TW201741298A - Compound, colorant composition comprising the same and resin composition comprising the same, photosensitive material, color filter, display device capable of improving color reproduction, brightness and contrast ratio - Google Patents

Abstract

Disclosed are a compound, a colorant composition comprising the same, and a resin composition comprising the same. The disclosed provides a compound represented by Formula 1. In the formula, each Y1 and Y2 independently represents a direct bond, or CQ1Q2; among Q1, Q2, R6-R3, two or more groups adjacent to one another bond with one another to form at least one or more monocyclic or multicyclic aromatic hydrocarbon rings optionally substituted and having a carbon number of 6-30, or monocyclic or multicyclic heterocyclic rings optionally substituted and having a carbon number of 2-30; among Q1, Q2, R1-R5 and R6-R13, each of those groups which do not form rings with adjacent groups is independently selected from the group consisting of hydrogn, heavy hydrogen, a halo group, a nitro group, a hydroxyl group, optionally substituted alkyl group having a carbon number of 1-30, optionally substituted alkoxy group having a carbon number of 1-30, optionally substituted monocyclic or multicyclic aryl group having a carbon number of 6-30, and optionally substituted monocyclic or multicyclic heteroaryl group having a carbon number of 2-30.

Description

Compound, coloring agent composition containing the same, resin composition containing the same, photosensitive material, color filter, display device

The present specification relates to a compound, a color former composition comprising the same, and a resin composition comprising the same.

Recently, for color filters, performance characterized by high brightness and high light to dark ratio is required. In addition, one of the main purposes of the development of display elements is the differentiation of display element performance and the improvement of productivity in manufacturing steps due to the improvement in color purity.

Previously, the type of pigment used as a color filter of a color filter was present in a color dispersion in a particle-dispersed state, and therefore, it was difficult to adjust the brightness and the light-dark ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, aggregation occurs in the color filter, solubility and dispersibility are lowered, and multiple scattering of light occurs due to large particles of aggregation. It has been pointed out that the scattering of such polarized light is the main reason for the reduction in the light to dark ratio. In order to increase the brightness and the light-dark ratio by the ultrafine particle size and dispersion stabilization of the pigment, efforts are being made continuously, but the degree of freedom is limited in the selection of the coloring agent for realizing the color coordinates of the high-color purity display device. Further, the pigment dispersion method using the developed coloring material, particularly the pigment, is limited in terms of improving the color purity, brightness, and brightness ratio of the color filter using the color filter.

Accordingly, it is required to develop a novel coloring agent which can enhance color reproduction, brightness, and brightness ratio by improving color purity. [Prior Art Document] [Patent Literature]

[Patent Document 1] Korean Patent Publication No. 2012-0139606

[Problems to be Solved by the Invention] The present specification provides a compound, a color former composition containing the same, and a resin composition containing the compound. [Means for solving the problem]

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Chemical Formula 1]

In the chemical formula 1, Y1 and Y2 are each independently a direct bond or CQ1Q2, and two or more mutually adjacent groups of Q1, Q2 and R6 to R13 are bonded to each other to form at least one or more substituted or Unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms or substituted or unsubstituted heterocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, Q1, Q2, R1 to R5 and R6 to R13, which are not independently bonded to each other, are independently selected from hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to A group consisting of 30 monocyclic or polycyclic heteroaryl groups.

Another embodiment of the present specification provides a color former composition comprising the compound represented by Chemical Formula 1.

Yet another embodiment of the present specification provides a resin composition comprising the colorant composition. [Effects of the Invention]

A compound of an embodiment of the present specification can be used as a dye and thus can be used as a color filter material.

The resin composition containing the compound according to an embodiment of the present specification is excellent in color characteristics, heat resistance, and solvent resistance.

Further, the resin composition containing the compound according to an embodiment of the present invention functions to prevent re-agglomeration and foreign matter formation of the finely divided pigment, and when applied to a color filter, the light-dark ratio is improved.

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

One embodiment of the present specification provides a compound represented by the above Chemical Formula 1. The chemical formula 1 is characterized in that at least one of the substituents R6 to R13 is a nitro group. The nitro group can function as a pull electron in the entire compound.

