KR102016619B1

KR102016619B1 - Novel compound, colorant composition comprising the same and resin composition comprising the same

Info

Publication number: KR102016619B1
Application number: KR1020160002608A
Authority: KR
Inventors: 박종호; 이다미
Original assignee: 주식회사 엘지화학
Priority date: 2016-01-08
Filing date: 2016-01-08
Publication date: 2019-08-30
Also published as: KR20170083307A

Abstract

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

Description

Novel compounds, colorant compositions comprising the same and resin compositions comprising the same {NOVEL COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING 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 overcome these problems and satisfy the requirements, the development of new color materials is required.

Korean Laid-Open Patent No. 2001-0009058

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,

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 ';

; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, R 1 and R 2; R3 and R4; And at least one of R5 and R6 may combine with each other to form a substituted or unsubstituted ring,

R7 to R14 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; or a substituted or unsubstituted aryl group,

m and n are each an integer of 1 to 4,

when m and n are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,

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.

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 resin composition comprising the color material composition.

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

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

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

According to the exemplary embodiment of the present specification, the color material composition including the compound represented by Chemical Formula 1 is excellent in heat resistance and light resistance, and may be used as a coloring material as well as a small amount, and an absorption and transmission spectrum suitable for a desired light source It is possible to obtain higher color reproducibility, higher luminance, higher contrast ratio, and the like.

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 silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide 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 two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

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, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

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

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.

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

When the fluorenyl group is substituted,

,

,

And

And so on. However, the present invention 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 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 2 to 7.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

[Formula 7]

In Chemical Formulas 2 to 7,

The definitions of R 1 to R 14, m, n and X ⁻ are the same as in the general 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; -RO (C = O) R ';

; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

; An alkyl group unsubstituted or substituted with a hydroxy group; Cycloalkyl group; Or an aryl group unsubstituted or substituted with an alkyl group.

; An ethyl group unsubstituted or substituted with a hydroxy group; n-propyl group; n-butyl group; Cyclohexyl group; Or a phenyl group unsubstituted or substituted with one or more selected from the group consisting of a methyl group and an ethyl group.

According to yet an embodiment of the present disclosure, wherein R and R "are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group.

According to yet an embodiment of the present disclosure, wherein R and R "are the same as or different from each other, and each independently an alkylene group; or an arylene group.

According to yet an embodiment of the present disclosure, wherein R and R "are the same as or different from each other, and each independently an ethylene group; or a phenylene group.

According to another exemplary embodiment of the present specification, R 'and R "' are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

According to another exemplary embodiment of the present specification, R 'and R "' are the same as or different from each other, and each independently hydrogen; an alkyl group; or an aryl group.

According to another exemplary embodiment of the present specification, R 'and R "' are the same as or different from each other, and each independently hydrogen; t-butyl group; or phenyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 and R2; R3 and R4; And at least one of R5 and R6 combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 and R2 may be bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 and R2 may be combined with each other to form a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 and R2 may be bonded to each other to form a ring of the following structure, but is not limited thereto.

The structure may include additional substituents.

According to an exemplary embodiment of the present specification, in the general formula 1, R3 and R4 may be bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R3 and R4 may be combined with each other to form a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R3 and R4 may be bonded to each other to form a ring of the following structure, but is not limited thereto.

The structure may include additional substituents.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 and R6 may be bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 and R6 may be combined with each other to form a substituted or unsubstituted hetero ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R5 and R6 may be bonded to each other to form a ring of the following structure, but is not limited thereto.

The structure may include additional substituents.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 to R14 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 to R14 are the same as or different from each other, and each independently hydrogen; Or an alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 1, R7 to R14 are the same as or different from each other, and each independently hydrogen; Or methyl group.

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 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; n-propylene 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; Or NR121COOR122.

According to yet an embodiment of the present disclosure, R118, R121 and R122 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to yet an embodiment of the present disclosure, R118, R121 and R122 are the same as or different from each other, and each independently hydrogen; Or an alkyl group.

According to yet an embodiment of the present disclosure, R118, R121 and R122 are the same as or different from each other, and each independently 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 is selected from the following compounds.

In the compound, the definition of Z ⁻ is the same as that of Chemical Formula 1.

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).

The colorant composition may further include at least one of dyes and pigments in addition to the compound represented by Chemical 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.

