JP6579452B2 - Compound, coloring material composition containing the same, and resin composition containing the same - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0072573 filed with the Korean Patent Office on June 10, 2016, the entire contents of which are included in this specification.
The present specification relates to a novel compound, a colorant composition containing the same, and a resin composition containing the same.

  Recently, as a light source of a liquid crystal display (LCD), an LED or an OLED element that emits light that is neither a drive nor a liquid crystal is used in place of the existing CCFL. When an LED or OLED is used as a light source, red, green, and blue light is emitted by itself, so that no separate color filter is required.

  However, it is generally not easy to adjust or adjust the required color coordinates using light emitted from an LED or OLED light source. In addition, methods for improving color purity, luminance, and light-to-dark ratio have reached the limit when manufacturing color filters that have already been developed, particularly color filters using pigment dispersion methods using pigments. In addition, the amount of color material used must be reduced in order to reduce the thickness of the color filter.

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

Korean Published Patent No. 2001-0009058

  The present specification provides a novel compound, a colorant 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.
[Chemical formula 1]

In Formula 1,
At least one of L1 and L2 is
Or
The rest is a direct bond,
Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted alkyl group; an aryl group substituted with at least one carboxy group; or an aryl group condensed with a cyclic anhydride;
L1 is
Or
And Ar1 is an aryl group substituted with at least one carboxy group; or an aryl group fused with a cyclic anhydride;
L2 is
Or
And Ar2 is an aryl group substituted with at least one carboxy group; or an aryl group fused with a cyclic anhydride;
R1 to R5 and R103 are the same or different from each other, and each independently represents hydrogen; deuterium; halogen group; hydroxy group; sulfonate group; sulfonamide group; substituted or unsubstituted alkoxy group; An alkyl group of
R101, R102, R104 and R105 are the same or different from each other, each independently independently a direct bond; or a substituted or unsubstituted alkylene group;
r1 and r2 are each an integer of 1 to 5,
r3 and r4 are each an integer of 1 to 3,
r5 is an integer of 1 to 4,
when each of r1 to r5 is 2 or more, the structures in the two or more brackets are the same or different from each other;
Is a site for linking N and Ar1 in Formula 1; or N and Ar2.

  According to another embodiment of the present specification, a color material composition including the compound represented by Formula 1 is provided.

  According to still another embodiment of the present specification, a resin composition including the color material composition is provided.

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

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

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

  In addition, according to one embodiment of the present specification, the color material composition containing the compound represented by the chemical formula 1 exhibits higher luminance, heat resistance, and chemical resistance than when a conventional pigment is used. In addition, it is possible to produce a color filter excellent in heat resistance and chemical resistance by using a colored resin composition using the same.

Hereinafter, the present specification will be described in more detail.
According to one embodiment of the present specification, a compound represented by Formula 1 is provided.

In the present specification, examples of the substituent are described below, but are not limited thereto.
The term “substituted” means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is a position where a hydrogen atom is substituted, that is, the substituent can be substituted. The position is not particularly limited, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

In this specification, the term “substituted or unsubstituted” refers to deuterium, halogen group, nitrile group, nitro group, imide group, amide group, carbonyl group, ester group, hydroxy group, sulfonate group, sulfonamide group, A substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted A substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; And one selected from the group consisting of substituted or unsubstituted heterocyclic groups Means not having either substituted with 2 or more substituents, or any substituent.
In this specification,
Means a site bonded to another substituent or bond.

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

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

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

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

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

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

In this specification, the sulfonate group is represented as —SO ₃ X, and X may be hydrogen or a Group 1 element. For example, the sulfonate group include _-SO 3 Na.
In the present specification, the carboxy group means —COOH.

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

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

  In the present specification, the alkoxy group may be a straight chain, a branched chain or a cyclic chain. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyl Examples include, but are not limited to, oxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. Absent.

In this specification, the amine group is —NH ₂ ; an alkylamine group; an N-arylalkylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1-30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group. , N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but are not limited thereto.

  In the present specification, the N-alkylarylamine group means 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-arylheteroarylamine group means 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-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted on N of the amine group.

  In the present specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specific examples of the alkylthioxy group include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, and an octylthioxy group. Examples of the alkylsulfoxy group include a methylsulfoxy group and an ethylsulfoxy group. Group, propylsulfoxy group, butylsulfoxy group and the like, but are not limited thereto.

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

In the present specification, the aryl group may be monocyclic or polycyclic.
When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, and a terphenyl group.

