TW201811926A - Photosensitive resin composition, photosensitive material, color filter and display device capable of improving color purity, color reproduction, brightness, and contrast ratio - Google Patents

Abstract

The present invention provides a photosensitive resin composition and a color filter including the same. The present description relates to a photosensitive resin composition comprising a compound represented by chemical formula 1 and a compound represented by chemical formula 2, and a color filter including the same, wherein the anionic group is selected from at least one of the groups consisting of -OH, -S03-, -S03 H, -S03-Z+, -C02H, -02-Z+, -C02Ra, -S03Rb, and -S03NRcRd, z+ represents N(Re)4+, Na+, or K+, Ra-Re which may be the same or different from each other, and each independently selected from the group consisting of substituted or unsubstituted alkyl groups of C1 to C30, substituted or unsubstituted monocyclic or polycyclic aryl groups of C6 to C30, and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups of C1 to C30.

Description

Photosensitive resin composition and color filter including the same

This specification relates to a photosensitive resin composition and a color filter including the same.

In recent years, for color filters, performance characterized by high brightness and high contrast ratio is required. In addition, one of the main goals of the development of display elements is to differentiate the performance of display elements and improve the productivity in manufacturing steps due to the improvement in color purity.

Previously, the type of pigment used as a coloring agent for a color filter existed in the color photoresist in a particle dispersed state, and therefore, it was difficult to adjust the brightness and contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, the particles are aggregated in a color filter, have poor dissolution and dispersibility, and cause multiple scattering of light due to aggregation of large particles. It has been pointed out that the scattering of such polarized light is the main reason for lowering the contrast ratio. Efforts are being made to improve brightness and contrast ratios by ultra-micronization and dispersion stabilization of pigments. However, the degree of freedom in the selection of colorants for color coordinates for display devices with high color purity is limited. limit. In addition, pigment dispersion methods using developed coloring materials, especially pigments, have reached the limit in terms of improving the color purity, brightness, and contrast ratio of color filters using them. Therefore, it is required to develop a coloring agent or a photosensitive resin composition containing the same that can improve color purity and improve color reproduction, brightness, and contrast ratio. [Prior Art Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open No. 9-87534

[Problems to be Solved by the Invention] The present invention relates to a photosensitive resin composition and a color filter manufactured using the same.

[Means for Solving the Problems] One embodiment of the present invention provides a photosensitive resin composition including a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2. [Chemical Formula 1] [Chemical Formula 2] [(RSiO _{1.5) n} ] In Chemical Formula 1, L _A and L _B may be the same as or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms, and R _A to R _F They may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, nitro, substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted Substituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic rings having 1 to 30 carbon atoms In the group consisting of polycyclic heteroaryl groups, R ₁ to R ₆ may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, substituted or unsubstituted carbon number 1 to 6 linear or branched alkyl groups, and substituted or unsubstituted alkoxy groups having 1 to 6 carbon atoms, sulfonic acid groups, sulfonic acid ester groups, sulfonate groups, -SO ₂ NHR ₇ groups, and In the group consisting of -SO ₂ NR ₈ R ₉ , R ₇ to R ₉ may be the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, and X ₁ to X ₅ Can be the same or different from each other , Each independently selected from the group consisting of hydrogen, deuterium, anionic group, hydroxyl group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic ring or more In the group consisting of a cyclic aryl group and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, at least one of X ₁ to X ₅ is an anionic group, R _AA and R _BB may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, and substituted or unsubstituted carbon having 1 to 30 carbon atoms. Alkoxy, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbons, Halogen atom, nitro group, phenoxy group, carboxyl group, carboxylate group, carboxylate group, alkoxycarbonyl group, hydroxyl group, sulfonate group, sulfonate group, sulfonate group, -SO ₂ NHR 'and- In the group composed of SO ₂ NR `` R ''', a and b may be the same as or different from each other, and are each independently an integer of 0 to 4. In the case where a and b are 2 or more, the Structures can be identical to each other May be different, R ', R''andR''' may be the same or different from each other, they are independently an alkyl group having 1 to 30 carbon atoms, in the formula 2, n is an even number of 4 or more, R a - (L ₁ ) _n1- R ₇ represents that multiple Rs may be the same as or different from each other, L ₁ is a direct bond, -O-, -S-, or an alkylene group having 1 to 30 carbon atoms, and n1 is an integer of 1 to 5 In the case where n1 is 2 or more, L ₁ may be the same as or different from each other, and R ₇ is hydrogen, deuterium, -OH, epoxy group, -SH, -NH ₂ , , -N = C = O, -C = C-, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms or heterocyclic group having 1 to 30 carbon atoms.

In addition, one embodiment of the present invention provides a photosensitive material manufactured using the photosensitive resin composition and a color filter including the same.

[Effects of the Invention] When the photosensitive resin composition according to an embodiment of the present invention is used to form a pattern for a color filter, when a hole is formed in the pattern, the sensitivity can be reduced and the brightness can be improved. In addition, the photosensitive resin composition according to an embodiment of the present invention is excellent in adhesion between a pattern and a substrate even if the sensitivity is low.

Hereinafter, this specification will be described in more detail. In the present specification, when a certain component is "included" in a certain component, as long as there is no particularly contrary description, this does not mean that other components are excluded, but it means that other components may be further included. According to an aspect of the present specification, a photosensitive resin composition including a compound represented by the chemical formula 1 and a compound represented by the chemical formula 2 is provided.

