TW201739844A - Compound, colorant composition comprising the same and resin composition comprising the same capable of providing excellent solubility and chemical resistance - Google Patents

Abstract

The present invention relates to a novel chemical compound, a colorant composition comprising the same and a resin composition comprising the same, in which the chemical compound is represented by the chemical formula 1. In the chemical formula 1, A is represented by the chemical formula A-1 or A-2, wherein at least one of R1 to R6 has a structure as shown in chemical formula "a" while the others may be the same with each other or different from each other, each independently being hydrogen,-R(C=O)R', -RO(C=O)R', -ROR', substituted or un-substituted alkyl, substituted or un-substituted alkenyl, substituted or un-substituted cycloalkyl, substituted or un-substituted aryl, or a cross-linking group, or at least one of the above R1, R2, R3, R4, and R5 and R6 can be bound with each other to form substituted or un-substituted ring; R7 to R22 are the same with each other or different from each other, each independently representing hydrogen, halogen, hydroxy, substituted or un-substituted alkoxy, or substituted or un-substituted alkyl; R and R'' are the same with each other or different from each other, each independently representing direct coupling, substituted or un-substituted alkylene, substituted or un-substituted allylene; R' and R''' are the same with each other or different from each other, each independently representing hydrogen, substituted or un-substituted alkyl, substituted or un-substituted alkenyl, or substituted or un-substituted aryl; Z- is an anionic group. In the chemical formula "a", Q is -R101C(=O)R102-, -R103OC(=O)R104-, -R105C(=O)OR106-, -R107OC(=O)OR108-, -SOOR115-, -SOR116-, -SR117-, substituted or un-substituted alkylene, or substited or un-substituted alkenylene; X is hydroxyl, amine, -OCOOR118, -CONR119R120, or -NR121COOR122; T is substituted or un-substituted alkyl; R101 to R109, R111, R112, and R114 to R117 are the same with each other or different from each other, each independently representing direct coupling, substituted or un-substituted alkylene, substituted or un-substituted cyclo-alkylene, substituted or un-substituted alkenylene; R110, R113, and R118 to R122 are the same with each other or different from each other, each independently representing hydrogen, substituted or un-substituted alkyl; p and q are each an integer of 1 to 4, where 2<=p+q<=5; the structures in two or more parentheses are the same with each other or different from each other when p and q are each an integer greater than 2; * is a part connected with N of the chemical formula 1.

Description

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

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

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

However, in the case of using a display such as an LED, an OLED, a QD or the like as a unit pixel, it is difficult to increase the area, and in the case of using an LED, an OLED, a QD or the like, it is also developed to include these elements as a light source and include color. The display of the filter is undergoing many efforts.

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

However, in the case of the pigment dispersion liquid, not only the pigment is scattered in the particle state but also the light is scattered, and the surface area of the pigment is rapidly increased by the refinement of the pigment, and unevenness is generated due to deterioration of the dispersion stability caused thereby. Pigment particles.

Therefore, it is considered that it is difficult to meet the most demanding high-quality requirements such as high brightness, high contrast, and high definition.

In order to solve the above problems and achieve high brightness, high contrast, and high resolution, it has recently been studied to use a dye instead of a pigment as a coloring agent. Among them, a large number of attempts have been made to use triarylmethane dyes as blue colorants. Generally, the triarylmethane dye has a high transmittance at 420 nm to 450 m, and the color characteristics are effective, but the chemical resistance is lowered due to the solubility higher than the pigment, and the color filter is lower than the heat resistance of the pigment. Used in restricted places.

[Prior Art Document] [Patent Document] Korean Patent Publication No. 2001-0009058 Korean Patent No. 2013-0130976

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

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

[Chemical 1]