According to an exemplary embodiment of the present specification, when Chemical Formula 1 includes a structure such as Chemical Formula a, it is not necessary to add an additional antioxidant known in the art, and the compound represented by Chemical Formula 1 may be It can be used for the use of colorant compositions and / or antioxidants.

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; 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 60% by weight, the content of the binder resin is 1% by weight to 60% by weight and The content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the multifunctional monomer is 0.1 wt% to 50 wt%.

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, Generally, a spin coating method is 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. 3.5 g of NaBH (OAc) ₃ were added slowly. After reaction at room temperature for 16 hours, the mixture was washed with distilled water several times and extracted with methylene chloride. After drying under reduced pressure, the residue was purified by a column (ethyl acetate: hexane = 1: 10) to obtain 2.48 g of an off-white oil (yield: 85.4%).

Preparation Example 2 Preparation of Compound B

Except for using 8-aminoquinoline instead of 5-aminoisoquinoline in Preparation Example 1 was prepared in the same manner. (Compound B 2.25g yield: 71.7%)

Preparation Example 3 Preparation of Compound C

4,4-Difluorobenzophenone (15 g, 1 eq.) And 2-ethylaminoethanol (31.1 g, 5 eq.) Were added to the flask under nitrogen atmosphere, and the mixture was heated to reflux at 160 ° C. for 48 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. Ethyl acetate was added to the obtained product, the mixture was stirred at room temperature for 2 hours, and then filtered to obtain 21 g of an off-white compound C. (Yield 86%)

Preparation Example 4 Preparation of Compound D

Dissolve 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid (9.6 g, 3 eq) in 70 mL of tetrahydrofuran under a nitrogen atmosphere, and then install an ice bath (ice bath) at 0 ° C. Cooled to. Then 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (5.30g, 2.4eq) was added thereto, followed by stirring for about 15 minutes, and 4-dimethylaminopyridine (0.56g, 0.4eq) was added thereto. After 15 minutes, 4.10 g (1 eq) of Compound C 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. Purification by column (ethyl acetate: hexane = 1: 3) afforded 4.51 g of compound C (yield 44.7%). If 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid remained after the column, the mixture was washed with NaHCO3 (pH10-11) solution, extracted with methylene chloride, and dried under reduced pressure.

Preparation Example 5 Preparation of Compound E

3- (3,5-di-t-butyl-4-hydroxyphenyl instead of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid (3eq.) In Preparation Example 4 ) Was prepared identically except using propionic acid (1.5 eq.). (Compound E 2.9g yield 40.8%)

Preparation Example 6 Preparation of Compound F

Compound D (2.0 g, 1.0 eq) was dissolved in 10 mL of pyridine, and di-t-butyl-dicarbonate (1.49 g, 3.0 eq) was slowly added. After 15 minutes, 4-dimethylaminopyridine (0.6 g, 2.0 eq) was added and stirred at 60 ° C. for 3 hours. After the reaction was completed, distilled water was added and the mixture was extracted with methylene chloride. The separated organic layer was dried over sodium sulfate and then dried under reduced pressure. The obtained product was purified by column (ethyl acetate: hexane = 1: 3) to obtain 2.09 g of an off-white oil compound F. (Yield 85%)

Preparation Example 7 Preparation of Compound G

Except using 3,5-di-t-butyl-4-hydroxybenzoic acid instead of 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid in Preparation Example 4 And prepared in the same manner. (Compound G 5.75 g yield 62%)

Preparation Example 8 Preparation of Compound H

Except for using the compound G instead of compound D in Preparation Example 6, the same was prepared. (Compound H 2g Yield 80%)

Preparation Example 9 Preparation of Compound I-1

1.0 g (1 eq) of Compound D was dissolved in chloroform. In a nitrogen atmosphere, 0.52 g of phosphoryl chloride (3.0eq) was added thereto, stirred for about 30 minutes, and 0.38 g (1.5eq) of Compound A was slowly added to dissolve in chloroform. After reaction at 60 ° C. for 16 hours, the reaction was terminated with distilled water and extracted with methylene chloride. The solvent was removed under reduced pressure, and then the methylene chloride: ethyl acetate = 1: 1 column was used to remove the precursors. Purification by column (methylene chloride: methanol: ethyl acetate = 6: 1: 2) to give a blue powder of compound I 0.13 (yield 10.2%)

