TW201710404A - Xanthene-based compound and photosensitive resin composition comprising the same - Google Patents

Abstract

The present specification provides a xanthene-based compound having a novel structure, a photosensitive resin composition including the same, a photosensitive material manufactured by using the same, a color filter, and a display device.

Description

Dibenzopyrans and photosensitive resin compositions containing the same

The present application claims priority to and the benefit of the Korean Patent Application No. 10-2015-0086200, filed on Jun. 17, 2015, in the Korean Intellectual Property Office, the entire contents of which is incorporated herein by reference. in.

The present invention relates to a dibenzopipen compound and a photosensitive resin composition containing the same. Further, the present invention relates to a color filter manufactured using the photosensitive resin composition and a display device including the same.

Recently, there is a need for an effect characterized by high brightness and high contrast ratio in color filters. In addition, one of the main objectives of the development of display devices is to differentiate the performance of the display device by improving the color purity and to improve the productivity of the manufacturing process.

Since the type of pigment used as the color material of the conventional color filter exists in a state in which the particles are dispersed in the color resist, it is difficult to adjust the brightness and the contrast ratio according to the adjustment of the size and distribution of the pigment particles. The pigment particles are aggregated in the color filter, and thus, the dilution and dispersibility are lowered, and multiple light scattering occurs due to the aggregated larger particles. The main cause of the decrease in contrast ratio is polarized light scattering. Efforts to improve brightness and contrast ratio by forming ultrafine pigment particles and stabilizing the pigment dispersion are continuing, but the freedom to select color materials to construct color coordinates of higher color purity display devices is limited. In addition, the use of developed color materials, particularly pigments, to disperse pigments has reached a critical point in improving the color purity, brightness and contrast ratio of color filters by using colored materials.

Therefore, there is a need to develop novel color materials that can improve color reproduction, brightness, and contrast ratio by enhancing color purity. [citation list] [patent document] Japanese Patent Laid-Open Application No. H9-87534

[Technical Problem] The present inventors intend to provide a dibenzopyran compound having a novel structure, a photosensitive resin composition containing the same, a color filter manufactured by using the same, and a display containing the same Device. [Technical solutions]

An exemplary embodiment of the present invention provides a compound represented by the following Chemical Formula 1. [Chemical Formula 1] In Chemical Formula 1, R ₁ to R ₆ are each independently selected from the group consisting of hydrogen; hydrazine; a halogen atom; a nitro group; a substituted or unsubstituted linear or branched group having 1 to 30 carbon atoms; An alkyl group; 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; To a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of up to 30 carbon atoms, R ₇ to R ₁₁ are each independently selected from the group consisting of: hydrogen; anthracene; an anionic group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group of 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and 2 to 30 carbons a substituted or unsubstituted monocyclic or polycyclic heteroaryl group, at least one of R ₇ to R ₁₁ being an anionic group, and R ₁₂ to R ₁₄ are each independently selected from the group consisting of: hydrogen; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; having 2 to 30 carbon atoms The substituted or unsubstituted monocyclic or polycyclic heteroaryl group; and anhydride group containing two nitrogen atoms, R ₁₅ and R ₁₆ are each independently selected from the group comprising of the: hydrogen; deuterium; anionic group; hydroxy a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic heteroaryl groups of up to 30 carbon atoms, or combined with each other to form substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon rings having 6 to 30 carbon atoms Or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, and L ₁ and L ₂ are each independently a direct bond; or a divalent linking group.

An exemplary embodiment of the present invention provides a color material composition comprising the compound of Chemical Formula 1.

An exemplary embodiment of the present invention may provide a resin composition comprising: a compound represented by Chemical Formula 1; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

An exemplary embodiment of the present invention provides a photosensitive material produced by using the resin composition.

An exemplary embodiment of the present invention provides a color filter including the photosensitive material.

An exemplary embodiment of the present invention provides a display device including the color filter. [Advantageous effect]

The dibenzopyran compound according to an exemplary embodiment of the present invention can be used as a color material in a photosensitive resin composition, and the color purity can be emitted from the light source by blending as compared with the color material of the related art. The absorption and transmission spectra of the spectrum and color filters are enhanced.

Further, a dibenzopyran compound according to an exemplary embodiment of the present invention can be used as a color material to improve color reproduction, brightness, and contrast ratio.

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

When a component "includes" a constituent element in the present invention, unless otherwise specifically described, it is not intended to exclude another constituent element, and it is intended to include another constituent element.

An exemplary embodiment of the present invention provides a compound represented by Chemical Formula 1.

Examples of the substituent of the compound represented by Chemical Formula 1 will be described below, but are not limited thereto.

In the present invention, the term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: hydrazine; halogen atom; alkyl group; alkenyl group; alkoxy group; Alkyl; arylalkyl; aryl; aryloxy; aralkyl; aralkenyl; alkylthiol; alkylsulfonyloxy; arylsulfonyloxy; boron; Amine; arylalkylamine; arylamine; heteroaryl; carbazolyl; propylene sulfhydryl; acrylate group; ether group; nitrile group; nitro group; hydroxyl group; cyano group; heterocyclic group, including N One or more of O, S and P atoms, and an anionic group, or no substituent.

In the present invention, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms thereof is not particularly limited, but may be from 1 to 30. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and the like, but are not limited thereto.

In the present invention, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms thereof is not particularly limited, but may be 2 to 25. Specific examples thereof include an alkenyl group in which an aryl group is substituted, such as an anthracenyl group and a styryl group, but are not limited thereto.

In the present invention, the alkoxy group may be a straight chain or a branched chain, and the number of carbon atoms thereof is not particularly limited, but may be from 1 to 30.

In the present invention, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof may be from 3 to 20, and the cycloalkyl group may especially be a cyclopentyl group or a cyclohexyl group.

In the present invention, examples of the halogen atom include fluorine, chlorine, bromine or iodine.

In the present invention, the phenoxy group is not particularly limited, but may have a carbon number of from 3 to 20.

