KR102059235B1 - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

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

Description

Compound, color material composition comprising the same and resin composition containing the same {COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}

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

Recently, as a light source of a liquid crystal display (LCD), in place of the conventional CCFL, LED or OLED devices that emit light by itself, not driving or liquid crystal, have been used. If LED or OLED is used as a light source, it emits red, green, and blue light by itself, and thus does not require a separate color filter.

However, in general, using the light from the LED or OLED light source, it is not easy to adjust or adjust the required color coordinates. In addition, a method for improving color purity, brightness, and contrast ratio in manufacturing a color filter using a pigment material dispersion method using a color material, especially a pigment, which has already been developed, has reached a limit point.

In order to solve this problem and to achieve high brightness, high contrast ratio and high resolution, it has recently been considered to use a dye instead of a pigment as a colorant. Many attempts have been made using triarylmethane dyes as blue colorants. In general, triarylmethane dyes are effective in color characteristics due to high transmittance at 420 to 450 nm, but have been used in color filters due to lower chemical resistance and lower heat resistance than pigments due to higher solubility than pigments.

Korean Laid-Open Patent No. 2001-0009058 Korean Patent Publication No. 2013-0130976

The present specification provides a novel compound, a colorant composition including the same, and a resin composition including the same.

According to an exemplary embodiment of the present specification, a compound represented by the following formula (1) is provided.

[Formula 1]

In Chemical Formula 1,

Y1 is N or CR9, Y2 is N or CR10, Y3 is N or CR11, Y4 is N or CR12, Y5 is N or CR13, Y6 is N or CR14,

At least one of Y1 to Y6 is N,

; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 가교성기이거나, 상기 R1과 R2; R3와 R4; 및 R5와 R6 중 적어도 하나는 서로 결합하여 치환 또는 비치환된 고리를 형성할 수 있으며, At least one of R1 to R6 is a structure represented by the formula (a), the rest are the same as or different from each other, and each independently hydrogen; -R (C = 0) R '; -RO (C = O) R '; -ROR ';

; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a crosslinkable group, or R1 and R2; R3 and R4; And at least one of R5 and R6 may combine with each other to form a substituted or unsubstituted ring,

R9 to R14 and G1 to G8 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,

R and R "are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

R 'and R "' are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; or a substituted or unsubstituted aryl group,

Z ^- is an anionic group,

[Formula a]

In Chemical Formula a,

;

; -SOOR115-; -SOR116-; -SR117-; 치환 또는 비치환된 알킬렌기; 또는 치환 또는 비치환된 알케닐렌기이고,Q is - R101C (= O) R102-; -R 103 OC (= 0) R 104-; -R105C (= 0) OR106-; -R107OC (= 0) OR108-;

;

; -SOOR115-; -SOR116-; -SR117-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,

X is a hydroxy group; 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 as or different from each other, and each independently a direct bond; Substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted alkenylene group,

R110, R113 and R118 to R122 are the same as or different from each other, and each independently 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 two or more parentheses are the same as or different from each other,

* Is a moiety linked to N in Chemical Formula 1.

According to yet an embodiment of the present disclosure, there is provided a polymer compound comprising a monomer released from the compound represented by the formula (1).

According to yet an embodiment of the present disclosure, it provides a color material composition comprising a compound represented by the formula (1).

According to yet an embodiment of the present disclosure, it provides a color material composition comprising the polymer compound.

According to yet an embodiment of the present disclosure, it provides a resin composition comprising the color material composition.

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

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

The compound represented by Formula 1 according to an exemplary embodiment of the present specification has excellent solubility in solvents and excellent chemical resistance.

In addition, according to an exemplary embodiment of the present specification, the color material composition comprising the compound represented by the formula (1) exhibits a higher brightness than the case of using a conventional pigment, the brittle that triaryl methane dye has by introducing a crosslinkable group It is possible to improve the chemical resistance, and also to produce a color filter having excellent chemical resistance by using the colored resin composition using the same.

