KR102067858B1 - Compound, colorant composition comprising the same and resin composition comprising the same - Google Patents

Abstract

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

Description

Compound and colorant composition comprising same and resin composition comprising same {COMPOUND, COLORANT COMPOSITION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}

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

In recent years, the performance of the color filter characterized by high brightness and high contrast ratio has been demanded. In addition, one of the main objectives of the display device development is to differentiate the display device performance by improving color purity and to improve productivity in the manufacturing process.

Since the pigment type conventionally used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, the light particles are aggregated in the color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to the aggregation of large particles. The scattering of the polarized light has been pointed out as a main factor for lowering the contrast ratio. Efforts have been made to improve the luminance and contrast ratio through ultrafine atomization and dispersion stabilization of pigments, but the degree of freedom in selecting colorants to implement color coordinates for high color purity display devices is limited. In addition, the pigment dispersion method using the already developed color material, especially pigment has reached the limit to improve the color purity, brightness and contrast ratio of the color filter using the same.

Accordingly, there is a demand for the development of a new color material that can improve color purity and improve color reproduction, brightness, and contrast ratio.

Korean Unexamined Patent Publication 2012-0139606

The present specification is to provide a compound, a color material composition comprising the same and a resin composition comprising the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Y1 and Y2 are each independently a direct bond; Or CQ1Q2,

Two or more adjacent groups of Q1, Q2, R6 to R13 combine with each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms,

Each of Q 1, Q 2, R 1 to R 5, and R 6 to R 13 that does not form a ring with an adjacent group is independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; 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.

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

Another embodiment of the present specification provides a resin composition including the color material composition.

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.

The resin composition comprising the compound according to an exemplary embodiment of the present specification is excellent in color characteristics, heat resistance and solvent resistance.

In addition, the resin composition comprising the compound according to the exemplary embodiment of the present specification serves to prevent reaggregation and generation of foreign matters of the atomized pigment, and thus the contrast ratio is improved.

Hereinafter, this specification is demonstrated in detail.

An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1. Formula 1 is characterized in that at least one or more of the substituents R6 to R13 is a nitro group. The nitro group may serve as an electron withdrawal throughout the compound.

Examples of substituents herein 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; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Silyl groups; Aralkyl group; Ar alkenyl group; Ester group; Carbonyl group; Aryl group; Aryloxy group; Alkyl thioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Boron group; Alkylamine group; Aralkyl amine groups; Arylamine group; Heteroaryl group; Carbazole groups; Acryloyl group; Acrylate group; Ether group; Nitrile group; Nitro group; Hydroxyl group; Substituted with one or more substituents selected from the group consisting of a cyano group and a heterocyclic group containing one or more of N, O, S, or P atoms, or two or more substituents among the above-described substituents are substituted with a linked substituent, or any It means that it does not have a substituent. 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 and can be interpreted as a substituent to which two phenyl groups are linked.

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

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50. 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.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. 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 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-C20. 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 cycloalkyl group is not particularly limited, but may have 3 to 20 carbon atoms, and in particular, may be a cyclopentyl group and a cyclohexyl group.

In the present specification, the aryl moiety may specifically be described below with respect to the aryl moiety, and 6 to 49 carbon atoms and the alkyl moiety are 1 to 44 carbon atoms. Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, α-methylbenzyl group, α, α-dimethylbenzyl Group, α, α-methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, α, α-ditrifluoromethylbenzyl group , p-methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyl groupoxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrole Ethyl group, aminobenzyl group, nitrobenzyl group, cyanobenzyl group, 1-hydroxy-2-phenyl isopropyl group, 1-chloro-2-phenyl isopropyl group and the like, but is not limited thereto.

In the present specification, the aryl portion of the aralkenyl group may be described below with respect to aryl, and the alkenyl portion may be applied with the description of the alkenyl group described above.

In this specification, although carbon number of an ester group is not specifically limited, It is preferable that it is C1-C50. 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-C50. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 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 C10-24. Specifically, the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl 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.