In the present invention, the carboxyl group is not particularly limited, but the number of carbon atoms thereof may be from 1 to 30.

In the present invention, the carboxylate group is not particularly limited, but the number of carbon atoms thereof may be 2 to 30. Specific examples thereof include a carboxylic acid methyl group, a carboxylic acid ethyl group, an carboxylic acid isopropyl group, a carboxylic acid benzyl group, and the like, but are not limited thereto.

In the present invention, the carboxylate group and the sulfonate group are each a salt having a monovalent cation, and the monovalent cation may be any one selected from the group consisting of Na ⁺ , K ⁺ and quaternary ammonium cations, but are not limited thereto. Specific examples of the quaternary ammonium cation include a tetraalkylammonium cation such as a tetramethylammonium cation, an ethyltrimethylammonium cation, and a tetrapropylammonium cation, but are not limited thereto.

In the present invention, the alkoxycarbonyl group is not particularly limited, but may have a number of carbon atoms of from 1 to 30. As a specific example of one of the alkyl groups in the alkoxycarbonyl group, the same description as the description of the alkyl group can be applied. Specific examples thereof include an alkoxycarbonyl group having an alkyl group described in a specific example of the alkyl group, but are not limited thereto.

In the present invention, the sulfonic acid group is not particularly limited, but may have a number of carbon atoms of from 1 to 30.

In the present invention, specific examples of the sulfonate group include an alkylsulfonyl group having 1 to 4 carbon atoms, such as a methanesulfonyl group, an ethanesulfonyl group, and a hexanesulfonyl group, but are not limited thereto.

In the present invention, for the aralkyl group, specifically, the number of carbon atoms in the aryl moiety is from 6 to 49, and the number of carbon atoms in the alkyl moiety is from 1 to 44. Specific examples thereof include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, α-A Benzomethyl, α,α-dimethylbenzyl, α,α-methylphenylbenzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p-fluorobenzyl, 3,5-difluorobenzyl, α,α-trifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α-phenoxybenzyl, α- Benzyloxybenzyl, naphthylmethyl, naphthylethyl, naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanobenzo Base, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl and the like, but are not limited thereto.

In the present invention, the description of the aryl group which will be described later can be applied to the aryl moiety of the aralkenyl group, and the description of the alkenyl group described above can be applied to the alkenyl moiety.

In the present invention, 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 thereof is not particularly limited, but may be from 6 to 40. 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 thereof is not particularly limited, but may be from 10 to 40. Specific examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group, and the like, but are not limited thereto.

In the present invention, the mercapto group may have a substituent, and the substituents may be combined with each other to form a spiro structure. Examples of 茀基 include , , , And similar groups.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbon atoms thereof is not particularly limited, but may be 2 to 30. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, anthracenyl Azinyl, quinolyl, isoquinolyl, fluorenyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, dibenzo Thienyl, benzofuranyl, dibenzofuranyl and the like, but are not limited thereto.

In the present invention, alkylene means that there are two bonding sites in the alkane. The alkylene group may be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms of the alkyl group is not particularly limited, but may be 2 to 25.

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

In the present invention, the description of the heteroaryl group can be applied to the heterocyclic ring except that the heterocyclic ring is not a monovalent group.

According to an exemplary embodiment described above, R ₁ to R ₆ may each independently be selected from the group consisting of: hydrogen; hydrazine; a halogen atom; a nitro group; a substituted with 1 to 30 carbon atoms or An unsubstituted linear or branched alkyl group; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; and a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms or Polycyclic aryl; and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms.

According to another exemplary embodiment of the present invention, R ₁ to R ₆ may each independently be selected from the group consisting of hydrogen; hydrazine; a substituted or unsubstituted linear chain having 1 to 20 carbon atoms; Or branched alkyl; substituted or unsubstituted alkoxy having 1 to 20 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to still another exemplary embodiment of the present invention, R ₁ to R ₆ may each independently be selected from the group consisting of hydrogen; hydrazine; a substituted or unsubstituted linear chain having 1 to 10 carbon atoms; Or branched alkyl; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 10 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic having 2 to 10 carbon atoms Heteroaryl.

According to still another exemplary embodiment of the present invention, R ₁ to R ₆ may be hydrogen.

Further, R ₇ to R ₁₁ may each independently be selected from the group consisting of hydrogen; hydrazine; an anionic group; a hydroxyl group; a substituted or unsubstituted linear or branched alkane 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; And at least one of R7 to R11 may be an anionic group.

According to another exemplary embodiment of the present invention, R ₇ to R ₁₁ may each independently be selected from the group consisting of hydrogen; hydrazine; an anionic group; substituted or unsubstituted having 1 to 20 carbon atoms a straight or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic ring having 2 to 20 carbon atoms Or a polycyclic heteroaryl group, and at least one of R7 to R11 may be an anionic group.

According to still another exemplary embodiment of the present invention, R ₇ to R ₁₁ may each independently be selected from the group consisting of hydrogen; hydrazine; an anionic group; substituted or unsubstituted having 1 to 10 carbon atoms a straight or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms; and a substituted or unsubstituted monocyclic ring having 2 to 10 carbon atoms Or a polycyclic heteroaryl group, and at least one of R7 to R11 may be an anionic group.

According to still another exemplary embodiment of the present invention, R ₇ to R ₁₁ may each independently be hydrogen; or an anionic group, and at least one of R ₇ to R ₁₁ may be an anionic group.

Further, R ₁₂ may be selected from the group consisting of hydrogen; hydrazine; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; substituted with 2 to 30 carbon atoms or An unsubstituted monocyclic or polycyclic heteroaryl group; and a dianhydride group containing a nitrogen atom.

According to another exemplary embodiment of the present invention, R ₁₂ may be selected from the group consisting of: hydrogen; hydrazine; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group to 20 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to still another exemplary embodiment of the present invention, R ₁₂ may be selected from the group consisting of hydrogen; hydrazine; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group to 10 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to still another exemplary embodiment of the present invention, R ₁₂ may be a dianhydride group containing a nitrogen atom.