In the present specification, the following description of the substituents will be given, but the invention is not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is substituted with another substituent, and the position substituted is a position at which a hydrogen atom is substituted, that is, a position at which a substituent can be substituted. It is not limited, and in the case of replacing two or more, two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used in the specification means selected from the group consisting of heavy hydrogen, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, nonylalkyl, aralkyl, aralkenyl. , ester group, carbonyl group, aryl group, aryloxy group, alkyl thiooxy group, alkyl sulfonate oxy group, aryl sulfonate oxy group, boron group, alkyl amine group, aralkyl group, aryl group An amine group, a heteroaryl group, a carbazolyl group, an acryloyl group, an acrylate group, an ether group, a nitrile group, a nitro group, a hydroxyl group, a cyano group, and one or more impurities including N, O, S, or P atoms One or more substituents in the group consisting of a cyclic group are substituted or substituted with a substituent in which two or more substituents in the above-exemplified substituent are bonded, or have no substituent. For example, the "substituent in which two or more substituents are bonded" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent in which two phenyl groups are bonded.

In the present specification, examples of the halogen group are fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, and is preferably from 1 to 50. Specific examples are: methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, t-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, third amyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl Benzyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl , n-octyl, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-decyl, 2,2-dimethylheptyl, 1-ethyl-propyl The group is 1,1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples are: vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentene , 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, but are not limited thereto.

In the present specification, the alkoxy group may be a straight chain, a branched chain or a cyclic chain. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be: methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, second butoxy , n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy The group, n-decyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group and the like are not limited thereto.

In the present specification, the cyclohexyl group is not particularly limited, and may have a carbon number of 3 to 20, and particularly may be a cyclopentyl group or a cyclohexyl group.

In the present specification, the arylalkyl group, specifically, the aryl moiety can be used in the description of the aryl group described later, and has a carbon number of 6 to 49 and an alkyl group of 1 to 44 carbon atoms. Specific examples are: benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, α-methylbenzyl, α, α-Dimethylbenzyl, α,α-methylphenylbenzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p-fluorobenzyl, 3,5-difluorobenzyl, α,α -di-trifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α-phenoxybenzyl, α-benzyloxybenzyl, naphthylmethyl, naphthylethyl, Naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanobenzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-benzene The isopropyl group or the like is not limited thereto.

In the present specification, as for the aryl moiety of the aralkenyl group, a description relating to an aryl group to be described later can be applied, and a description relating to the alkenyl group can be applied to the alkenyl moiety.

In the present specification, the carbon number of the ester group is not particularly limited, but is preferably from 1 to 50 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 from 1 to 50 carbon atoms. Specifically, it may be a compound having the structure described below, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the carbon number is not particularly limited, and is preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group is a phenyl group, a biphenyl group, a biphenyl group or the like, but is not limited thereto.

In the case where the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, and is preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group is a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group, a fluorenyl group, Base, base, etc., but not limited to these.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

In the case where the thiol group is substituted, , , ,and Etc., but not limited to these.

In the present specification, a heteroaryl group is a hetero atom having one or more non-carbon atoms, and specifically, the hetero atom may include one or more groups selected from the group consisting of O, N, Se, and S. atom. The carbon number of the heteroaryl group is not particularly limited, but is preferably from 2 to 60 carbon atoms. Examples of heterocyclic groups are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, tri Azyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, pyrazolopyrimidinyl, pyrazolopyrazinyl, pyrazinopyridinium Azinyl, isoquinolyl, decyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, dibenzothiophenyl, benzene And furanyl, phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl and dibenzofuranyl, but not limited For that.

In the present specification, the description of the aryl group can be applied to the aromatic hydrocarbon ring except that it is not a monovalent group.

In the present specification, the heterocyclic ring can be applied to the description of the heteroaryl group, except that it is not a monovalent group.

In the present specification, the "adjacent" group may mean a substituent substituted on an atom directly bonded to an atom to which the substituent is substituted, a substituent closest to the position of the substituent in a steric structure, or Other substituents substituted on the atom to which the substituent is substituted. For example, two substituents substituted at the ortho position in the phenyl ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the adjacent groups are bonded to each other to form a ring, and as described above, the adjacent groups are bonded to each other to form a hydrocarbon ring of 5 to 8 members or a heterocyclic ring of 5 to 8 members. It may be monocyclic or polycyclic, and may be aliphatic, aromatic, or a form of such condensation, and is not limited thereto.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or not. a substituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 30 In the group consisting of a heterocyclic or polycyclic heteroaryl group, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more. A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

According to an embodiment of the present specification, R1 to R13 are each independently selected from hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or not. Substituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted carbon number 2 to 20 In the group consisting of a heterocyclic or polycyclic heteroaryl group, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more. A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted, mono- or polycyclic aryl having 6 to 15 carbon atoms. In the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, at least one of R6 to R13 is a nitro group, and at least one of R6 to R13 Two or more mutually adjacent groups are bonded to each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms, or substituted or unsubstituted A monocyclic or polycyclic heterocyclic ring having 2 to 15 carbon atoms.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, a nitro group, and a hydroxyl group, and at least one of R6 to R13 is a nitro group, R6. At least two or more mutually adjacent groups of -R13 are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms, or substituted or not A substituted monocyclic heterocyclic ring having 2 to 10 carbon atoms.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, a nitro group, and a hydroxyl group, and at least one of R6 to R13 is a nitro group, R6. At least two or more adjacent groups in the group -R13 are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms.