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

  In the present specification, an “adjacent” group means a substituent substituted by an atom directly connected to an atom to which the corresponding substituent is substituted, a substituent closest to the corresponding substituent in terms of a three-dimensional structure, or It can mean other substituents in which the substituent is replaced by a substituted atom. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as “adjacent” groups to each other.

  In the present specification, the aryl groups in the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group and arylphosphine group are the same as the examples of the aryl group described above. It is. Specifically, as the aryloxy group, a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. And thioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group and the like, and arylsulfoxy The benzene sulfoxide groups include, p- toluenesulfonic sulfoxide group, and the like, but is not limited thereto.

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

  In the present specification, a heteroaryl group contains one or more atoms that are not carbon atoms and heteroatoms. Specifically, the heteroatoms are atoms selected from the group consisting of O, N, Se, S, and the like. The above can be included. The number of carbon atoms is not particularly limited, but preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, triazolyl, acridyl, pyridazinyl, pyrazinyl Group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzothiazolyl group Carbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group And dibenzofuranyl group, and the like, but not limited thereto.

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

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

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

  In the present specification, an alkylene group means an alkyl group having two bonding positions, that is, a divalent substituent. The above explanation of the alkyl group can be applied except that these are each a divalent substituent.

  In the present specification, examples of the cyclic anhydride include maleic anhydride, fumaric anhydride, glutaric anhydride, and the like, but are not limited thereto.

  According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.

[Chemical formula 1-1]

[Chemical formula 1-2]

[Chemical formula 1-3]

[Chemical formula 1-4]

In the chemical formulas 1-1 to 1-4,
The definitions of R1 to R5, r1 to r5, R101 to R105, Ar1 and Ar2 are the same as those in Chemical Formula 1,
R203 is hydrogen; deuterium; halogen group; hydroxy group; substituted or unsubstituted alkoxy group; or substituted or unsubstituted alkyl group;
R201, R202, R204 and R205 are the same or different from each other and are each independently a direct bond; or a substituted or unsubstituted alkylene group.

  According to one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-5 to 1-12.

[Chemical formula 1-5]

[Chemical formula 1-6]

[Chemical formula 1-7]

[Chemical formula 1-8]

[Chemical formula 1-9]

[Chemical formula 1-10]

[Chemical formula 1-11]

[Chemical formula 1-12]

In the chemical formulas 1-5 to 1-12,
The definitions of R1 to R5, r1 to r5, R101 to R105, Ar1, Ar2, and R201 to R205 are as described above.

  According to one embodiment of the present specification, in Formulas 1-5 to 1-8, Ar 1 is a substituted or unsubstituted alkyl group.

  According to one embodiment of the present specification, in Formulas 1-5 to 1-8, Ar1 is an alkyl group substituted or unsubstituted with an amino group, a carboxy group, or a hydroxy group.

  According to one embodiment of the present specification, in Formulas 1-5 to 1-8, Ar1 is an n-propyl group that is substituted or unsubstituted with an amino group, a carboxy group, or a hydroxy group.

  According to one embodiment of the present specification, in Formulas 1-5 to 1-8, Ar1 is an n-propyl group substituted with an amino group, a carboxy group, or a hydroxy group.

  According to one embodiment of the present specification, in Formulas 1-9 to 1-12, Ar2 is a substituted or unsubstituted alkyl group.

  According to one embodiment of the present specification, in Formulas 1-9 to 1-12, Ar2 is an alkyl group substituted or unsubstituted with an amino group, a carboxy group, or a hydroxy group.

  According to one embodiment of the present specification, in Formulas 1-9 to 1-12, Ar2 is an n-propyl group substituted or unsubstituted with an amino group, a carboxy group, or a hydroxy group.

  According to one embodiment of the present specification, in Formulas 1-9 to 1-12, Ar2 is an n-propyl group substituted with an amino group, a carboxy group, or a hydroxy group.

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

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

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

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

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

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

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

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

  According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represents hydrogen; a sulfonate group; a sulfonamide group; or a substituted or unsubstituted alkyl group.

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

According to one embodiment of the present specification, the R1 to R5 are the same as or different from each other, and are each independently hydrogen; —SO ₃ Na; 2-ethylhexylsulfonamido group; methyl group; ethyl group; A propyl group; or an isopropyl group.

  According to one embodiment of the present specification, R103 is hydrogen.

  According to one embodiment of the present specification, the R101, R102, R104 and R105 are the same or different from each other, and are each independently a direct bond; or an alkylene group.