Further, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of: hydrogen; hydrazine; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 30 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to another exemplary embodiment of the present invention, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of hydrogen; hydrazine; a substituted or unsubstituted monocyclic ring having 6 to 20 carbon atoms; Or a polycyclic aryl group; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to still another exemplary embodiment of the present invention, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of hydrogen; hydrazine; a substituted or unsubstituted monocyclic ring having 6 to 10 carbon atoms; Or a polycyclic aryl group; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to still another exemplary embodiment of the present invention, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of: hydrogen; substituted or unsubstituted phenyl; and dianhydride group containing a nitrogen atom. .

According to still another exemplary embodiment of the present invention, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of: hydrogen; a phenyl group substituted with at least one selected from the group consisting of a methyl group and an anionic group; And a dianhydride group containing a nitrogen atom.

Further, R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen; hydrazine; an anionic group; a hydroxyl group; a substituted or unsubstituted linear or branched 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, or Combination of each other to form a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms .

According to another exemplary embodiment of the present invention, R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen; hydrazine; an anionic group; a hydroxyl group; substituted or unsubstituted having 1 to 20 carbon atoms a straight or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic ring having 2 to 20 carbon atoms Or a polycyclic heteroaryl group, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted having 2 to 20 carbon atoms; Monocyclic or polycyclic heteroaryl.

According to still another exemplary embodiment of the present invention, R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen; hydrazine; an anionic group; a hydroxyl group; substituted or unsubstituted having 1 to 20 carbon atoms a straight or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic ring having 2 to 20 carbon atoms Or a polycyclic heteroaryl group, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted having 2 to 20 carbon atoms; Monocyclic or polycyclic heteroaryl.

According to another exemplary embodiment of the present invention, R ₁₅ and R ₁₆ are each independently selected from the group consisting of hydrogen; hydrazine; an anionic group; a hydroxyl group; substituted or unsubstituted having 1 to 10 carbon atoms a straight or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms; and a substituted or unsubstituted monocyclic ring having 2 to 10 carbon atoms Or a polycyclic heteroaryl group, or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted having 2 to 10 carbon atoms; Monocyclic or polycyclic heteroaryl.

According to still another exemplary embodiment of the present invention, R ₁₅ and R ₁₆ may each independently be selected from the group consisting of hydrogen; hydrazine; and an anionic group, and may be combined with each other to form a substituted or unsubstituted benzene. ring.

Further, L ₁ and L ₂ may each independently be a direct bond; or a divalent linking group, more specifically, a direct bond or an alkyl group, and even more specifically, have 1 to 6 carbon atoms. Unsubstituted alkylene.

Further, another exemplary embodiment of the present invention can provide a compound in which Chemical Formula 1 is represented by the following Chemical Formula 2. [Chemical Formula 2]

In Chemical Formula 2, R ₁ to R ₁₁ , R ₁₃ to R ₁₆ and L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₇ and R ₁₈ are each independently the same as those described for R ₁₅ and R ₁₆ .

Further, another exemplary embodiment of the present invention can provide a compound in which Chemical Formula 1 is represented by the following Chemical Formula 3. [Chemical Formula 3]

In Chemical Formula 3, R ₁ to R ₁₄ , L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₉ may be selected from the group consisting of hydrogen; hydrazine; substituted with 1 to 20 carbon atoms or Unsubstituted linear or branched alkyl group; substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; substituted or unsubstituted monocyclic or poly 6 to 30 carbon atoms a cycloaryl group; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; a halogen atom; a nitro group; a phenoxy group; a carboxyl group; a carboxylate group; a carboxylate group; Alkoxycarbonyl; hydroxy; sulfonate; sulfonate; sulfonate; -SO ₂ NHR ₂₁ group; and -SO ₂ NR ₂₂ R ₂₃ , R ₂₁ to R ₂₃ may each independently have 1 to The alkyl group of 30 carbon atoms, m may be an integer of 1 to 4, and when m is 2 or more, R ₁₉ may be the same or different from each other.

According to another exemplary embodiment of the present invention, R ₁₉ may be selected from the group consisting of hydrogen; hydrazine; a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted alkoxy group to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; substituted with 2 to 20 carbon atoms Or unsubstituted monocyclic or polycyclic heteroaryl; sulfonic acid group; sulfonate group; sulfonate group; -SO ₂ NHR ₂₁ group; and -SO ₂ NR ₂₂ R ₂₃ , R ₂₁ to R ₂₃ Each may independently be an alkyl group having 1 to 20 carbon atoms, m may be an integer of 1 to 4, and when m is 2 or more, R ₁₉ may be the same or different from each other.

According to yet another exemplary embodiment of the present invention, the group consisting of R ₁₉ may be selected from: hydrogen; deuterium; a sulfonic acid group; a sulfonic acid ester group; sulfonate group; -SO ₂ NHR ₂₁ group; and -SO ₂ NR ₂₂ R ₂₃ , R ₂₁ to R ₂₃ may each independently be an alkyl group having 1 to 10 carbon atoms, m may be an integer of 1 to 4, and when m is 2 or more, R ₁₉ may be each other Same or different.

According to still another exemplary embodiment of the present invention, R ₁₉ may be hydrogen; or hydrazine.

Further, another exemplary embodiment of the present invention can provide a compound in which Chemical Formula 1 is represented by the following Chemical Formula 4. [Chemical Formula 4]

In Chemical Formula 4, R ₁ to R ₁₁ , R ₁₃ , R ₁₄ , L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₉ and R ₂₀ are each independently the same as described for R ₁₉ .

However, in addition, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be a substituted monocyclic aryl group having 6 to 30 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be a substituted phenyl group having 6 to 30 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be an alkyl-substituted phenyl group having 6 to 30 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be an alkyl-substituted phenyl group having 6 to 10 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be a methyl substituted phenyl group having 6 to 10 carbon atoms.

Further, in Chemical Formula 4, R ₁₃ and R ₁₄ may each independently be 2,6-dimethylphenyl.