According to an embodiment of the present specification, the compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2 or Chemical Formula 3.

[Chemical Formula 2]

[Chemical Formula 3]

In the chemical formula 2 and the chemical formula 3, Y1, Y2, R1 to R13 are as defined in the chemical formula 1, and R14, R15 and R6' to R15' are each independently selected from hydrogen, a heavy hydrogen, a halogen group, a nitro group, a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 6 to 30 a group consisting of a cyclic or polycyclic aryl group and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms of a monocyclic or polycyclic ring, wherein R6' to R9' of the chemical formula 2 One or more of the above and one or more of R10' to R13' of the chemical formula 3 are a nitro group.

In the chemical formula 2 and the chemical formula 3, R1 to R13 are each independently selected from hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or not. a substituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 2 to 30 In the group consisting of a heterocyclic or polycyclic heteroaryl group, at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one substituted or unsubstituted carbon number 6 to a monocyclic or polycyclic aromatic hydrocarbon ring of 30, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, R14, R15 and R6' to R15' are each independently selected from Hydrogen, heavy hydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, and substituted or An unsubstituted group of 6 to 30 monocyclic or polycyclic aryl groups, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms of a monocyclic or polycyclic group. At least one of R6' to R13' is a nitro group.

According to an embodiment of the present specification, R1 to R13 are each independently selected from hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or not. Substituted alkoxy groups having 1 to 10 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms, and substituted or unsubstituted carbon number 2 to 20 In the group consisting of a heterocyclic or polycyclic heteroaryl group, at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one substituted or unsubstituted carbon number 6 to a monocyclic or polycyclic aromatic hydrocarbon ring of 20 or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted, mono- or polycyclic aryl having 6 to 15 carbon atoms. a group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, wherein at least two or more adjacent groups of R6 to R13 are bonded to each other And forming at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms, or substituted or unsubstituted monocyclic or polycyclic ring having 2 to 15 carbon atoms; Heterocyclic.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, a nitro group, and a hydroxyl group, and at least two of R6 to R13 are adjacent to each other. The groups are bonded to each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms, or a substituted or unsubstituted carbon number of 2 to 15 A cyclic or polycyclic heterocyclic ring.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, a nitro group, and a hydroxyl group, and at least two of R6 to R13 are adjacent to each other. The groups are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms, or substituted or unsubstituted heterocyclic carbon having 2 to 10 carbon atoms ring.

According to an embodiment of the present specification, R1 to R13 are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, a nitro group, and a hydroxyl group, and at least two of R6 to R13 are adjacent to each other. The groups are bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms.

According to an embodiment of the present specification, R14, R15 and R6' to R15' are each independently selected from the group consisting of hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 10 carbon atoms. a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted aryl group In the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, at least one of R6' to R13' is a nitro group.

According to an embodiment of the present specification, R14, R15 and R6' to R15' are each independently selected from the group consisting of hydrogen, dihydrogen, halogen, nitro, hydroxy, and substituted or unsubstituted carbon number 6-10. In the group consisting of a monocyclic aryl group and a substituted or unsubstituted heterocyclic group having 2 to 10 carbon atoms, at least one of R6' to R13' is a nitro group.

According to an embodiment of the present specification, R14, R15 and R6' to R15' are each independently selected from the group consisting of hydrogen, a heavy hydrogen, a halogen group, and a nitro group, and at least one of R6' to R13' The above is a nitro group.

According to an embodiment of the present specification, a compound represented by the following Chemical Formula 4 can be provided.

[Chemical Formula 4]

In the chemical formula 4, R1 to R5, R14, R15 and R6' to R15' are the same as described above.

According to an embodiment of the present invention, in the chemical formula 1, at least one of R6 to R9 is a halogen element.

According to one embodiment of the present specification, a compound in which at least one of R9' and R13' is a nitro group in Chemical Formula 2 and Chemical Formula 3 is provided.

According to an embodiment of the present invention, there is provided a compound represented by any one of the following compounds.

According to another embodiment of the present specification, a color former composition comprising a compound of an embodiment of the present specification is provided.

The colorant composition may further contain at least one of a dye and a pigment in addition to the compound of Chemical Formula 1. For example, the colorant composition may include only a compound of one embodiment of the present specification, or may include the compound of the chemical formula 1 and one or more dyes, or a compound containing one embodiment of the present specification and one or more A pigment, or a compound of the above formula 1, one or more dyes, and one or more pigments.