After dissolving 0.13 g of Compound I in methanol, bistrifluoromethanesulfonimide (BMI) 1.5eq. After adding (0.05 g) and stirring at room temperature, distilled water was added and the blue powder precipitated was filtered to obtain 0.12 g of a blue powder of compound I-1. (79% yield)

Preparation Example 10 Preparation of Compound J-1

0.7 g (1 eq) of Compound F was dissolved in chloroform. 0.15 g (1.5 eq.) Of phosphoryl chloride was added under a nitrogen atmosphere, and stirred for 2 hours. Then, 1.4 g (1.3 eq.) Of Compound A was dissolved in chloroform and slowly added thereto. 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 methylene chloride was removed. The column was removed in an ethyl acetate = 1: 1 ratio to remove the precursor, and the composition was purified by changing the composition to methylene chloride: methanol: ethyl acetate = 6: 1: 2 to obtain 0.1 g of Compound J. (12% yield)

After dissolving 0.1 g of compound J in methanol, bistrifluoromethanesulfonimide (BMI) 1.5eq. (0.03 g) was added thereto, followed by stirring at room temperature. Distilled water was added thereto, and the precipitated blue powder was filtered to obtain 0.09 g of compound J-1. (Yield 75.9%)

Preparation Example 11 Preparation of Compound K-1

Except for using the compound G instead of compound D in Preparation Example 9 and was prepared in the same manner. (Compound K-1 0.85g yield 86.4%)

Preparation Example 12 Preparation of Compound L-1

Except for using the compound H instead of compound D in Preparation Example 9 was prepared in the same manner. (Compound L-1 0.09 g yield 83%)

Preparation Example 13 Preparation of Compound M-1

Except for using the compound B instead of compound A in Preparation Example 9 it was prepared in the same manner. (Compound M-1 0.15g Yield 74%)

Preparation Example 14 Preparation of Compound N-1

Except for using the compound B instead of compound A in Preparation Example 11 was prepared in the same manner. (Compound N-1 0.15 yield 74%)

Preparation Example 15 Preparation of Compound O-1

Except for using the compound E instead of compound D in Preparation Example 9 and was prepared in the same manner. (Compound O-1 0.25g Yield 81%)

Preparation Example 16 Preparation of Compound P

Compound X was prepared by the method of Synthesis Example 1 of Korean Patent Publication No. 10-2015-0009447. Thereafter, 0.20 g (1 eq.) Of Compound I was dissolved in 10 g of dimethylformamide, and 0.09 g (1.5 eq.) Of Compound X was added. After stirring at 55 ° C. for 3 hours, the mixture was cooled to room temperature and added dropwise while stirring to 1000 g of distilled water for 1 hour, followed by filtration under reduced pressure to obtain compound P 0.22 g. (Yield 88%)

Preparation Example 17 Preparation of Compound Q-1

1) Preparation of Compound Y

3.0 g (1 eq) of compound C was dissolved in 15 mL of methylene chloride. 2.13 g (2.5 eq) of triethylamine was added little by little after making it to 0 degreeC using an ice bath. After about 20 minutes, 2.73 g (2.3 eq) of benzoyl chloride was slowly added. The reaction was carried out at room temperature for 5 hours. After the reaction was terminated with distilled water, the reaction mixture was purified by methylene chloride: ethyl acetate = 10: 1 to obtain an off-white oil compound Y. (4.5g, yield 95%)

2) Preparation of Compound Q-1

Except for using the compound Y instead of compound D in Preparation Example 9 and was prepared in the same manner. (Compound Q-1 0.27g Yield 74%)

Preparation Example 18 Preparation of Compound R-1

1) Preparation of Compound Z

3.64 g (3eq) of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid (3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid under a nitrogen atmosphere Was dissolved in 30 mL of tetrahydrofuran and an ice bath was installed in the reactor 2.39 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1-ethyl-3- 3-dimethylaminopropyl carbodiimide) (3eq) was added and stirred for about 15 minutes, followed by 0.3 g (0.6eq) of 4-dimethylaminopyridine, and 15 g of 4,4'-Bis (methylamino) benzophenone was added to tetra It was dissolved in 10 mL of hydrofuran and slowly added, stirred for 24 hours, extracted with methylene chloride and dried under reduced pressure, and purified by column (ethyl acetate: hexane = 1: 3) to obtain 1.01 g of compound Z (yield 32.0%). NaHCO, after 3- (3,5-di-t-butyl-4-hydroxyphenyl) propionic acid (3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid remains _It was washed with ₃ (pH10-11) solution, extracted with methylene chloride, and dried under reduced pressure.

