JP6562470B2 - COMPOUND, COLOR MATERIAL COMPOSITION CONTAINING THE SAME AND RESIN COMPOSITION CONTAINING THE SAME {COMPUND, COLORANT COMPOSION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME} - Google Patents

Description

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

  In recent years, as a light source of a liquid crystal display (LCD), an element such as an LED, an OLED, or a QD is often used instead of the existing CCFL. However, display products have been developed and produced from which color filters have been removed in order to produce thin film displays, flexible displays, and the like, that is, LEDs, OLEDs, QDs, and other self-luminous elements are used as unit pixels.

  However, in the case of a display using LED, OLED, QD, etc. as a unit pixel, it is difficult to increase the area, and even when using LED, OLED, QD, etc., these are included as a light source, and a color filter is included. Much effort has been made to develop displays.

  In order to realize a desired color, a light source and an appropriate color filter are required. Currently, a pigment dispersion method using a pigment as a colorant is generally applied.

  However, in the case of a pigment dispersion, not only does the pigment exist in the form of particles and scatters light, but also the surface area of the pigment increases rapidly due to the finer pigment, resulting in poor dispersion stability and uneven pigment. Particles are generated.

  Therefore, it is recognized that the limit that is difficult to satisfy the high quality requirements such as high brightness, high contrast, and high definition that have recently been demanded is recognized.

  In order to solve such problems and achieve high brightness, high contrast and high resolution, recently, the use of a dye instead of a pigment as a colorant has been studied. Among them, many attempts have been made using triarylmethane dyes as blue colorants. In general, triarylmethane dyes have a high transmittance from 420 to 450 nm and are effective for color characteristics. However, the triarylmethane dye has a lower chemical resistance due to its higher solubility than a pigment and a color filter due to its lower heat resistance than a pigment. Has been used restrictively.

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

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

According to one embodiment of the present specification, a compound represented by the following Chemical Formula 1 is provided.
[Chemical 1]
In the above chemical formula 1,
A is represented by the following chemical formula A-1 or A-2,
[Chemical A-1]
[Chemical A-2]
At least one of R1 to R6 is a structure represented by the following chemical formula a, and the rest are the same or different from each other, and each independently represents 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 above; R3 and R4; And at least one of R5 and R6 can be bonded to each other to form a substituted or unsubstituted ring;
R7 to R22 are the same as or different from each other, and each independently represents hydrogen; a halogen; a hydroxy group; 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 each independently represents a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group;
R ′ and R ′ ″ are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; or a substituted or unsubstituted aryl group. Yes,
Z ⁻ is an anionic group,
[Chemical a]
In the above chemical formula a,
Q is -R101C (= O) R102-; -R103OC (= O) R104-; -R105C (= O) OR106-; -R107OC (= O) OR108-;
-SOOR115-; -SOR116-; -SR117-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; an amine group; -OCOOR118; -CONR119R120; or -NR121COOR122,
T is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112, and R114 to R117 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or An unsubstituted alkenylene group,
R110, R113 and R118 to R122 are the same or different from each other, and each independently represents hydrogen; or a substituted or unsubstituted alkyl group;
p and q are each an integer of 1 to 4,
2 ≦ p + q ≦ 5,
when p and q are each 2 or more, the structures in the brackets of 2 or more are the same or different from each other;
* Is a site linked to N in Formula 1.
Is a site linked to Chemical Formula 1 above.

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

  According to 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 one embodiment of the present specification, a display device including the above-described color filter 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 chemical resistance.

  Further, according to one embodiment of the present specification, the colorant composition containing the compound represented by the chemical formula 1 exhibits higher brightness than the case where an existing pigment is used, and introduces a crosslinkable group. Thus, the fragile chemical resistance of the triarylmethane dye can be improved. Furthermore, it is possible to produce a color filter having excellent chemical resistance by using a colored resin composition using the same.

It is a figure which shows the chemical-resistance evaluation result of Examples 1-3 and the comparative example 1 which concern on one embodiment of this specification.

  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 will be described below, but the present invention is not limited thereto.