When the small hydrogen (H) is substituted at the second and sixth positions, a plurality of absorption bands rotated by the substituent exist in the case of having a single bond characteristic, and therefore, the absorption wavelength region is widened, and the transmission of the short wavelength is performed. The rate is reduced.

Further, when a substituent having two or more than one carbon atom larger than a methyl group is introduced into the second and sixth positions, the substituent generates steric repulsion with another alkyl substituent of the nitrogen atom, and Therefore, it is difficult to maintain the flatness, and the wavelength at which λ is the _largest is shortened (hypsochromic shift) and the transmittance at the short wavelength is lowered.

When different substituents are introduced into the 2nd and 6th positions, the substituents may be more diversely rotated than in the case where the substituents are identical to each other, and for the reasons there are a plurality of absorption bands, and thus The absorption wavelength region is widened, and the transmittance of the short wavelength is lowered. Thus, the same substituents can be introduced into the 2nd and 6th positions, and in particular, the methyl group can exhibit the best color characteristics.

Further, the anionic group may be at least one selected from the group consisting of -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ ^- Z ⁺ , -CO ₂ Ra, -SO ₃ Rb and -SO ₃ NRcRd, Z ⁺ represents ⁺ N(Re) ₄ , Na ⁺ or K ⁺ , and Ra to Re may each independently represent a carbon atom having 1 to 20 carbon atoms. a substituted or unsubstituted linear or branched alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted having 2 to 30 carbon atoms Substituted monocyclic or polycyclic heteroaryl.

According to another exemplary embodiment of the present invention, the anionic group may be at least one selected from the group consisting of: -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ ^- Z ⁺ , -CO ₂ Ra, -SO ₃ Rb and -SO ₃ NRcRd, Z ⁺ represents ⁺ N(Re) ₄ , Na ⁺ or K ⁺ , and Ra to Re can each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and having 2 to A substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 20 carbon atoms.

According to still another exemplary embodiment of the present invention, the anionic group may be at least one selected from the group consisting of: -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -SO ₃ Rb, and -SO ₃ NRcRd, Z ⁺ represents Na ⁺ or K ⁺ , and Ra to Rd each independently represent a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; having 6 to 10 A substituted or unsubstituted monocyclic or polycyclic aryl group of one carbon atom; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms.

According to still another exemplary embodiment of the present invention, the anionic group may be -SO ₃ ^- or -SO ₃ ^- Na ⁺ .

The anionic group may itself have an anion or may exist as a complex with another cation. Thus, the sum of the total charges of the molecules of the compounds of the invention may vary depending on the number of substituted anionic groups. Since an amine group of the compound of the present invention has a cation, the sum of the total charges of the molecules may have a value derived from an anion having a value obtained by subtracting 1 from the number of substituted anionic groups to 0.

Further, when the alkylphthalimide is substituted with a nitrogen atom, the compound in which the alkylphthalimide is substituted enhances the dispersibility of the pigment and inhibits the conversion of the pigment crystal at a high temperature at a high temperature. Stabilize the pigment.

In addition, the phthalic acid substituted dibenzopyran can enhance the dispersibility of the pigment which is used together to expect better CR characteristics, and can stabilize the pigment in the crystal transformation of the pigment and at a high temperature. Reduce color changes. That is, by stabilizing the pigment, the dispersibility and storage stability can be improved and the color change can be reduced.

Therefore, the dibenzopyran compound in which the methyl substituted phenyl group and the phthalimido group are introduced into the second and sixth positions can exhibit excellent color characteristics and can have a stable pigment. Improves dispersion and storage stability and reduces the effects of color changes.

Further, the compound represented by Chemical Formula 1 may be represented by any of the following chemical formulas, but is not always limited thereto.

Furthermore, an exemplary embodiment of the present invention can provide a color material composition comprising the compound.

In addition to the compound of Chemical Formula 1, the color material composition may further comprise at least one of a dye and a pigment. For example, the color material composition may also include only the compound of Chemical Formula 1, but may include the compound of Chemical Formula 1 and one or more dyes, or may comprise the compound of Chemical Formula 1 and one or more pigments, or may comprise a compound of Chemical Formula 1. One or more dyes and one or more pigments.

An exemplary embodiment of the present invention may provide a resin composition comprising the color material composition.

According to an exemplary embodiment of the present invention, the resin composition may further include: a compound represented by Chemical Formula 1; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

The binder resin is not particularly limited as long as the binder resin can exhibit physical properties (such as strength and developability) of the film produced by using the resin composition.

As the binder resin, a copolymer resin which imparts mechanical strength to a polyfunctional monomer and an alkali-soluble monomer can be used, and may further contain a binder which is generally used in the art.

The polyfunctional monomer imparting mechanical strength to the film may be any one or more of an unsaturated carboxylic acid ester, an aromatic ethylene, an unsaturated ether, an unsaturated quinone imide, and an acid anhydride.

Specific examples of the unsaturated carboxylic acid ester may be selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, ( Methyl) dimethylaminoethyl acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, (A) Ethylhexyl acrylate, 2-phenoxyethyl (meth)acrylate, tetrahydrofuran (meth)acrylate, hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, ( 2-hydroxy-3-chloropropyl methacrylate, 4-hydroxybutyl (meth) acrylate, decyl octyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, methoxytriethylene glycol (methyl) Acrylate, methoxytripropylene glycol (meth) acrylate, poly(ethylene glycol) methyl ether (meth) acrylate, phenoxy diethylene glycol (meth) acrylate, p-nonyl phenoxy Polyethylene glycol (meth) acrylate, pair Phenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexa(meth)acrylate Fluoroisopropyl ester, octafluoropentyl (meth)acrylate, heptafluorodecyl (meth)acrylate, tribromophenyl (meth)acrylate, α-methylol methacrylate, α-hydroxymethyl Ethyl acrylate, propyl α-hydroxymethyl acrylate, and butyl α-hydroxymethacrylate, but are not limited thereto.

