KR102064631B1 - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

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

Description

Amine compound, colorant composition comprising the same, and resin composition containing same {COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}

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

Recently, as a light source of a liquid crystal display (LCD), devices such as LED, OLED, QD, etc. are used instead of the conventional CCFL. However, in order to manufacture thin-film displays and flexible displays, display products in which color filters have been removed, that is, self-luminescence such as LEDs, OLEDs, and QDs, are developed and produced.

However, displays using LEDs, OLEDs, QDs, etc. as unit pixels have difficulty in large area, and even when using LEDs, OLEDs, QDs, etc., they have a lot of efforts to develop displays that include them as light sources and include color filters. Doing.

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

However, in the case of the pigment dispersion, the pigment is present in the form of particles, not only to scatter light, but also to rapidly increase the pigment surface area due to the miniaturization of the pigment, resulting in uneven pigment particles due to deterioration of dispersion stability.

Therefore, it is recognized that the limit point which is difficult to satisfy high quality requirements such as high brightness, high contrast ratio, and high definition which is recently required is recognized.

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, triaryl methane dye has an advantage of high transmittance at 420 to 450 nm, but when used in a color filter coloring composition has a disadvantage of poor heat resistance.

As a method of improving the heat resistance, a combination of a triaryl methane dye and an aromatic sulfonic acid and use as a colorant have been proposed. However, even when a color filter is produced using this dye, there is a problem that both heat resistance and light resistance are insufficient. In addition, it has been proposed to introduce an alkyl group at the benzene ortho-position of the triaryl methane-based dye to form salts with phthalocyanine sulfonic acid or ankraquinone sulfonic acid as counter ions, but the heat resistance and light resistance are insufficient, and also pigments such as phthalocyanine sulfonic acid and Because of the salt formation, there is a problem that the high brightness of the original triaryl methane-based dye is lowered.

Therefore, new color material development is required to overcome this problem.

Korean Unexamined Patent No. 2012-0012393 Korean Patent Publication No. 2012-0028815 Japanese Laid-Open Patent 2012-017425 Japanese Laid-Open Patent 2011-133844

The present specification provides a amine compound having a novel structure, 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,

A is represented by the following formula A-1 or A-2,

[Formula A-1]

[Formula A-2]

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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or R1 and R2, R3 and R4 or R5 and R6 may combine with each other to form a substituted or unsubstituted ring,

R7 to R22 are the same as or different from each other, and each independently hydrogen; halogen; Hydroxyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,

R23, R25, R27 and R28 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 arylene group,

R24, R26, R29 and R30 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

Z ^- is an anionic group,

[Formula a]

In Chemical Formula a,

Q is -R101COR102-; -R103OCOR104-; -R105COOR106-; -R107OCOOR108-; -R109CONR110R111-; -R112OCNR113R114-; -R115OCNR116C1171; -SOOR118-; -SOR119-; -SR120-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,

X is a hydroxy group; Amine group; -OCOOR121; -CONR122R123; Or -NR124COOR125,

Y is a substituted or unsubstituted alkyl group,

R101 to R109, R111, R112, R114, R115 and R117 to R120 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 alkenylene group,

R110, R113, R116 and R121 to R125 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

2 ≦ n + m ≦ 5,

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

* Is a moiety linked to N in Formula 1,

는 상기 화학식 1에 연결되는 부위이다.

Is a site linked to the formula (1).

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 an exemplary embodiment of the present specification, a resin composition comprising the color material composition is provided.

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

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

The compound according to one embodiment of the present specification may act as a dye, and thus may be used as a color filter material. Specifically, according to the exemplary embodiment of the present specification, the resin composition including the compound may obtain an absorption and transmission spectrum suitable for a desired light source, thereby achieving higher color reproducibility, higher luminance, and high contrast ratio.

In addition, the color material composition according to an exemplary embodiment of the present specification is excellent in heat resistance, and can maintain excellent chromaticity characteristics even after a high temperature heating process.

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.

In the present specification, when a part "includes" a certain component, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

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 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.

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, and 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 methyl thioxy group, ethyl thioxy group, tert-butyl thioxy group, hexyl thioxy group, octyl thioxy group, and the like. 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 is not particularly limited, but preferably has 6 to 30 carbon atoms, and 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.