  According to one embodiment of the present specification, R101, R102, R104, and R105 are the same or different from each other, and are each independently a direct bond; or an alkylene group having 1 to 10 carbon atoms.

  According to one embodiment of the present specification, R101, R102, R104 and R105 are the same or different from each other, and each independently is a direct bond; or an n-propylene group.

According to one embodiment of the present specification, in Formula 1, L1 is
Or
And Ar1 is an aryl group substituted with at least one carboxy group; or an aryl group fused with a cyclic anhydride;
L2 is
Or
, Ar2 is an aryl group substituted with at least one carboxy group; or an aryl group fused with a cyclic anhydride.

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

[Chemical Formula 1-A]

In Formula 1-A,
At least one of G1 to G5 is a carboxy group and the rest is hydrogen, or adjacent rings are bonded to each other to form maleic anhydride,
Is a site bound to L1 or L2 in the chemical formula 1.

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

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

  According to one embodiment of the present specification, in Formula 1-A, three of G1 to G5 are carboxy groups, and the rest are hydrogen.

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

  According to one embodiment of the present specification, the chemical formula 1-A is selected from the following structural formulas.

In the structural formula:
Is a site bound to L1 or L2 in the chemical formula 1.

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

In the compound, R is
It is.

  The compound represented by Chemical Formula 1 can be produced with reference to the production examples described later.

  According to one embodiment of the present specification, a color material composition including the compound represented by Formula 1 is provided.

  The color material composition may further include at least one of a dye and a pigment in addition to the compound represented by Formula 1. For example, the colorant composition may include only the compound represented by the chemical formula 1, but includes the compound represented by the chemical formula 1 and one or more dyes, or the compound represented by the chemical formula 1 One or more pigments may be included, or the compound represented by Formula 1 above, one or more dyes, and one or more pigments may be included. In one embodiment of the present specification, a resin composition including the color material composition is provided.

According to an embodiment of the present specification, the dye is one or more dyes selected from xanthene dyes, cyanine dyes, anthraquinone dyes, and azaporphyrin dyes, and the pigment is a blue pigment or a violet pigment.
The xanthene dye, cyanine dye, anthraquinone dye and azaporphyrin dye are not particularly limited as long as they are used in this technical field.

  The blue pigment is not particularly limited as long as it is used in the art, and among them, a copper phthalocyanine blue pigment can be included. Examples of the copper phthalocyanine blue pigment include compounds classified as pigments by Color Index (published by The Society of Dyer's and Colorists). As a specific example, C.I. I. And blue pigment (Color Index Pigment Blue) 1, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60, and the like.

  The purple pigment is not particularly limited as long as it is used in the technical field, and is classified into C.I. I. Purple Index (Color Index Pigment Violet) 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 and the like.

  In one 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 the resin composition.
As the binder resin, a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility can be used, and a binder generally used in this technical field can be further included.

  The polyfunctional monomer imparting the mechanical strength of the film is any one or more of unsaturated carboxylic esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. Also good.

  Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth). Acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) Acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2 Hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene Glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) ) Acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafur Roisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxy It may be selected from the group consisting of methyl acrylate and butyl α-hydroxymethyl acrylate, but is not limited thereto.

  Specific examples of the aromatic vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, It may be selected from the group consisting of p) -chlorostyrene, but is not limited thereto.

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

  Specific examples of the unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. However, it is not limited to only these.

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

  The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2 -Selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, omega-carboxypolycaprolactone mono (meth) acrylate Although it is preferable to use 1 or more types, it is not limited only to these.

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

  The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol. Diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetra Methacrylate and dipentaerythritol hexame May be one or a mixture of two or more selected from the group consisting of acrylate.

  The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light and causes crosslinking. For example, the photoinitiator is selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. 1 or more types may be sufficient.

  Examples of the acetophenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2- Hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- ( 4-Bromo-benzyl-2-dimethylamino Examples include, but are not limited to, 1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one. is not.

  Examples of the biimidazole compound include 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′- Examples include tetraphenylbiimidazole, 2,2′-bis (o-chlorophenyl) -4,4,5,5′-tetraphenyl-1,2′-biimidazole, but are not limited thereto. .

  Examples of the triazine compound include 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, cyclohexyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloro) Methyl) -s-triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 3- {4 -[2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4- Bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc. Although it is mentioned, it is not limited to these.

