TW201804250A - Photosensitive resin composition, photosensitive material, color filter and display device capable of decreasing the sensitivity and increasing the brightness when realizing holes in a pattern - Google Patents

Abstract

The invention provides a photosensitive resin composition and a color filter including the same. The specification of the invention relates to a compound represented by chemical formula 1, a photosensitive resin composition represented by chemical formula 2, and a color filter having the same. In chemical formula 1, LA and LB may be the same or different from each other, and are each independently a direct bond or an alkylene group with a carbon number of 1 to 10; RA to RF may be the same or different from each other, and are each independently selected from the group consisting of hydrogen, heavy hydrogen, halogen atom, nitro group, substituted or unsubstituted alkyl group with a carbon number of 1 to 30, substituted or unsubstituted alkoxy group with a carbon number of 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl group with a carbon number of 6 to 30, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group with a carbon number of 1 to 30; R1 to R6 may be the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, substituted or unsubstituted linear chain or branched chain alkyl group with a carbon number of 1 to 6, substituted or unsubstituted alkoxy group with a carbon number of 1 to 6, sulfonic acid group, sulfonic acid ester group , sulfonate group, -SO2NHR7 group and -SO2NR8R9; R7 to R9 may be the same or different from each other, and are each independently a linear chain or branched chain alkyl group with a carbon number of 1 to 10; X1 to X5 may be the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, anionic group, hydroxyl group, substituted or unsubstituted alkyl group with a carbon number of 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl group with a carbon number of 6 to 30, and substituted or unsubstituted monocyclic or polycyclic heteroaryl group with a carbon number of 1 to 30; at least one of X1 to X5 is an anionic group; RAA and RBB may be the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted alkyl group with a carbon number of 1 to 30, substituted or unsubstituted alkoxy group with a carbon number of 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl group with a carbon number of 6 to 30, substituted or unsubstituted monocyclic or polycyclic heteroaryl group with a carbon number of 1 to 30, halogen atom, nitro group, phenoxy group, carboxyl group, carboxylate group, carboxylate group, alkoxycarbonyl group, hydroxyl group, sulfonic acid group, sulfonate group, sulfonate group, -SO2NHR' and -SO2NR''R'"; a and b may be the same or different from each other, and are each independently an integer of 0 to 4.

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 a color photoresist in a particle dispersed state, and therefore it was difficult to adjust brightness and contrast ratio by adjusting the size and distribution of 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 capable of improving color purity, and improving color reproduction, brightness, and contrast ratio, or a photosensitive resin composition containing the same. [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.

[化學式2]

化學式1中， L_A 及L_B 可彼此相同亦可不同，分別獨立地為直接鍵結或碳數1～10的伸烷基， R_A ～R_F 可彼此相同亦可不同，分別獨立地選自由氫、重氫、鹵素原子、硝基、經取代或未經取代的碳數1～30的烷基、經取代或未經取代的碳數1～30的烷氧基、經取代或未經取代的碳數6～30的單環或多環的芳基、及經取代或未經取代的碳數1～30的單環或多環的雜芳基所組成的群組中， R₁ ～R₆ 可彼此相同亦可不同，分別獨立地選自由氫、重氫、鹵素原子、經取代或未經取代的碳數1～6的直鏈或分支鏈的烷基、經取代或未經取代的碳數1～6的烷氧基、磺酸基、磺酸酯基、磺酸鹽基、-SO₂ NHR₇ 基及-SO₂ NR₈ R₉ 所組成的群組中， R₇ ～R₉ 可彼此相同亦可不同，分別獨立地為直鏈或分支鏈的碳數1～10的烷基， X₁ ～X₅ 可彼此相同亦可不同，分別獨立地選自由氫、重氫、陰離子性基、羥基、經取代或未經取代的碳數1～30的烷基、經取代或未經取代的碳數6～30的單環或多環的芳基、及經取代或未經取代的碳數1～30的單環或多環的雜芳基所組成的群組中， 所述X₁ ～X₅ 的至少一個為陰離子性基， R_AA 及R_BB 可彼此相同亦可不同，分別獨立地選自由氫、重氫、經取代或未經取代的碳數1～30的烷基、經取代或未經取代的碳數1～30的烷氧基、經取代或未經取代的碳數6～30的單環或多環的芳基、經取代或未經取代的碳數1～30的單環或多環的雜芳基、鹵素原子、硝基、苯氧基、羧基、羧酸酯基、羧酸鹽基、烷氧基羰基、羥基、磺酸基、磺酸酯基、磺酸鹽基、-SO₂ NHR'及-SO₂ NR''R'''所組成的群組中， a及b可彼此相同亦可不同，分別獨立地為0～4的整數， 於a及b為2以上的情況下，括號內的結構可彼此相同亦可不同， R'、R''及R'''可彼此相同亦可不同，分別獨立地為碳數1～30的烷基， 化學式2中， R為碳數1～5的烷基， M₁ 及L₁ 可彼此相同亦可不同，分別獨立地為直接鍵結或碳數1～10的伸烷基， n1及n2可彼此相同亦可不同，分別獨立地為1～4的整數， 於n1及n2為2以上的情況下，括號內的結構可彼此相同亦可不同， n3為0或1， n4為0～4的整數， 於n4為2以上的情況下，括號內的結構可彼此相同亦可不同， R₁₀₀ 為氫、重氫或碳數1～30的烷基。[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]