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

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.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, and N-arylheteroarylamine 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, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. 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, the alkenylene group refers to a divalent group having two bonding positions in the alkyl group. The description of the alkenyl group described above can be applied except that they are each divalent.

In the present specification, the term "adjacent groups" in the substituents combine with each other to form a ring "means combining with adjacent groups to form a substituted or unsubstituted hydrocarbon ring; or to form a substituted or unsubstituted hetero ring. .

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. The heterocycle 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 except that it is not monovalent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by the following formula 1-a or 1-b.

[Formula 1-a]

[Formula 1-b]

In Chemical Formulas 1-a and 1-b,

The definitions of R1 to R4, R7 to R14, and Z ⁻ are the same as those of Formula 1,

The definitions of R5, R6, R15 to R22 are the same as those of Formulas A-1 and A-2.

According to an exemplary embodiment of the present specification, in the general formula 1-a and 1-b, 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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, in the general formula 1-a and 1-b, 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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula 1-a and 1-b, 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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; A substituted or unsubstituted ethyl group; Substituted or unsubstituted n-propyl group; A substituted or unsubstituted cyclohexyl group; It is a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, in the general formula 1-a and 1-b, 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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; An ethyl group unsubstituted or substituted with a hydroxy group; n-propyl group; Cyclohexyl group; Or a phenyl group unsubstituted or substituted with an alkyl group.

According to an exemplary embodiment of the present specification, in the general formula 1-a and 1-b, 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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; An ethyl group unsubstituted or substituted with a hydroxy group; n-propyl group; Cyclohexyl group; Or a phenyl group unsubstituted or substituted with a methyl group.

According to an exemplary embodiment of the present specification, the R23, R25, R27 and R28 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the R23, R25, R27 and R28 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted ethylene group; Or a substituted or unsubstituted phenylene group.

According to an exemplary embodiment of the present specification, the R23, R25, R27 and R28 are the same as or different from each other, and each independently a direct bond; Ethylene group; Or a phenylene group.

According to an exemplary embodiment of the present specification, the R23, R25, R27 and R28 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the R24, R26, R29 and R30 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted t-butyl group; Or a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, the R24, R26, R29 and R30 are the same as or different from each other, and each independently hydrogen; t-butyl group; Or a phenyl group.

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 A-1 and A-2, 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 A-1 and A-2, 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, the R7 to R22 are the same as or different from each other, and each independently hydrogen; halogen; Hydroxyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, the R7 to R22 are the same as or different from each other, and each independently hydrogen; halogen; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, the R7 to R22 are the same as or different from each other, and each independently hydrogen; Fluorine; bromine; Goat; iodine; Or a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, the R7 to R22 are the same as or different from each other, and each independently hydrogen; Fluorine; Or a substituted or unsubstituted methyl group.

According to an exemplary embodiment of the present specification, the R7 to R22 are the same as or different from each other, and each independently hydrogen; Fluorine; Or methyl group.

According to an exemplary embodiment of the present specification, in the general formula a, Q is -R101COR102-; -R103OCOR104-; -R105COOR106-; -R107OCOOR108-; -R109CONR110R111-; -R112OCNR113R114-; -R115OCNR116C1171; -SOOR118-; -SOR119-; -SR120-; A substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted linear or branched alkenylene group having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula a, Q is -R101COR102-; -R103OCOR104-; -R105COOR106-; -R107OCOOR108-; -R109CONR110R111-; -R112OCNR113R114-; -R115OCNR116C1171; -SOOR118-; -SOR119-; -SR120-; Substituted or unsubstituted ethylene group; Or a substituted or unsubstituted 2-methylhexylene group.

According to an exemplary embodiment of the present specification, in the general formula a, Q is -R101COR102-; -R103OCOR104-; -R105COOR106-; -R107OCOOR108-; -R109CONR110R111-; -R112OCNR113R114-; -R115OCNR116C1171; -SOOR118-; -SOR119-; -SR120-; Ethylene group; Or 2-methylhexylene group.

According to another exemplary embodiment, the R101 to R109, R111, R112, R114, R115, and R117 to R120 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms; Or a substituted or unsubstituted linear or branched alkenylene group having 2 to 20 carbon atoms.

According to another exemplary embodiment, the R101 to R109, R111, R112, R114, R115, and R117 to R120 are the same as or different from each other, and each independently a direct bond; Methylene group; Ethylene group; n-propylene group; n-butylene group; n-pentylene group; Or n-butenylene group.