In the chemical formula 1, A is represented by the following chemical formula A-1 or A-2, [Chemical A-1] [化A-2] At least one of R1 to R6 is a structure represented by the following chemical formula a, and the others are the same or different from each other, and are independently hydrogen, -R(C=O)R', -RO(C=O)R', - ROR', a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a crosslinkable group; R1 and R2, R3 and R4, and at least one of R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring, and R7 to R22 are the same or different from each other, and are independently hydrogen, halogen, hydroxyl, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group, R and R'' are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group. Or a substituted or unsubstituted extended aryl group, R' and R''' are the same or different, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl Or a substituted or unsubstituted aryl group, Z ^- is an anionic group, [a] In the chemical formula a, Q is -R101C(=O)R102-, -R103OC(=O)R104-, -R105C(=O)OR106-, -R107OC(=O)OR108-, ; , -SOOR115-, -SOR116-, -SR117-, substituted or unsubstituted alkylene, or substituted or unsubstituted alkenyl, X is hydroxy, amine, -OCOOR118, -CONR119R120, or -NR121COOR122, T is a substituted or unsubstituted alkyl group, and R101 to R109, R111, R112 and R114 to R117 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted extended alkenyl group, R110, R113 and R118 to R122 which are the same or different from each other, independently hydrogen or substituted or unsubstituted The alkyl group, p and q are each an integer of 1 to 4, 2≦p+q≦5, and when p and q are each 2 or more, the structures in the two or more brackets are the same or different, and * is The N-linked portion of Chemical Formula 1, It is a site to which the chemical formula 1 is bonded.

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

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

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

Further, in accordance with an embodiment of the present specification, a display device including the color filter is provided. [Effects of the Invention]

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

Further, according to an embodiment of the present specification, in the case of using an existing pigment, the coloring material composition containing the compound represented by the chemical formula 1 exhibits high luminance, and a crosslinkable group can be introduced to improve triarylmethane. The weak chemical resistance of dyes. Further, a color filter having excellent chemical resistance can be produced by using the colored resin composition using the same.

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

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

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 changed to another substituent, and a position substituted is a position at which a hydrogen atom is substituted, that is, a position at which a substituent can be substituted, and Without limitation, when two or more are substituted, two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used in the specification means a substituent substituted by a substituent selected from the group consisting of an anthracene, a halogen group, a nitrile group, a nitro group, and a nitro group.醯imino, amidino, carbonyl, ester, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted Or unsubstituted aryloxy, substituted or unsubstituted alkylthiooxy, substituted or unsubstituted arylthiooxy, substituted or unsubstituted alkylsulfonic acidoxy, Substituted or unsubstituted arylsulfonic acid oxy group, substituted or unsubstituted alkenyl group, substituted or unsubstituted amino group, substituted or unsubstituted aryl group, and substituted or unsubstituted One or two or more substituents in the group consisting of substituted heterocyclic groups.

In this manual, It refers to the part bonded to other substituents or bonding moieties.

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

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

In the present specification, in the guanamine group, the nitrogen of the guanamine 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 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, and is preferably from 1 to 30 carbon atoms. Specifically, it may be a compound having the structure described below, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted 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 of the following structural formula, but is not limited thereto.

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 30. 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, 4-methylhexyl or 5-methylhexyl, but is not limited thereto.

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

In the present specification, the alkoxy group may be a straight chain, a branched chain or a cyclic group. The carbon number of the alkoxy group is not particularly limited, and is preferably from 1 to 30 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 is a fluorenyloxy group, a n-decyloxy group, a benzyloxy group or a p-methylbenzyloxy group, but is not limited thereto.

In the present specification, the amine group may be selected from -NH ₂ , alkylamino group, N-arylalkylamino group, arylamine group, N-arylheteroarylamino group, N-alkylheteroarylamine. In the group consisting of a group and a heteroarylamine group, the number of carbon atoms is not particularly limited, and is preferably from 1 to 30. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamino group, a naphthylamino group, a biphenylamino group, a decylamino group, 9-Methyl-decylamino group, diphenylamino group, N-phenylnaphthylamino group, xylylamino group, N-phenylmethylphenylamino group, triphenylamine group, etc., but not Limited to this.

In the present specification, the N-alkylarylamino group means an amine group substituted with an alkyl group and an aryl group on the N group of the amine group.

In the present specification, the N-arylheteroarylamino group means an amine group substituted with an aryl group and a heteroaryl group on the N group of the amine group.

In the present specification, the N-alkylheteroarylamino group means an amine group substituted with an alkyl group and a heteroarylamino group on the N group of the amine group.