In an embodiment of the present specification, a resin composition comprising the colorant composition is provided.

In an embodiment of the present specification, the resin composition may further comprise a binder resin, a polyfunctional monomer, 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 the film produced from the resin composition.

The binder resin may be a copolymerized resin of a polyfunctional monomer imparting mechanical strength and a monomer which imparts alkali solubility, and may further contain a binder which is generally used in the art.

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

Specific examples of the unsaturated carboxylic acid esters may 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, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, (methyl) 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, decyl octyloxy-2-hydroxypropyl (meth) acrylate Ester, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy diethylene glycol (meth) acrylate Ester, methoxytriethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, p-nonyl phenoxy polyethyl Glycol (meth) acrylate, p-nonyl phenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, (meth) acrylate 1, 1,1,3,3,3-hexafluoroisopropyl ester, octafluoropentyl (meth)acrylate, heptadecafluoro(meth)acrylate, tribromophenyl (meth)acrylate, α-hydroxyl Methyl methacrylate, α-hydroxyethyl methacrylate, α-hydroxypropyl methacrylate, and α-hydroxy methacrylate butyl ester are not limited thereto.

Specific examples of the aromatic vinyl monomer may be selected from styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxystyrene. And the group consisting of (o-, m-, p-)-chlorostyrene, but not limited to these.

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

Specific examples of the unsaturated quinone imines may be selected from N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxybenzene The group consisting of butylenediamine and N-cyclohexylmethyleneimine is, but not limited to, only those groups.

The acid anhydride is maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride or the like, but is not limited thereto.

The monomer which imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, and antibutene. Diacid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth)acryloxy)ethyl phthalate, succinic acid mono-2 One or more of the group consisting of -((meth)acryloxy)ethyl ester and ω-carboxypolycaprolactone mono(meth)acrylate, but it is not limited to these.

In an embodiment of the present specification, the binder resin has an acid value of 50 KOHmg/g to 130 KOHmg/g and a weight average molecular weight of 1,000 to 50,000.

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

The photoinitiator is not particularly limited as long as it is a radical generating a radical by light to cause cross-linking, and may be, for example, selected from the group consisting of an acetophenone-based compound, a biimidazole-based compound, and a triazine-based compound. And one or more of the group consisting of lanthanoid compounds.

The acetophenone-based compound is: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane- 1-ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether Benzoin, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholinyl-1-propan-1-one , 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino 1-(4-morpholinylphenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one It is not limited to these.

The biimidazole-based compound is: 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)- 4,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. It is not limited to these.

The triazine-based compound is: 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4 - bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid 1,1,1,3,3,3-hexafluoroisopropyl, 2-{4-[2,4 - bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl 2-Phenylthio}acetic acid 2-epoxyethyl ester, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetic acid cyclohexyl ester, 2 -{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}benzyl acetate, 3-{chloro-4-[2,4-bis(trichloromethyl) -)-triazine-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propanoid 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., not limited thereto These.

The lanthanide compounds are: 1,2-octanedione,-1-(4-phenylthio)phenyl,-2-(o-benzylidene fluorene) (Ciba-Geigy) Company, CGI124), ethyl ketone, 1-(9-ethyl)-6-(2-methylbenzimid-3-yl)-, 1-(O-ethylindenyl) (CGI242), N-1919 (ADEKA), etc., is not limited to these.

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, tert-butanol, 2-ethoxypropanol, 2-methoxy Propanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol diethyl 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.

In one embodiment of the present specification, the content of the compound of the chemical formula 1 is 5% by weight to 60% by weight based on the total weight of the solid content in the resin composition, and the content of the binder resin is 1% by weight to 60% by weight, the content of the initiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is 0.1% by weight to 50% by weight.

The total weight of the solid component means the sum of the weights of the components other than the solvent in the resin composition. The basis of the solid content and the weight % based on the solid content of each component can be measured by a general analytical method used in the art, such as liquid chromatography or gas chromatography.

In one embodiment of the present specification, the resin composition further comprises a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, an antioxidant, a thermal polymerization inhibitor, an ultraviolet absorber, One or two or more additives selected from the group consisting of antioxidants, dispersants, and leveling agents.