2) Preparation of Compound R-1

Except for using the compound Z instead of compound D in Preparation Example 9 and was prepared in the same manner. (Compound R-1 0.18g Yield 79.6%)

Preparation Example 19 Preparation of Comparative Compound 1

Except for using bistrifluoromethanesulfonimide as an anion in Example 7 of Korean Patent Publication No. 10-2012-0014111, 0.8g of Comparative Example Compound 1 was obtained. (Yield 80%)

Preparation and Evaluation of Resin Compositions

Comparative Example 1

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

0.04 part by weight of Comparative Example Compound 1 prepared in Preparation Example 19 as a blue dye compound and a binder resin (mass ratio benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: 11: 25) Copolymer) 8.0 parts by weight, propylene glycol monomethyl ether acetate 1.9 parts by weight, a leveling agent (TF-1740) and 0.06 parts by weight of the adhesion aid (KRM-503) was stirred to uniformly mixed to prepare a photosensitive blue resin composition.

Example 1

Except for using the compound I-1 instead of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

Example 2

Except for using the compound J-1 instead of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

Example 3

Except for using the compound K-1 in place of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

Example 4

Except for using the compound L-1 instead of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

Example 5

Except for using the compound M-1 instead of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

Example 6

Except for using the compound N-1 instead of Comparative Example 1 in Comparative Example 1 was prepared in the same manner.

PCB manufacturing method

The photosensitive resin composition was spincoated on glass (5 cm × 5 cm) and pre-bake at 100 ° C. for 100 seconds to form a film.

Heat resistance measurement

In order to measure heat resistance, each of the blue resin compositions for color filters prepared in Examples 1 to 6 and Comparative Example 1 was spin-coated on a glass substrate of 5 cm × 5 cm, and pre-bake for 2 minutes on a hot plate at 100 ° C. After the reaction, the mixture was cooled at room temperature for 2 minutes. Then, after 20 minutes post-bake in the convection oven at 230 ℃, using a spectrophotometer to check the color characteristics, and further heat treatment in 230 ℃ convection oven for 1 hour, and then again Checking the color characteristics to obtain the ΔEab * value of the substrate prepared by the resin composition prepared in Examples 1 to 4 and Comparative Example 1 are shown in Table 1 below.

division Example 1 Example 2 Example 3 Example 4 Comparative Example 1 ΔEab * 1.75 2.82 3.13 3.07 4.01

When the coloring photosensitive resin composition of Examples 1-4 and Comparative Example 1 was compared, the result which was excellent in the heat resistance of said Examples 1-4 was shown.

Light resistance measurement

Test boards were prepared in the same order as the heat resistance test, and after 20 minutes postbake at 230 ° C., the color difference was measured at the C light source. Thereafter, the measuring substrate was placed in the light tester Sun test CPS + and left for 6 hours. Then, the color difference was measured in the C light source, and the color difference change rate ΔEab * was calculated and shown in Table 2.

division Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Comparative Example 1 ΔEab * 22.99 22.08 16.92 18.75 22.36 19.87 33.84

By using the pigment | dye which introduce | transduced the specific substituent of this invention from the above, it becomes possible to obtain the coloring composition for color filters and color filter excellent in heat resistance and light resistance.

Claims

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 ';

; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, R 1 and R 2; R3 and R4; And at least one of R5 and R6 may combine with each other to form a substituted or unsubstituted ring,
R7 to R14 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; or a substituted or unsubstituted aryl group,
m and n are each an integer of 1 to 4,
when m and n are each 2 or more, the structures in the two or more parentheses are the same as or different from each other,
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 groups; -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 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 4.

The color material composition according to claim 5, further comprising at least one of dyes and pigments.

A compound according to any one of claims 1 to 4; Antioxidants; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent.

A color filter comprising the resin composition of claim 7.

A display device comprising the color filter of claim 8.