In the present specification, an alkyl group in an alkylamino group, an N-arylalkylamino group, an alkylthio group, an alkylsulfonyloxy group or an N-alkylheteroarylamino group is an alkyl group as described. The illustration is as follows. Specifically, the alkylthio group has a methylthiooxy group, an ethylthiooxy group, a tert-butylthiooxy group, a hexylthiooxy group, an octylthiooxy group, etc., and an alkylsulfonic acidoxy group has a methyl group. The base, ethyl sulfonate oxy group, propyl sulfonate oxy group, butyl sulfonate oxy group, etc. are 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, and is preferably 2 to 30. 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 is not limited thereto.

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

In the case where the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, and is preferably from 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may, for example, be a phenyl group, a biphenyl group or a biphenyl group, 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 30 carbon atoms. Specifically, the polycyclic aryl group may, for example, be a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group or a fluorenyl group. Base, base, etc., but is not limited thereto.

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 on the ortho position at the ortho position and two substituents substituted on the same carbon on the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, an aryloxy group, an arylthiooxy group, an arylsulfonic acidoxy group, an N-arylalkylamino group, an N-arylheteroarylamino group, and an aryl group in the arylphosphino group are As exemplified by the aryl group described. Specifically, the aryloxy group is a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, and a 2,4,6-trimethylphenoxy group. , p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy , 5-methyl-2-naphthyloxy, 1-decyloxy, 2-indenyloxy, 9-fluorenyloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9 - phenanthryloxy and the like, the arylthio group has a phenylthio group, a 2-methylphenylthio group, a 4-tert-butylphenylthio group, etc., and an arylsulfonic acid group has : benzenesulfonic acid oxy group, p-toluenesulfonic acid oxy group, etc., but is not limited thereto.

In the present specification, examples of the arylamine group are a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. . The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing 2 or more of the aryl group may include a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group can be selected from the exemplification of the aryl group.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and a hetero atom, and specifically, the hetero atom may include one or more selected from the group consisting of O, N, Se, and S. The atoms in the group. The carbon number is not particularly limited, and is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, anthracenyl Pyridyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, pyridazinyl, pyrazolopyrimidinyl, pyrazolopyrazinyl, pyrazinopyrazinyl, iso Quinolinyl, fluorenyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, Phenanthroline, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl and dibenzofuranyl, but not limited thereto.

In the present specification, examples of the heteroarylamino group are a substituted or unsubstituted monoheteroarylamino group, a substituted or unsubstituted diheteroarylamino group, or a substituted or unsubstituted three. Heteroarylamine group. The heteroarylamino group containing 2 or more of the heteroaryl group may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or both a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group can be selected from the exemplification of the heteroaryl group.

In the present specification, the exemplification of the heteroaryl group in the N-arylheteroarylamino group and the N-alkylheteroarylamino group is as exemplified as the heteroaryl group.

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

In the present specification, alkylene means that there are two bonding sites on the alkyl group, that is, a divalent group. The description of the alkyl group may be applied in addition to the divalent group.

In the present specification, a cycloalkyl group means that there are two bonding sites on the cycloalkyl group, that is, a divalent group. The description of the cycloalkyl group may be applied in addition to the divalent group.

In the present specification, an extended aryl group means that there are two bonding sites on the aryl group, that is, a divalent group. The description of the aryl group may be applied in addition to being a divalent group, respectively.

In the present specification, a heteroaryl group means that there are two bonding sites on the heteroaryl group, that is, a divalent group. The description of the heteroaryl group can be applied in addition to being a divalent group, respectively.

According to an embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 1-1 or 1-2. [Chem. 1-1] [Chem. 1-2] In Chemical Formula 1-1 and 1-2, R1 to R4, R7 to R14 and Z ^- is the same as defined in Chemical Formula 1, R5, definition of R6, R15 to R22 and the chemical formulas A-1 and A- 2 is the same.

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

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

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the others are the same or different from each other, and are independently hydrogen, -ROR', substituted by a hydroxyl group or not A substituted alkyl group, an alkenyl group, an alkyl group substituted or unsubstituted aryl group, or a crosslinkable group.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the others are the same or different from each other, and are independently hydrogen, -ROR', substituted by a hydroxyl group or not Substituted ethyl, vinyl, alkyl, substituted or unsubstituted phenyl, or crosslinkable.

According to an embodiment of the present specification, at least one of R1 to R6 is a structure represented by the chemical formula a, and the others are the same or different from each other, and are independently hydrogen, -ROR', substituted by a hydroxyl group or not a substituted ethyl group, a vinyl group, a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a methyl group and an ethyl group, or a crosslinkable group.