  Examples of the oxime compound include 1,2-octadion-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (CGI124, manufactured by Ciba Geigy Co.), ethanone-1- (9-ethyl) -6- ( Examples thereof include, but are not limited to, 2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGI242) and N-1919 (Adeka).

  As the solvent, acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether , Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropano , Propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl It may be at least one selected from the group consisting of 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but is not limited thereto. It is not something.

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

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

  According to one embodiment of the present specification, the resin composition comprises a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and It further includes one or more additives selected from the group consisting of leveling agents.

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

  The photocrosslinking sensitizer includes benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9- Fluorenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; Xanthone compounds such as 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, Acridine compounds such as 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7 -Dicarbonyl compounds such as trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxy) Benzoyl) -2,4,4-trimethylpentylphosphineoxy Phosphine oxide compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5 -Amino such as bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone Synergists; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7-methoxy -Coumarin, 10,10-carbonylbis [1,1,7, Coumarin compounds such as 7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolizin-11-one; 4-diethylaminochalcone 1 or more types selected from the group consisting of chalcone compounds such as 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthothiazoline.

  The curing accelerator is used to increase the curing and mechanical strength. Specifically, 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) It can be used one or more selected.

  As the adhesion promoter used in this specification, one or more methacryloylsilane coupling agents such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, and methacryloyloxypropyldimethoxysilane are selected. As the alkyltrimethoxysilane, one or more selected from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like can be used.

  The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, examples of the silicone-based surfactant include BYK-077, BYK-085, BYK-300, BYK manufactured by BYK-Chemie. -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 or the like can be used, and the fluorine-based surfactant is D. F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, manufactured by C (DaiNippon Ink & Chemicals) 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, TF1442 and the like can be used. It is not limited only thereto.

  The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant. However, it is not limited to only these.

  Specific examples of the antioxidant include phosphoric acid-based heat stabilizers 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, tetrabis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl -2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 3,5-di-tert-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4′-butylidene-bis (3-methyl-6-t-butyl) Phenol), 4,4′-thiobis (3-methyl-6-tert-butylphenol) or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester (Bis Hindered phenol-based primary antioxidants such as [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester); phenyl-α-naphthylamine; Amine-based secondary antioxidants such as phenyl-β-naphthylamine, N, N′-diphenyl-p-phenylenediamine or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, di Lauryl thiopropionate, distearyl thiopropionate Thio-based secondary antioxidants such as thio, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenyl phosphite, tris (nonylphenyl) phosphite, triiso Decyl phosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Pentaerythritol Diphosphite or (1,1′-biphenyl) -4,4′-diylbisphosphonite tetrakis [ 2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1′-Biphenyl) -4,4′-Diylbisphosphono acid acid tetrakis [2,4 -Bis (1,1-dimethylethyl) phenyl] ester), and the like.

  As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but are not limited thereto. Any of those commonly used in the art may be used.

  Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenylhydroxyamine aluminum salt. , P-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2-methylenebis (4-methyl-6-t) -Butylphenol), 2-mercaptoimidazole and phenothiazine, but may include one or more selected from the group consisting of, but not limited to, generally known in the art It can contain the.

  The dispersant can be used by a method of internally adding the pigment to the pigment in a form in which the pigment is surface-treated in advance or a method of adding the pigment to the pigment externally. As the dispersant, a compound type, nonionic, anionic or cationic dispersant can be used, and examples thereof include fluorine-based, ester-based, cationic-based, anionic-based, non-ionic and amphoteric surfactants. . These can be used alone or in combination of two or more.

  Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonate ester, sulfonate, carboxylate ester, carboxylate , One or more selected from the group consisting of an alkylamide alkylene oxide adduct and an alkylamine, but is not limited thereto.

  The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamidoamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen. Including compounds, but not limited thereto, any of those commonly used in the art may be used.

According to one embodiment 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 color material composition. The resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed and cured to form a color filter.

  The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and the spin coating method is generally widely used. Moreover, after forming a coating film, a part of residual solvent can be removed under reduced pressure depending on the case.

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

  The resin composition according to the present specification includes a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or a black matrix forming photosensitive material for an organic light emitting diode, and an overcoat layer. It is used for forming photosensitive materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, photosensitive materials for printed wiring boards, plasma display panel (PDP) photosensitive materials, and the like. And there are no particular restrictions on its use.

  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. Therefore, the color filter has a high color reproducibility even in the curing process during the production of the color filter, and has a high luminance and light / dark ratio. Can be provided.

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

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
According to another embodiment, the color filter may further include an overcoat layer.