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

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

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; Substituted or unsubstituted alkyl group; A 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 alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or means having no substituent.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Means a site which is bonded to another substituent or binding moiety.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group is 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.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the ester group may be substituted with oxygen of the ester group having 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 linear or branched chain, carbon number 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

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

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number 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, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.

In the present specification, the N-alkylarylamineamine group means an amine group in which an alkyl group and an aryl group are substituted for 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 for N in 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 for N of the amine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy and butyl sulfoxy groups Etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, carbon number 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-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

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

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.

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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, in the present specification, the heteroaryl group includes one or more atoms other than carbon and hetero atoms, and specifically, the hetero atoms include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. It may include. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, 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, tria Zolyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, 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 including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

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

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

In the present specification, the alkylene group refers to a divalent group having two bonding positions in the alkyl group. The description of the aforementioned alkyl groups can be applied except that they are each divalent.

In the present specification, a cycloalkylene group means a bivalent group having two bonding positions in a cycloalkyl group. The description of the cycloalkyl group described above can be applied except that they are each divalent.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

According to an exemplary embodiment of the present specification, in the general formula 1, one of Y1 to Y6 is N.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-6.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

In Chemical Formulas 1-1 to 1-6,

The definitions of R1 to R6, R9 to R14, G1 to G8, and Z ⁻ are the same as in Chemical Formula 1.

According to an exemplary embodiment of the present specification, in the general formula 1, at least one of R1 to R6 is a structure represented by the general formula a, the remaining are the same as or different from each other, and each independently hydrogen; -ROR '; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkale group; Substituted or unsubstituted aryl group; Or a crosslinkable group.

According to an exemplary embodiment of the present specification, in the general formula 1, at least one of R1 to R6 is a structure represented by the general formula a, the remaining are the same as or different from each other, and each independently hydrogen; -ROR '; An alkyl group unsubstituted or substituted with a hydroxy group; Alkenyl groups; An aryl group unsubstituted or substituted with an alkyl group; Or a crosslinkable group.

According to an exemplary embodiment of the present specification, in the general formula 1, at least one of R1 to R6 is a structure represented by the general formula a, the remaining are the same as or different from each other, and each independently hydrogen; -ROR '; An ethyl group unsubstituted or substituted with a hydroxy group; Vinyl group; A phenyl group unsubstituted or substituted with an alkyl group; Or a crosslinkable group.

According to an exemplary embodiment of the present specification, in the general formula 1, at least one of R1 to R6 is a structure represented by the general formula a, the remaining are the same as or different from each other, and each independently hydrogen; -ROR '; An ethyl group unsubstituted or substituted with a hydroxy group; Vinyl group; A phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group and an ethyl group; Or a crosslinkable group.

According to yet an embodiment of the present disclosure, wherein R is a substituted or unsubstituted alkylene group.

According to yet an embodiment of the present disclosure, wherein R is an alkylene group.

According to yet an embodiment of the present disclosure, wherein R is an ethylene group.

According to yet an embodiment of the present disclosure, wherein R is a substituted or unsubstituted alkyl group.

According to yet an embodiment of the present disclosure, wherein R is an alkyl device.

According to yet an embodiment of the present disclosure, wherein R is a vinyl group.

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

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,

R201 to R203 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

R204 to R207 are the same as or different from each other, and each independently, a direct bond; O; NR208; 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 an exemplary embodiment of the present specification, in the general formula 2, R201 is hydrogen; Or an alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 2, R201 is hydrogen; Or methyl group.

According to an exemplary embodiment of the present specification, in the general formula 2, R204 is a direct bond; O; NR208; Alkylene group; Or a cycloalkylene group.

According to an exemplary embodiment of the present specification, in the general formula 2, R204 is a direct bond; O; NR208; Ethylene group; Or a cyclohexylene group.