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

The photocrosslinking sensitizer may be one or more selected from the group consisting of benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4- Bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,3-dimethyl- a benzophenone compound such as 4-methoxybenzophenone or 3,3,4,4-tetrakis(t-butylperoxycarbonyl)benzophenone; 9-fluorenone, 2-chloro-9 Anthrone-based compounds such as anthrone and 2-methyl-9-fluorenone; thioxanthone, 2,4-diethylthiazinone, 2-chlorothiazepinone, 1-chloro-4- a thioxanthone compound such as propyloxy thioxanthone, isopropyl thioxanthone or diisopropyl thioxanthone; oxazepine such as xanthone or 2-methyloxaxanone; Ketone compounds; anthraquinone compounds such as hydrazine, 2-methyl hydrazine, 2-ethyl hydrazine, tert-butyl hydrazine, 2,6-dichloro-9,10-fluorene; 9-benzene Acridine such as pyridinium, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane a compound; benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrenequinone Dicarbonyl compound; 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, bis(2,6-dimethoxybenzylidene)-2,4,4-trimethylpentyl a phosphine oxide compound such as phosphine oxide; methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, 2-n-butoxyethyl a benzoate compound such as -4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis (4) -Amino-aminobenzylidene)cyclohexanone, 2,6-bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone and other amine synergists; 3,3 -carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzylidene-7 -(diethylamino)coumarin, 3-benzylidene-7-methoxy-coumarin, 10,10-carbonyl bis[1,1,7,7-tetramethyl-2, Coumarin compound such as 3,6,7-tetrahydro-1H,5H,11H-C1]-benzopyrano[6,7,8-ij]-quinolizin-11-one; 4-2-B A chalcone compound such as a sulfhydryl ketone or a 4-azidobenzylidene acetophenone; 2-benzimidylmethylene, 3-methyl-b-naphthylthiazoline.

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

The adhesion promoter used in the present specification may be selected from methacryloxypropyltrimethoxydecane, methacryloxypropyldimethoxydecane, methacryloxypropyltriethoxylate. One or more of a methacryl decyl decane coupling agent such as decane or methacryloxypropyldimethoxydecane, which may be derived from octyltrimethoxydecane or dodecyl group. One or more of trimethoxydecane, octadecyltrimethoxydecane, and the like are used.

The surfactant is an anthrone-based surfactant or a fluorine-based surfactant. Specifically, an anthrone-based surfactant can be used: BYK-077, BYK-085 of 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: DIC (DaiNippon Ink & Chemicals) company's F-114, F-177, F-410, F-411, F- 450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF- 1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., but not limited to these .

The antioxidant may be one or more selected from the group consisting of a hindered phenol-based antioxidant, an amine-based antioxidant, a sulfur-based antioxidant, and a phosphine-based antioxidant, but is not limited thereto.

Specific examples of the antioxidant include a phosphate-based heat stabilizer such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl- 3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl) Propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,5-di- Diethyl tert-butyl-4-hydroxybenzyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g, t-butylphenol 4 , 4'-butylidene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or double [3, 3-bis-(4'-hydroxy-3'-t-butylphenyl)butanoic acid]diol (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid] Hindered phenol such as glycol ester is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N , an amine-based secondary antioxidant such as N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl a sulfur-based secondary antioxidant such as thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrakis[methylene-3-(laurylthio)propionate]methane; or Phenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl)pentaerythritol diphosphite (Bis(2,4-ditbutylphenyl) ) Pentaerythritol Diphosphite) or (1,1 '-biphenyl)-4,4'-diylbisphosphonic acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester (( A phosphite secondary antioxidant such as 1,1'-Biphenyl)-4,4'-Diylbis phosphonic acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester).

The ultraviolet absorber may be used: 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc., but It is not limited to these, and is generally available to users in the art.

The thermal polymerization preventing agent may, for example, comprise one or more 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-tert-butyl-p-cresol, ortho-benzene Trisphenol, benzoquinone, 4,4-thiobis(3-methyl-6-tert-butylphenol), 2,2-methylenebis(4-methyl-6-tert-butylphenol) 2-mercaptoimidazole and phenothiazine, but are not limited thereto only, and may be generally included in the art.

The dispersing agent can be used in the following method: a method of internally adding to a pigment in a form in which a pigment is surface-treated in advance, or a method of externally adding to a pigment. As the dispersant, a compound type, a nonionic, an anionic or a cationic dispersant can be used, and examples thereof include a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactant.

These can be used separately or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene alkyl polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonates, sulfonates And one or more of the group consisting of a carboxylate, a carboxylate, a alkylguanamine alkylene oxide adduct, and an alkylamine, but is not limited thereto.

The leveling agent can be polymeric or non-polymeric. Specific examples of the polymer leveling agent include polyethyleneimine, polyamidamine, an amine and an epoxide reaction product, and specific examples of the non-polymeric leveling agent include a non-polymer sulfur-containing compound. And a non-polymer nitrogen-containing compound, but it is not limited thereto, and can be generally used by a user in the art.