According to another exemplary embodiment, the R110, R113 and R116 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, the R110, R113 and R116 are the same as or different from each other, and each independently hydrogen; Methyl group; n-propyl group; Or t-butyl group.

According to an exemplary embodiment of the present specification, in Chemical Formula a, Q may be selected from the following structures, but is not limited thereto.

는 화학식 a에 연결되는 부위이다.The structure may include additional substituents, * is a moiety linked to N of Formula 1,

Is a moiety linked to formula a.

According to an exemplary embodiment of the present specification, in the general formula a, Q is -R101COR102-; Or -R105COOR106-.

According to another exemplary embodiment, the R101, R102, R105, and R106 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted alkylene group.

According to another exemplary embodiment, the R101, R102, R105, and R106 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.

According to another exemplary embodiment, the R101, R102, R105, and R106 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted ethylene group.

According to another exemplary embodiment, the R101, R102, R105, and R106 are the same as or different from each other, and are each independently a direct bond; Or an ethylene group.

According to an exemplary embodiment of the present specification, in the general formula a, X is a hydroxy group; Primary amine group; Secondary amine groups; Tertiary amine groups; -OCOOR121; -CONR122R123; Or -NR 124 COOR 125.

According to an exemplary embodiment of the present specification, in the general formula a, X is a hydroxy group; -NH ₂ (amino group); Ethylamine group; t-butylamine group; Dimethylamine group; -OCOOR121; -CONR122R123; Or -NR 124 COOR 125.

According to another exemplary embodiment, the R121 to R125 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, the R121 to R125 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Or t-butyl group.

According to an exemplary embodiment of the present specification, in Chemical Formula a, X may be selected from the following structures, but is not limited thereto.

The structure may include additional substituents, and * is a moiety linked to formula (a).

According to an exemplary embodiment of the present specification, in the general formula a, X is a hydroxy group; Or -OCOOR121.

According to another exemplary embodiment, R121 is a linear or branched alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, R121 is a t-butyl group.

According to an exemplary embodiment of the present specification, in the general formula a, Y is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

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

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

According to an exemplary embodiment of the present specification, Chemical Formula a may be selected from the following structures, but is not limited thereto.

In the above structure, * is a site linked to the formula (1).

According to an exemplary embodiment of the present disclosure, in the general 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, the compound represented by Formula 1 is selected from the following compounds.

The compound represented by Chemical Formula 1 may be prepared by referring to the preparation examples described later.

Another embodiment of the present specification provides a color material composition including the compound represented by Chemical Formula 1.

The color material 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.

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 an antioxidant; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.

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).

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.

In one 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, and is, for example, from an acetophenone compound, a biimidazole compound, a triazine compound, and an oxime compound. It may be one or more selected.

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.

In one embodiment of the present specification, based on the total weight of solids in the resin composition, the compound represented by the formula (1) or the content of the compound represented by the formula (1) is 5% by weight to 60% by weight, The content of the antioxidant is 0.001% to 20% by weight, the content of the binder resin is 1% to 60% by weight, the content of the initiator is 0.1% to 20% by weight, 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.

In one embodiment of the present specification, the resin composition further comprises one or two or more additives selected from the group consisting of photocrosslinking agents, curing accelerators, adhesion promoters, surfactants, thermal polymerization inhibitors, ultraviolet absorbers, dispersants and leveling agents. It includes.

In one embodiment of the present specification, the amount 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, TF-1740, etc. may be used, but is not limited thereto.

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.

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.

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.

In one embodiment of the present specification, a color filter including the resin composition is provided.

The color filter may be manufactured using a resin composition containing the compound represented by Chemical Formula 1. 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.

In 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.

It provides a label device comprising a color filter according to the present disclosure.