According to an exemplary embodiment of the present specification, in the general formula 3, R205 is a direct bond; Or an alkylene group.

According to an exemplary embodiment of the present specification, in the general formula 3, R205 is a direct bond; Or methylene group.

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

According to an exemplary embodiment of the present specification, in the general formula 4, R206 is a direct bond; Or an alkylene group.

According to an exemplary embodiment of the present specification, in the general formula 4, R206 is a direct bond; Or methylene group.

According to an exemplary embodiment of the present specification, in the general formula 5, R203 is hydrogen; It is a C1-C4 alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 5, R207 is a direct bond; Or an alkylene group.

According to an exemplary embodiment of the present specification, in the general formula 5, R207 is a direct bond; Or methylene group.

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

According to an exemplary embodiment of the present specification, in the formula a, X is bonded to the ortho position with respect to the bonded position of the phenyl group of the formula (a).

According to an exemplary embodiment of the present specification, in Formula 1 Z ⁻ is an anionic group, the anionic group is not particularly limited, 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. 2007-7028897, Japanese Patent Laid-Open No. 2005-071680, Korean Patent Application Laid-Open No. 2007-7000693, Japanese Patent Laid-Open No. 2005-111696, Japanese Laid-Open Patent 2008- The anions described in 249663 can be applied.

Specific examples of the anion include trifluoromethanesulfonate anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion and tetra Kis (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 and the like.

In addition, Z ^- is boron; Anions including aluminum; An anion comprising oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus. In particular, Z ⁻ may include an anion of tungstophosphoric acid, an anion of tungstosilicic acid, or an anion of tungsten-based isopoly acid.

According to an exemplary embodiment of the present specification, in the general formula 1, Z ^- sulfonimide acid containing a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion comprising oxygen and one or more elements selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus.

According to an exemplary embodiment of the present specification, in the general formula a, Q is - R101C (= O) R102-; Or -R103OC (= 0) R104-.

According to yet an embodiment of the present disclosure, the R101 to R104 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted cycloalkylene group.

According to yet an embodiment of the present disclosure, the R101 to R104 are the same as or different from each other, and each independently a direct bond; Alkylene group; Or a cycloalkylene group.

According to yet an embodiment of the present disclosure, the R101 to R104 are the same as or different from each other, and each independently a direct bond; Methylene group; Ethylene group; Or a cyclohexylene group.

According to an exemplary embodiment of the present specification, in the general formula a, X is a hydroxy group; -OCOOR118.

According to yet an embodiment of the present disclosure, R118 is hydrogen; Or a substituted or unsubstituted alkyl group.

According to yet an embodiment of the present disclosure, R118 is hydrogen; Or an alkyl group.

According to yet an embodiment of the present disclosure, R118 is hydrogen; Or t-butyl group.

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

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

According to an exemplary embodiment of the present specification, in the general formula a, T is a t-butyl group.

According to an exemplary 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 may be prepared by referring to the preparation examples described later.

According to an exemplary embodiment of the present specification, it provides a color material composition comprising a compound represented by the formula (1).

According to one embodiment of the present specification, a polymer compound including a monomer derived from the compound represented by Chemical Formula 1 is provided.

In the present specification, "monomer" means a structure in which the compound is included in the form of two or more in the polymer by the polymerization reaction.

According to one embodiment of the present specification, it provides a color material composition comprising the polymer compound.

The color material composition may further include at least one of dyes and pigments in addition to the compound or the polymer compound represented by the formula (1). For example, the colorant composition may include only the compound represented by Chemical Formula 1, but may include the compound represented by Chemical Formula 1 and one or more dyes, or may include the compound represented by Chemical Formula 1 and one or more pigments It may also include a compound represented by the formula (1), at least one dye and at least one pigment.

In one embodiment of the present specification, a resin composition containing the color material composition is provided.

In one embodiment of the present specification, the resin composition is a binder resin; Polyfunctional monomers; Antioxidants; Photoinitiators; And a solvent may be further included.