In an embodiment of the present specification, a photosensitive material produced from the resin composition is provided.

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

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 usually widely used. Further, after the coating film is formed, a part of the residual solvent can be removed under reduced pressure as the case may be.

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

The resin composition of the present specification can be used for: a thin film transistor liquid crystal display device (TFT LCD), a pigment dispersion type photosensitive material for color filter manufacturing, a thin film transistor liquid crystal display device (TFT LCD), or a black matrix of an organic light emitting diode. Photographic material for forming, overcoat layer forming photosensitive material, columnar spacer photosensitive material, photocurable coating material, photocurable ink, photocurable adhesive, printing plate, photosensitive member for printed wiring board, and plasma display In the photosensitive material for a panel (Plasma Display Panel, PDP), the use thereof is not particularly limited.

In an embodiment of the present specification, a color filter including the photosensitive material is provided.

The color filter can be produced using a resin composition containing the compound of the chemical formula 1. A coating film is formed by applying the resin composition onto a substrate, and the coating film is exposed, developed, and cured to form a color filter.

The resin composition of one embodiment of the present specification is excellent in heat resistance, and has little color change due to heat treatment, and the color reproduction rate is high even when the color filter is used for the hardening process, and the brightness and the light-dark ratio are high. Color filter.

The substrate may be a glass plate, a tantalum wafer, a plate of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), and 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.

In another embodiment, the color filter may further comprise an overcoat layer.

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

A black matrix of an embodiment of the present specification may use a black pigment or a black dye as a colorant. For example, carbon black may be used alone or in combination with a color pigment. In this case, since the coloring pigment having insufficient light shielding property is mixed, there is an advantage that the strength of the film or the substrate is increased even if the amount of the colorant is relatively increased. The adhesion will not decrease.

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

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), or a liquid crystal display device (Liquid Crystal Display, Any of LCD, Thin Film Transistor-Liquid Crystal Display (LCD-TFT), and Cathode Ray Tube (CRT).

Hereinafter, the present specification will be described in detail by way of examples. The following examples are intended to be illustrative of the present invention, and the scope of the present invention is intended to cover the scope of the invention and the scope of the invention.

Synthesis Example 1 Reaction Formula 1

10 g (50.459 mmol) of 2,3-naphthalenedicarboxylic anhydride (A-1) was added to 30 ml of HNO ₃ , and the reaction solution was gradually warmed up and stirred at 95 ° C for 2 hours. The reaction solution was cooled to room temperature and precipitated in water. The precipitate was filtered under reduced pressure, and dried in a convection oven at 80 ° C for 1 day to obtain the A-2. The A-2 was added to 50 ml of acetic anhydride, and the temperature was raised to 150 ° C and stirred for 2 hours. The reactant was cooled to room temperature, filtered under reduced pressure, and washed with water with a small amount of water to obtain 8.3 g (34.132 mmol) of the A-3 in a yield of 67.64%.

Synthesis Example 2 Reaction Formula 2

3 g (18.963 mmol) of 8-aminoquinoxadine (A-4) and 2.809 g (18.963 mmol) of phthalic anhydride (A) were added to 3 g of benzoic acid and 3 g of methyl benzoate. -5), slowly warmed up and stirred at 180 ° C for 5 hours. The reaction was cooled to ambient temperature and taken up in 100 mL MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried by a convection oven at 80 ° C for 1 day to obtain 4.67 g (16.198 mmol) of the A-6 in a yield of 85.4%.

Synthesis Example 3 Reaction Formula 3

1.687 g (6.937 mmol) of the A-3 and 2 g (6.937 mmol) of the A-6 were added to 3 g of benzoic acid and 3 g of methyl benzoate, and the temperature was gradually raised at 200 ° C. Stir for 3 hours. The reaction was cooled to ambient temperature and taken up in 100 mL MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried by a convection oven at 80 ° C for 1 day to obtain 12.422 g (4.717 mmol) of the product of the reaction formula 3 in a yield of 68.0%.

Synthesis Example 4 Reaction Formula 4

The product of the above Reaction Formula 4 was synthesized under the same conditions as those of Reaction Formula 2 and Reaction Formula 3.

Synthesis Example 5 Reaction Formula 5

The product of the reaction formula 5 was synthesized under the same conditions as those of the reaction formula 2 and the reaction formula 3.

Synthesis Example 6 Reaction Formula 6

The product of the reaction formula 6 was synthesized under the same conditions as those of the reaction formula 2 and the reaction formula 3.

Synthesis Example 7 Reaction Formula 7

The product of the reaction formula 7 was synthesized under the same conditions as those of the reaction formula 2 and the reaction formula 3.