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 C-2

 1) Preparation of Compound A

15 g (1 eq) of 4,4-difluorobenzophenone and 31.1 g of 2-ethylamino ethanol (5 eq) were added to the flask under a nitrogen atmosphere, and the mixture was heated to 160 ° C. I was. After reaction at 160 ° C. for 48 hours, the reaction mixture was cooled to room temperature. Distilled water was added, followed by extraction with methylene chloride or ethyl acetate and dried under reduced pressure. Recrystallization and purification of ethyl acetate at room temperature gave off-white compound A. (20 g, yield 82%)

2) Preparation of Compound C

9.6 g (3eq) of 3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid (3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid under nitrogen atmosphere Was dissolved in 70 mL of tetrahydrofuran and an ice bath was installed in the reactor 5.30 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide (1-ethyl-3- 3-dimethylaminopropyl carbodiimide) (2.4eq) was added and stirred for about 15 minutes, followed by 0.56 g of 4-dimethylaminopyridine (0.4eq), and after 15 minutes, 4.10 g (1eq) of Compound A was slowly added to 30 mL of tetrahydrofuran. After stirring for 24 hours, the mixture was extracted with methylene chloride and dried under reduced pressure, and purified by column (ethyl acetate: hexane = 1: 3 or 100% ethyl acetate) to obtain 4.31 g (yield 43%) of compound C. After column 3 -(3,5-di-t-butyl-4-hydroxyphenyl) propionic acid ((3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid) may remain In the case, the mixture was washed with NaHCO ₃ (pH 10-11) solution, extracted with methylene chloride, and dried under reduced pressure.

3) Preparation of Compound C-1

Dissolve 3.55 g (1 eq) of Compound C in chloroform. In a nitrogen atmosphere, 1.0 g of phosphoryl chloride (1.5eq) was added thereto, stirred for about 30 minutes, and 1.5 g (1.3eq) of 1-cyclohexyl-1-naphthylamine was slowly added to 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 then the methylene chloride: ethyl acetate = 1: 1 column was used to remove the precursor. Purification by column (methylene chloride: methanol: ethyl acetate = 6: 1: 2) to give a 0.67g blue powder of compound C-1. (Yield 15%)

4) Preparation of Compound C-2

Dissolve 0.67 g of Compound C-1 in methanol, add 0.25 g (1.5 eq) of bistrifluoromethanesulfonimide, stir at room temperature, and add distilled water to filter the precipitated blue powder to filter Compound C-2, 0.62 g. A blue powder was obtained. (Yield 76%)

Preparation Example 2 Preparation of Compound D-2

1) Preparation of Compound D

Compound C 4.31 was dissolved in 40 mL of pyridine, and then di-tert-butyl dicarbonate was slowly added. After 15 minutes, 1.20 g of 4-dimethylaminopyridine was added thereto. After the reaction at 60 ° C. for 3 hours, distilled water was added, the mixture was extracted with methylene chloride, and the solvent was removed under reduced pressure, and then purified by column chromatography (methylene chloride: ethyl acetate = 10: 1) to obtain 3.87 g of an off-white oil compound D. (73% yield)

2) Preparation of Compound D-1

3.87 g (1 eq) of Compound D was dissolved in chloroform. Phosphoryl chloride 0.88g (1.3eq) was added under a nitrogen atmosphere and stirred for about 30 minutes. Then, 1.4g (1.3eq) of 1-cyclohexyl-1-naphthylamine was slowly added to 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 methylene chloride: ethyl acetate = 1: 1 ratio was used to remove the precursors. The methylene chloride: methanol: ethyl acetate = 6: 1: 1 compound was purified to give 1.13 g of compound D-1. . (Yield 24%)

3) Preparation of Compound D-2

Dissolve 1.13 g of compound D-1 in methanol, add 1.5 eq (0.8 g) of bistrifluoromethanesulfonimide (BMI), stir at room temperature, and add distilled water to filter the precipitated blue powder, compound D-2. 1.21 g was obtained. (Yield 90.34%)

Preparation Example 3 Preparation of Compound F-2

3,5-di-t-butyl-4-hydroxybenzoic acid instead of 3- (3,5-di-tert-buthyl-4-hydroxyphenyl) propanoic acid in Preparation Example 1 (3,5-Di-tert- Compound A 4.0 g, 3,5-di-t-butyl-4-hydroxybenzoic acid (3,5-di-) in the same manner as in Preparation Example 1, except that butyl-4-hydroxybenzoic acid) was used. Using 8.4 g of tert-butyl-4-hydroxybenzoic acid), Compound F 5.83 g (yield 63%), Compound F-1 1.3 g (yield 17%) and blue powder Compound F-2 1.5 g (yield 94%) Was prepared.