In the present specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen atom, alkyl, alkenyl, alkoxy, cycloalkyl, arylalkenyl, aryl, Aryloxy, aralkyl, arylalkenyl, alkylamino, aralkylamino, arylamino, heteroaryl, carbazolyl, acryloyl, acrylate, ether, nitrile , Nitro, hydroxy, cyano, one or more substituents in the group containing one or more heteroaryl groups and anionic groups containing N, O, S, or P atoms, or do not have any substitution base.

In this specification, the alkyl group may be a straight chain or a branched chain, and is not particularly limited, and the carbon number may be 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, third butyl, pentyl, hexyl, and heptyl. In this specification, the alkenyl group may be a straight chain or a branched chain, and is not particularly limited, and the carbon number may be 2 to 25. Specific examples include alkenyl groups in which aryl groups such as a stylbenyl group and a styrenyl group are substituted, but are not limited thereto. In this specification, the alkoxy group may be a straight chain or a branched chain, and is not particularly limited, and the carbon number may be 1 to 30. In the present specification, the cycloalkyl group is not particularly limited, and the carbon number may be 3 to 20, and particularly may be a cyclopentyl group or a cyclohexyl group. In this specification, examples of the halogen atom include fluorine, chlorine, bromine, and iodine.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. When the aryl group is a monocyclic aryl group, it is not particularly limited, and the carbon number may be 6 to 40. Specifically, examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a bitriphenyl group, but are not limited thereto. When the aryl group is a polycyclic aryl group, it is not particularly limited, and the carbon number may be 10 to 40. Specific examples of the polycyclic aryl group include, but are not limited to, naphthyl, anthracenyl, phenanthryl, fluorenyl, fluorenyl, fluorenyl, and fluorenyl. In the case where the fluorenyl group is substituted, it may become , And so on (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups. However, it is not limited to this.

In this specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited. According to an embodiment, the carbon number of the heterocyclic group is 1-30. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, and isothiazolyl , Triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thianyl, pyrazinyl, oxazinyl, thiazinyl, dioxinyl , Triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthene, Morphinidyl, diazanaphthyl, triazaindenyl, indolyl, indolyl, indazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl , Benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, di Benzocarbazolyl, indolocarbazolyl, indencarbazolyl, phenazine, imidazopyridyl, phenoxazinyl, morphinyl, phenanthroline, phenothia zine) group, imidazoloridinyl, benzimidazoquinazolinyl, or benzimidazoridinyl, but are not limited to these.

In one embodiment of the present specification, the number of the ring-forming elements of the heterocyclic group is 3 to 60. In one embodiment, the number of the ring-forming elements of the heterocyclic group is 3 to 40. Furthermore, in an embodiment, the number of the ring-forming elements of the heterocyclic group is 3-20.

In the present specification, the heteroaryl group is an aromatic heterocyclic group containing O, N, S, or P as a hetero atom, and is not particularly limited, and the carbon number may be 1 to 30. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridine (Acridyl), pyridazinyl, quinolinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzo Thienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, and the like are not limited to these. In the present specification, in addition to the aromatic group, the description about the heterocyclic group can be applied.

In the present specification, an alkylene group refers to a group having two bonding positions in an alkane. The alkylene group may be linear, branched, or cyclic. The number of carbons of the alkylene group is not particularly limited, but may be 2 to 25.

In this specification, in addition to the arylene group being a divalent group, the description about the aryl group can be applied.

In this specification, in addition to a heterovalent diaryl group, a description about the heteroaryl group can be applied.

In the present specification, adjacent groups are bonded to each other to form a substituted or unsubstituted ring, which means that a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, A substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring, or these condensed rings.

As used herein, the term "aliphatic hydrocarbon ring" refers to a ring that is not aromatic, and refers to a ring containing only carbon atoms and hydrogen atoms. Specifically, examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, Cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like are not limited to these.

In the present specification, an aromatic hydrocarbon ring refers to an aromatic ring containing only carbon atoms and hydrogen atoms. In the present specification, specific examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, fluorene, fluoranthene, diphenyltriphenylene, fluorene, fluorene, fused tetrabenzene, fluorene, pentacene, and fluorene. , Indene, pyrene, benzofluorene, spirofluorene, and the like, but are not limited to these.

As used herein, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms. Specifically, examples of the aliphatic heterocyclic ring include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, and morpholine. , Oxepan, azocane, thiocane, etc., but it is not limited to these.

In the present specification, the term "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms. Specifically, examples of the aromatic heterocyclic ring include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, and oxadiazole. , Thiadiazole, dithiazole, tetrazole, pyran, thioan, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, hydroquinone (quinol), Quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzene Benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, morphinidine, indolocarbazole , Indenecarbazole, etc., but not limited to these.

In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring, and aromatic heterocyclic ring may be monocyclic or polycyclic.

In one embodiment of the present specification, L _A and L _B may be the same as or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms. In one embodiment, L _A and L _B are respectively propyl.

In one embodiment of the present specification, R _A to R _F may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, nitro, substituted or unsubstituted carbon having 1 to 30 carbon atoms. Alkyl, substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted A group of monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms. In one embodiment, R _A to R _F are hydrogen. According to an embodiment of the present specification, R ₁ to R ₆ may be the same as or different from each other, and are each independently selected from the group consisting of straight or branched chain of carbon number 1 to 6 consisting of hydrogen, deuterium, or substituted. A group consisting of an alkyl group, a sulfonate group, a sulfonate group, -SO ₂ NHR ₇ group, and -SO ₂ NR ₈ R ₉ group. R ₇ to R ₉ may be the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms. According to an embodiment of the present specification, R ₁ to R ₆ may be the same as or different from each other, and are each independently selected from the group consisting of straight or branched chain of carbon number 1 to 6 consisting of hydrogen, deuterium, or substituted. Alkyl and sulfonate groups.

