a yield of 74%.

[Production Example 5] Production of Compound E

Under nitrogen atmosphere, 2.92 g (0.01 mol, 1.5 eq) of 3- (3,5-di-third-butyl-4-hydroxyphenyl) propionic acid was dissolved in 30 mL of tetrahydrofuran (THF), and then set Ice bath. Then, 2.54 g (0.017 mol, 2.4 eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (EDC) was added, and after stirring for about 15 minutes, 0.34 g ( 0.003mol, 0.4eq) of 4-Dimethylamino pyridine, DMAP). After 15 minutes, 1.69 g (0.007 mol, 1 eq) of 4- (naphthalene-1-ylamino) cyclohex-1-ol was dissolved in 10 mL of tetrahydrofuran and slowly added. After stirring for 24 hours, it was extracted with dichloromethane and dried under reduced pressure. Purification was performed in a column (in a ratio of ethyl acetate: hexane = 1: 5) to obtain 2.3 g (yield 65%) of Compound E.

[Production Example 6] Production of Compound F

Under a nitrogen atmosphere, 15 g (0.069 mol, 1 eq) of 4,4-difluorobenzophenone and 31.1 g (0.35 mol, 5 eq) of 2-ethylaminoethanol were added, and the mixture was stirred at 160 ° C. with It heats up. After reacting at 160 ° C for 48 hours, it was cooled to normal temperature. Distilled water was added, and extraction was performed with dichloromethane, followed by drying under reduced pressure. Compound F was obtained by recrystallization purification with ethyl acetate at normal temperature. (20g, yield 82%)

[Production Example 7] Production of Compound G

In a nitrogen environment, 9.6 g (0.035 mol, 3 eq) of 3- (3,5-di-third-butyl-4-hydroxyphenyl) propionic acid was dissolved in 70 mL of tetrahydrofuran, and then an ice bath (ice bath). Add 4.28 g (0.028 mol, 2.4 eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide to the reactor, and after stirring for about 15 minutes, add 0.56 g (0.005 mol, 0.4 eq) of 4-Dimethylamino pyridine. After 15 minutes, 4.10 g (0.011 mol, 1 eq) of Compound F was dissolved in 30 mL of tetrahydrofuran and slowly added. After stirring for 24 hours, it was extracted with dichloromethane and dried under reduced pressure. Purification was performed in a column (in a ratio of ethyl acetate: hexane = 1: 3) to obtain 4.31 g of Compound G in a yield of 43%. After purification in a column, the compound was purified in 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propanoic acid ((3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid). In the case of), it was washed with NaHCO ₃ (pH 10) solution, extracted with dichloromethane, and dried under reduced pressure.

[Production Example 8] Production of Compound H and Compound I

Except that 1.5 eq of 3- (3,5-di-third-butyl-4-hydroxyphenyl) propionic acid was added to Production Example 7, it was produced by the same method as Production Example 7, and then placed in a tube. Purification was performed in a column (at a ratio of ethyl acetate: hexane = 1: 3), and 2.5 g of compound H was obtained in a yield of 31.7%. At 2.5 g (0.004 mol, 1 eq) of Compound H To this was added 30 mL of dichloromethane. Slowly add 0.53 g (0.0053 mol, 1.3 eq) of triethylamine at room temperature. Then, 0.77 g (0.009 mol, 2.2 eq) of methacrylic acid was added and stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate: hexane = 1: 5) to obtain 1.9 g of Compound I in a yield of 68%.

[Production Example 9] Production of Compound J

To 2 g (0.006 mol, 1 eq) of compound F was added 30 mL of dichloromethane. 1.42 g (0.028 mol, 2.5 eq) of triethylamine was slowly added at room temperature. Then, 2.16 g (0.025 mol, 2.5 eq) of methacrylic acid was added and stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate: hexane = 1: 3), and 1.5 g of compound J was obtained in a yield of 54%.

[Production Example 10] Production of Compound K

After dissolving 4.31 g (0.005 mol, 1 eq) of Compound G in 40 mL of pyridine, 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 reacting at 60 ° C for 3 hours, distilled water was added, and the solvent was extracted with dichloromethane and the solvent was removed under reduced pressure. The residue was purified in a column (dichloromethane: ethyl acetate = 10: 1 ratio) to 73 % Yield of 3.87 g of compound K.

[Production Example 11] Production of Compound L

Except for using 3,5-di-third-butyl-4-hydroxybenzoic acid in place of 3- (3,5-di-third-butyl-4-hydroxyphenyl) propionic acid in Production Example 7 described above It was produced by the same method as in Production Example 7, and 5.83 g of Compound L was obtained in a yield of 63%.