Synthesis Example 8 Reaction Formula 8

The product of the reaction formula 8 was synthesized under the same conditions as those of the reaction formula 2 and the reaction formula 3.

In the chemical formula 3 of the present application, a specific example of the nitro group in any one of R10' to R15' is synthesized by the same procedures and methods as those of the synthesis examples 3 to 8.

Synthesis Example 9 Reaction Formula 9

5 g (20.562 mmol) of the A-3 and 3.253 g (20.562 mmol) of 8-aminoquinoxadine (A-4) were added to 5 g of benzoic acid and 10 g of methyl benzoate. The temperature was gradually raised and stirred at 180 ° C for 5 hours. The reaction was cooled to ambient temperature and taken up in 150 mL MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried by a convection oven at 80 ° C for 1 day to obtain 7.094 g (18.505 mmol) of the A-17 in a yield of 90.0%.

Synthesis Example 10 Reaction Formula 10

5 g (13.043 mmol) of the A-17, 1.932 g (13.043 mmol) of phthalic anhydride (A-5) were added to 5 g of benzoic acid and 10 g of methyl benzoate, and the temperature was gradually raised. It was stirred at 200 ° C for 3 hours. The reaction was cooled to ambient temperature and taken up in 150 mL MeOH. The precipitate was filtered under reduced pressure and washed with MeOH. It was dried by a convection oven at 80 ° C for 1 day to obtain 5.022 g (9.781 mmol) of the product of the reaction formula 10 in a yield of 74.97%.

Synthesis Example 11 Reaction Formula 11

The product of the above Reaction Formula 11 was synthesized under the same conditions as those of Reaction Formula 9 and Reaction Formula 10.

Synthesis Example 12 Reaction Formula 12

The product of the above Reaction Formula 12 was synthesized under the same conditions as those of Reaction Formula 9 and Reaction Formula 10.

Synthesis Example 13 Reaction Formula 13

The product of the reaction formula 13 was synthesized under the same conditions as those of the reaction formula 9 and the reaction formula 10.

In the chemical formula 2 of the present application, a specific example in which any one of R6' to R9', R14 and R15 is a nitro group is synthesized by the same procedures and methods as those of the synthesis examples 10 to 13 .

Example 1 5.554 g of the product of Synthesis Example 3, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (mol ratio 70:30, acid value 113 KOH mg/g, by GPC) The weight average molecular weight measured was 20,000, the molecular weight distribution (PDI) was 2.0 g, the solid content (SC) was 25%, and the solvent PGMEA was contained in 10.376 g, and I-369 (BASF) 2.018 g as a photoinitiator was used. Photopolymerizable compound DPHA (Nippon Chemical Co., Ltd.) 12.443 g, Solylene Glycol Monomethyl Ether Acetate (PGMEA) 68.593 g, and 1.016 g of DIC Corporation's F-475 as an additive were mixed to prepare a compound. .

Example 2 A compound was produced in the same manner except that the product of Synthesis Example 4, 5.554 g, was used instead of the product of Synthesis Example 3 of Example 1.

Example 3 A compound was produced in the same manner except that the product of Synthesis Example 5 was used instead of the product of Synthesis Example 3 of Example 1.

Example 4 A compound was produced in the same manner except that the product of Synthesis Example 6 was used instead of the product of Synthesis Example 3 of Example 1.

Example 5 A compound was produced in the same manner except that the product of Synthesis Example 7 was used instead of the product of Synthesis Example 3 of Example 1.

Example 6 A compound was produced in the same manner except that the product of Synthesis Example 8 was used instead of the product of Synthesis Example 3 of Example 1.

Example 7 A compound was produced in the same manner except that the product of Synthesis Example 10, 5.554 g, was used instead of the product of Synthesis Example 3 of Example 1.

Example 8 A compound was produced in the same manner except that the product of Synthesis Example 11 was used instead of the product of Synthesis Example 3 of Example 1.

Example 9 A compound was produced in the same manner except that the product of Synthesis Example 12 was used instead of the product of Synthesis Example 3 of Example 1.

Example 10 A compound was produced in the same manner except that the product of Synthesis Example 13 was used instead of the product of Synthesis Example 3 of Example 1.

Comparative Example 1 A compound was produced in the same manner except that the compound represented by the following Chemical Formula 5 was used instead of the product of Synthesis Example 3 of Example 1.

Chemical formula 5

Comparative Example 2 A compound was produced in the same manner except that the compound represented by the following Chemical Formula 6 was used instead of the product of Synthesis Example 3 of Example 1.

