KR20170034767A - Xanthene-based compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

The present invention relates to a novel xanthene-based compound which is represented by chemical formula 1. The present invention further relates to a coloring material composition containing the same, and to a resin composition containing the xanthene-based compound and the coloring material composition. According to an embodiment of the present invention, the xanthene-based compound functions as a dye, and thus can be used as a material for color filters.

Description

XANTHENE-BASED COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME,

This application claims the benefit of Korean Patent Application No. 10-2015-0133199 filed on September 21, 2015, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel xanthene-based compound, a colorant composition containing the same, and a resin composition containing the same.

BACKGROUND ART [0002] In recent years, LEDs or OLED devices which do not drive liquid crystal but perform self-luminescence instead of conventional CCFL have been widely used as a light source of a liquid crystal display (LCD). When an LED or an OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required.

However, it is generally not easy to adjust or adjust the required color coordinates using light emitted from an LED or OLED light source. In addition, the method of improving the color purity, luminance and contrast ratio in the production of a color filter using a pigment dispersion method using already developed color materials, in particular, a pigment has reached a limit. In addition, in order to make the color filter thinner, the use amount of the color material should be reduced.

Development of a new color material is required to overcome such a problem and satisfy the requirement.

Korean Patent Publication No. 2001-0009058

The present invention describes a novel xanthane-based compound, a colorant composition containing the same, and a resin composition containing the same.

According to one embodiment of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R ₁ and R ₃ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C2-C30 linear or branched alkenyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

R ₂ is a direct bond; Or a divalent linking group,

R ₄ to R ₁₃ are the same or different and each independently hydrogen; heavy hydrogen; SO ₃ ^- ; COOH; COO ^- ; A hydroxy group; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

At least one of R ₄ to R ₁₃ is SO ₃ ^- ; COOH; Or COO ^- and,

R ₁₄ to R ₁₇ are the same or different and each independently hydrogen; Or deuterium,

X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C2-C30 linear or branched alkenyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

r2, m, n, p and q are each an integer of 1 to 3,

When r 2 is 2 or more, R ₂ are the same or different from each other,

When m is 2 or more, R ₁₄ are the same or different from each other,

When n is 2 or more, R ₁₅ are the same or different from each other,

When p is 2 or more, R ₁₆ are the same or different from each other,

When q is 2 or more, R ₁₇ are the same or different from each other.

According to another embodiment of the present invention, there is provided a colorant composition comprising the compound represented by Formula 1 above.

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

The compound according to one embodiment of the present disclosure can act as a dye and therefore can be used as a color filter material. Specifically, according to one embodiment of the present invention, the resin composition comprising the compound can obtain absorption and transmission spectra suitable for a desired light source, thereby achieving higher color reproducibility, high brightness, and high contrast ratio. According to one embodiment of the present invention, the resin composition containing the compound has a high degree of crosslinking and is excellent in heat resistance and / or chemical resistance. Therefore, the resin composition according to one embodiment of the present invention has less color change due to heat treatment and less elution into a solvent.

Hereinafter, the present invention will be described in detail.

According to one embodiment of the present invention, there is provided a compound represented by the above formula (1).

Examples of substituents of the compound represented by the formula (1) are described below, but are not limited thereto.

As used herein, the term " substituted or unsubstituted " A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; -NH ₂ ; An alkylamine group; An aralkylamine group; An arylamine group; Carbazole group; Acryloyl group; Acrylate groups; Ether group; A nitrile group; A nitro group; A hydroxy group; A nitrile group; An epoxy group; (Meth) acrylate groups; Hydrocarbon ring group; And a heterocyclic group containing at least one of N, O, S, or P atoms, or has no substituent group.

 In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 25.

In the present specification, the alkenyloxy group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 25.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the aralkyl group is specifically an aryl moiety having 6 to 49 carbon atoms, and the alkyl moiety has 1 to 44 carbon atoms. Specific examples include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, Group, an?,? -Methylphenylbenzyl group, a 1-naphthylbenzyl group, a 2-naphthylbenzyl group, a p-fluorobenzyl group, a 3,5-difluorobenzyl group, , p-methoxybenzyl group, m-methoxybenzyl group,? -phenoxybenzyl group,? -benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, But are not limited to, an ethyl group, an aminobenzyl group, a nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like.