In one embodiment of the present specification, X ₁ to X ₅ may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, anionic group, hydroxyl group, substituted or unsubstituted carbon number 1 to 30. Alkyl, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbons In the group, at least one of X ₁ to X ₅ is an anionic group.

An embodiment aspect of the present specification, the anionic group is selected from the group consisting of ^{_{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, -O 2 - Z +, - At least one of the group consisting of CO ₂ R _a , -SO ₃ R _b and -SO ₃ NR _c R _d , Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺ , and R _a ～ R _e are each independently selected from 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 at least one of the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms. According to another aspect of the present specification, the anionic group may be -SO ₃ ^- or -SO ₃ ^- Na ⁺ . The anionic group may have an anion by itself, or may exist in the form of a complex compound together with other cations. Therefore, depending on the number of substituted anionic groups, the sum of the total charges of the molecules of the compound of Chemical Formula 1 may be changed. Since the compound of the present invention has a cation in one amine group, the sum of the total charge of the molecule may have a value from an anion to a value obtained by subtracting 1 from the number of substituted anionic groups.

In one embodiment of the present specification, R ′, R ″, and R ′ ″ may be the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L ₁ may be the same as or different from each other, and are each independently a direct bond, -O-, -S-, or an alkylene group having 1 to 30 carbon atoms. In one embodiment, L ₁ is -O-. In one embodiment, L ₁ is methylene, ethylene or propyl. In one embodiment of the present specification, R ₁ is hydrogen, deuterium, -OH, epoxy group, -SH, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and aromatic group having 6 to 30 carbon atoms. Or a heterocyclic group having 1 to 30 carbon atoms. In one embodiment, R ₇ is -SH. In one embodiment, R ₇ is an epoxy group. In one embodiment, R ₇ is phenyl.

In one embodiment of the present specification, the R may be represented by any one of the following Chemical Formulas 2-a to 2-e. [Chemical Formula 2-a] [Chemical Formula 2-b] [Chemical Formula 2-c] [Chemical Formula 2-d] [Chemical Formula 2-e]

In one embodiment, the R may be represented by any one of the chemical formula 2-b and the chemical formula 2-c. In one embodiment of the present specification, the compound represented by the chemical formula 2 may be SQ506 of Arakawa Chemical Industry Co., Ltd. In one embodiment of the present specification, the compound represented by the chemical formula 2 may be KBM-503 of Shin-Etsu Chemical Industry Co., Ltd.

In an embodiment of the present specification, the photosensitive resin composition may further include a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

The binder resin is not particularly limited as long as it exhibits physical properties such as strength and developability of a film produced from a resin composition. As the binder resin, a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility can be used, and a binder commonly used in the technical field may be further included. In one embodiment, the binder resin may be an acrylic binder resin.

Examples of the polyfunctional monomer that imparts mechanical strength to the film include those selected from the group consisting of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated sulfonimines, and acid anhydrides. Any of the above. Specific examples of the unsaturated carboxylic acid esters are selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and (meth) ) Dimethylaminoethyl acrylate, isobutyl (meth) acrylate, tertiary butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, (methyl ) Ethylhexyl acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, fluorenyl octyloxy-2-hydroxypropyl (meth) acrylate, glycerol (methyl ) Acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene Alcohol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, Nonylphenoxy polyethylene glycol (meth) acrylate, para Phenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexamethacrylate Fluoroisopropyl, octafluoropentyl (meth) acrylate, heptafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, α-hydroxymethyl methacrylate, α-hydroxymethyl The group consisting of ethyl acrylate, α-hydroxymethacrylate, and α-hydroxymethacrylate is not limited to these groups. Specific examples of the aromatic vinyl-based monomer are selected from the group consisting of styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxy The group consisting of styrene and (o-, m-, p-)-chlorostyrene is not limited to these. Specific examples of the unsaturated ethers are selected from the group consisting of vinyl methyl ether, vinyl ether, and allyl glycidyl ether, but are not limited to these. Specific examples of the unsaturated fluorene imines are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, and N- (4-hydroxyphenyl) horse The group consisting of lymeimide and N-cyclohexylmaleimide is not limited to these. Examples of the acid anhydride include, but are not limited to, maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride.

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group. For example, a monomer selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid is preferably used. Acid, monomethyl maleate, 5-norbornene-2-carboxylic acid, mono-2-(((meth) acryloxy) ethyl) phthalate, mono-2-((methyl One or more of the group consisting of acryl) propenyloxy) ethyl ester and ω-carboxy polycaprolactone mono (meth) acrylate, but it is not limited to these.

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

The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light. Specifically, the polyfunctional monomer may be selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, Neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanate Ureate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate One or a mixture of two or more in the group.

The photo-initiator is not particularly limited as long as it is a initiator that catalyzes crosslinking by generating free radicals by light. For example, the photo-initiator may be selected from acetophenone-based compounds, biimidazole-based compounds, and triazine-based compounds. One or more of the group consisting of a compound and an oxime-based compound.

Examples of the acetophenone-based compound include 2-hydroxy-2-methyl-1-phenylpropane-1-one and 1- (4-isopropylphenyl) -2-hydroxy-2-methyl Propane-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ether, benzoin iso Butyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholinyl-1-propane-1 -Ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butane-1-one, 2- (4-bromo-benzyl-2-dimethyl Amino-1- (4-morpholinylphenyl) -butane-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinylpropane-1- Ketones and the like are not limited thereto.