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

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

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

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

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

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

According to an embodiment of the present specification, the crosslinkable group is a structure represented by any one of the following Chemical Formulas 2 to 5. [Chemical 2] [Chemical 3] [Chemical 4] [Chemical 5] In the chemical formulas 2 to 5, the R201 to R203 are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group, and R204 to R207 are the same or different from each other, and are each independently a direct bond. , O, NR208, substituted or unsubstituted alkylene, or substituted or unsubstituted cycloalkyl, R208 is hydrogen, or substituted or unsubstituted alkyl, r, s, t and u is 1 or 2, respectively. When the r, s, t, and u are 2, respectively, the structures in the two brackets may be the same or different.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

According to an embodiment of the present specification, in the chemical formula 1, Z ^- is an anionic group, and the anionic group is not particularly limited, and for example, US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080 Japanese Patent Laid-Open No. 2006-001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. Hei No. 2007-7028897, Japanese Patent Laid-Open No. Hei No. 2005-071680, Korean Patent Application No. 2007-7000693, Japanese Patent Laid-Open An anion described in Japanese Patent Laid-Open No. 2008-249663.

Specific examples of the anion include: trifluoromethanesulfonate anion, bis(trifluoromethylsulfonyl)guanamine anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, four Phenylborate anion, tetrakis(4-fluorophenyl)borate, tetrakis(pentafluorophenyl)borate, tris-trifluoromethanesulfonyl methide, phosphate ion, nitrate ion, carbonate ion , sulfite ion, halogen group, such as bromo group, fluorine group, iodine group, chlorine group and the like.

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

According to an embodiment of the present specification, in the chemical formula 1, Z ^- is: a sulfonium imide containing a halogenated hydrocarbon group; an anion comprising a sulfonic acid; an anion comprising halogen, boron, aluminum; or comprising selected from the group consisting of tungsten, One or more elements and anions of oxygen in a group consisting of molybdenum, rhenium, and phosphorus.

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

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

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

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

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

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

According to another embodiment of the present specification, R118 is hydrogen or an alkyl group.

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

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

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

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

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

The compound represented by Chemical Formula 1 can be produced by reference to a production example described later.

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

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

In an embodiment of the present specification, the resin composition may further comprise 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 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 to which the alkali solubility is imparted is not particularly limited as long as it contains an acid group. For example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, and anti- Butenedioic acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth)acryloxy)ethyl phthalate, succinic acid One or more of the group consisting of -2-((meth)acryloxy)ethyl ester and ω-carboxypolycaprolactone mono(meth)acrylate, but is not limited thereto.

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

The polyfunctional monomer is a monomer having a function of forming a photoresist image by light, and specifically may be selected from 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 radical to trigger 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 Etc., is not limited to this.

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 this.

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 this.

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 this.

The solvent may be one or more selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-Dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ether , chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane , heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, 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.

According to an embodiment of the present specification, the content of the coloring material composition is 5% by weight to 90% 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 30% by weight, the antioxidant is contained in an amount of 0.001% by weight to 20% by weight, the photoinitiator is contained in an amount of 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 refers to the total weight of the components of the resin composition excluding the solvent. 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.

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

According to an embodiment of the present specification, the additive is contained in an amount of from 0.1% by weight to 20% by weight based on the total mass of the solid component 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 derived from methacryloxypropyltrimethoxydecane, methacryloxypropyldimethoxydecane, methacryloxypropyltriethoxylate. One or more selected from the group consisting of a methacryl decyl decane coupling agent such as decane or methacryloxypropyl dimethoxy decane, and an alkyltrimethoxy decane, which may be derived from octyltrimethoxynonane or twelve. One or more selected from the group consisting of alkyl trimethoxy decane and octadecyl trimethoxy decane 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, and the like are not limited thereto.