In the present specification, the aryl moiety of the aralkenyl group may be an explanation of the aryl moiety described below, and the alkenyl moiety may be the description of the alkenyl moiety described above.

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

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 40 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

,

,

및

등이 있다. In the present specification, the fluorenyl group may have a substituent, and the substituents may combine to form a spiro structure. Examples of the fluorenyl group include

,

,

And

.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but is preferably 2-40 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, And the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group may be exemplified by a heterocyclic group.

In the present specification, the hydrocarbon ring group may be an aromatic, aliphatic or aromatic and aliphatic condensed ring group, and examples thereof may be selected from the above-mentioned cycloalkyl group or aryl group.

In the present specification, an alkylene group means that the alkyl group has two bonding positions. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, but an example of the alkyl group can be applied, except that the number of carbon atoms is 2 to 25 and the number of carbon atoms is 2.

In the present specification, an arylene group means that there are two bonding positions in an aryl group. The arylene group may be monocyclic or polycyclic, and examples of the aryl group may be applied except that the arylene group is a divalent group.

In the present specification, the epoxy group is an alicyclic epoxy group and preferably has 2 to 20 carbon atoms.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted phenyl group.

According to another embodiment of the present invention, in Formula 1, R ₁ and R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a phenyl group substituted with a methyl group.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; Or a divalent linking group.

For example, the divalent linking group may be an oxy group (-O-); Thiogen (-S-); Carbonyl group (-CO-); A sulfonyl group (-SO ₂ -) amino group; A substituted or unsubstituted, linear or branched alkylene group having 1 to 30 carbon atoms; A substituted or unsubstituted C2-C30 linear or branched alkenylene group; A substituted or unsubstituted monocyclic or polycyclic cycloalkylene group having 3 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A substituted or unsubstituted, linear or branched alkylene group having 1 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A substituted or unsubstituted, straight or branched chain 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 one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A substituted or unsubstituted, straight or branched chain alkylene group having 1 to 10 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 10 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A linear or branched alkylene group having 1 to 10 carbon atoms; Or a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms which is substituted or unsubstituted with a straight or branched alkyl group having 1 to 10 carbon atoms.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A substituted or unsubstituted methylene group; Or a phenylene group substituted or unsubstituted with an alkyl group.

According to one embodiment of the present disclosure, r2 is 3.

According to one embodiment of the present invention, in Formula 1, R ₂ is a direct bond; A methylene group; Or a methylene group, or a phenylene group substituted or unsubstituted with an ethyl group.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted straight or branched alkyl group having 1 to 20 carbon atoms.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted straight or branched alkyl group having 1 to 15 carbon atoms.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; And a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring group which may be substituted with a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , an epoxy group, a (meth) acrylate group, a dihydrocarbyl group containing a nitrogen atom, a monocyclic or polycyclic heterocyclic group, And an alkyl group having from 1 to 10 carbon atoms.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; And a substituted or unsubstituted monocyclic or polycyclic aryl group which is substituted with a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , an epoxy group, a (meth) acrylate group, a dihydrocarbyl group including a nitrogen atom, a monocyclic or polycyclic heterocyclic group, And an alkyl group having 1 to 10 carbon atoms.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; And a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , an epoxy group, a (meth) acrylate group, an oxiranyl group, an oxetanyl group, a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group, A thiomorpholinyl group, a piperidyl group, a piperidino group, a piperazinyl group, a homopiperazinyl group, a 1,3-dioxolan-2-yl group, a pyridyl group, a pyrazinyl group, a pyrimidyl group, , A quinolyl group, an isoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, an imidazolyl group, a pyrazolyl group, a triazoyl group, a tetrazolyl group, a thiazolyl group, a benzothiazolyl group, A straight or branched chain alkylene group having 1 to 10 carbon atoms which is unsubstituted or substituted with an oxazolyl group, an indolyl group, an indazolyl group, a benzoimidazolyl group, a phthalimide group, a thienyl group, a furyl group, a pyranyl group, Alkyl group.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; And a linear or branched alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , a phthalimide group, or a (meth) acrylate group.

According to another embodiment of the present invention, in Formula 1, X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; Methyl group; An ethyl group; And a n-propyl group substituted or unsubstituted with a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , a phthalimide group, or a methyl methacrylate group.