Examples of the biimidazole-based compound include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) ) -4,4 ', 5,5'-tetra (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'-diphenyl Imidazole and the like are not limited thereto.

Examples of the triazine-based compound include 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, and 3- {4- [2 , 4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanoic acid 1,1,1,3,3,3-hexafluoroisopropyl ester, 2- {4- [2 , 4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} ethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -mesytriazine-6 -Yl] phenylthio} 2-epoxyethyl acetate, 2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} cyclohexyl acetate , 2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} benzyl acetate, 3- {chloro-4- [2,4-bis (tri (Chloromethyl) -mesytriazine-6-yl] phenylthio} propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} Promethazine, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-dimethylene Aminoaminophenyl) -1,3, -butadienyl-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc., but not Not limited to this.

Examples of the oxime-based compound include 1,2-octanedione, 1- (4-phenylsulfanyl) phenyl, and 2- (o-benzoylsulfanyloxime) (ciba-geki (Ciba- Geigy), CGI124), ethyl ketone, -1- (9-ethyl) -6- (2-methylbenzylidene-3-yl)-, 1- (O-acetamidooxime) ( CGI242), N-1919 (manufactured by Adeka), etc., but it is not limited to this.

Examples of the solvent include those selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, and ethylene glycol. Methyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl 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, tertiary butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol , Cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellulose One or more of the group consisting of esters, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether are not limited to these.

In an embodiment of the present specification, based on the total weight of solid components in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 0.1 parts by weight to 50 parts by weight. The content of the compound is 0.01 to 10 parts by weight, the content of the binder resin is 1 to 60 parts by weight, and the content of the photoinitiator is 0.1 to 20 parts by weight. The content of the functional monomer is 0.1 to 50 parts by weight.

The total weight of the solid content refers to the total weight of the components after the solvent is removed from the resin composition. The solid content and the weight basis of the solid content of each component based on the solid content can be measured by a usual analysis means used in the art such as liquid chromatography or gas chromatography.

In an embodiment of the present specification, the photosensitive resin composition may further include at least one of a dye and a pigment. Dyes and pigments are those who take on a range of wavelengths required for absorption and exhibit color. They can be divided into dyes and pigments based on their solubility in solvents. Dyes are those with high solubility in solvents and are easy to dissolve, and pigments are those with relatively low solubility and are difficult to dissolve. The dye may be at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye. The anthraquinone dye may be represented by the following Chemical Formula 3. [Chemical Formula 3] In the chemical formula 3, R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. By.

In addition, according to an embodiment of the present specification, the anthraquinone-based dye may be any one selected from the following compounds.

In addition, according to an embodiment of the present specification, the tetraazaporphyrin-based dye may be selected from the following compounds.

In addition, according to an embodiment of the present specification, the triarylmethane-based dye may be any one selected from the following compounds.

In one aspect of the present specification, the pigment is a blue pigment. As the blue organic pigment, the blue pigment may include, for example, C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4, C.I. Pigment Blue 15: 6, C.I. Pigment Blue 60, and the like. In one embodiment, the pigment may include a copper phthalocyanine pigment. The blue dye may include, for example, a methyl-based dye, an anthraquinone-based dye, an azo-based dye, a triarylmethane-based dye, or a phthalocyanine-based dye. In addition, the blue pigment may include, as a blue lake pigment, for example, a blue pigment that is laked as described above with a lake-forming agent. The lake-forming agent is not particularly limited, and examples thereof include phosphotungstic acid, phosphomolybdic acid, phosphotungstic molybdic acid, tannic acid, lauric acid, 3,4,5-trihydroxybenzoic acid, ferricyanide, and Ferricyanide etc. Examples of specific blue lake pigments include: CI Pigment Blue 1, CI Pigment Blue 1: 2, CI Pigment Blue 2, CI Pigment Blue 3, CI Pigment Blue 8, CI Pigment Blue 9, CI Pigment Blue 10, CI Pigment Blue 12, CI Pigment Blue 14, CI Pigment Blue 17: 1, CI Pigment Blue 18, CI Pigment Blue 19, CI Pigment Blue 24, CI Pigment Blue 24: 1, CI Pigment Blue 53, CI Pigment Blue 56, CI Pigment Blue 56: 1, CI Pigment Blue 61, CI Pigment Blue 61: 1, CI Pigment Blue 62, CI Pigment Blue 63, CI Pigment Blue 78, and the like.

In one embodiment of the present specification, the photosensitive resin composition further includes a dispersant, and the dispersant may include a polymer including a repeating unit represented by the following chemical formula 11 or a repeating unit represented by the following chemical formula 12. [Chemical Formula 11] [Chemical Formula 12] In Chemical Formula 11 and Chemical Formula 12, R ₃₀₁ and R ₄₀₁ may be the same as or different from each other, and are independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and R ₃₀₂ , R ₃₀₃ , R _402, and R ₄₀₃ may be the same as each other or may be different from each other. Different, each may be hydrogen, alkyl having 1 to 30 carbons, aryl having 6 to 30 carbons or heteroaryl having 1 to 30 carbons, or R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ each other Bonded to form a substituted or unsubstituted ring, Ar ₃ and Ar ₄ may be the same as or different from each other, and are each independently directly bonded, an alkylene group having 1 to 10 carbon atoms, and-[CH (R ₃₁₁ ) -CH (R ₃₁₂ ) -O] _x -CH (R ₃₁₃ ) -CH (R ₃₁₄ ) _-or -[(CH ₂ ) _y1 -O] _z- (CH ₂ ) _y2 -represented by a divalent linking group, R ₃₁₁ to R ₃₁₄ may be the same as or different from each other, and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses may be mutually different The same or different, y1 and y2 may be the same or different from each other, and are each independently an integer of 1 to 5, z is an integer of 1 to 18, and when the z is 2 or more, the structures in the brackets may be the same as each other. May be different, Q is selected from direct bonding, carbon number 1 Any one or two or more of a group consisting of an alkylene group of 10 to 10, an alkylene group of 6 to 30 carbon atoms, -CONH-, -COO-, and an ether group of 1 to 10 carbon atoms Linker.