Preparation Example 4 Preparation of Compound G-2

Proceed in the same manner as in Preparation Example 3 to obtain 0.8 g of G-2. (Yield 11%)

Preparation Example 5 Preparation of Compound H-2

Compound H-2 was obtained in the same manner as in Production Example 1, except that the compound H prepared in an asymmetric structure was purified and separated. To obtain compound H-2, 1.03 g (yield 76%).

Preparation Example 6 Preparation of Compound I

1) Preparation of Compound I

3.0 g (1 eq) of Compound A was dissolved in 15 mL of methylene chloride. 2.13 g (2.5 eq) of triethylamine was added dropwise after making the mixture at 0 ° C. using an ice bath. After about 20 minutes, 2.73 g (2.3 eq) of benzoyl chloride was slowly added. The reaction was performed at room temperature for about 5 hours. After completion of the reaction with distilled water and purified by methylene chloride: ethyl acetate = 10: 1 to give an off-white oil compound I. (4.5g, yield 95%)

2) Preparation of Compound I-2

In the same manner as in Example 1 except that C-1 Dash I-1 was used, 1.12 g of Compound I-2 was obtained. (74% yield)

Preparation Example 7 Preparation of Compound C-3

To Compound C-1, 0.98 g (1 eq), 5 g of 2-aminonaphthalene sulfonate 0.54 g (2.5 eq) dichloromethane and 10 g of water were added and stirred at room temperature for 2 hours. Thereafter, the organic layer was washed with an extract, and the organic layer was concentrated under reduced pressure. Drying under reduced pressure yielded 0.8 g of compound C-3. (Yield 70%)

Preparation Example 8 Preparation of Compound C-4

0.42 g (2.5eq) of sodium benzene sulfonate, 5 g of dichloromethane, and 10 g of water were added to 1.04 g (1 eq) of Compound C-1, followed by stirring at room temperature for 2 hours. Thereafter, the organic layer was washed with an extract, and the organic layer was concentrated under reduced pressure. Drying under reduced pressure yielded 0.75 g of compound C-4. (Yield 65%)

Preparation Example 9 Preparation of Compound L-2

1) Preparation of Compound K

3.75 g (1.5 eq) of 3,5-Di-tert-butyl-4-hydroxybenzoic acid is dissolved in 20 g of tetrahydrofuran. Ice bath (ice bath) was set to 0 ℃, EDC 4.78g (2.5eq), add 15 minutes after DMAP 0.48g (0.4eq) and add 10g tetrahydrofuran. After stirring for 30 minutes, 1.43 g (1.0eq) of 1-naphthylamine was added thereto and stirred. After stirring for 16 hours, the mixture was washed with 200 g of distilled water and brine, extracted with methylene chloride, and dried under reduced pressure. Purification with ethyl acetate: n-hexane = 1: 5 afforded 3.2 g of compound K (yield 85%).

2) Preparation of Compound L-2

In the same manner as in Production Example 1 except that K was used instead of 1-cyclohexyl-1-naphthylamine to give a compound L-2, 0.83g. (Yield 88%)

Preparation Example 10 Comparative Example Compound 1

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

Preparation and Evaluation of Coloring Composition

Comparative Example 1

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

2.0 parts of Comparative Example Compound 1 prepared by Production Example 10 as a blue dye compound, and a binder resin (mass ratio benzyl methacrylate: N-phenylmaleimide: styrene: methacrylic acid = 55: 9: 11: 25) 43.0 parts of dipentaerythritol hexaacrylate, an acrylic monomer, 47.0 parts of propylene glycol monomethyl ether acetate, 2.0 parts of a photoinitiator (PBG-3057), a leveling agent (TF-1740) and an adhesion aid (KRM- 503) was stirred to uniformly mix 0.7 parts to prepare a photosensitive blue resin composition.

Example 1

A photosensitive blue resin composition was manufactured in the same composition as in Comparative Example 1, except that 2.8 parts of Compound C-2 prepared according to Preparation Example 1 was used instead of 2.0 parts of Comparative Example Compound 1 as a blue dye compound.

Example 2

A photosensitive blue resin composition was manufactured in the same composition as in Comparative Example 1, except that 3.0 parts of Compound D-2 prepared according to Preparation Example 2 was used instead of 2.0 parts of Comparative Example Compound 1 as a blue dye compound.