  A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the black matrix material. In this case, it is possible to use a method in which chromium is deposited on the entire glass substrate and a pattern is formed by etching. However, a resin black matrix by a pigment dispersion method capable of fine processing can be used in consideration of high process costs, high reflectivity of chromium, and environmental contamination due to chromium waste liquid.

  The black matrix according to an embodiment of the present specification can use a black pigment or a black dye as a colorant. For example, carbon black can be used alone, or carbon black and a color pigment can be mixed and used. At this time, the amount of the coloring material is relatively increased because the color pigment lacking in light shielding properties is mixed. However, there is an advantage that the strength of the film or the adhesion to the substrate does not decrease.

A display device including a color filter according to the present description is provided.
The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting device (OLED), a liquid crystal display, and a liquid crystal display (LCD). It may be any one of a display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

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

Production Example Production Example 1 Production of compound 1

NMP 230 g to B-1 19.92g (38.42mmol), A-1 21.36g (153.68mmol), NaI 23.04g (153.68mmol), K 2 CO 3 21.24g of (153.68mmol) The mixture was stirred at 95 ° C. for 15 hours. The reaction product was cooled to room temperature, stirred in DI-Water for 1 hour, the precipitate was filtered and washed under reduced pressure, and dried at 80 ° C. for 12 hours to obtain B-2. B-2 was used in the next reaction without separation.

  B-2 and A-2 24.27g (115.26mmol) were put into 700g of pyridine (Pyridine), and it stirred at normal temperature for 24 hours. The reaction was placed in DI-Water and stirred for 1 hour. The precipitate was filtered and washed under reduced pressure, and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was subjected to column chromatography to obtain Compound 1.

  Ionization mode =: APCI +: m / z = 983 [M + H] +, Exact Mass: 982

Production Example 2 Production of compound 2

  Compound 2 was obtained in the same manner as in Production Example 1 except that C-1 was used instead of B-1 and C-2 was used instead of B-2.

  Ionization mode =: APCI +: m / z = 1039 [M + H] +, Exact Mass: 1038

Production Example 3 Production of compound 3

  Compound 3 was obtained in the same manner as in Production Example 1 except that D-1 was used instead of B-1 and D-2 was used instead of B-2.

  Ionization mode =: APCI +: m / z = 1095 [M + H] +, Exact Mass: 1094

Production Example 4 Production of compound 4

  Compound 4 was obtained in the same manner as in Production Example 1 except that E-1 was used instead of B-1 and E-2 was used instead of B-2.

  Ionization mode =: APCI +: m / z = 1151 [M + H] +, Exact Mass: 1150

Production Example 5 Production of compound 5

  Compound 5 was obtained in the same manner as in Production Example 1 except that F-1 was used instead of B-1 and F-2 was used instead of B-2.

  Ionization mode =: APCI +: m / z = 1067 [M + H] +, Exact Mass: 1066

Production Example 6 Production of Compound 6

Acid Red 289 26 g (38.42 mmol), A-1 21.36 g (153.68 mmol), NaI 23.04 g (153.68 mmol), K ₂ CO ₃ 21.24 g (main compound as the main compound) in 230 g of NMP 153.68 mmol) was added, and the mixture was stirred at 95 ° C. for 15 hours. The reaction product was cooled to room temperature, stirred in EA for 1 hour, and then the precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours to obtain G-2 having the above structure as the main compound. G-2 was used in the next reaction without separation.

  G-2 and 24.27 g (115.26 mmol) of A-2 were added to 700 g of pyridine, and the mixture was stirred at room temperature for 24 hours. The reaction was placed in DI-Water and stirred for 1 hour. The precipitate was filtered and washed under reduced pressure, and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was subjected to column chromatography to obtain Compound 6 having the above structure as the main compound.

Production Example 7 Production of Compound 7 In Production Example 1, instead of B-2
Manufactured in the same way except that
(Compound 7) was produced.

Production Example 8 Production of Compound 8 In Production Example 2, instead of C-2
Manufactured in the same way except that
(Compound 8) was produced.

Production Example 9 Production of Compound 9 In Production Example 3, instead of D-2
Manufactured in the same way except that
(Compound 9) was produced.

Production Example 10 Production of Compound 10 In Production Example 4, instead of E-2
Manufactured in the same way except that
(Compound 10) was produced.

Production Example 11 Production of Compound 11 In Production Example 5, instead of F-2
Manufactured in the same way except that
(Compound 11) was produced.