In one embodiment, the dispersant may be contained in an amount of 0.5 to 50 parts by weight based on the total weight of the solid content in the resin composition. According to an embodiment of the present specification, the resin composition may further include an antioxidant. According to an embodiment of the present specification, a content of the antioxidant is 0.1 to 20 parts by weight based on a total weight of solid components in the resin composition.

According to an embodiment of the present specification, the resin composition further includes a member selected from the group consisting of a photocrosslinking sensitizer, a hardening accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and One or two or more additives in a group of leveling agents. According to an embodiment of the present specification, a content of the additive is 0.1 to 20 parts by weight based on a total weight of solid components in the resin composition.

As the photo-crosslinking sensitizer, one or more members selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl o-benzoyl benzoate, 3,3-dimethyl-4 -Benzophenone-based compounds such as methoxybenzophenone, 3,3,4,4-tetrakis (third butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9- Fluorenone compounds such as fluorenone, 2-methyl-9-fluorenone; thioanthrone, 2,4-diethylthioxanthone, 2-chlorothiaxanthone, 1-chloro-4-propane Thioxanthone compounds such as oxanthone, isopropylthioxanthone, and diisopropylxanthone; xanthone such as xanthone and 2-methylxanthone Compounds; anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, third butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone and other anthraquinone compounds; 9-phenyl Acridine, acridine, 1,7-bis (9-acridyl) heptane, 1,5-bis (9-acridylpentane), 1,3-bis (9-acridyl) propane and other acridine systems Compounds; benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrene Dicarbonyl compounds such as quinone; 2,4,6-trimethylbenzylidene diphenylphosphine oxide, bis (2,6-dimethoxybenzylidene) -2,4,4-trimethyl Phosphine oxide compounds such as amylphosphine oxide; methyl 4- (dimethylamino) benzoate, ethyl 4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- ( Benzoate-based compounds such as dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzylidene) cyclopentanone, 2,6-bis (4-diethyl Amine benzyl) cyclohexanone, 2,6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone and other amine synergists; 3,3-carbonylvinyl -7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzylidene-7- (diethyl Propylamino) coumarin, 3-benzylidene-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6, Coumarin compounds such as 7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinazine-11-one; 4-diethylamino group Chalcone compounds such as ear ketone, 4-azidobenzylideneacetophenone; 2-benzylidene methylene, 3-methyl-b-naphthothiazoline.

The hardening accelerator is used by a user for improving hardening and mechanical strength. Specifically, a hardening accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2,5- Dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) ), Pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tri (2-mercaptoacetate), and trimethylolpropane-tri ( 3-mercaptopropionate).

As the adhesion promoter used in the present specification, methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltrimethoxysilane can be selected. One or more of methacrylfluorenylsilane coupling agents such as ethoxysilane and methacryloxypropyldimethoxysilane are used. As the alkyltrimethoxysilane, octyltrimethoxysilane can be selected. , Dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc.

The surfactant is a silicon-based surfactant or a fluorine-based surfactant. Specifically, as the silicon-based surfactant, BYK-077 and BYK from BYK-Chemie can be used. BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK ( 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, BI BYK-375, BYK-380, BYK-390, etc. As fluorine-based surfactants, DIC (DaiNippon Ink & Chemicals) can be used. Company's 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. are not limited to these.

Examples of the antioxidant include one or more members selected from the group consisting of a hindered phenol-based antioxidant, an amine-based antioxidant, a sulfur-based antioxidant, and a phosphine-based antioxidant, but the invention is not limited to this. some. Specific examples of the antioxidant include phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; 2,6-di-third-butyl-p-cresol, and octadecyl- 3- (4-hydroxy-3,5-di-third-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-third-butyl-4-hydroxyphenyl) ) Propionate] methane, 1,3,5-trimethyl-2,4,6-tri (3,5-di-third-butyl-4-hydroxybenzyl) benzene, 3,5-di- Diethyl tertiary butyl-4-hydroxybenzyl phosphite, 2,2-thiobis (4-methyl-6-third butylphenol), 2,6-g, t-butylphenol 4 , 4'-butylene-bis (3-methyl-6-tert-butylphenol), 4,4'-thiobis (3-methyl-6-tert-butylphenol) or bis [3, 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] diol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol ester) and other hindered phenol (Hindered phenol) primary antioxidants; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-bis-β-naphthyl-p-phenylenediamine and other amine-based secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate , Sulfur-based secondary antioxidants such as mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite Ester, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite) Or (1,1'-biphenyl) -4,4'-diylbisphosphinic acid tetra [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1 Phosphite secondary antioxidants such as' -Biphenyl) -4,4'-Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-thirdbutyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but It is not limited to this, and can be used if it is a user generally used in this field.

The thermal polymerization inhibitor may include, for example, a compound selected from p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, and N-nitroso. Phenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-third-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thio Bis (3-methyl-6-tert-butylphenol), 2,2-methylenebis (4-methyl-6-tert-butylphenol), 2-mercaptoimidazole and phenothiazine One or more of the formed groups are not limited to these, and may include those generally known in the art.