Specific examples of the aromatic vinyl monomer may be selected from the group consisting of styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxy Styrene and (o-, m-, p-)-chlorostyrene, but are not limited thereto.

Specific examples of the unsaturated ether 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 quinone imine may be selected from the group consisting of N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4- Hydroxyphenyl) maleimide and N-cyclohexyl maleimide, but are not limited thereto.

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

The monomer which imparts alkali solubility is not particularly limited as long as the monomer contains an acid group, and it is preferred to use one or more selected from the group consisting of (meth)acrylic acid, crotonic acid, and clothing. Tannic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth)acryloyloxyphthalate) Ethyl ester, mono-2-((meth)propenyloxy) succinate, and ω-carboxypolycaprolactone mono(meth)acrylate, but the monomer is not limited thereto.

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

The polyfunctional monomer is a monomer for forming a photoresist phase by light, and may especially be a mixture of one selected from the group consisting of or a mixture of two or more of the following: propylene glycol methacrylic acid Ester, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, double Phenoxyethanol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol IV Methacrylate and dipentaerythritol hexamethacrylate.

The photoinitiator is not particularly limited as long as the photoinitiator is an initiator which generates a radical by light to initiate crosslinking, but may be one or more selected from the group consisting of: For example, an acetophenone compound, a biimidazole compound, a triazine compound, and an anthraquinone compound.

Examples of the acetophenone compound include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1 a ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Benzoin, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholinyl-1-propan-1-one, 2-Benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino-1 -(4-morpholinylphenyl)-butan-1-one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one, and the like , but not limited to this.

Examples of biimidazole compounds include 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 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'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, and Analogous, but not limited to.

Examples of triazine compounds include 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-double (trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine- 6-yl]phenylthio}acetate, benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]thio} acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloro) Methyl)-s-triazin-6-yl]phenylthio}propanamide, 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2, 4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3,-butadienyl-s-triazine, 2-trichloromethyl-4-amino -6-p-methoxystyryl-s-triazine, and the like, and is not limited thereto.

Examples of terpenoids include 1-(4-phenylthio)phenyl-2-(p-benzoylhydrazinyl)-1,2-octanedione (CIBA-GEIGY Corp., CGI 124), 1-(9-ethyl)-6-(2-methylbenzimid-3-yl)-1-(O-acetyl)-ethanone (CGI 242), N-1919 (Adeka Corporation), and the like, without being limited thereto.

The solvent may be one or more selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, cellosolve, ethyl stilbene, tetrahydrofuran, 1 ,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol ether, propylene glycol dimethyl ether, propylene glycol ethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether , chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, hexane , heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxy Propanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate , ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but are not limited thereto.

According to an exemplary embodiment of the present invention, the content of the compound represented by Chemical Formula 1 is from 5% by weight to 60% by weight based on the total weight of the solid content of the resin composition, and the content of the binder resin is from 1% by weight to 60% by weight. The content of the photoinitiator is from 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight.

The total weight of the solid content means the sum of the total weights of the components other than the solvent in the resin composition. The basis of the weight % of the solid content and the solid content of each component can be measured by a general analytical method (such as liquid chromatography or gas chromatography) used in the art.

According to an exemplary embodiment of the present invention, the resin composition may further contain an antioxidant.

According to an exemplary embodiment of the present invention, the antioxidant is contained in an amount of from 0.1% by weight to 20% by weight based on the total of the solid content of the resin composition.

According to an exemplary embodiment of the present invention, the resin composition further comprises one or two or more additives selected from the group consisting of: a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, Surfactants, thermal polymerization inhibitors, UV absorbers, dispersants, and leveling agents.

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

It is possible to use one or more of the following groups to be used as a photocrosslinking sensitizer: a benzophenone compound such as benzophenone or 4,4-bis(dimethylamino)diphenyl Methyl ketone, 4,4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-p-benzoyl benzoate, 3, 3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetrakis(t-butylperoxycarbonyl)benzophenone; anthrone compounds such as 9-fluorenone, 2-Chloro-9-fluorenone and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1- Chloro-4-propoxythioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthone compounds such as xanthones and 2-methyloxaxanone Terpenoids such as hydrazine, 2-methyl hydrazine, 2-ethyl hydrazine, tert-butyl hydrazine, and 2,6-dichloro-9,10-fluorene; acridine compounds, Such as 9-phenyl acridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), and 1,3-bis(9-acridinyl) Propane; dicarbonyl compound, such as benzyl, 1,7 , 7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione and 9,10-phenanthrenequinone; phosphine oxide compounds such as 2,4,6-trimethylbenzene oxide Mercapto diphenylphosphine and bis(2,6-dimethoxybenzylidene)-2,4,4-trimethylpentylphosphine; benzoate compounds such as methyl-4-(di) Methylamino)benzoate, ethyl-4-(dimethylamino)benzoate and 2-n-butoxyethyl-4-(dimethylamino)benzoate; amine group Agents such as 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene)cyclohexanone, and 2,6- Bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; coumarine compounds such as 3,3-carbonylvinyl-7-(diethylamino) Bean, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzylidinyl-7-(diethylamino)coumarin, 3-benzamide Benzyl-7-methoxy-coumarin and 10,10-carbonyl bis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1] - benzopyrano[6,7,8-ij]-quinolizin-11-one; chalcone compounds such as 4-diethylamine-chalcone and 4-azidobenzylidene Acetophenone (4-azidebenzalacetophe None); and 2-benzylidene methylene and 3-methyl-b-naphthylthiazoline.

A curing accelerator is used in order to increase curing and mechanical strength, and in particular, it is possible to use one or more of the following groups: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoene Oxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis(3-mercaptopropionate), pentaerythritol-three ( 3-mercaptopropionate), pentaerythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate), and trishydroxyl Methylpropane-tris(3-mercaptopropionate).