The binder resin is not particularly limited as long as it can exhibit physical properties such as strength, developability, and the like of the film made of the resin composition.

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

Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene 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-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.

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

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

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.

Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.

The monomer which imparts the 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, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.

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

The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.

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

The acetophenone-based compound is 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-hydroxycyclohexylphenylketone, 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] -2-morpholinopropan-1-one, and the like.

As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 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'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.

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-triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-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-triazine-6 -Yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloro Methyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto. .

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.

The solvent is 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 Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.

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

The total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition. The weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.

According to one embodiment of the present specification, the resin composition is one or more selected from the group consisting of a photocrosslinking agent, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and a leveling agent. Further additives.

According to an exemplary 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 solids in the resin composition.

The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.

The curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.

As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's BYK-077, BYK-085, 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, and the like. (DaiNippon 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. may be used, but is not limited thereto.

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid thermal 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-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' Phosphite-based secondary antioxidants such as -diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.

The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.

The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.

According to one embodiment of the present specification, a photosensitive material manufactured using the resin composition is provided.

In more detail, the resin composition of this specification is apply | coated on a base material by a suitable method, and forms the photosensitive material of a thin film or a pattern form.

Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, and spin coating method is generally used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.

As a light source for curing the resin composition according to the present specification, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc., which emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.

The resin composition according to the present disclosure may be a pigment dispersion photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, It can be used for photosensitive material for forming overcoat layer, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed circuit board, photosensitive material for plasma display panel (PDP), and the like. There is no special place.

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

The color filter may be manufactured using a resin composition including the color material composition. The resin composition may be applied onto a substrate to form a coating film, and the color filter may be formed by exposing, developing, and curing the coating film.

The resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having a high color reproducibility and a high luminance and contrast ratio by the curing process during the manufacture of the color filter. have.

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

The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.

According to another exemplary embodiment, the color filter may further include an overcoat layer.

A black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix according to one embodiment of the present specification may use black pigment or black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.

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

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a thin film transistor. The liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, the present specification will be described in detail with reference to Examples. The following examples are provided to illustrate the present specification, and the scope of the present specification includes the ranges described in the following claims, their substitutions and changes, and is not limited to the examples.

Preparation Example 1 Preparation of Compound A

To 2 g (1 eq) of 8-aminoquinoline, 5 ml of acetic acid, 5 ml of methylene chloride, and 1.64 g (1.2 eq) of cyclohexanone were added and stirred for 30 minutes. Add 3.5 g of NaBH (OAC) ₃ slowly. After reacting for 16 hours at room temperature, washed several times with distilled water and then extracted with MC. After drying under reduced pressure, the residue was purified by a column (ethyl acetate: hexane = 1:10 ratio) to obtain 2.48 g of an off-white oil compound A (yield 85.4%).

Preparation Example 2 Preparation of Compound B

Add 50 mL of dimethylformamide (DMF) to 3.75 g (0.026 mol, 1 eq) of 8-aminoquinoline, slowly add 17.97 g (0.13 mol, 5 eq) at room temperature and stir for 30 minutes. Then 7.86 g (0.065 mol, 2.5 eq) of aryl bromide was added and stirred at room temperature for 4 hours. Reaction completion water and distilled water were added, extraction was performed with ether, the organic layer was dried over sodium sulfate, and dried under reduced pressure. The obtained product was purified by a column (ethyl acetate: hexane = 1: 100 to 1: 80 ratio) to obtain a compound B 1.2g, 27% yield.

Preparation Example 3 Preparation of Compound C

To 3.03 g (0.021 mol, 1 eq) of 8-aminoquinoline, 30 mL of methylene chloride is added, and 2.73 g (0.027 mol, 1.3 eq) of triethylamine are added slowly at room temperature. Then 4.8 g (0.056 mol, 2.7 eq) of methacrylic acid is added and stirred at room temperature for 16 hours.