The dispersant can be used by a method in which the pigment is internally added to the pigment in a form in which the pigment is surface-treated in advance, or a method in which the pigment is externally added to the pigment. As the dispersant, a compound-type, nonionic, anionic, or cationic dispersant can be used, and examples thereof include fluorine-based, ester-based, cationic, anionic, non-ionic, and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, examples of the dispersant include polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonate esters, One or more members selected from the group consisting of a sulfonate, a carboxylic acid ester, a carboxylate, an alkylamidoalkylene oxide adduct, and an alkylamine, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamine, reaction products of amines and epoxides, and specific examples of the non-polymeric leveling agent include non-polymeric sulfur The compound and the non-polymeric nitrogen-containing compound are not limited thereto, and can be used if they are generally used in the art.

An embodiment of the present specification provides a photosensitive resin composition including a compound represented by the following Chemical Formula 15, a compound represented by the following Chemical Formula 2, a dye, and a dispersant, and the dye is a triarylmethane-based dye. [Chemical Formula 15] [Chemical Formula 2] In Chemical Formula 15, the definitions of R ₁ to R ₆ , R _A to R _D , R _AA , R _BB, and X ₁ to X _{5 and} the definition of Chemical Formula 2 are referred to those mentioned above.

An embodiment of the present specification provides a photosensitive material manufactured using the resin composition. More specifically, a photosensitive material in the form of a film or a pattern obtained by applying a resin composition according to an embodiment of the present invention to a substrate by an appropriate method is provided. The coating method is not particularly limited, and a spray method, a roll coating method, a spin coating method, or the like can be used. Generally, a spin coating method can be widely used. In addition, after forming the coating film, a part of the residual solvent may be removed under reduced pressure as appropriate.

Examples of the light source for hardening the resin composition of the present specification include light mercury vapor arc (arc), carbon arc, Xe arc, etc., which emits a wavelength of 250 nm to 450 nm, but it is not necessarily limited to this.

The resin composition of this specification can be used in pigment-dispersed photosensitive materials for thin film transistor liquid crystal display (TFT LCD) color filter manufacturing, thin-film transistor liquid crystal display (TFT LCD), or organic light-emitting diodes. Photosensitive material for forming black matrix of polar body, photosensitive material for forming overcoat layer, photosensitive material for column spacer (colomn spacer), photocurable paint, photocurable ink, photocurable adhesive, printed board, printed wiring There are no particular restrictions on the use of photosensitive materials for boards, photosensitive materials for plasma display panels (PDP), and the like.

According to an aspect of the present specification, a color filter including the photosensitive material is provided. The color filter includes the photosensitive resin composition. The photosensitive resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to form a color filter.

A resin composition according to an embodiment of the present specification can provide a color filter capable of reducing sensitivity and realizing high brightness when a hole is realized in a pattern. The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (Polycarbonate, PC), and 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 addition, according to an aspect, the color filter may further include an overcoat layer. Between the color pixels of the color filter, for the purpose of improving the contrast, a grid-like black pattern called a black matrix can be arranged. As a material of the black matrix, chromium can be used. In this case, a method can be used in which chromium is deposited on the entire glass substrate and a pattern is formed by an etching process. However, in consideration of the high cost in steps, the high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix using a pigment dispersion method capable of fine processing can be used.

The black matrix according to an embodiment of the present specification may use a black pigment or a black dye as a colorant. For example, carbon black can be used alone, or carbon black can be mixed with colored pigments. At this time, because colored pigments with insufficient light-shielding properties are mixed, there are advantages such that even if the amount of colorant is relatively increased, the strength of the film or the The adhesion of the substrate does not decrease.

A display device including the color filter of the present specification is provided. The display device may be a plasma display panel (PDP), a light emitting diode (Light Emitting Diode, LED), an organic light emitting element (Organic Light Emitting Diode, OLED), or a liquid crystal display (Liquid Crystal Display, LCD). ), Any of a Thin Film Transistor-Liquid Crystal Display (LCD-TFT), and a Cathode Ray Tube (CRT).

Hereinafter, in order to specifically describe this specification, examples will be described in detail. However, the embodiments of this specification can be modified into various other forms, and the scope of this specification cannot be interpreted as being limited to the embodiments described below. The examples in this specification are provided to explain the specification more completely to those with average knowledge in the art.

Synthesis of Compound In order to produce a photosensitive resin composition according to an embodiment of the present specification, Compound 1 is produced by the following reaction formula 1. [Reaction formula 1] Put 5 g of A-1 (8.710 mmol), 8.233 g of B-1 (34.838 mmol), and 4.815 g of K ₂ CO ₃ (34.5838 mmol) into 100 ml of N-Methylpyrrolidone (N-Methyl Pyrrolidone (NMP), and stirred at 95 ° C for 12 hours. After that, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 6 g of Compound 1 (3.322 mmol) was obtained with a yield of 72%. The results are described below. Ionization mode =: Atmospheric Pressure Chemical Ionization (APCI) +: m / z = 949 [M + H] +, Exact Mass: 948 ¹ H-NMR measurement result of the compound 1 As described below. ¹ H NMR (500 MHz, dimethylsulfoxide (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)

[Reaction formula 2] As described in Reaction Scheme 2, 1.43 g of C-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), and 1.31 g of K ₂ CO ₃ (9.490 mmol) were placed in 20 ml of NMP. Stir at 95 ° C for 12 hours. After that, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 1.622 g of Compound 2 (1.912 mmol) was obtained with a yield of 70%. Ionization mode =: APCI +: m / z = 977 [M + H] +, Exact Mass: 976