  The term “substituted” means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substituted position is the position where the hydrogen atom is substituted, that is, the substituent is substituted. The position is not limited as long as it is possible, 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, substituted or unsubstituted alkyl group, Substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted aryloxy group; substituted or unsubstituted alkylthioxy group; substituted or unsubstituted arylthioxy group; substituted or unsubstituted 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 a substituted or unsubstituted heterocyclic group Substituted with one or more substituents selected from the group, or any It means that do not have even 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 this 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, the amide group may be substituted by hydrogen, a straight chain, branched chain 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 can 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 alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-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, Sohekishiru, 4-methylhexyl, 5-methylhexyl there are 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, Examples include, but are not limited to, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl. It is not a thing.

  In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyl Oxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like are limited thereto. It is not a thing.

In this specification, an amine group consists of —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 carbons that can be selected from the group and are included in the substituent is not particularly limited, but is preferably 1 to 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. Groups, N-phenylnaphthylamine groups, ditolylamine groups, N-phenyltolylamine groups, triphenylamine groups, 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 heteroarylamine group are substituted on N of the amine group.

  In this specification, the alkyl group in the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is as exemplified above for the alkyl group. 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 methyl, ethylsulfoxy group, and propyl. Although there are a sulfoxy group, a butylsulfoxy group and the like, it is not limited thereto.

  In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 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- Examples include, but are not limited to, 1-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, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, and fluorenyl group.

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

  In this specification, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is an example of the aryl group described above. Street. Specifically, the aryloxy group includes 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, etc. Thioxy group, 2-methylphenylthioxy group, 4-tert-butylphenylthioxy group, etc., arylsulfoxy group Is then benzene sulphoxide group, there are such p- toluenesulfonic sulfoxy group, 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 can 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 can be selected from the examples of the aryl group described above.

  In the present specification, a heteroaryl group includes one or more atoms that are not carbon atoms and hetero atoms, and specifically, the hetero atoms are atoms selected from the group consisting of O, N, Se, and S. 1 or more can be included. The number of carbons contained in the substituent is not particularly limited, but is preferably 2 to 30 carbons, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, triazolyl group, acridyl group, pyridazinyl group, Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzoimidazolyl group, benzothiazolyl group, benzothiazolyl group Carbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group Thiadiazolyl group, a benzothiazolyl group, it is such a phenothiazinyl group and dibenzofuranyl group, but is 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 containing two or more heteroaryl groups can 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 can 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 as described above for the heteroaryl group.

  In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic. Can be selected.

  In the present specification, the alkylene group means that the alkyl group has two bonding positions, that is, a divalent group. Except that these are each a divalent group, the above explanation of the alkyl group can be applied.

  In the present specification, the cycloalkylene group means that the cycloalkyl group has two bonding positions, that is, a divalent group. The explanation of the cycloalkyl group described above can be applied except that each of these is a divalent group.

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

  In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. The explanation of the heteroaryl group described above can be applied except that each of them is a divalent group.

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

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

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

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

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

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

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

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

  According to another embodiment of the present specification, R is an ethylene group; or a cyclohexylene group.

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

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

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

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

  According to one embodiment of the present specification, in Chemical Formula 2, R201 is hydrogen; or an alkyl group.

  According to one embodiment of the present specification, in Chemical Formula 2, R201 is hydrogen; or a methyl group.

  According to one embodiment of the present specification, in Formula 2 above, R204 is a direct bond; O; NR208; an alkylene group; or a cycloalkylene group.

  According to one embodiment of the present specification, in Chemical Formula 2, R204 is a direct bond; O; NR208; an ethylene group; or a cyclohexylene group.

  According to one embodiment of the present specification, in Formula 3 above, R205 is a direct bond; or an alkylene group.

  According to one embodiment of the present specification, in Formula 3 above, R205 is a direct bond; or a methylene group.

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

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

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

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

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

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

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

  According to one embodiment of the present specification, in Formula (a), X is bonded to the ortho position with respect to the position where T is bonded to the phenyl group of Formula (a).