[Production Example 12] Production of Compound M and Compound M-1

1.5 g (0.002 mol, 1 eq) of Compound I was completely dissolved in chloroform. Under a nitrogen environment, 0.44 g (0.003 mol, 1.3 eq) of phosphorus phosphonium chloride was added, and after stirring for about 30 minutes, 0.58 g (0.0026 mol, 1.3 eq) of 1-cyclohexyl-1-naphthylamine was dissolved in Add slowly in chloroform. After reacting at 60 ° C for 2 hours, the reaction was terminated with distilled water and extracted with dichloromethane. After removing the solvent under reduced pressure, the column was purified by dichloromethane: ethyl acetate = 1: 1 to remove the precursor, and then the composition was changed to dichloromethane: methanol: ethyl acetate = 6: 1: 2. While purification was performed, 1.0 g of compound M was obtained in a yield of 49%. Then, 1.0 g (0.001 mol, 1 eq) of Compound M was dissolved in 30 mL of methanol, and then 0.46 g (0.0016 mol, 1.5 eq) of bistrifluoromethanesulfonimide (BMI) was added and stirred at normal temperature. The blue powder precipitated by adding distilled water was filtered to obtain 1.1 g of compound M-1 in a yield of 87%.

[Production Example 13] Production of Compound N and Compound N-1

The same method as in Production Example 12 was used, except that Compound J was used instead of Compound I and Compound E was used in Production Example 12, and 0.95 g of Compound N was obtained in a yield of 31%. And, 1.1 g of compound N-1 was obtained in a yield of 93%.

[Production Example 14] Production of Compound O and Compound O-1

Except for using Compound G instead of Compound I and using Compound B instead of Compound A in Production Example 12, the same method as in Production Example 12 was used to produce 0.48 g of Compound O in a yield of 26%. And obtained in 85% yield 0.5 g of compound O-1 was obtained.

[Production Example 15] Production of Compound P and Compound P-1

Except for using Compound G instead of Compound I and using Compound C instead of Compound A in Production Example 12, the same method as in Production Example 12 was used to produce 0.77 g of Compound P in a yield of 41%. And 0.75 g of compound P-1 was obtained in a yield of 79%.

[Production Example 16] Production of Compound Q and Compound Q-1

Except for using Compound G instead of Compound I and using Compound D instead of Compound A in Production Example 12, the same method as in Production Example 12 was used to produce 0.82 g of Compound Q in a yield of 39%. And at a yield of 76% 0.75 g of compound Q-1 was obtained.

[Production Example 17] Production of Compound R

The anion was produced in the same manner as the method of Synthesis Example 1 of Korean Laid-Open Patent 2015-0009447. 0.5 g (0.0005 mol, 1 eq) of Compound M was thoroughly dissolved in 10 g of dimethylformamide. 0.27 g (0.0008 mol, 1.5 eq) of anion was added. After stirring at 55 ° C for 3 hours, it was cooled to room temperature. The solution was added dropwise to 1000 g of distilled water while stirring for 1 hour, and then filtered under reduced pressure to obtain 0.48 g of Compound R in a yield of 74%.

[Production Example 18] Production of Compound 1 of Comparative Example

Except that bistrifluoromethanesulfenimide was used as an anion in Example 7 of Korean Laid-Open Patent 2012-0014111, it was produced in the same manner, and 0.8 g of Compound 1 of Comparative Example was obtained in a yield of 80%.

[Production and evaluation of coloring composition]

Comparative Example 1

A photosensitive blue resin composition was produced with the composition described below.

A compound of Comparative Example manufactured in Production Example 18 as a blue dye compound and 0.85 wt% of a binder resin (mass ratio is benzyl methacrylate: N-phenylcis butylene difluorene) Imine: styrene: methacrylic acid = 55: 9: 11: 25 copolymer), 20.46% by weight of dipentaerythritol hexaacrylate as acrylic monomer, 56.57% by weight of propylene glycol monomethyl ether acetate, 0.68 The photopolymerization initiator (PBG-3142), leveling agent (TF-1740), and adhesion assistant (KRM-503) were mixed by 0.66% by weight in a uniformly mixed manner to produce a photosensitive blue resin composition. .

Example 1

A blue resin composition was produced with the same composition as that of Comparative Example 1 except that Compound M-1 was used instead of Compound 1 of Comparative Example as a blue dye compound.

Example 2

A blue resin composition was produced with the same composition as that of Comparative Example 1 except that Compound N-1 was used instead of Compound 1 of Comparative Example as a blue dye compound.