As the adhesion promoter used in the present specification, it is possible to select and use a methacrylonitrile decane coupling agent (such as methacryloxypropyltrimethoxydecane or methacryloxypropyldimethoxy). One or more of decane, methacryloxypropyltriethoxydecane, and methacryloxypropyldimethoxydecane, and as alkyltrimethoxydecane, it is possible to select and One or more of octyltrimethoxydecane, dodecyltrimethoxydecane, octadecyltrimethoxydecane, and the like are used.

The surfactant is an anthrone-based surfactant or a fluorine-based surfactant, and in particular, as an anthrone-based surfactant, it is possible to use 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, manufactured by BYK-Chemie Co., Ltd.; Fluorine surfactants, it is possible to use 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-14 41. TF-1442 and the like, which are manufactured by Dai Nippon Ink & Chemicals (DIC) Co., Ltd., but the surfactant is not limited thereto.

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

Specific examples of antioxidants include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; hindered phenol-based primary antioxidants such as 2,6-di-t-butyl-p-cresol, octadecyl -3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[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-hydroxybenzyl)benzene, 3,5-di third Diethyl butyl-4-hydroxybenzyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g, tert-butylphenol 4,4 '-Butyl-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or bis[3,3-dual (4'-hydroxy-3'-t-butylphenyl)butyric acid] glycol ester; amine secondary antioxidant such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N , N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl p-phenylenediamine; sulfur secondary antioxidants such as dilauryl disulfide, dilauryl thiopropionate Ester, distearyl thiopropionate, mercaptobenzothiazole or tetramethylbismethylthiocarbamate disulfide -3-(laurylthio)propionate]methane; or a phosphite secondary antioxidant such as triphenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, Bis(2,4-dibutylphenyl)pentaerythritol diphosphite or (1,1'-biphenyl)-4,4'-diylbisphosphinic acid tetra[2,4-bis(1,1 -Dimethylethyl)phenyl]ester.

As the UV absorber, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but The UV absorber is not limited thereto, and those generally used in the art can be used.

The thermal polymerization inhibitor may comprise one or more selected from the group consisting of: p-anisole, hydroquinone, catechol, tert-butylcatechol, N-nitrosophenylhydroxyl Amine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, pyrrogarole, benzoquinone, 4,4-thiol (3 -methyl-6-tert-butylphenol), 2,2-methylenebis(4-methyl-6-tert-butylphenol), 2-mercaptoimidazole, and phenothiazine, but are not limited thereto. And may include those generally known in the art.

The dispersing agent can be used in a method of adding the inside of the dispersing agent to the pigment (in a form in which the pigment is subjected to surface treatment in advance) or a method of externally adding the dispersing agent to the pigment. As the dispersing agent, a composite type, nonionic, anionic or cationic dispersing agent can be used, and examples thereof include fluorines, esters, cationics, anionics, amphoteric surfactants, and the like. These can be used singly or in combination of two or more thereof.

Specific examples of the dispersing agent include one or more selected from the group consisting of polyalkylene glycol and esters thereof, polyalkylene oxide polyols, ester alkylene oxide adducts, and alcohol alkylene oxide additions. And sulfonate, sulfonate, carboxylic acid ester, carboxylate, alkylguanamine alkylene oxide adduct and alkylamine, but are not limited thereto.

The leveling agent can be polymeric or non-polymeric. Specific examples of the polymerization leveling agent include polyethyleneimine, polyamine amine, and a reaction product of an amine and an epoxide, and specific examples of the non-polymerization leveling agent include a non-polymerized sulfur-containing and non-polymerized nitrogen-containing compound, but the examples are not Limited thereto, and those generally used in the art can be used.

An exemplary embodiment of the present invention provides a photosensitive material produced from the resin composition.

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

The coating method is not particularly limited, but a spray coating method, a roll coating method, a spin coating method, and the like can be used, and in general, a spin coating method is widely used. Further, a coating film is formed, and then, in some cases, the residual solvent may be partially removed under reduced pressure.

Examples of the light source for curing the resin composition according to the present invention include a mercury vapor arc, a carbon arc, an Xe arc, and the like, which emit light at a wavelength of from 250 nm to 450 nm, but are not limited thereto.

The resin composition according to the present invention can be used in the following: a pigment dispersion type photosensitive material for producing a color filter of a thin film transistor liquid crystal display (TFT LCD), for forming a thin film transistor liquid crystal a black matrix of a display (TFT LCD) or a photosensitive material of an organic light emitting diode, a photosensitive material for forming an overcoat layer, a pillar spacer photosensitive material, a photocurable coating material, a photocurable ink, and a photocurable An adhesive, a printing plate, a photosensitive material for a printed circuit board, a photosensitive material for a plasma display panel (PDP), and the like, and the use thereof is not particularly limited.

An exemplary embodiment of the present invention provides a color filter including the photosensitive material.

The color filter can be produced by using a resin composition containing the compound represented by Chemical Formula 1. The color filter can be formed by coating a resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.

The resin composition according to an exemplary embodiment of the present invention has excellent heat resistance and thus undergoes a slight color change by heat treatment, and thus can provide higher color reproduction even when a color filter is manufactured by a curing process Range and high brightness and high contrast color filters.

The substrate may be a glass plate, a tantalum wafer, and a plastic base material such as a polyethersulfone (PES) and a polycarbonate (PC) plate, and the type thereof is not particularly limited.

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

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

A lattice-type black pattern called a black matrix can be placed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as a material for a black matrix. In this case, it is possible to use a method of depositing chromium on the entire glass substrate and patterning by etching. However, in view of the higher cost in the process, the higher reflectivity of chromium, and the environmental pollution caused by chromium wastewater, it is possible to use a resin black matrix by a pigment dispersion method in which fine treatment is possible.

The black matrix according to an exemplary embodiment of the present invention may use a black pigment or a black dye as a color material. For example, carbon black may be used alone, or a mixture of carbon black and color pigment may be used, and in this case, since the coloring pigment having a light-shielding property is mixed, there is an advantage that the strength of the film or the adhesion to the substrate is not Reduce, even if the amount of color material is relatively increased.