According to one embodiment of the present specification, in Chemical Formula 1, Z ⁻ is an anionic group, and the anionic group is not particularly limited. For example, in US Pat. No. 7,939,644, Japanese Unexamined Patent Publication No. 2006-003080, Japanese Unexamined Patent Application Publication No. 2006-001917, Japanese Unexamined Patent Application Publication No. 2005-159926, Japanese Unexamined Patent Application Publication No. 2007-7028897, Japanese Unexamined Patent Application Publication No. 2005-071680, Japanese Unexamined Patent Application Publication No. 2007-7000693, Japanese Unexamined Patent Application Publication No. 2007-700653. Anions described in JP-A-2005-111696 and JP-A-2008-249663 can be applied.

  Specific examples of the anion include trifluoromethanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis (4- Fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tristrifluoromethanesulfonylmethide, phosphate ion, nitrate ion, carbonate ion, sulfite ion, halogen group such as bromo group, fluorine group, iodine group, chlorine group, etc. There is.

Z ⁻ means boron, an anion containing aluminum, an anion containing one or more elements selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and oxygen. In particular, the Z ⁻ may include an anion of tungstophosphoric acid, an anion of tungstosilicate, or an anion of tungsten isopolyacid.

According to one embodiment of the present specification, in Formula 1 above, Z ⁻ represents a sulfonimidic acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; boron; an anion containing aluminum; or tungsten, molybdenum And an anion containing oxygen and at least one element selected from the group consisting of silicon and phosphorus.

  According to one 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, R101 to R104 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted group. A cycloalkylene group;

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

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

  According to one embodiment of the present specification, in the chemical formula a, X is a hydroxy 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 herein, R118 is hydrogen; or a t-butyl group.

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

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

  According to one embodiment of the present specification, in the chemical formula a, T is a t-butyl group.

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

  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 comprising the compound represented by Formula 1 is provided.

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

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

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

  The binder resin may be a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further include a binder generally used in the art.

  The polyfunctional monomer imparting the mechanical strength of the film is at least one of unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. May be.

  Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) ) Acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (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- -Hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri Propylene 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-hexaph Oroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxy It can 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 , P) -chlorostyrene can be selected from the group consisting of, but not limited to.

  Specific examples of the unsaturated ethers can 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 are 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 these.

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

  The monomer imparting 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- From the group consisting of norbornene-2-carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate Although it is preferable to use one or more selected, it is not limited 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 Tetramethacrylate and dipentaerythritol hexa May be one kind or a mixture of two or more selected from the group consisting of methacrylate.

  The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light and triggers crosslinking. For example, a group consisting of an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound It may be one or more selected.

  The acetophenone compounds 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-1 (4-morpholinophenyl) - butan-1-one or 2-methyl-1- [4- (methylthio) phenyl)] - include 2-morpholino-1-one, but is not limited thereto.

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

  The triazine compound is 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 (trichloromethyl) ) -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 and the like Yes, it is not limited to this.

  The oxime compounds are 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), ethanone, -1- (9-ethyl) -6. There are-(2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGI242), N-1919 (Adeka) and the like, but not limited thereto.

  The above solvents are 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, isopropanol 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, It may be at least one selected from the group consisting of ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, It is not limited to only.

  According to an 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 to 30% by weight, the antioxidant content is 0.001 to 20% by weight, the photoinitiator content is 0.1 to 20% by weight, The content of the functional monomer is 0.1% to 50% by weight.

  The said total weight of solid content means the sum total of the total weight of the component except a solvent in a resin composition. The weight percentage standard based on the solid content and the solid content of each component can be measured by a 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 includes a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and a dispersant. And one or more additives selected from the group consisting of leveling agents.

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

  The photocrosslinking sensitizers are 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 A fluorenone compound such as fluorenone; a thioxanthone compound such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; Xanthone compounds such as nthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone and 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; Dicarbonyl compounds such as 7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione and 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6- Dimethoxybenzoyl) -2,4,4-trimethylpentylpho Phosphine oxide compounds such as fin oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2 , 5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone, etc. 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7 -Methoxy-coumarin, 10,10-carboni Such as rubis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolizin-11-one One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthothiazoline can be used. .