According to another embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of the following compounds.

The compound of formula (1) can be prepared by referring to the following Production Examples.

Another embodiment of the present disclosure provides a colorant composition comprising the compound of formula (1).

The colorant composition may further include at least one of a dye and a pigment in addition to the compound of the formula (1). For example, the colorant composition may contain only the compound of Formula 1, but may include the compound of Formula 1 and at least one dye, or may include the compound of Formula 1 and at least one pigment, , One or more dyes, and one or more pigments.

According to one embodiment of the present invention, there is provided a resin composition comprising the color material composition.

According to one embodiment of the present invention, the resin composition comprises the compound represented by Formula 1 above; Binder resin; Multifunctional monomers; Photoinitiators; And a solvent.

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

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

The multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; 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, isobutyl (Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) , Methyl [alpha] -hydroxymethyl acrylate, ethyl [alpha] -hydroxymethyl acrylate, propyl [alpha] -hydroxymethyl acrylate and butyl [alpha] -hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the unsaturated imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.

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

The alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.

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

The multifunctional monomer is a monomer that functions to form a photoresist phase by light. Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate. Species or a mixture of two or more species.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking. For example, the photoinitiator is selected from the group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound Or more.

The acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.

Examples of the biimidazole-based compounds include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.

The triazine-based compound may be at least one selected from the group consisting of 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl 2- {4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2- epoxyethyl-2- {4- [ Yl] phenylthio} acetate, benzyl-2- {4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, 3- {chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloromethyl) -s-triazine-6-yl] 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 .

The oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.

The solvent is selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroethane, 1,1,2-trichloroethane, hexane, heptane, Methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl It may be at least one selected from the group consisting of citrate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether. But is not limited thereto.

According to one embodiment of the present invention, the content of the compound represented by Formula 1 is 5 wt% to 60 wt% based on the total weight of the solid content of the resin composition, 60 wt%, the content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the polyfunctional 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 standard of weight percentage based on solid content and solid content of each component can be measured by general analytical means used in the art such as liquid chromatography or gas chromatography.

According to one embodiment of the present invention, the resin composition may further comprise an antioxidant.

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

According to one embodiment of the present invention, the resin composition further comprises one or more additives selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersing agent and a leveling agent .

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

The photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone 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-acridinylpentane), 1,3-bis (9-acridinyl) propane, and the like Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, and 9,10-phenanthrenequinone; Phosphine oxide-based compounds such as 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide; Benzoate-based compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis Amino-synergists such as methyl-cyclopentanone; (Diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl- -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- Pyran o [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylaminokalone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline, and the like.

As the curing accelerator, curing and mechanical strength are used, and 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) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.

Examples of the adhesion promoter used in the present invention include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.

Specifically, the silicone surfactant is 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-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F- TF-1116SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1025SF, TF- , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, and the like.

The antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-? -Naphthylamine, phenyl-? -Naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-? -Naphthyl- Secondary antioxidant; Thio such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethyl thiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] Secondary antioxidant; (2,4-ditbutylphenyl) pentaerythritol diphosphite or (1, 2,4-dibutylphenyl) pentaerythritol diphosphite or bis (2,4-dibutylphenyl) (1,1'-biphenyl) -4,4'-diisopropylphosphonic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] -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 and alkoxybenzophenone may be used. Anything that is commonly used can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.

The dispersant may be used either in a manner of internally adding to the pigment in the form of surface-treating the pigment in advance, or in a method of externally adding the pigment. As the dispersing agent, compound type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic, amphoteric surfactants and the like. These may be used individually or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, Alkyl amide alkylene oxide adducts, and alkyl amines, but are not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.

According to one embodiment of the present invention, there is provided a photosensitive material made of the resin composition.

More specifically, the resin composition of the present invention is applied onto a substrate by a suitable method to form a photosensitive material in the form of a thin film or a pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.

Examples of the light source for curing the resin composition according to the present invention include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emits light having a wavelength of 250 nm to 450 nm.

The resin composition according to the present invention can be used as a pigment dispersing type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of an organic light emitting diode or a thin film transistor liquid crystal display (TFT LCD) And can be used for a photosensitive material for overcoat layer formation, a column spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printing wiring board and a photosensitive material for a plasma display panel (PDP) Is not specifically set.