[Reaction formula 3] As described in Reaction Scheme 3, 1.608 g of D-1 (2.732 mmol), 2.99 g of B-1 (9.490 mmol), and 1.31 g of K ₂ CO ₃ (9.490 mmol) were placed in 20 ml of NMP. Stir at 95 ° C for 12 hours. After that, the solvent was removed under reduced pressure, and 200 ml of water was put into the precipitate and stirred for 1 hour. The precipitate was filtered under reduced pressure and dried at 80 ° C. for 12 hours. Thereafter, the dried precipitate was separated by column chromatography. (Eluent-MC: MeOH) As a result, 1.526 g of Compound 3 (1.622 mmol) was obtained with a yield of 59%. Ionization mode =: APCI +: m / z = 963 [M + H] +, Exact Mass: 962

[Reaction formula 4] As described in Reaction Scheme 4, put 289.5 g of Acid Red (7.388 mmol), 8.1 g of B-1 (25.8 mmol), and 4.09 g of K ₂ CO ₃ (29.554 mmol) into 100 ml of In NMP, it stirred at 95 degreeC for 12 hours. Thereafter, the solvent was removed under reduced pressure, and brine 100 was added to the precipitate and stirred for 1 hour. Then, the precipitate was filtered under reduced pressure, and dried at 80 ° C. for 12 hours. As a result, 7.3 g of a colorant (6.945 mmol) containing Compound 4 as the main product was obtained, and the yield was 94%.

Experimental Examples Example 1 to Example 4 and Comparative Example 1 to Comparative Example 4 were produced at the ratios shown in Table 1 below. The input unit of each component is gram (g).

[Table 1]

Preparation of the substrate The prepared compound was spin-coated on glass (5 cm × 5 cm) on which SiN _x was vapor-deposited, and prebake at 110 ° C. for 70 seconds to form a film. The interval between the substrate on which the film was formed and the photo mask was set to 300 μm, and the entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm ² using an exposure device. Thereafter, the exposed substrate was developed with a developing solution (KOH, 0.04%) for 55 seconds, and post-bake was performed at 230 ° C for 20 minutes to prepare a substrate.

Measurement of the pore size The inside length of the pore was measured using a microspectrophotometer (manufactured by Olympus Optical Industry Co., Ltd., OSPSP200) at a magnification of 1000 times on a substrate prepared under the above-mentioned conditions.

Measurement of Adhesion Using a microspectrophotometer (manufactured by Olympus Optical Industry Co., Ltd., OSPSP200), the substrate produced under the above-mentioned conditions was measured. [Table 2]

As shown in Table 1, it can be seen that a color filter was produced using the photosensitive resin composition of Examples 1 to 4 including both the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2. In the case of a sheet, fine pattern adhesion is excellent. The result obtained by measuring the adhesion of the fine pattern is shown in FIG. 1.

no

FIG. 1 shows the results of measuring the adhesion between a color filter pattern using a photosensitive resin composition according to an embodiment of the present invention and a fine pattern of a comparative example.

Claims (18)