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, octadecane 3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[methylene-3-(3,5-di-t-butyl-4-hydroxyl) Phenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,5- Di-t-butyl-4-hydroxybenzyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g, t-butyl Phenol 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or double [ 3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]diol (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl) Hindered phenol such as butanoic acid]glycol ester) is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine Or an amine-based secondary antioxidant such as N,N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, and second hard Sulfur-based thiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetras[methylene-3-(laurylthio)propionate]methane (Thio) secondary Antioxidant; or triphenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl)pentaerythritol diphosphite (Bis ( 2,4-ditbutylphenyl)Pentaerythritol Diphosphite) or (1,1'-biphenyl)-4,4'-diylbisphosphinic acid tetra[2,4-bis(1,1-dimethylethyl) Phosphite-based secondary antioxidants such as (1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester) .

The ultraviolet absorber may be used: 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc., but Not limited to this, any one of ordinary users in the art can use either.

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 may 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, a reaction product of an amine and an epoxide, and specific examples of the non-polymeric leveling agent include a non-polymer sulfur-containing compound and a non-polymer. The polymer contains a nitrogen-containing compound, but is not limited thereto, and any one of ordinary users in the art can use any one.

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

The color filter can be produced using a resin composition containing the coloring material composition. 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 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 hardening 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 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 Diasplay Panel, PDP), the use thereof is not particularly limited.

The resin composition according to an embodiment of the present invention is excellent in heat resistance, and has little color change due to heat treatment, and has a high color reproduction rate even when a color filter is used for the curing process, thereby providing high brightness and contrast. 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.

According to 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, a method may be employed in which chromium is vapor-deposited on the entire glass substrate, and a pattern is formed by an etching treatment. 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 coloring material. 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 coloring material 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.

[Manufacturing Example 1] Production of Compound A To 0.55 g (0.38 mmol, 1.2 eq) of naphthalene-1-amine, 1 mL of AcOH, 0.3 g (0.31 mmol, 1 eq) of cyclohexanone, and 1 mL of dichloromethane were added and stirred for about 30 minutes. Then, 1.0 g (4.7 mmol, 1.5 eq) of NaBH(OAC) _{3 was} slowly added. After stirring at room temperature for about 16 hours, distilled water was added thereto, and the mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:9) to obtain 0.74 g of Compound A. (yield 86%)

[Manufacturing Example 2] Production of Compound B Add 50 ml of dimethylformamide (DMF) to 3.7 g (0.026 mol, 1 eq) of naphthalen-1-amine, and slowly add 17.85 g (0.13 mol, 5 eq) of potassium carbonate at room temperature. After that, stir for 30 minutes. Then, 7.8 g (0.065 mol, 2.5 eq) of bromopropene was added, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, distilled water was added, and the mixture was extracted with ether, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:100 to 1:80) to obtain 1.5 g of Compound B in a yield of 34%.

[Manufacturing Example 3] Production of Compound C To 3.0 g (0.021 mol, 1 eq) of naphthalen-1-amine, 30 mL of dichloromethane was added, and 2.75 g (0.027 mol, 1.3 eq) of triethylamine was slowly added at room temperature. Then, 4.8 g (0.056 mol, 2.7 eq) of methacrylic acid was added, and the mixture was stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:10 to 1:15) to obtain 0.9 g of Compound C in 20% yield.

[Manufacturing Example 4] Production of Compound D Add 2.5 mL of dichloromethane to 2.41 g (0.01 mol, 1 eq) of 4-(naphthalen-1-ylamino)cyclohexan-1-ol, and slowly add 1.32 g (0.013 mol, at room temperature). 1.3 eq) of triethylamine. Then, 2.3 g (0.022 mol, 2.2 eq) of methacrylic acid was added, and the mixture was stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:5) to obtain 2.3 g of Compound D in a yield of 74%.

[Manufacturing Example 5] Production of Compound E After dissolving 2.92 g (0.01 mol, 1.5 eq) of 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid in 30 mL of tetrahydrofuran under nitrogen, an ice bath was set up. (ice bath). Then, 2.54 g (0.017 mol, 2.4 eq) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added, and after stirring for about 15 minutes, 0.34 g (0.003 mol, 0.4 eq) 4-Dimethylamino pyridine. After 15 minutes, 1.69 g (0.007 mol, 1 eq) of 4-(naphthalen-1-ylamino)cyclohexan-1-ol was dissolved in 10 mL of tetrahydrofuran and added slowly. After stirring for 24 hours, it was extracted with dichloromethane and dried under reduced pressure. Purification was carried out in a column (in a ratio of ethyl acetate:hexane = 1:5) to obtain 2.3 g (yield: 65%) of Compound E.