Example 3

A blue resin composition was produced with the same composition as that of Comparative Example 1 except that Compound Q-1 was used instead of Compound 1 of Comparative Example as a blue dye compound.

Substrate manufacturing method

The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and pre-bake was performed 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 machine at an exposure amount of 40 mJ / cm ² .

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

Evaluation of chemical resistance

A substrate was prepared by the above method, and after cutting into 1 cm × 5 cm, two substrates cut into 1 cm × 5 cm were immersed in 16 g of N-methyl-2-pyrrolidone solvent, and then convection oven at 30 ° C. Further, baking was performed for 40 minutes. The absorbance of the solvent from which the substrate sheet was taken out was measured and shown in Table 1 and FIG. 1 below.

By using a coloring material composition containing a compound represented by Chemical Formula 1 according to an embodiment of the present specification, a coloring composition for a color filter and a color filter having excellent chemical resistance can be obtained.

Claims (11)

A compound represented by the following chemical formula 1:

In the above chemical formula 1, A is represented by the following chemical formula A-1 or A-2,

At least one of R1 to R6 is a structure represented by the following chemical formula a, and the rest are the same as or different from each other, and are independently hydrogen, -R (C = O) R ', -RO (C = O) R',- ROR ',

, Substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or crosslinkable groups; or At least one of R1 and R2, R3 and R4, and R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring; R7 to R22 are the same or different from each other, and are independently hydrogen, halogen, hydroxyl, Substituted or unsubstituted alkoxy, or substituted or unsubstituted alkyl, R and R "are the same as or different from each other, and are independently directly bonded, substituted or unsubstituted alkylene, Or substituted or unsubstituted arylene groups, R ′ and R ″ ′ are the same or different from each other, and are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, Or a substituted or unsubstituted aryl group, Z ^- is an anionic group,

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

,

, -SOOR115-, -SOR116-, -SR117-, substituted or unsubstituted alkylene, or substituted or unsubstituted alkenyl, X is hydroxyl, amine, -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 from each other, and are independently directly bonded, substituted or unsubstituted alkylene, Substituted or unsubstituted cycloalkylene, or substituted or unsubstituted alkenyl, R110, R113 and R118 to R122 are the same as or different from each other, and are independently hydrogen, or substituted or unsubstituted Alkyl groups, p and q are integers of 1 to 4, respectively 2 ≦ p + q ≦ 5, in the case where p and q are 2 or more, the structures in two or more brackets are the same or different from each other, * is the same as The N-linked part of the chemical formula 1,

It is a site linked to the above Chemical Formula 1. The compound as described in Item 1 of the patent application, wherein the crosslinkable group is a structure represented by any one of the following Chemical Formulas 2 to 5: [Chemical Formula 2]

In the chemical formulae 2 to 5, R201 to R203 are the same as or different from each other, and are independently hydrogen or substituted or unsubstituted alkyl, and R204 to R207 are the same or different from each other, and are independently direct bonding,- O-, -N (R208)-, substituted or unsubstituted alkylene, or substituted or unsubstituted cycloalkyl, R208 is hydrogen, or substituted or unsubstituted alkyl, r , S, t, and u are 1 or 2, respectively. In the case where r, s, t, and u are 2, respectively, the structures within the two brackets may be the same or different. The compound according to item 1 of the scope of the patent application, wherein the X is bonded to the ortho position relative to the position where the T is bonded to the phenyl group of the chemical formula a. The compound as described in item 1 of the patent application, wherein Z ^- is: a sulfonylimide containing a halogenated hydrocarbon group, an anion containing a sulfonic acid, an anion containing halogen, boron, aluminum, or containing One or more elements in the group consisting of phosphorus and anions of oxygen. The compound according to item 1 of the patent application scope, wherein the chemical formula 1 is selected from the following compounds:

A coloring material composition comprising the compound according to any one of items 1 to 5 of the patent application. The coloring material composition as described in Item 6 of the patent application scope further includes at least one of dyes and pigments. The coloring material composition as described in item 7 of the patent application scope, wherein the dye is one or more dyes selected from the group consisting of xanthene dyes, cyanine dyes and azaporphyrin dyes, and the pigments are blue pigments Or purple paint. A resin composition comprising a compound represented by Chemical Formula 1 as described in item 1 of the patent application, a binder resin, a multifunctional monomer, a photoinitiator, an antioxidant, and a solvent. A color filter comprising the resin composition as described in item 9 of the patent application scope. A display device including the color filter as described in item 10 of the patent application scope.