A photosensitive resin composition comprising a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2; [Chemical Formula 1] [Chemical Formula 2] [(RSiO _{1.5) n} ] (In Chemical Formula 1, L _A and L _B may be the same as or different from each other, and are each independently a direct bond or an alkylene group having 1 to 10 carbon atoms, and R _A to R _F may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, a halogen atom, a nitro group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number 1 -30 alkoxy, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted monocyclic or polycyclic heterocyclic having 1 to 30 carbons In the group consisting of aryl groups, R ₁ to R ₆ may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, substituted or unsubstituted straight chain or Branched alkyl group, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, sulfonic acid group, sulfonic acid ester group, sulfonic acid salt group, -SO ₂ NHR ₇ group and -SO ₂ NR ₈ R _In the group consisting of ₉ , R ₇ to R ₉ may be the same as or different from each other, and are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, and X ₁ to X ₅ may be the same as or different from each other. , Each independently selected Free hydrogen, deuterium, anionic group, hydroxyl group, substituted or unsubstituted alkyl 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 1 to 30 carbon atoms, at least one of X ₁ to X ₅ is an anionic group, R _AA and R _BB They may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted alkoxy having 1 to 30 carbons, Substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl having 1 to 30 carbon atoms, halogen atom, nitro group , Phenoxy, carboxyl, carboxylate, carboxylate, alkoxycarbonyl, hydroxyl, sulfonate, sulfonate, sulfonate, -SO ₂ NHR 'and -SO ₂ NR'' In the group consisting of R ''', a and b may be the same as or different from each other, and are each independently an integer of 0 to 4. When a and b are 2 or more, the structures in the brackets may be the same as each other. Can be different, R ', R''AndR''' may be the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms. In Chemical Formula 2, n is an even number of 4 or more, and R is represented _by- (L ₁ ) _n1 -R ₇ , Multiple Rs may be the same as or different from each other. L ₁ is a direct bond, -O-, -S-, or an alkylene group having 1 to 30 carbon atoms, n1 is an integer of 1 to 5, and when n1 is 2 or more In the following, L ₁ may be the same as or different from each other, and R ₇ is hydrogen, deuterium, -OH, epoxy, -SH, -NH ₂ , , -N = C = O, -C = C-, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms or heterocyclic group having 1 to 30 carbon atoms). The patentable scope of the application as a first item a photosensitive resin composition, wherein said anionic group is selected from the group consisting of ^{_{-OH, -SO 3 -, -SO 3}} H, -SO 3 - Z +, -CO 2 H, - At least one of the group consisting of O ₂ ^- Z ⁺ , -CO ₂ R _a , -SO ₃ R _b and -SO ₃ NR _c R _d , Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ or K ⁺ and R _a to R _e may be the same as or different from each other, and are each independently selected from the group consisting of substituted or unsubstituted alkyl having 1 to 30 carbons, and substituted or unsubstituted having 6 to 30 carbons. At least one of a group consisting of a monocyclic or polycyclic aryl group and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms. The photosensitive resin composition according to item 1 of the scope of patent application, wherein the R is represented by any one of the following Chemical Formula 2-a to Chemical Formula 2-e; [Chemical Formula 2-a] [Chemical Formula 2-b] [Chemical Formula 2-c] [Chemical Formula 2-d] [Chemical Formula 2-e] . The photosensitive resin composition according to item 1 of the scope of patent application, further comprising: a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The photosensitive resin composition according to item 4 of the scope of patent application, wherein the content of the compound represented by the chemical formula 1 is 0.1 parts by weight to 50 weight based on the total weight of solid components in the photosensitive resin composition. Parts, the content of the compound represented by the chemical formula 2 is 0.01 parts by weight to 10 parts by weight, the content of the binder resin is 1 part by weight to 60 parts by weight, and the content of the photoinitiator is 0.1 parts by weight to The content of the polyfunctional monomer is 20 parts by weight to 0.1 to 50 parts by weight. The photosensitive resin composition according to item 4 of the scope of patent application, further comprising at least one of a dye and a pigment. The photosensitive resin composition according to item 6 of the scope of the patent application, wherein the dye is at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye. The photosensitive resin composition according to item 7 of the scope of patent application, wherein the anthraquinone dye is represented by the following Chemical Formula 3; [Chemical Formula 3] (In the chemical formula 3, R ₁₁ and R ₁₂ are each independently at least one selected from the group consisting of an amino group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. One). The photosensitive resin composition according to item 7 of the scope of application for a patent, wherein the anthraquinone dye is any one selected from the following compounds; . The photosensitive resin composition according to item 7 of the scope of application for a patent, wherein the tetraazaporphyrin-based dye is any one selected from the following compounds; . The photosensitive resin composition according to item 7 of the scope of patent application, wherein the triarylmethane-based dye is any one selected from the following compounds; . The photosensitive resin composition according to item 4 of the scope of patent application, further comprising a dispersant, the dispersant being a polymer containing a repeating unit represented by the following Chemical Formula 11 or a repeating unit represented by the Chemical Formula 12; [Chemical Formula 11] [Chemical Formula 12] (In Chemical Formula 11 and Chemical Formula 12, R ₃₀₁ and R ₄₀₁ may be the same as or different from each other, and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and R ₃₀₂ , R ₃₀₃ , R _402, and R ₄₀₃ may be the same as each other or May be different, and are each independently hydrogen, alkyl having 1 to 30 carbons, aryl having 6 to 30 carbons or heteroaryl having 1 to 30 carbons, or R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ each other Bonded to form a substituted or unsubstituted ring, Ar ₃ and Ar ₄ may be the same as or different from each other, and are each independently directly bonded, an alkylene group having 1 to 10 carbon atoms, and-[CH (R ₃₁₁ ) -CH (R ₃₁₂ ) -O] _x -CH (R ₃₁₃ ) -CH (R ₃₁₄ ) _-or -[(CH ₂ ) _y -O] _z- (CH ₂ ) _y -represented by a divalent linking group, R ₃₁₁ to R ₃₁₄ may be the same as or different from each other, and are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, x is an integer of 1 to 18, and when x is 2 or more, the structures in parentheses may be mutually different The same or different, y is an integer from 1 to 5, and z is an integer from 1 to 18. When z is 2 or more, the structures in the brackets may be the same as or different from each other. Q is selected from the group consisting of direct bonding, carbon 1 to 10 alkylene groups, 6 to 30 carbon atoms, -CONH- Any one or two or more of the group consisting of -COO-, and an ether group having 1 to 10 carbon atoms; A photosensitive resin composition comprising a compound represented by the following Chemical Formula 15, a compound represented by the following Chemical Formula 2, a dye, and a dispersant, and the dye is a triarylmethane-based dye; [Chemical Formula 15] [Chemical Formula 2] (In Chemical Formula 15, the definitions of R ₁ to R ₆ , R _A to R _D , R _AA , R _BB, and X ₁ to X _{5 and} the definition of Chemical Formula 2 refer to the definition in item 1 of the scope of patent application). The photosensitive resin composition according to item 13 of the scope of application for a patent, wherein the triarylmethane-based dye is any one selected from the following compounds; . The photosensitive resin composition according to item 13 of the scope of patent application, wherein the dispersant is a polymer containing a repeating unit represented by the following Chemical Formula 11 or a repeating unit represented by the Chemical Formula 12; [Chemical Formula 11] [Chemical Formula 12] (In Chemical Formula 11 and Chemical Formula 12, the definitions of R ₃₀₁ , R ₃₀₂ , R ₃₀₃ , R ₄₀₁ , Ar ₃ , Ar ₄ , R ₃₁₁ to R ₃₁₄ , x, y, z, and Q refer to the 12th scope of the patent application. Definition). A photosensitive material manufactured by using the resin composition according to any one of claims 1 to 15 of the scope of patent application. A color filter includes the photosensitive material according to item 16 of the patent application scope. A display device includes the color filter according to item 17 of the scope of patent application.