  The curing accelerator is used to increase 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-mercapto) Acetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate). It is possible to use one or more of that.

  The adhesion promoter used in the present specification is one of methacryloylsilane coupling agents such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, and methacryloyloxypropyldimethoxysilane. The above can be selected and used, and one or more kinds of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like can be selected and used as the alkyltrimethoxysilane.

  The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301 manufactured by BYK-Chemie. 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., and as a fluorinated surfactant, DIC Dai-Nippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446 F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., It is not limited only to the LES.

  The antioxidant may be one or more selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant and a phosphine antioxidant. Although it is good, it is not limited only to this.

  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-tert-butylphenol), 2,6-g, tert-butylphenol 4,4′-butylidene-bis (3-methyl-6-tert-butylphenol) Nol), 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) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl-β Amine-based secondary antioxidants such as naphthylamine, N, N′-diphenyl-p-phenylenediamine or N, N′-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilaurylthiopropio , Distearyl thiopropionate, mercap Thio secondary antioxidants such as tobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl 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′-Diylbisphosphonoacid acid tetrakis [2,4-bis ( , 1-dimethylethyl) phenyl] ester phosphite secondary antioxidant such as) 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 can be used.

  Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine 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 is not limited thereto and is generally known in the art. It can include those who are.

  The dispersing agent can be used by a method of internally adding the pigment in a form in which the pigment is surface-treated in advance or a method of externally adding the pigment to the pigment. 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, nonionic-based, and amphoteric surfactants. These can be used either individually or in combination of two or more.

  Specifically, the dispersant includes polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylic acid There is at least one selected from the group consisting of a salt, 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 leveling agents. Any of those commonly used in the art can be used, including but not limited to polymeric nitrogen-containing compounds.

  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 applied onto a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

  Although it does not restrict | limit especially as said application | coating method, A spray method, a roll coat method, a spin coat method, etc. can be used, A spin coat method is generally used widely. 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 a mercury vapor arc (arc), a carbon arc, and a Xe arc that emit light having a wavelength of 250 nm to 450 nm, but are not necessarily limited thereto. It is not something.

  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. Used for layer forming photosensitive materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, printed wiring board photosensitive materials, plasma display panel (PDP) photosensitive materials, etc. The application is not particularly limited.

  The resin composition according to one embodiment of the present specification is a color filter having excellent heat resistance, little color change due to heat treatment, high color reproducibility even during the curing process during color filter manufacture, and high brightness and contrast. Can be provided.

  The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (Polycarbonate, PC), etc., and the type 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 in order to improve contrast. Chrome 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 that can be finely processed can be used in consideration of high cost in the process, high reflectivity of chromium, and environmental contamination due to chromium waste liquid.

  In the black matrix according to one embodiment of the present specification, a black pigment or a black dye can be used as a coloring material. For example, carbon black can be used alone, or carbon black and colored pigment can be mixed and used. At this time, the amount of coloring material is relatively increased because of the mixing of colored pigments with insufficient light shielding properties. However, there is an advantage that the strength of the film or the adhesion to the substrate is not lowered.

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

  The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a liquid crystal display (LCD). Any one of a liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT) may be used.

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

[Production Example 1] Production of Compound A
1 mL of AcOH, 0.3 g (0.31 mmol, 1 eq) of Cyclohexane and 1 mL of methylene chloride were added to 0.55 g (0.38 mmol, 1.2 eq) of Naphtharene-1-amine and stirred for about 30 minutes. Thereafter, 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 and extracted with methylene chloride. The organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified by a column (ratio of ethyl acetate: hexane = 1: 9) to obtain 0.74 g of Compound A. (Yield 86%)

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

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

[Production Example 4] Production of Compound D
4- (Naphthalen-1-ylamino) cyclohexan-1-ol (2.41 g, 0.01 mol, 1 eq) was added with 25 mL of methylene chloride, and 1.32 g (0.013 mol, 1.3 eq) of triethylamine was slowly added at room temperature. Added. Then, 2.3 g (0.022 mol, 2.2 eq) of methacrylic acid was added and stirred at room temperature for 16 hours. After completion of the reaction, distilled water was added and extracted with methylene chloride, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified with a column (ratio of ethyl acetate: hexane = 1: 5) to obtain 2.3 g of Compound D in a yield of 74%.