,

,

및

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

,

,

And

Etc., but is not limited thereto.

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 of a heteroaryl group is not specifically limited, It is preferable that it is C2-C60. Examples of heteroaryl groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), thiazolyl group, Isooxazolyl group, oxdiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, the description of the aryl group may be applied except that the aromatic hydrocarbon ring is not a monovalent group.

In the present specification, the description of the heteroaryl group may be applied except that the hetero ring is not a monovalent group.

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

In the present specification, the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups are bonded to each other, as described above, to form a 5 to 8 membered hydrocarbon ring or a 5 to 8 membered hetero ring. , Monocyclic or polycyclic, and may be aliphatic, aromatic or condensed form thereof, but is not limited thereto.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; 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 R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other At least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other. At least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other At least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; And a hydroxy group, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic having 6 to 10 carbon atoms. Aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic hetero ring having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; And a hydroxy group, at least one of R6 to R13 is a nitro group, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic having 6 to 10 carbon atoms. To form an aromatic hydrocarbon ring.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by the following formula (2) or (3).

[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,

Y1, Y2, R1 to R13 are the same as defined in Formula 1,

R14, R15 and R6 'to R15' are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,

At least one of R6 'to R9' of Formula 2, and at least one of R10 'to R13' of Formula 3 is a nitro group.

In Formulas 2 and 3, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; 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, and at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted carbon atoms of 30 to 30 carbon atoms. Monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms, R14, R15 and R6 'to R15' are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; And 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, and at least one of R6 'to R13' is a nitro group.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, and at least two or more adjacent groups of R6 to R13 are bonded to each other to combine at least one or more substituted or unsubstituted carbon atoms of 6 to 20 carbon atoms. Monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, and at least two or more adjacent groups of R6 to R13 combine with each other to form at least one or more substituted or unsubstituted carbon atoms of 15 to 15 carbon atoms. Monocyclic or polycyclic aromatic hydrocarbon rings; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; And at least two or more adjacent groups selected from the group consisting of hydroxy groups and R 6 to R 13 bonded to each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 15 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; And at least two or more adjacent groups selected from the group consisting of hydroxy groups and R 6 to R 13 bonded to each other to form at least one substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 10 carbon atoms; Or a substituted or unsubstituted monocyclic hetero ring having 2 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R1 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; And it is selected from the group consisting of a hydroxyl group, at least two or more adjacent groups of R6 to R13 are bonded to each other to form at least one or more substituted or unsubstituted monocyclic aromatic hydrocarbon ring of 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, R14, R15 and R6 'to R15' are each independently, hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 15 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 15 carbon atoms, and at least one of R6 'to R13' is a nitro group.

According to an exemplary embodiment of the present specification, R14, R15 and R6 'to R15' are each independently, hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; And a substituted or unsubstituted monocyclic aryl group having 6 to 10 carbon atoms; And a substituted or unsubstituted monocyclic heteroaryl group having 2 to 10 carbon atoms, and at least one of R6 'to R13' is a nitro group.

According to an exemplary embodiment of the present specification, R14, R15 and R6 'to R15' are each independently, hydrogen; heavy hydrogen; Halogen group; And nitro groups, and at least one of R6 'to R13' is a nitro group.

According to an exemplary embodiment of the present specification, Formula 1 may provide a compound represented by Formula 4.

[Formula 4]

In Chemical Formula 4,

R1 to R5, R14, R15 and R6 'to R15' are the same as described above.

According to an exemplary embodiment of the present specification, in the general formula 1, at least one or more of R6 to R9 is provided a compound that is a halogen element.

According to an exemplary embodiment of the present specification, in the general formula 2 and 3, at least one or more of R9 'and R13' provides a compound that is a nitro group.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 provides a compound represented by any one of the following compounds.

Another embodiment of the present specification provides a colorant composition comprising the compound according to one embodiment of the present specification.