After the reaction was completed, distilled water was added, the mixture was extracted with methylene chloride, the organic layer was dried over sodium sulfate, and dried under reduced pressure. The obtained product was purified by column (ethyl acetate: hexane = 1: 10 to 1: 15 ratio) to obtain a compound C 0.5g, 11% yield.

Preparation Example 4 Preparation of Compound D

To 2 g (1 eq) of 5-amino-isoquinoline, 5 ml of acetic acid, 5 ml of methylene chloride, and 1.64 g (1.2 eq) of cyclohexanone were added and stirred for 30 minutes. Add 3.5 g of NaBH (OAC) ₃ slowly. After reacting for 16 hours at room temperature, washed several times with distilled water and then extracted with MC. After drying under reduced pressure, the residue was purified by a column (ethyl acetate: hexane = 1:10 ratio) to obtain a off-white oil compound D of 2.25 g, yielding 71.7%.

Preparation Example 5 Preparation of Compound E

15 g (0.069 mol, 1 eq) of 4,4-difluorobenzophenone and 31.1 g (0.35 mol, 5 eq) of 2-ethylamino ethanol were added under a nitrogen atmosphere, and the temperature was increased while stirring at 160 ° C. After reaction at 160 ° C. for 48 hours, the reaction mixture was cooled to room temperature. Distilled water was added thereto, followed by extraction with methylene chloride and dried under reduced pressure. Recrystallized and purified with ethyl acetate at room temperature to give a compound E 20g, 82% yield.

Preparation Example 6 Preparation of Compound F

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, followed by installing an ice bath. . 4.28g (0.028mol, 2.4eq) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide was added to the reactor and stirred for about 15 minutes, followed by 0.56g (0.005mol) of 4-dimethylaminopyridine. , 0.4eq) was added. After 15 minutes, 4.10 g (0.011 mol, 1 eq) of Compound E was dissolved in 30 mL of tetrahydrofuran and added slowly. After stirring for 24 hours, the mixture was extracted with methylene chloride and dried under reduced pressure. The resultant was purified by column (ethyl acetate: hexane = 1: 3 ratio) to obtain 4.31 g of compound F, yield 43%. 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid ((3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid) remaining after the column The mixture was washed with NaHCO ₃ (pH 10) solution, extracted with methylene chloride, and dried under reduced pressure.

Preparation Example 7 Compounds G and H

After the preparation in the same manner as in the compound F, the mixture was purified by a column (ethyl acetate: hexane = 1: 3 ratio) to give 2.5 g of a compound G and a yield of 31.7%. To 2.5 g (0.004 mol, 1 eq) of compound G is added 30 mL of methylene chloride. Slowly add 0.53 g (0.0053 mol, 1.3 eq) of triethylamine at room temperature. Thereafter, 0.77 g (0.009 mol, 2.2 eq) of methacrylic acid is added and stirred at room temperature for 16 hours. After the reaction was completed, distilled water was added, the mixture was 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 (ethyl acetate: hexane = 1: 5 ratio) to obtain a compound H 1.9g, 68% yield.

Preparation Example 8 Preparation of Compound I

4.31 g (0.005 mol, 1 eq) of Compound F was dissolved in 40 mL of pyridine, and then 2.68 g (0.012 mol, 2.5 eq) of Di-tert-butyl dicarbonate was slowly added thereto. After 15 minutes, 1.20 g (0.01 mol, 2 eq) of 4-dimethylaminopyridine was added thereto. After the reaction at 60 ° C. for 3 hours, distilled water was added, extraction was performed with methylene chloride, and the solvent was removed under reduced pressure, and then purified by column (methylene chloride: ethyl acetate = 10: 1 ratio) to obtain a compound I with a yield of 3.87 g and 73%.