[Production Example 5] Production of Compound E
In a nitrogen atmosphere, 2.92 g (0.01 mol, 1.5 eq) of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid was dissolved in 30 mL of tetrahydrofuran, and then an ice bath. Was installed. Thereafter, 2.54 g (0.017 mol, 2.4 eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added and stirred for about 15 minutes, and then 0.34 g of 4-dimethylaminopyridine (4-dimethylaminopyridine). (0.003 mol, 0.4 eq) was added. 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 slowly added. After stirring for 24 hours, the mixture was extracted with methylene chloride and dried under reduced pressure. Purification by column (ratio of ethyl acetate: hexane = 1: 5) gave 2.3 g of compound E (yield 65%).

[Production Example 6] Production of Compound F
Under a nitrogen atmosphere, 15 g (0.069 mol, 1 eq) of 4,4-difluorobenzophenone and 31.1 g (0.35 mol, 5 eq) of 2-ethylaminoethanol were added, and the temperature was raised at 160 ° C. with stirring. After reacting at 160 ° C. for 48 hours, it was cooled to room temperature. Distilled water was added and extracted with methylene chloride, followed by drying under reduced pressure. Recrystallization and purification with ethyl acetate at room temperature gave Compound F. (20 g, 82% yield)

[Production Example 7] Production of Compound G
In a nitrogen atmosphere, 9.6 g (0.035 mol, 3 eq) of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid was dissolved in 70 mL of tetrahydrofuran, and then an ice bath was installed. did. The reactor was charged with 4.28 g (0.028 mol, 2.4 eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide, stirred for about 15 minutes, and then 4-dimethylaminopyridine (0. 4-dimethylaminopyridine). 56 g (0.005 mol, 0.4 eq) was added. After 15 minutes, 4.10 g (0.011 mol, 1 eq) of Compound F was dissolved in 30 mL of tetrahydrofuran and slowly added. After stirring for 24 hours, the mixture was extracted with methylene chloride and dried under reduced pressure. Purification by column (ratio of ethyl acetate: hexane = 1: 3) gave 4.31 g of compound G in a yield of 43%. When 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid ((3- (3,5-di-tert-butyl-4-hydroxyphenyl) propanoic acid) remains after the column , Washed with NaHCO ₃ (pH 10) solution, extracted with methylene chloride, and dried under reduced pressure.

[Production Example 8] Production of compounds H and I
Except for adding 1.5 eq of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid in Preparation Example 7 above, the same procedure as in Preparation Example 7 was followed by Purification was performed to obtain 2.5 g of Compound H in a yield of 31.7%. 30 mL of methylene chloride was added to 2.5 g (0.004 mol, 1 eq) of Compound H. Slowly 0.53 g (0.0053 mol, 1.3 eq) of triethylamine was added at room temperature. Thereafter, 0.77 g (0.009 mol, 2.2 eq) of methacrylic acid was added and stirred at room temperature for 16 hours. After completion of the reaction, distilled water was added and extracted with methylene chloride, and the organic layer was dried over sodium sulfate and dried under reduced pressure. The obtained product was purified with a column (ratio of ethyl acetate: hexane = 1: 5) to obtain 1.9 g of Compound I in a yield of 68%.

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

[Production Example 10] Production of Compound K
After dissolving 4.31 g (0.005 mol, 1 eq) of Compound G in 40 mL of pyridine, 2.68 g (0.012 mol, 2.5 eq) of di-tert-butyl dicarbonate is slowly added. did. After 15 minutes, 1.20 g (0.01 mol, 2 eq) of 4-dimethylaminopyridine (4-dimethylaminopyridine) was added. After reacting at 60 ° C. for 3 hours, distilled water was added, and the solvent was removed by extraction and decompression with methylene chloride, followed by purification with a column (ratio of methylene chloride: ethyl acetate = 10: 1) to obtain compound K 3 , 87 g, 73% yield.