Chemical formula 6

Preparation of the substrate The compound produced in the above Example 1, Example 2, and Comparative Example 1 was spin-coated on glass (5 cm × 5 cm), and heat treatment was performed at 100 ° C for 100 seconds. Prebake) to form a film. The interval between the substrate on which the film was formed and the photo mask was set to 250 μm, and the entire surface of the substrate was irradiated with an exposure amount of 40 mJ/cm ² using an exposure machine. Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-baked at 230 ° C for 20 minutes to prepare a substrate.

Evaluation of heat resistance A transmittance spectrum of a visible light region in the range of 380 nm to 780 nm was obtained using a spectrometer (MCPD-Otsuka Co., Ltd.) on a prebake substrate prepared under the above-described conditions. Further, a prebake substrate was additionally subjected to post bake at 230 ° C for 20 minutes, and a transmittance spectrum was obtained by the same equipment and measurement range. Using the obtained transmittance spectrum and the C light source backlight, ΔEab was calculated using the obtained values E (L*, a*, b*), and is shown in Table 1 below. ΔE(L*, a*, b*)={(ΔL*)2+(Δa*)2+(Δb*)2} ^1/2 A small value of ΔE indicates excellent color heat resistance. In general, when it has a value of ΔEab<3, it is a coloring agent excellent in heat resistance.

The results of measurement of heat resistance of the compound of one embodiment of the present application and Comparative Example 1 are shown in Table 1 below. Further, as shown in Table 1, a compound of an embodiment of the present application is similar to Comparative Example 1 (current commercial product), and exhibits a color change of 3 or less (ΔEab).

[Table 1]

Long-wavelength evaluation Accurately weigh 0.05 g of the compound samples of Example 1, Example 4, and Example 7 and Comparative Example 2, and add it to a 200 ml volumetric flask to fill DMF to 200 ml. Display line. The solution was piped 5 ml, added to a 100 ml volumetric flask, and filled to a 100 ml display line with DMF. Using this solution, an ultraviolet-visible (UV-Vis) absorption spectrum was measured using a UV-Vis Spectrophotometer, and the results are shown in Table 2 below.

[Table 2]

As is clear from the above Table 2, it is understood that the compound of one embodiment of the present application is longer-wavelength than Comparative Example 2 in which the nitro group is not substituted. Thereby, the compound of one embodiment of the present application can have an advantage that the amount of the coloring agent used is reduced by the long wavelength of the absorption spectrum.

no

no

no

Claims (14)

a compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the chemical formula 1, Y1 and Y2 are each independently a direct bond or CQ1Q2, and two or more mutually adjacent groups of Q1, Q2 and R6 to R13 are bonded to each other to form at least one or more substituted or Unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms or substituted or unsubstituted heterocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, Q1, Q2, R1 to R5 and R6 to R13, which are not independently bonded to each other, are independently selected from hydrogen, dihydrogen, halogen, nitro, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted carbon number 2 to A group consisting of 30 monocyclic or polycyclic heteroaryl groups. The compound according to claim 1, wherein the chemical formula 1 is represented by Chemical Formula 2 or Chemical Formula 3: [Chemical Formula 2] [Chemical Formula 3] In the chemical formula 2 and the chemical formula 3, Y1, Y2, R1 to R13 are as defined in the chemical formula 1, and R14, R15 and R6' to R15' are each independently selected from hydrogen, a heavy hydrogen, a halogen group, a nitro group, a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number of 6 to 30 a group consisting of a cyclic or polycyclic aryl group and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms of a monocyclic or polycyclic ring, wherein R6' to R9' of the chemical formula 2 One or more of the above and one or more of R10' to R13' of the chemical formula 3 are a nitro group. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 4: [Chemical Formula 4] In the chemical formula 4, R1 to R5, R14, R15 and R6' to R15' are the same as defined in the second item of the patent application. The compound according to claim 1, wherein one or more of R6 to R13 is a nitro group. The compound according to claim 1, wherein one or more of R6 to R9 is a halogen element. The compound of claim 2, wherein one or more of R9' and R13' is a nitro group. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following compounds: . A coloring agent composition comprising the compound according to any one of claims 1 to 7. The coloring agent composition according to claim 8, which further comprises at least one of a dye and a pigment. A resin composition further comprising the compound according to any one of claims 1 to 7, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The resin composition according to claim 10, wherein the content of the compound is from 5% by weight to 60% by weight based on the total weight of the solid components in the resin composition, the binder resin The content of the polyfunctional monomer is from 0.1% by weight to 50% by weight, and the content of the initiator is from 0.1% by weight to 20% by weight. A photosensitive material produced by using the resin composition as described in claim 10 of the patent application. A color filter comprising the photosensitive material according to claim 12 of the patent application. A display device comprising the color filter of claim 13 of the patent application.