Preparation Example 9 Preparation of Compounds J and J-1

1.5 g (0.002 mol, 1 eq) of Compound H was dissolved in chloroform. 0.44 g (0.003 mol, 1.3 eq) of phosphoryl chloride was added in a nitrogen atmosphere, followed by stirring for about 30 minutes, and 0.59 g (0.0026 mol, 1.3 eq) of Compound A was slowly added to dissolve in chloroform. After the reaction at 60 ° C. for 2 hours, the reaction was terminated with distilled water and extracted with methylene chloride. The solvent was removed under reduced pressure, and the precursor was removed by columning at a ratio of methylene chloride: ethyl acetate = 1: 1, followed by purification by changing the composition to methylene chloride: methanol: ethyl acetate = 6: 1: 1 to yield a compound J 1.0g, 49% yield. Got it. Thereafter, 1.0 g (0.001 mol, 1 eq) of compound J was dissolved in 30 mL of methanol, and then 0.46 g (0.0016 mol, 1.5 eq) of bistrifluoromethanesulfonimide (BMI) was added thereto, followed by stirring at room temperature. Distilled water was added to precipitate the blue powder was filtered to obtain a compound J-1 1.1g, 87% yield.

Preparation Example 10 Preparation of Compounds K and K-1

Compound F was prepared in the same manner as in Example 9, except that Compound F was used instead of Compound H, and Compound B was used instead of Compound A, and a compound K was obtained in a yield of 0.52 g, 28%, and compound K-1 0.56 g, Obtained in 87% yield.

Preparation Example 11 Preparation of Compounds L and L-1

Compound F was prepared in the same manner as in Example 9, except that Compound F was used instead of Compound H and Compound C was used instead of Compound A, and the compound L 0.8g was obtained in a yield of 42%, and the compound L-1 0.82g, Obtained in 83% yield.

Preparation Example 12 Preparation of Compounds M and M-1

Compound I was prepared in the same manner as in Example 9, except that Compound I was used instead of Compound H and Compound C was used instead of Compound A, thereby obtaining Compound M 0.61 g, 33% yield, and Compound M-1 0.62 g, Obtained in a yield of 85%.

Preparation Example 13 Preparation of Compounds N and N-1

Compound F was prepared in the same manner as in Example 9, except that Compound F was used instead of Compound H and Compound D instead of Compound A was obtained in a yield of 0.45 g, 22%, and Compound N-1 0.50 g, Obtained in a yield of 88%.

Preparation Example 14 Preparation of Compound O

The anion was prepared in the same manner as in Synthesis example 1 of Korean Laid-Open Patent 2015-0009447. 0.5 g (0.0005 mol, 1 eq) of compound J-1 is dissolved in 10 g of dimethylformamide. 0.27 g (0.0008 mol, 1.5 eq) of anion is added. Stir at 55 ° C. for 3 hours and then cool 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 0.40 g of Compound O in a yield of 69%.

Preparation Example 15 Preparation of Comparative Example Compound 1

Except for using bistrifluoromethanesulfonimide as an anion in Example 7 of Korean Patent Publication No. 2012-0014111, Comparative Example 1 was obtained in a yield of 0.8 g and 80%.

[Production and Evaluation of Coloring Composition]

Comparative Example 1

The photosensitive blue resin composition was manufactured with the following composition.

0.85% by weight of the comparative compound prepared in Preparation Example 15 as a blue dye compound, a binder resin (mass ratio benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: 11: 25 Coalescence) 20.78% by weight, 20.46% by weight of dipentaerythritol hexaacrylate, an acrylic monomer, 56.57% by weight of propylene glycol monomethyl ether acetate, 0.68% by weight of photopolymerization initiator (PBG-3142), leveling agent (TF-1740) and adhesion 0.66 wt% of the preparation (KRM-503) was stirred to uniformly mix to prepare a photosensitive blue resin composition.

Example 1

A blue resin composition was prepared in the same composition as in Comparative Example 1, except that Compound J-1 was used instead of Comparative Example Compound 1 as a blue dye compound.