The color material composition may further include at least one of dyes and pigments in addition to the compound of Formula 1. For example, the color material composition may include only a compound according to an exemplary embodiment of the present specification, the compound of Formula 1 and one or more dyes, or a compound and one or more pigments according to an exemplary embodiment of the present specification Or a compound of Formula 1, one or more dyes, and one or more pigments.

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

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

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

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

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

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate , p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1 , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.

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

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

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

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

The monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.

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 ar Tate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but It is not limited only.

In one embodiment of the present specification, based on the total weight of solids in the resin composition, the content of the compound of Formula 1 is 5% by weight to 60% by weight, the content of the binder resin is 1% by weight to 60% by weight %, The content of the initiator is 0.1% to 20% by weight, the content of the multifunctional monomer is 0.1% to 50% by weight.

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

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

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, etc. may be used, but is not limited thereto.

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

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

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

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

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

These can be used individually or in combination of 2 or more types.

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

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

In an exemplary embodiment of the present specification, a photosensitive material prepared from the resin composition is provided.

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

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

Light sources for curing the resin composition according to the present specification include, but are not limited to, mercury vapor arcs, carbon arcs, Xe arcs, etc., which emit light having a wavelength of 250 nm to 450 nm.

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

In one embodiment of the present specification, a color filter including the photosensitive material is provided.

The color filter may be prepared using a resin composition containing the compound of 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.

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

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

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

Synthesis Example 1

Scheme 1

10 g (50.459 mmol) of 2,3-naphthalenedicarboxylic anhydride (A-1) was added to 30 ml of HNO3, and the reaction solution was gradually heated up and stirred at 95 ° C for 2 hours. The reaction solution was cooled to room temperature and precipitated in water. The precipitate was filtered under reduced pressure and dried in an 80 ° C. convection oven for one day to obtain A-2. A-2 was added to 50 ml of Acetic anhydride, and heated to 150 ° C. and stirred for 2 hours. The reaction was cooled to room temperature, filtered under reduced pressure, washed with a small amount of water to obtain 8.3 g (34.132 mmol) of A-3, with a yield of 67.64%.

Synthesis Example 2

Scheme 2

3 g (18.963 mmol) of 8-Aminoquinaldine (A-4) and 2.809 g (18.963 mmol) of Phthalic anhydride (A-5) were added to 3 g of Benzoic acid and 3 g of Methyl benzoate, and the mixture was gradually heated and stirred at 180 ° C. for 5 hours. The reaction was cooled to room temperature and precipitated in 100 ml of MeOH. The precipitate was filtered off under reduced pressure and washed with MeOH. Drying in an 80 ° C. convection oven for one day yielded 4.67 g (16.198 mmol) of A-6, with a yield of 85.4%.

Synthesis Example 3

Scheme 3

1.6-3 g (6.937 mmol) of A-3 and 2 g (6.937 mmol) of A-6 were added to 3 g of Benzoic acid and 3 g of Methyl benzoate, and the temperature was gradually increased and stirred at 200 ° C. for 3 hours. The reaction was cooled to room temperature and precipitated in 100 ml of MeOH. The precipitate was filtered off under reduced pressure and washed with MeOH. Drying in an 80 ° C. convection oven for 1 day yielded 12.422 g (4.717 mmol) of the product according to Scheme 3, with a yield of 68.0%.

Synthesis Example 4

Scheme 4

Under the same conditions as in Scheme 2 and Scheme 3, the resultant according to Scheme 4 was synthesized.

Synthesis Example 5

Scheme 5

Under the same conditions as in Scheme 2 and Scheme 3, the resultant according to Scheme 5 was synthesized.

Synthesis Example 6

Scheme 6

Under the same conditions as in Scheme 2 and Scheme 3, the resultant according to Scheme 6 was synthesized.

Synthesis Example 7

Scheme 7

Under the same conditions as in Scheme 2 and Scheme 3, the resultant according to Scheme 7 was synthesized.