[Production Example 11] Production of Compound L
Except for using 3,5-di-t-butyl-4-hydroxybenzoic acid instead of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid in Preparation Example 7 above Was produced in the same manner as in Production Example 7 to obtain 5.83 g of Compound L in a yield of 63%.

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

[Production Example 13] Production of compounds N and N-1
A compound N was prepared in the same manner as in Preparation Example 12 except that Compound J was used instead of Compound I in Example 12 and Compound E was used instead of Compound A. This was obtained in a yield of 31%, and 1.1 g of Compound N-1 was obtained in a yield of 93%.

[Production Example 14] Production of compounds O and O-1
Except that Compound G was used in place of Compound I and Compound B was used in place of Compound A in Production Example 12 above, this was produced in the same manner as in Production Example 12, and 0.48 g of Compound O was obtained. Obtained in 26% yield, compound 0-1 was obtained in 0.5 g, 85% yield.

[Production Example 15] Production of compounds P and P-1
Except that Compound G was used instead of Compound I and Compound C was used instead of Compound A in Preparation Example 12, the same procedure as in Preparation Example 12 was carried out to prepare 0.77 g of Compound P. Obtained in a yield of 41%, 0.75 g of compound P-1 was obtained in a yield of 79%.

[Production Example 16] Production of compounds Q and Q-1
Except that Compound G was used in place of Compound I in Example 12 and Compound D was used in place of Compound A, the compound was prepared in the same manner as in Example 12, and 0.82 g of Compound Q was obtained. Obtained in a yield of 39%, 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 in Synthesis Example 1 of Korean Patent Publication No. 2015-0009447. Compound M (0.5 g, 0.0005 mol, 1 eq) is dissolved in 10 g of dimethylformamide. Anion 0.27 g (0.0008 mol, 1.5 eq) was added. After stirring at 55 ° C. for 3 hours, it is cooled to room temperature. The mixture was added dropwise to 1000 g of distilled water with stirring for 1 hour, and then filtered under reduced pressure to obtain 0.48 g of Compound R in a yield of 74%.

[Production Example 18] Production of Compound 1 of Comparative Example
Except that bistrifluoromethanesulfonimide was used as an anion in Example 7 of Korean Published Patent Application No. 2012-0014111, 0.8 g, 80% yield of Compound 1 of Comparative Example was obtained. Obtained at a rate.

[Production and Evaluation of Colored Composition]
Comparative Example 1
A photosensitive blue resin composition was produced with the following composition.

  The compound of the comparative example manufactured by manufacture example 18 as a blue dye compound is 0.85 weight%, binder resin (mass ratio benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: 11: 25). Copolymer) 20.78 wt%, acrylic monomer dipentaerythritol hexaacrylate 20.46 wt%, propylene glycol monomethyl ether acetate 56.57 wt%, photopolymerization initiator (PBG-3142) 0.68 wt% %, A leveling agent (TF-1740) and an adhesion aid (KRM-503) 0.66% by weight were stirred so as to be uniformly mixed to produce a photosensitive blue resin composition.

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

Example 2
A blue resin composition was produced with the same composition as Comparative Example 1 except that Compound N-1 was used instead of Compound 1 of Comparative Example as the blue dye compound.

Example 3
A blue resin composition was produced with the same composition as Comparative Example 1 except that Compound Q-1 was used instead of Compound 1 of Comparative Example as the blue dye compound.

Substrate preparation method The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm), and pre-baked at 100 ° C. for 100 seconds to form a film. The entire surface of the substrate on which the film was formed was irradiated with an exposure 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-baked at 230 ° C. for 20 minutes to obtain a color pattern.