Example 2

A blue resin composition was manufactured in the same composition as in Comparative Example 1, except that Compound N-1 was used instead of Comparative Example Compound 1 as the blue dye compound.

PCB manufacturing method

The photosensitive resin composition was spincoated on glass (5 × 5 cm) and pre-bake at 100 ° C. for 100 seconds to form a film. The exposure amount of 40 mJ / cm ² was irradiated to the front surface of the board | substrate which formed the film using the exposure machine.

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

Chemical resistance evaluation

The substrate was prepared by the above method, cut into 1 × 5 cm, and two pieces of the substrate cut into 1 × 5 cm were immersed in 16 g of N-methyl-2-pyrrolidone solvent, followed by additional baking for 40 minutes in an 80 ° C. convection oven. . The absorbance of the solvent from which the substrate pieces were taken out was measured and shown in Table 1 below.

division Absorbance % Improvement compared to the comparative example Comparative Example 1 0.761 - Example 1 0.054 92.95% Example 2 0.072 90.61%

By using the color material composition containing the compound represented by General formula (1) which concerns on one Embodiment of this specification from the above, it becomes possible to obtain the coloring composition for color filters and color filter excellent in chemical resistance.

Claims (10)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
Y1 is N or CR9, Y2 is N or CR10, Y3 is N or CR11, Y4 is N or CR12, Y5 is N or CR13, Y6 is N or CR14,
At least one of Y1 to Y6 is N,
At least one of R1 to R6 is a structure represented by the formula (a), the rest are the same as or different from each other, and each independently hydrogen; -R (C = 0) R '; -RO (C = O) R '; -ROR ';

; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a crosslinkable group, or R1 and R2; R3 and R4; And at least one of R5 and R6 may combine with each other to form a substituted or unsubstituted ring,
At least one of R1 to R6 is -ROR '; Substituted or unsubstituted alkenyl group; Or a crosslinkable group,
R9 to R14 and G1 to G8 are the same as or different from each other, and each independently hydrogen; Halogen group; Hydroxyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,
R and R "are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,
R 'and R "' are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkenyl group; or a substituted or unsubstituted aryl group,
Z ^- is an anionic group,
[Formula a]

In Chemical Formula a,
Q is - R101C (= O) R102-; -R 103 OC (= 0) R 104-; -R105C (= 0) OR106-; -R107OC (= 0) OR108-;

;

; -SOOR115-; -SOR116-; -SR117-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; 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 as or different from each other, and each independently a direct bond; Substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Or a substituted or unsubstituted alkenylene group,
R110, R113 and R118 to R122 are the same as or different from each other, and each independently 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 two or more parentheses are the same as or different from each other,
* Is a moiety linked to N in Chemical Formula 1. The compound according to claim 1, wherein the crosslinkable group has a structure represented by any one of Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,
R201 to R203 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
R204 to R207 are the same as or different from each other, and each independently, a direct bond; O; NR208; 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. The compound of claim 1, wherein X is bonded at the ortho position relative to the bonded position of the phenyl group of formula a. The compound of claim 1, wherein Z ⁻ is sulfonimide acid including a halogenated hydrocarbon group; Anions including sulfonic acids; halogen; boron; Anions including aluminum; Or an anion comprising oxygen and one or more elements selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus. The compound of claim 1, wherein Formula 1 is selected from the following compounds:

A color material composition comprising the compound according to any one of claims 1 to 5. The color material composition according to claim 6, further comprising at least one of dyes and pigments. The method according to claim 7, wherein the dye is at least one dye selected from xanthene dyes, cyanine dyes and azapopyrine dyes,
The pigment is a color material composition is a blue pigment or a purple pigment. A compound represented by formula 1 according to claim 1; Binder resins; Polyfunctional monomers; Photoinitiators; Antioxidants; And a solvent. The color filter containing the resin composition of Claim 9.