Production Example 12. Production of Compound 12 In Production Example 6, instead of G-2
Manufactured in the same way except that
(Compound 12) was produced.

Comparative compound 1

Comparative compound 2

  The comparative compound 1 is Basic blue 7, and the comparative compound 2 is rhodamine 6G.

Examples Color material compositions were produced at the ratios shown in Table 1 below. The dosage unit of the compound is grams (g).

Fabrication of Substrate The compound produced by the above synthesis was spin coated on glass (5 × 5 cm) and prebaked at 100 ° C. for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photomask was 250 μm, and the entire surface of the substrate was irradiated with light having an exposure amount of 40 mJ / cm ² using an exposure device.

  Thereafter, the exposed substrate was developed with a developing solution (KOH, 0.05%) for 60 seconds, and post-baked at 230 ° C. for 20 minutes to produce a substrate.

Evaluation of heat resistance A transmittance spectrum of a visible light region in a range of 380 nm to 780 nm was obtained using a prebake substrate manufactured under the above conditions using a spectroscope (MCPD-Otsuka). In addition, a prebake substrate was further post-baked at 230 ° C. for 20 minutes, and a transmittance spectrum was obtained with the same equipment and measurement range.

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

ΔE (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2
A small ΔE value means excellent color heat resistance.

  Table 2 shows the measurement results of heat resistance for the substrates manufactured in Examples 1 to 6 and the substrates manufactured in Comparative Examples 1 and 2. As shown in Table 2, it was confirmed that the substrates produced in Examples 1 to 6 had a smaller color change (ΔEab) than Comparative Examples 1 and 2.

Claims (11)

Compound represented by the following chemical formula 1:
[Chemical Formula 1]
In Formula 1,
L1 and L2 are
Or
L1 and L2 are the same substituent ,
Ar1 and Ar2 are the same or different from each other, each independently an aryl group substituted by at least one carboxy group; a fused aryl group or a cyclic anhydride,
R1 to R5 and R103 are the same as or different from each other, and each independently represents hydrogen; deuterium; halogen group; hydroxy group; sulfonate group; sulfonamide group ; alkoxy group ;
R101, R102, R104 and R105 are as or different are identical to each other, each independently direct bond; is a or an alkylene group, R101 to bind to the N atom in Formula 1 is an alkylene group,
r1 and r2 are each an integer of 1 to 5,
r3 and r4 are each an integer of 1 to 3,
r5 is an integer of 1 to 4,
when each of r1 to r5 is 2 or more, the structures in the two or more brackets are the same or different from each other;
Is a site for linking N and Ar1 in Formula 1; or N and Ar2. The compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4.
[Chemical Formula 1-1]
[Chemical formula 1-2]
[Chemical formula 1-3]
[Chemical formula 1-4]
In the chemical formulas 1-1 to 1-4,
The definitions of R1 to R5, r1 to r5, R101 to R105, Ar1 and Ar2 are the same as those in Chemical Formula 1,
R203 is hydrogen; deuterium; halogen group; hydroxy group; substituted or unsubstituted alkoxy group; or substituted or unsubstituted alkyl group;
R201, R204, and R205 are the same or different from each other and are each independently a direct bond ; or an alkylene group , but R201 in Formula 1-1 is an alkylene group . The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other and are each independently represented by the following chemical formula 1-A:
[Chemical Formula 1-A]
In Formula 1-A,
At least one of G1 to G5 is a carboxy group and the rest is hydrogen, or adjacent rings are bonded to each other to form maleic anhydride,
Is a site bound to L1 or L2 in the chemical formula 1.   The compound according to claim 1, wherein Ar1 and Ar2 are the same or different from each other, and each independently represents a phenyl group substituted with 1 to 3 carboxy groups. The compound according to claim 1, wherein Formula 1 is selected from the following compounds:
In the compound, R is
It is.   The coloring material composition containing the compound of any one of Claims 1-5.   The colorant composition according to claim 6, further comprising at least one of a dye and a pigment. The dye is one or more dyes selected from xanthene dyes, cyanine dyes, anthraquinone dyes and azaporphyrin dyes;
The colorant composition according to claim 7, wherein the pigment is a blue pigment or a violet pigment.   A resin composition comprising the compound represented by Chemical Formula 1 according to claim 1, a binder resin, a polyfunctional monomer, a photoinitiator, an antioxidant, and a solvent.   A color filter comprising the resin composition according to claim 9.   A display device comprising the color filter according to claim 10.