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

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

Hereinafter, the present invention will be described in detail with reference to examples for specifically describing the present invention. However, the examples according to the present invention may be modified in various forms, and should not be construed as limiting the scope of the invention to the examples described below. The present invention is provided to more fully explain the present invention to those of ordinary skill in the art. [Experimental Example 1] Synthesis of a compound

Compound 1 is produced by a reaction such as the following Reaction Formula 1. Reaction formula 1

5 grams (8.710 millimoles) A-1, 8.233 grams (34.838 millimoles) B-1 and 4.815 grams (34.5838 millimoles) K ₂ CO _{3 were} placed in 100 ml of NMP and stirred at 95 ° C. The resulting mixture was allowed to stand for 12 hours. Then, the solvent was removed under reduced pressure, 200 ml of water was placed in the precipitate, and the resulting mixture was stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. And subsequently, the dried precipitate was separated by column chromatography. (solubilizer-MC: MeOH)

Thus, 6 g (3.322 mmol) of Compound 1 was obtained, and the yield was 72%.

The results are as follows. Ionization mode = APCI +: m / z = 949 [M + H] +, accurate mass: 948

The measurement results of ¹ H-NMR of Compound 1 are as follows. ¹ H NMR (500MHz, DMSO, ppm): 8.03 (m, 11H), 7.69~7.18 (m, 10H), 6.99~6.95 (t, 1H), 6.80~6.01 (dd, 1H), 5.93~5.85 (dd , 1H), 4.06~3.79(m, 4H), 3.72~3.60(m, 4H), 2.17~1.70(m, 16H)

Further, Compound 2 was produced by the following Reaction Formula 2. Reaction formula 2

5 g (7.388 mmol) of Acid Red 289 and 4.09 g (29.554 mmol) of K ₂ CO _{3 were} placed in 100 ml of NMP, and the resulting mixture was stirred at 95 ° C for 12 hours. And then, the solvent was removed under reduced pressure, brine 100 was added to the precipitate, and the resulting mixture was stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours.

Thus, 7.3 g (6.945 mmol) of a color material containing Compound 2 as a main product was obtained, and the yield was 94%.

Further, Compound 3 was produced by the following Reaction Formula 3. Reaction formula 3

CHCl ₃ and 7.4 g of DMF were placed in a container at 0 °C. 2.479 g (20.835 mmol) of SOCl _{2 was} placed in the mixture, and the resulting mixture was additionally stirred at 0 ° C for 30 minutes. To this was slowly added dropwise 7.3 g (6.945 mmol) of a color material containing Compound 2 as a main product. And then, the resulting mixture was warmed to 35 ° C and stirred for 1 hour and 30 minutes. Further, the mixture was cooled to 0 ° C, 2.593 g (20.835 mmol) of 2-ethylhexylamine was added dropwise thereto, and 7.028 g (69.45 mmol) of Et ₃ N was added thereto dropwise, and stirred at normal temperature. The resulting mixture was 16 hours. The solvent was removed under reduced pressure, and water and MC were added thereto for extraction. The organic layer MgSO _4, and then the solvent was removed under reduced pressure and the product was dried at 80 deg.] C for 12 hours.

Thus, 2.772 g (2.431 mmol) of a color material containing Compound 3 as a main product was obtained, and the yield was 35%.

Further, Compound 4 was produced by the following Reaction Formula 4. Reaction formula 4

1.43 g (2.732 mmol) D-1, 2.99 g (9.490 mmol) B-1 and 1.31 g (9.490 mmol) K ₂ CO _{3 were} placed in 20 ml of NMP and stirred at 95 ° C. The resulting mixture was allowed to stand for 12 hours. Then, the solvent was removed under reduced pressure, 200 ml of water was placed in the precipitate, and the resulting mixture was stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. And subsequently, the dried precipitate was separated by column chromatography. (solubilizer-MC: MeOH)

Thus, 1.622 g (1.912 mmol) of Compound 4 was obtained, and the yield was 70%.

Ionization mode = APCI +: m / z = 977 [M + H] +, accurate mass: 976

Further, Compound 5 is produced by the following Reaction Formula 5. Reaction formula 5

The 1.608 g (2.732 mmol) E-1,2.99 g (9.490 mmol) B-1 and 1.31 g (9.490 mmol) K ₂ CO ₃ into 20 ml of NMP and stirred at 95 deg.] C The resulting mixture was allowed to stand for 12 hours. Then, the solvent was removed under reduced pressure, 200 ml of water was placed in the precipitate, and the resulting mixture was stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. And subsequently, the dried precipitate was separated by column chromatography. (solubilizer-MC: MeOH)

Thus, 1.526 g (1.622 mmol) of Compound 4 was obtained, and the yield was 59%.

Ionization mode = : APCI +: m / z = 963 [M + H] +, exact mass: 962

The compounds used as subjects to be compared are as follows. Comparative compound 1 Comparative compound 2

Comparative Example 1 is basic blue 7 and Comparative Example 2 is Rhodamine 6G.

The ratios are described in the following Table 1 for manufacturing examples and comparative examples. The unit used to administer the compound is grams (g). Table 1 Manufacturing substrate

The compound prepared in the synthesis was spin-coated on glass (5 × 5 cm), and pre-heat treated (prebaked) at 100 ° C for 100 seconds to form a film. The interval between the substrate on which the film was formed and the reticle was set to 250 μm, and an exposure amount of 40 mJ/cm 2 was radiated on the entire surface of the substrate using an exposer.

Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-heat treatment (post-baking) was performed at 230 ° C for 20 minutes to further manufacture a substrate. Evaluation of heat resistance

Using a spectrometer (MCPD-Otsuka Electronics Co., Ltd.), a preheated (prebaked) substrate fabricated under the foregoing conditions was used to obtain a range of 380 nm to 780 nm in the visible light region. Transmission spectrum inside. In addition, the pre-heat treated (prebaked) substrate was additionally subjected to post-heat treatment (post-baking) at 230 ° C for 20 minutes to obtain a transmission spectrum using the same equipment and measurement range.