Example 3

A photosensitive blue resin composition was manufactured in the same composition as in Comparative Example 1, except that 2.7 parts of Compound F-2 prepared according to Preparation Example 3 was used instead of 2.0 parts of Comparative Example Compound 1 as a blue dye compound.

Example 4

A photosensitive blue resin composition was manufactured in the same composition as in Comparative Example 1, except that 2.9 parts of Compound G-2 prepared according to Preparation Example 4 was used instead of 2.0 parts of Comparative Example Compound 1 as a blue dye compound.

Example 5

A photosensitive blue resin composition was manufactured in the same composition as in Comparative Example 1, except that 2.4 parts of Compound H-2 prepared according to Preparation Example 5 was used instead of 2.0 parts of Comparative Example Compound 1 as a blue dye compound.

PCB manufacturing method

The photosensitive resin composition was spincoated onto glass (5 × 5 cm) and pre-bake at 100 ° C. for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photo mask was set to 200 μm, and the exposure amount of 40 mJ / cm ² was irradiated on the entire surface of the substrate using an exposure machine.

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

Experimental Example 1. Measurement of heat resistance

In order to measure heat resistance, each of the blue resin compositions for color filters prepared in Examples 1 to 5 and Comparative Example 1 was spin-coated on a glass substrate of 5 cm x 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 5 minutes. This was exposed (365 nm standard) by the exposure amount of 40mJ / cm <^2> using the exposure machine.

Then, after 20 minutes post-bake in a 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 is shown in Table 1 below.

division Example 1 Example 2 Example 3 Example 4 Example 5 Comparative Example 1 ΔEab * 3.60 3.22 1.68 1.03 4.92 9.13

When the coloring photosensitive resin composition of Examples 1-5 and Comparative Example 1 was compared, the result which was excellent in the heat resistance of said Examples 1-5 was shown.

Experimental Example 2 Measurement of Light Resistance

A test substrate was produced in the same order as the heat resistance test, and the color difference was measured at C light source after post-bake at 230 ° C. for 20 minutes. Thereafter, the substrate was placed in a light resistance tester Sun test CPS + and left for 6 hours. Color difference was measured by the several C light source which taken out the board | substrate, and color difference change rate (DELTA) Eab was computed, and it is shown in Table 2.

division Example 1 Example 2 Example 3 Example 4 Example 5 Comparative Example 1 ΔEab * 12.90 16.46 14.62 18.57 16.64 21.99

By using the amine 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 (9)

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

In Chemical Formula 1,
A is represented by the following formula A-2,
[Formula A-2]

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; -R23COR24; -R25OCOR26; -R27OCOR28NR29COOR30; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group, or R1 and R2, R3 and R4 or R5 and R6 may combine with each other to form a substituted or unsubstituted ring,
R7 to R14, R17, R18 and R19 to R22 are the same as or different from each other, and each independently hydrogen; halogen; Hydroxyl group; Substituted or unsubstituted alkoxy group; Or a substituted or unsubstituted alkyl group,
R23, R25, R27 and R28 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 arylene group,
R24, R26, R29 and R30 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
Z ^- is an anionic group,
[Formula a]

In Chemical Formula a,
Q is -R101COR102-; -R103OCOR104-; -R105COOR106-; -R107OCOOR108-; -R109CONR110R111-; -R112OCNR113R114-; -R115OCNR116C1171; -SOOR118-; -SOR119-; -SR120-; Substituted or unsubstituted alkylene group; Or a substituted or unsubstituted alkenylene group,
X is a hydroxy group; Amine groups; -OCOOR121; -CONR122R123; Or -NR124COOR125,
Y is a substituted or unsubstituted alkyl group,
R101 to R109, R111, R112, R114, R115 and R117 to R120 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 alkenylene group,
R110, R113, R116 and R121 to R125 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
2 ≦ n + m ≦ 5,
when n and m are each 2 or more, the structures in two or more parentheses are the same as or different from each other,
* Is a moiety linked to N in Formula 1,

Is a site linked to the formula (1). delete 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 method 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. Colorant composition comprising a compound represented by the formula (1) according to any one of claims 1, 3 and 4. The color material composition according to claim 5, further comprising at least one of dyes and pigments. A compound represented by formula 1 according to any one of claims 1, 3, and 4; Antioxidants; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent further comprising a solvent. A color filter comprising the resin composition of claim 7. A display device comprising the color filter of claim 8.