Synthesis Example 8

Scheme 8

Under the same conditions as in Scheme 2 and Scheme 3, the resultant according to Scheme 8 was synthesized.

In the general formula (3) of the present application, any one of R10 'to R15' is a nitro group was synthesized in the same order and method as the result of Synthesis Examples 3 to 8.

Synthesis Example 9

Scheme 9

5 g (20.562 mmol) of A-3 and 3.253 g (20.562 mmol) of 8-Aminoquinaldine (A-4) were added to 5 g of Benzoic acid and 10 g of Methyl benzoate, and the mixture was gradually heated and stirred at 180 ° C. for 5 hours. The reaction was cooled to room temperature and precipitated in 150 ml of MeOH. The precipitate was filtered off under reduced pressure and washed with MeOH. Drying in an 80 ° C. convection oven for one day yielded 7.094 g (18.505 mmol) of A-17, with a yield of 90.0%.

Synthesis Example 10

Scheme 10

5 g (13.043 mmol) of A-17 and 1.932 g (13.043 mmol) of Phthalic anhydride (A-5) were added to 5 g of Benzoic acid and 10 g of Methyl benzoate, and the mixture was gradually heated and stirred at 200 ° C. for 3 hours. The reaction was cooled to room temperature and precipitated in 150 ml of MeOH. The precipitate was filtered off under reduced pressure and washed with MeOH. Drying in an 80 ° C. convection oven for one day yielded 5.022 g (9.781 mmol) of the product according to Scheme 10, with a yield of 74.97%.

Synthesis Example 11

Scheme 11

 Under the same conditions as in Scheme 9 and Scheme 10, the resultant according to Scheme 11 was synthesized.

Synthesis Example 12

Scheme 12

 Under the same conditions as in Scheme 9 and Scheme 10, the resultant according to Scheme 12 was synthesized.

Synthesis Example 13

Scheme 13

 Under the same conditions as in Scheme 9 and Scheme 10, the resultant according to Scheme 13 was synthesized.

In Formula 2 of the present application, any one of R6 'to R9', R14 and R15 is a nitro group was synthesized in the same order and method as the result of Synthesis Examples 10 to 13.

Example 1

5.554 g of the product according to Synthesis Example 3, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 measured by GPC, molecular weight distribution (PDI ) 2.0g, solid content (SC) 25%, solvent PGMEA) 10.376g, I-369 (BASF) 2.018g as photoinitiator, DPHA (Japanese gunpowder) 12.443g as photopolymerizable compound, solvent PGMEA (Propylene Glycol Mnomethyl Ether) Acetate) was prepared by mixing 68.593g and 1.016g of DIC F-475 with an additive.

Example 2

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 4 was used instead of the result of Synthesis Example 3 of Example 1.

Example 3

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 5 was used instead of the result of Synthesis Example 3 of Example 1.

Example 4

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 6 was used instead of the result of Synthesis Example 3 of Example 1.

Example 5

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 7 was used instead of the result of Synthesis Example 3 of Example 1.

Example 6

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 8 was used instead of the result of Synthesis Example 3 of Example 1.

Example 7

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 10 was used instead of the result of Synthesis Example 3 of Example 1.

Example 8

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 11 was used instead of the result of Synthesis Example 3 of Example 1.

Example 9

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 12 was used instead of the result of Synthesis Example 3 of Example 1.

Example 10

A compound was prepared in the same manner except that 5.554 g of the result of Synthesis Example 13 was used instead of the result of Synthesis Example 3 of Example 1.

Comparative Example 1

A compound was prepared in the same manner as in Example 1, except that the compound represented by Formula 5 was used instead of the result of Synthesis Example 3.

Formula 5

PCB Fabrication

The compounds prepared in Examples 1 and 2 and Comparative Example 1 were spincoated on glass (5 × 5 cm) and prebake 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 250 µm, and the exposure amount of 40 mJ / cm ² was irradiated on the entire surface of the substrate using an exposure machine.