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

The color filter can be produced using a resin composition containing the compound represented by the general formula (1). The resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

The resin composition according to one embodiment of the present invention can provide a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance, 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 kind thereof is not particularly limited.

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

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

Between the color pixels of the color filter, a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast. As the material of the black matrix, chromium can be used. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectivity of chrome, and environmental pollution caused by a 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 invention can use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or a mixture of carbon black and a color pigment may be used. In this case, since the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.

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

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 liquid crystal display (LCD), and a cathode ray tube (CRT).

Hereinafter, the present invention will be described in detail with reference to examples. The following examples are intended to illustrate the present disclosure and the scope of the present disclosure includes the scope of the following claims and their substitutions and modifications, which are not intended to limit the scope of the embodiments.

Production Example 1. Preparation of Compound 1

1) Preparation of Compound A-3

3.000 g (7.403 mmol) of A-1 and 0.753 g (2.96 mmol) of A-2 were added to 30 g of N-methylpyrrolidone (NMP) under light shielding conditions and reacted at 150 ° C. for 4 hours. The solvent was removed under reduced pressure, and the Crude compound was subjected to column chromatography to obtain 1.174 g (1.184 mmol) of Compound A-3.

2) Preparation of Compound A-5

5.000 g (5.041 mmol) of Compound A-3 and 2.443 g (20.162 mmol) of Compound A-4 were added to 50 g of N-methylpyrrolidone (NMP) and reacted at 150 ° C for 5 hours. It was cooled to room temperature, 35% HCl was added and stirred. The solvent was removed under reduced pressure and 1.756 g (1.512 mmol) of Compound A-5 was obtained by column chromatography.

3) Preparation of compound 1

1.756 g (5.041 mmol) of Compound A-5, 3.427 g (20.162 mmol) of Compound A-6 and 2.786 g (20.162 mmol) of K ₂ CO ₃ were added to 50 g of N-methylpyrrolidone (NMP) . The solvent was removed under reduced pressure and 1.341 g (1.008 mmol) of Compound 1 was obtained through column chromatography.

Ionization mode =: APCI +: m / z = 1329 [M + H] < + >, Exact Mass: 1328

Production Examples 2 to 10. Preparation of the compounds 2 to 10

Compounds 2 to 10 were prepared in the same manner as in Preparation Example 1, except that the substituents were applied differently.

Examples and Comparative Examples were prepared in the same ratios as in Table 1 below. The addition unit of the compound is gram (g).

compound Binder resin (g) Photoinitiator (g) The multifunctional monomer (g) Additive (g) Solvent (g) Example 1 Compound 1 5.554 10.376 2.018 12.443 1.016 68.593 Example 2 Compound 2 Example 3 Compound 3 Example 4 Compound 4 Example 5 Compound 5 Example 6 Compound 6 Example 7 Compound 7 Example 8 Compound 8 Example 9 Compound 9 Example 10 Compound 10 Comparative Example 1 Comparative Example Compound 1 Comparative Example 2 Comparative Example Compound 2

Binder resin: Copolymer of benzyl methacrylate and methacrylic acid (mole ratio 70:30, acid number 113
KOH mg / g, weight average molecular weight measured by GPC 20,000, molecular weight distribution (PDI) 2.0
Solids (SC) 25%, solvent PGMEA)
Photoinitiator: I-369 (BASF)
Multifunctional monomer: DPHA (Japanese explosive)
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Additive: DIC F-475
* Evaluation after insoluble ingredient filter
Comparative Example Compound 1 (Basic blue 7) Comparative Example Compound 2 (rhodamine 6G)

Board Fabrication

The compound prepared by the above synthesis was spin-coated on glass (5 x 5 cm) and pre-baked 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 at 250 mu m and the entire surface of the substrate was irradiated with an exposure dose of 40 mJ / cm < ² > Subsequently, the exposed substrate was developed in a developer (KOH, 0.05%) for 60 seconds and post baked at 230 캜 for 20 minutes to prepare a substrate.

Heat resistance evaluation

A prebake substrate manufactured under the above conditions was subjected to spectral analysis using a spectroscope (MCPD-Otsuka) to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm. In addition, the prebake substrate was further post baked at 230 ° C for 20 minutes to obtain the transmittance spectrum in the same equipment and measurement range.