[Manufacturing Example 6] Production of Compound F Under nitrogen, 15 g (0.069 mol, 1 eq) of 4,4-difluorobenzophenone and 31.1 g (0.35 mol, 5 eq) of 2-ethylaminoethanol were added at 160 ° C. Allow to warm while stirring. After reacting at 160 ° C for 48 hours, it was cooled to normal temperature. Distilled water was added thereto, and the mixture was extracted with dichloromethane, and then dried under reduced pressure. Recrystallization purification with ethyl acetate at normal temperature gave Compound F. (20 g, yield 82%)

[Production Example 7] Production of Compound G After dissolving 9.6 g (0.035 mol, 3 eq) of 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid in 70 mL of tetrahydrofuran under nitrogen, an ice bath was set up. (ice bath). 4.28 g (0.028 mol, 2.4 eq) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added to the reactor, and after stirring for about 15 minutes, 0.56 g (0.005) was added. Mol, 0.4 eq) 4-Dimethylamino pyridine. After 15 minutes, 4.10 g (0.011 mol, 1 eq) of Compound F was dissolved in 30 mL of tetrahydrofuran and added slowly. After stirring for 24 hours, it was extracted with dichloromethane and dried under reduced pressure. Purification was carried out in a column (in a ratio of ethyl acetate:hexane = 1:3) to obtain 4.31 g of Compound G in a yield of 43%. After 3-column, 3-(3,5-di-tert-buthyl-4-hydroxyphenyl)propanoic acid In the case of a NaHCO ₃ (pH 10) solution, it was washed with water, extracted with dichloromethane, and dried under reduced pressure.

[Production Example 8] Production of Compound H and Compound I In the same manner as in Production Example 7, except that 1.5 eq of 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid was added to the above Production Example 7, Purification was carried out in a column (in a ratio of ethyl acetate:hexane = 1:3) to obtain 2.5 g of Compound H in a yield of 31.7%. 30 mL of dichloromethane was added to 2.5 g (0.004 mol, 1 eq) of compound H. 0.53 g (0.0053 mol, 1.3 eq) of triethylamine was slowly added at room temperature. Then, 0.77 g (0.009 mol, 2.2 eq) of methacrylic acid was added, and the mixture was stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:5) to obtain 1.9 g of Compound I in 68% yield.

[Manufacturing Example 9] Production of Compound J 30 mL of dichloromethane was added to 2 g (0.006 mol, 1 eq) of compound F. 1.42 g (0.028 mol, 2.5 eq) of triethylamine was slowly added at room temperature. Then, 2.16 g (0.025 mol, 2.5 eq) of methacrylic acid was added, and the mixture was stirred at normal temperature for 16 hours. After completion of the reaction, distilled water was added thereto, and the mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified in a column (in a ratio of ethyl acetate:hexane = 1:3) to obtain 1.5 g of Compound J in 54% yield.

[Manufacturing Example 10] Production of Compound K After dissolving 4.31 g (0.005 mol, 1 eq) of Compound G in 40 mL of pyridine, 2.68 g (0.012 mol, 2.5 eq) of Di-tert-butyl dicarbonate was slowly added. . After 15 minutes, 1.20 g (0.01 mol, 2 eq) of 4-Dimethylaminopyridine was added. After reacting at 60 ° C for 3 hours, distilled water was added thereto, and the mixture was extracted with dichloromethane and decompressed to remove the solvent, followed by purification in a column (dichloromethane: ethyl acetate = 10:1 ratio). The yield of % gave 3.87 g of compound K.

[Production Example 11] Production of Compound L Except for the use of 3,5-di-tert-butyl-4-hydroxybenzoic acid instead of 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid in Production Example 7. It was produced in the same manner as in Production Example 7, and 5.83 g of Compound L was obtained in a yield of 63%.