Using the obtained transmission spectrum and the C light source backlight, Δ Eab was calculated using the obtained value E (L*, a*, b*), and the calculated values are shown in Table 2 below. ΔE(L*, a*, b*)={(ΔL*) 2+(Δa*)2+(Δb*)2}1/2

A smaller ΔE value indicates that the color heat resistance is excellent.

The heat resistance measurement results of the experimental examples and the compounds obtained in Comparative Example 1 and Comparative Example 2 are shown in Table 2. As shown in Table 2, it was confirmed that the color change (Δ Eab) of the compound was smaller than that of Comparative Example 1 and Comparative Example 2. Table 2

In addition, FIG. 1 is a graph illustrating transmittance in the case where a phenyl group substituted with a methyl group in R13 and R14 of Chemical Formula 1 according to an exemplary embodiment of the present application is substituted with an isopropyl group. Phenyl, and phenyl substituted by ethyl. Referring to Figure 1, it can be seen that in the case of a compound according to an exemplary embodiment of the present application, the desired transmittance can be obtained.

no

1 is a view illustrating the transmittance of a compound according to an exemplary embodiment of the present invention.

Claims (16)

A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R ₁ to R ₆ are each independently selected from the group consisting of hydrogen; hydrazine; a halogen atom; a nitro group; a substituted or unsubstituted linear chain having 1 to 30 carbon atoms or a branched alkyl group; 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; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 30 carbon atoms, each of R ₇ to R _{11 being} independently selected from the group consisting of hydrogen; anthracene; an anionic group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group of 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and 2 to 30 a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of one carbon atom, at least one of R ₇ to R ₁₁ being an anionic group, and R ₁₂ to R ₁₄ are each independently selected from the group consisting of the following: : hydrogen; hydrazine; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms; having 2 to 30 By atoms of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group; and a group containing a dianhydride of a nitrogen atom, R ₁₅ and R ₁₆ are each independently selected from the group consisting of the following: hydrogen; anion; deuterium a hydroxyl group; a substituted or unsubstituted linear or branched 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, or a combination of each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic having 6 to 30 carbon atoms a hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms, and L ₁ and L ₂ are each independently a direct bond; or a divalent linking group. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2: [Chemical Formula 2] In Chemical Formula 2, R ₁ to R ₁₁ , R ₁₃ to R ₁₆ , L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₇ and R ₁₈ are each independently selected from the group consisting of: hydrogen; An anion group; a hydroxyl group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic ring having 6 to 30 carbon atoms; An aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or a combination of each other to form a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms or a polycyclic aromatic hydrocarbon ring; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 3: [Chemical Formula 3] In Chemical Formula 3, R ₁ to R ₁₄ , L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₉ is selected from the group consisting of hydrogen; hydrazine; substituted with 1 to 30 carbon atoms. Or unsubstituted linear or branched alkyl; substituted or unsubstituted alkoxy having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms or Polycyclic aryl; substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms; halogen atom; nitro; phenoxy; carboxyl group; carboxylate group; carboxylate group ; alkoxycarbonyl; hydroxy; sulfonate; sulfonate; sulfonate; -SO ₂ NHR ₂₁ group; and -SO ₂ NR ₂₂ R ₂₃ , R ₂₁ to R ₂₃ are each independently 1 to An alkyl group of 30 carbon atoms, and m is an integer of 1 to 4, and when m is 2 or more, R _{19 is the} same or different from each other. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 4: [Chemical Formula 4] In Chemical Formula 4, R ₁ to R ₁₁ , R ₁₃ , R ₁₄ , L ₁ and L ₂ are the same as those defined in Chemical Formula 1, and R ₁₉ and R ₂₀ are each independently selected from the group consisting of: hydrogen; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; having 6 to 30 carbons a substituted or unsubstituted monocyclic or polycyclic aryl group; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; a halogen atom; a nitro group; Carboxyl; carboxylate; carboxylate; alkoxycarbonyl; hydroxy; sulfonate; sulfonate; sulfonate; -SO ₂ NHR ₂₁ group; and -SO ₂ NR ₂₂ R ₂₃ , m is an integer of 1 to 4; n is an integer of 1 to 4, when m is 2 or more, R _{19 is the} same or different from each other, and when n is 2 or more, R _{20 is the} same or different from each other. The compound of claim 1, wherein the anionic group is at least one selected from the group consisting of: -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ ^- Z ⁺ , -CO ₂ H, -CO ₂ ^- Z ⁺ , -CO ₂ Ra, -SO ₃ Rb, and -SO ₃ NRcRd, and Z ⁺ represents ⁺ N(Re) ₄ , Na ⁺ or K ⁺ , and Ra to Re each Independently representing at least one selected from the group consisting of substituted or unsubstituted straight or branched alkyl groups having from 1 to 30 carbon atoms; substituted with from 6 to 30 carbon atoms or Unsubstituted monocyclic or polycyclic aryl; and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 2 to 30 carbon atoms. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following chemical formulae: . The compound of claim 1, wherein R ₁₃ and R ₁₄ are each independently an alkyl-substituted phenyl group having 6 to 10 carbon atoms. The compound of claim 1, wherein R ₁₃ and R ₁₄ are each independently 2,6-dimethylphenyl. A color material composition containing the compound according to any one of claims 1 to 8. The color material composition according to claim 9 further comprising: at least one of a dye and a pigment. A resin composition comprising: the compound represented by Chemical Formula 1 according to any one of claims 1 to 8; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. The resin composition according to claim 11, wherein the content of the compound represented by Chemical Formula 1 is from 5% by weight to 60% by weight based on the total weight of the solid content of the resin composition. The content of the binder resin is from 1% by weight to 60% by weight, the content of the photoinitiator is from 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight. The resin composition as described in claim 11 further contains: an antioxidant. A photosensitive material produced by using the resin composition as described in claim 11 of the patent application. A color filter comprising the photosensitive material as described in claim 14 of the patent application. A display device comprising the color filter of claim 15 of the patent application.