The obtained transmittance spectrum and C light source backlight are used and ΔEab is calculated using the obtained value E (L *, a *, b *) and shown in Table 2 below.

? E (L *, a *, b *) = {(? L *) 2+ (? A *) 2+

The smaller ΔE value means that the color heat resistance is excellent.

Table 2 shows the results of measurement of heat resistance of the color material compositions of Examples 1 to 10 and Comparative Examples 1 and 2. As shown in Table 2, it was confirmed that Examples 1 to 10 had less color change (? Eab) than Comparative Examples 1 and 2.

? Eab (PB-PrB) Example 1 2.86 Example 2 3.45 Example 3 3.24 Example 4 3.04 Example 5 2.98 Example 6 3.12 Example 7 3.05 Example 8 2.96 Example 9 3.01 Example 10 3.34 Comparative Example 1 26.52 Comparative Example 2 23.95

Claims (14)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
R ₁ and R ₃ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C2-C30 linear or branched alkenyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
R ₂ is a direct bond; Or a divalent linking group,
R ₄ to R ₁₃ are the same or different and each independently hydrogen; heavy hydrogen; SO ₃ ^- ; COOH; COO ^- ; A hydroxy group; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
At least one of R ₄ to R ₁₃ is SO ₃ ^- ; COOH; Or COO ^- and,
R ₁₄ to R ₁₇ are the same or different and each independently hydrogen; Or deuterium,
X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C2-C30 linear or branched alkenyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
r2, m, n, p and q are each an integer of 1 to 3,
When r 2 is 2 or more, R ₂ are the same or different from each other,
When m is 2 or more, R ₁₄ are the same or different from each other,
When n is 2 or more, R ₁₅ are the same or different from each other,
When p is 2 or more, R ₁₆ are the same or different from each other,
When q is 2 or more, R ₁₇ are the same or different from each other. 2. The compound of claim 1, wherein R ₁ and R ₃ are the same or different and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted phenyl group. _{2. The} compound of claim 1, wherein R < ₂ > A linear or branched alkylene group having 1 to 10 carbon atoms; Or a monocyclic or polycyclic arylene group having 6 to 10 carbon atoms which is substituted or unsubstituted with a straight or branched alkyl group having 1 to 10 carbon atoms. The compound according to claim 1, wherein X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; And a substituted or unsubstituted C 1 -C 20 linear or branched alkyl group. The compound according to claim 1, wherein X ₁ to X ₄ are the same or different from each other, and each independently hydrogen; And a hydroxyl group, a thiol group, a nitrile group, -NH ₂ , an epoxy group, a (meth) acrylate group, an oxiranyl group, an oxetanyl group, a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group, A thiomorpholinyl group, a piperidyl group, a piperidino group, a piperazinyl group, a homopiperazinyl group, a 1,3-dioxolan-2-yl group, a pyridyl group, a pyrazinyl group, a pyrimidyl group, , A quinolyl group, an isoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, an imidazolyl group, a pyrazolyl group, a triazoyl group, a tetrazolyl group, a thiazolyl group, a benzothiazolyl group, A straight or branched chain alkylene group having 1 to 10 carbon atoms which is unsubstituted or substituted with an oxazolyl group, an indolyl group, an indazolyl group, a benzoimidazolyl group, a phthalimide group, a thienyl group, a furyl group, a pyranyl group, Alkyl group. ≪ / RTI > The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following compounds:

A colorant composition comprising the compound of any one of claims 1 to 6. The colorant composition according to claim 7, further comprising at least one of a dye and a pigment. A compound represented by formula (1) according to claim 1; Binder resin; Multifunctional monomers; Photoinitiators; And a solvent. The method of claim 9,
Based on the total weight of the solid content in the resin composition
The content of the compound represented by Formula 1 is 5 wt% to 60 wt%
The content of the binder resin is 1 wt% to 60 wt%
The content of the photoinitiator is 0.1 wt% to 20 wt%
And the content of the polyfunctional monomer is 0.1 wt% to 50 wt%. The resin composition according to claim 9, further comprising an antioxidant. A photosensitive material produced using the resin composition according to claim 9. A color filter comprising the photosensitive material according to claim 12. A display device comprising a color filter according to claim 13.