[Production Example 12] Production of Compound M and Compound M-1 1.5 g (0.002 mol, 1 eq) of Compound I was thoroughly dissolved in chloroform. 0.44 g (0.003 mol, 1.3 eq) of phosphonium chloride was added under a nitrogen atmosphere, and after stirring for about 30 minutes, 0.58 g (0.0026 mol, 1.3 eq) of 1-cyclohexyl-1-naphthylamine was dissolved. In chloroform, add slowly. After reacting at 60 ° C for 2 hours, the reaction was terminated with distilled water and extracted with dichloromethane. After removing the solvent under reduced pressure, the column was removed in a ratio of dichloromethane:ethyl acetate=1:1 to remove the precursor, and the composition was changed to dichloromethane:methanol:ethyl acetate=6:1:2. Purification was carried out to obtain 1.0 g of Compound M in a yield of 49%. Then, 1.0 g (0.001 mol, 1 eq) of Compound M was dissolved in 30 mL of methanol, and then 0.46 g (0.0016 mol, 1.5 eq) of bistrifluoromethanesulfonimide (BMI) was added at room temperature. Stir. The blue powder which was precipitated by adding distilled water was filtered, and 1.1 g of the compound M-1 was obtained in a yield of 87%.

[Production Example 13] Production of Compound N and Compound N-1 The compound N was used in the same manner as in Production Example 12 except that the compound J was used instead of the compound I in the production example 12, and 0.95 g of the compound N was obtained in a yield of 31%. And 1.1 g of the compound N-1 was obtained in a yield of 93%.

[Production Example 14] Production of Compound O and Compound O-1 Except that the compound G was used instead of the compound I in the production example 12, and the compound B was used instead of the compound A, the same procedure as in Production Example 12 was carried out, and 0.48 g of the compound O was obtained in a yield of 26%. And 0.5 g of compound 0-1 was obtained in 85% yield.

[Production Example 15] Production of Compound P and Compound P-1 The compound P was obtained in the same manner as in Production Example 12 except that the compound G was used instead of the compound I in the production example 12, and 0.77 g of the compound P was obtained in a yield of 41%. And 0.75 g of the compound P-1 was obtained in a yield of 79%.

[Production Example 16] Production of Compound Q and Compound Q-1 The compound Q was used in the same manner as in Production Example 12 except that the compound G was used instead of the compound I in the production example 12, and 0.82 g of the compound Q was obtained in a yield of 39%. And 0.75 g of compound Q-1 was obtained in a yield of 76%.

[Production Example 17] Production of Compound R The anion was produced in the same manner as the method of Synthesis Example 1 of Korean Laid-Open Patent Publication No. 2015-0009447. 0.5 g (0.0005 mol, 1 eq) of Compound M was thoroughly dissolved in 10 g of dimethylformamide. 0.27 g (0.0008 mol, 1.5 eq) of anion was added. After stirring at 55 ° C for 3 hours, it was cooled to room temperature. After dropwise addition to 1000 g of distilled water while stirring for 1 hour, filtration under reduced pressure was carried out to obtain 0.48 g of Compound R in a yield of 74%.

[Manufacturing Example 18] Production of Compound 1 of Comparative Example Except that bistrifluoromethanesulfonimide was used as an anion in Example 7 of Korean Patent Publication No. 2012-0014111, it was produced in the same manner, and 0.8 g of Compound 1 of Comparative Example was obtained in a yield of 80%.

[manufacture and evaluation of coloring composition]

Comparative Example 1 A photosensitive blue resin composition was produced in the following composition. 0.88 wt% of a compound of Comparative Example manufactured by Production Example 18 as a blue dye compound, 20.78% by weight of a binder resin (mass ratio of benzyl methacrylate: N-phenylbutylene dioxime) Imine: styrene: methacrylic acid = 55:9:11:25 copolymer), 20.46% by weight of dipentaerythritol hexaacrylate as acrylic monomer, 56.57 wt% of propylene glycol monomethyl ether acetate, 0.68 A photosensitive blue resin composition was prepared by uniformly mixing a weight percentage of a photopolymerization initiator (PBG-3142), a leveling agent (TF-1740), and a bonding aid (KRM-503) at 0.66% by weight. .

Example 1 A blue resin composition was produced in the same manner as in Comparative Example 1, except that the compound M-1 was used as the blue dye compound instead of the compound 1 of the comparative example.

Example 2 A blue resin composition was produced in the same manner as in Comparative Example 1, except that the compound N-1 was used as the blue dye compound instead of the compound 1 of the comparative example.

Example 3 A blue resin composition was produced in the same manner as in Comparative Example 1, except that the compound Q-1 was used instead of the compound 1 of the comparative example as the blue dye compound.