Evaluation of chemical resistance After producing a substrate by the above method and cutting it out to 1 cm × 5 cm, after immersing two pieces of the substrate cut out to 1 cm × 5 cm in 16 g of N-methyl-2-pyrrolidone solvent, convection at 30 ° C. Baking was further performed in an oven for 40 minutes. The absorbance of the solvent from which the substrate piece was taken out was measured and shown in Table 1 and FIG.

  By using the color material composition containing the compound represented by Chemical Formula 1 according to one embodiment of the present specification, it is possible to obtain a color filter coloring composition and a color filter excellent in chemical resistance.

Claims (11)

Represented by the following chemical formula 1 ,
Compound:
[Chemical Formula 1]
In Formula 1,
A is represented by the following chemical formula A-1 or A-2,
[Chemical formula A-1]
[Chemical formula A-2]
At least one of R1 to R6 is a crosslinkable group,
At least one of R1 to R6 is a structure represented by the following chemical formula a, and the rest are the same as or different from each other, and each independently represents 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 can be bonded to each other to form a substituted or unsubstituted ring;
R7 to R22 are the same as or different from each other, and each independently represents hydrogen; a halogen; a hydroxy group; 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 each independently represents a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group;
R ′ and R ′ ″ are the same or different from each other, and each independently represents hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; or a substituted or unsubstituted aryl group. Yes,
Z ⁻ is an anionic group,
[Chemical formula a]
In the chemical formula a,
Q is -R101C (= O) R102-; -R103OC (= O) R104-; -R105C (= O) OR106-; -R107OC (= O) OR108-;
-SOOR115-; -SOR116-; -SR117-; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; an amine group; -OCOOR118; -CONR119R120; or -NR121COOR122,
T is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112, and R114 to R117 are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted alkylene group; a substituted or unsubstituted cycloalkylene group; or a substituted or An unsubstituted alkenylene group,
R110, R113 and R118 to R122 are the same or different from each other, and each independently represents hydrogen; or a substituted or unsubstituted alkyl group;
p and q are each an integer of 1 to 4,
2 ≦ p + q ≦ 5,
when p and q are each 2 or more, the structures in the brackets of 2 or more are the same or different from each other;
* Is a site linked to N in Formula 1.
Is a site linked to Formula 1. The crosslinkable group has a structure represented by any one of the following chemical formulas 2 to 5 .
The compound of claim 1:
[Chemical formula 2]
[Chemical Formula 3]
[Chemical Formula 4]
[Chemical Formula 5]
In Formulas 2 to 5,
R201 to R203 are the same or different from each other, and each independently represents hydrogen; or a substituted or unsubstituted alkyl group;
R204 to R207 are the same as or different from each other, and each independently represents a direct bond; —O—; —N (R208) —; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted cycloalkylene group. And
R208 is hydrogen; or a substituted or unsubstituted alkyl group;
r, s, t and u are each 1 or 2,
When r, s, t and u are each 2, the structures in the two parentheses are the same or different. X is bonded to the ortho position with respect to the position to which the phenyl group of Formula a is bonded .
The compound according to claim 1 or 2 . Z ⁻ represents one or more elements selected from the group consisting of a sulfonimidic acid containing a halogenated hydrocarbon group; an anion containing a sulfonic acid; a halogen; a boron; an anion containing aluminum; or tungsten, molybdenum, silicon, and phosphorus. And an anion containing oxygen ,
The compound according to any one of claims 1 to 3 . Formula 1 are those selected from the following compounds,
The compound of claim 1:
Comprising a compound according to any one of claims 1 to 5 ,
Color material composition. Further comprising at least one of a dye and a pigment ,
The color material composition according to claim 6. The dye is one or more dyes selected from xanthene dyes, cyanine dyes and azaporphyrin dyes,
The pigment is a blue pigment or a violet pigment .
The color material composition according to claim 7. Compound of any one of claims 1 to 5;
Binder resin;
Multifunctional monomers;
Photoinitiator;
An antioxidant; and a solvent ,
Resin composition. The resin composition according to claim 9 is included .
Color filter. The color filter according to claim 10 is included .
Display device.