Thereafter, the exposed substrate was developed in a developer (KOH, 0.05%) for 60 seconds, and post-baked at 230 ° C. for 20 minutes to prepare a substrate.

Heat resistance rating

Using a spectrometer (MCPD-Otsuka Co., Ltd.), a prebake substrate prepared under the above conditions was used to obtain a transmittance spectrum in the visible light range of 380 nm to 780 nm. In addition, the prebake substrate was further subjected to post bake at 230 ° C. for 20 minutes to obtain transmittance spectra in the same equipment and measurement range.

Using the obtained transmittance spectrum and C light source backlight, ΔEab was calculated using the obtained values E (L *, a *, b *) and shown in Table 2 below.

ΔE (L *, a *, b *) = {(ΔL *) 2+ (Δa *) 2+ (Δb *) 2} ^1/2

Small ΔE values indicate excellent color heat resistance.

Generally, when the value of ΔEab <3, it can be said that the color material is excellent in heat resistance.

The heat resistance measurement results of the compound according to the exemplary embodiment of the present application and Comparative Example 1 are shown in Table 1 below. In addition, as shown in Table 1, the compound according to an exemplary embodiment of the present application showed a color change (ΔEab) of 3 or less similarly to Comparative Example 1 (currently commercialized product).

ΔEab (PB-PrB) Example 1 0.87 Example 2 1.20 Example 3 0.14 Example 4 0.15 Example 5 0.62 Example 6 0.42 Example 7 0.35 Example 8 1.23 Example 9 0.39 Example 10 0.40 Comparative Example 1 0.29

Claims (14)

As a compound represented by the following formula (1),
Formula 1 is a compound represented by the following formula (2) or (3):
[Formula 1]

In Chemical Formula 1,
Y1 and Y2 are each independently a direct bond; Or CQ1Q2,
Two or more adjacent groups of Q1, Q2, R6 to R13 may combine with each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms,
Each of Q 1, Q 2, R 1 to R 5, and R 6 to R 13 that does not form a ring with an adjacent group is independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
[Formula 2]

[Formula 3]

In Chemical Formulas 2 and 3,
Y1, Y2, R1 to R13 are the same as defined in Formula 1,
R14, R15 and R6 'to R15' are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
At least one of R6 'to R9' of Formula 2, and at least one of R10 'to R13' of Formula 3 is a nitro group. delete As a compound represented by the following formula (1),
Formula 1 is a compound represented by the following formula (4):
[Formula 1]

In Chemical Formula 1,
Y1 and Y2 are each independently a direct bond; Or CQ1Q2,
Two or more adjacent groups of Q1, Q2, R6 to R13 may combine with each other to form at least one substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic hetero ring having 2 to 30 carbon atoms,
Each of Q 1, Q 2, R 1 to R 5, and R 6 to R 13 that does not form a ring with an adjacent group is independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
[Formula 4]

In Chemical Formula 4,
R1 to R5 are the same as defined in Formula 1,
R14, R15 and R6 'to R15' are each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
At least one of R6 'to R9', or at least one of R10 'to R13' is a nitro group. delete The method according to claim 1,
At least one of R 6 to R 9 of Formula 3 is a halogen element. The method according to claim 1,
At least one of R9 'and R13' is a nitro group. Compound represented by any one of the following compounds:

. Colorant composition comprising a compound according to any one of claims 1, 3 and 5 to 7. The color material composition according to claim 8, further comprising at least one of dyes and pigments. A compound according to any one of claims 1, 3 and 5 to 7; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent further comprising a solvent. The method according to claim 10,
The content of the compound is 5% to 60% by weight based on the total weight of solids in the resin composition,
The content of the binder resin is 1% by weight to 60% by weight,
The content of the multifunctional monomer is 0.1% by weight to 50% by weight,
The content of the photoinitiator is a resin composition of 0.1% by weight to 20% by weight. The photosensitive material manufactured using the resin composition of Claim 10. A color filter comprising the photosensitive material of claim 12. A display apparatus comprising the color filter of claim 13.