In the method of producing a substrate, the photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and pre-bake was performed at 100 ° C for 100 seconds to form a film. The substrate on which the film was formed was entirely irradiated with an exposure amount of 40 mJ/cm ² using an exposure machine. The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-bake was performed at 230 ° C for 20 minutes to obtain a color pattern.

Evaluation of chemical resistance The substrate was fabricated by the above method, and after cutting to 1 cm × 5 cm, two substrates cut to 1 cm × 5 cm were immersed in 16 g of N-methyl-2-pyrrolidone solvent. Afterwards, a Baking was carried out for 40 minutes in a convection oven at 30 °C. The absorbance of the solvent from which the substrate piece was taken out was measured and shown in Table 1 below and FIG.

[Table 1]

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

no

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

Claims (11)

a compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the chemical formula 1, A is represented by the following chemical formula A-1 or A-2, [Chemical A-1] [化A-2] At least one of R1 to R6 is a structure represented by the following chemical formula a, and the others are the same or different from each other, and are independently hydrogen, -R(C=O)R', -RO(C=O)R', - ROR', a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a crosslinkable group; R1 and R2, R3 and R4, and at least one of R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring; R7 to R22 are the same or different from each other, and are independently hydrogen, halogen, hydroxyl, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted alkyl group, R and R'' are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group. Or a substituted or unsubstituted extended aryl group, R' and R''' are the same or different, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl Or a substituted or unsubstituted aryl group, Z ^- is an anionic group, [a] In the chemical formula a, Q is -R101C(=O)R102-, -R103OC(=O)R104-, -R105C(=O)OR106-, -R107OC(=O)OR108-, , , -SOOR115-, -SOR116-, -SR117-, substituted or unsubstituted alkylene, or substituted or unsubstituted alkenyl, X is hydroxy, amine, -OCOOR118, -CONR119R120, or -NR121COOR122, T is a substituted or unsubstituted alkyl group, and R101 to R109, R111, R112 and R114 to R117 are the same or different from each other, and are each independently a directly bonded, substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted extended alkenyl group, R110, R113 and R118 to R122 which are the same or different from each other, independently hydrogen or substituted or unsubstituted The alkyl group, p and q are each an integer of 1 to 4, 2≦p+q≦5, and when p and q are each 2 or more, the structures in the two or more brackets are the same or different, and * is The N-linked portion of Chemical Formula 1, It is a site to which the chemical formula 1 is bonded. The compound according to claim 1, wherein the crosslinkable group is a structure represented by any one of the following Chemical Formulas 2 to 5: [Chemical 2] [Chemical 3] [Chemical 4] [Chemical 5] In the chemical formulas 2 to 5, the R201 to R203 are the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted alkyl group, and R204 to R207 are the same or different from each other, and are each independently a direct bond. , -O-, -N(R208)-, substituted or unsubstituted alkylene, or substituted or unsubstituted cycloalkyl, R208 is hydrogen, or substituted or unsubstituted alkyl r, s, t, and u are 1 or 2, respectively. When the r, s, t, and u are 2, respectively, the structures in the two brackets may be the same or different. The compound of claim 1, wherein the X is bonded to the ortho position relative to the position of the phenyl bond of T with the chemical formula a. The compound according to claim 1, wherein Z ^- is: a sulfonimide comprising a halogenated hydrocarbon group, an anion comprising a sulfonic acid, an anion comprising halogen, boron, aluminum or comprising selected from the group consisting of tungsten, molybdenum and rhenium And one or more elements of the group consisting of phosphorus and anions of oxygen. The compound of claim 1, wherein the chemical formula 1 is selected from the group consisting of: . A coloring material composition comprising the compound according to any one of claims 1 to 5. The coloring material composition according to claim 6, which further comprises at least one of a dye and a pigment. The coloring material composition according to claim 7, wherein the dye is one or more dyes selected from the group consisting of xanthene dyes, cyanine dyes, and azaporphyrin dyes, and the pigment is a blue pigment. Or purple pigment. A resin composition comprising the compound represented by Chemical Formula 1 according to the first aspect of the invention, a binder resin, a polyfunctional monomer, a photoinitiator, an antioxidant, and a solvent. A color filter comprising the resin composition as described in claim 9 of the patent application. A display device comprising the color filter of claim 10 of the patent application.