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 independently selected Free hydrogen, deuterium, halogen atom, nitro, substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted In the group consisting of a substituted 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, 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, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, substituted or unsubstituted In the group consisting of 1 to 6 carbon alkoxy groups, sulfo groups, sulfonate groups, sulfonate groups, -SO ₂ NHR ₇ groups and -SO ₂ NR ₈ R ₉ , R ₇ to R ₉ may be the same or different, and are each independently a straight or branched chain alkyl having 1 to 10, X ₁ ~ X ₅ may be the same or different from each other, are independently selected from the group consisting of hydrogen, deuterium, anionic Group, hydroxy, substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbons, and substituted or unsubstituted In a group consisting of a monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, at least one of X ₁ to X ₅ is an anionic group, and R _AA and R _BB may be the same as or different from each other, respectively. 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 carbon 6 to 30 monocyclic or polycyclic aryl groups, substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms, halogen atoms, nitro, phenoxy, carboxyl, carboxyl A group consisting of an ester group, a carboxylate group, an alkoxycarbonyl group, a hydroxyl group, a sulfonate group, a sulfonate group, a sulfonate group, -SO ₂ NHR ', and -SO ₂ NR `` R''' In the group, 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 or different from each other, and R ', R''AndR''' may be the same as each other The same, each independently alkyl having 1 to 30, Chemical Formula 2, R is alkyl of 1 to 5, M ₁ and L ₁ may be identical or different from each other, they are independently a direct bond or For alkylene groups having 1 to 10 carbon atoms, n1 and n2 may be the same as or different from each other, and are each independently an integer of 1 to 4. When n1 and n2 are 2 or more, the structures in the brackets may be the same as each other Different, n3 is 0 or 1, and n4 is an integer from 0 to 4. When n4 is 2 or more, the structures in the brackets may be the same as or different from each other. R ₁₀₀ is hydrogen, deuterium, or a carbon number of 1 to 30. alkyl.

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 color filter manufactured using the photosensitive resin composition according to one embodiment of the present invention reduces the surface cutting phenomenon of the pattern during the development step, and has excellent solvent resistance to solvents.

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.

、

等螺茀基，

(9,9-二甲基茀基)及

(9,9-二苯基茀基)等經取代而成的茀基。但是，並不限定於此。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 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, 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 this specification, specific examples of the aromatic hydrocarbon ring include phenyl, naphthyl, anthracenyl, benzene, naphthalene, anthracene, phenanthrene, fluorene, fluoranthene, triphenylene, fluorene, fluorene, and fused tetraphenyl Benzene, fluorene, pentacene, fluorene, indene, fluorene, benzofluorene, spirofluorene, and the like 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. In the group consisting of alkyl group, sulfonate group, sulfonate group, -SO ₂ NHR ₇ group, and -SO ₂ NR ₈ R ₉ , R ₇ to R ₉ may be the same as or different from each other. Alkyl group having 1 to 10 carbon atoms in the chain or branch chain. 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 to L ₄ 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 ₁ to L ₄ are ethylene. In an embodiment of the present specification, R _{1 1} to R _{1 4} , R ₂₁ to R _24, and R ₃₁ to R ₃₄ may be the same as or different from each other, and are each independently hydrogen, deuterium, or a carbon number of 1 to 30. alkyl. In one embodiment of the present specification, R _{1 1} to R _{1 4} , R ₂₁ to R _24, and R ₃₁ to R ₃₄ 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. In one embodiment of the present specification, R _{1 1} to R _{1 4} , R ₂₁ to R _24, and R ₃₁ to R ₃₄ may be the same as or different from each other, and are each independently hydrogen or methyl. In one embodiment, R _{1 1} to R _{1 4} are methyl. In one embodiment, R ₂₂ to R ₂₄ and R ₃₁ to R ₃₄ are hydrogen.

According to an embodiment of the present specification, the compound represented by Chemical Formula 2 may be any one selected from the following compounds.

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- (Manufactured by Geigy), CGI124), ethyl ketone, -1- (9-ethyl) -6- (2-methylbenzylidene-3-yl)-, 1- (o-acetamidooxime) (CGI242 ), N-1919 (made 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, the content of the compound represented by the chemical formula 1 is 0.1 to 50 parts by weight based on the total weight of solid components in the photosensitive resin composition. 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.

所述化學式3中， R₁₁ 及R₁₂ 分別獨立地為選自由胺基、烷基胺基、二烷基胺基、苯基胺基及二苯基胺基所組成的群組中的至少一者。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. The blue pigment may include, as a blue organic pigment, 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.

[化學式12]

化學式11及化學式12中， R₃₀₁ 及R₄₀₁ 可彼此相同亦可不同，分別獨立地為氫或碳數1～10的烷基， R₃₀₂ 、R₃₀₃ 、R₄₀₂ 及R₄₀₃ 可彼此相同亦可不同，可分別獨立地為氫、碳數1～30的烷基、碳數6～30的芳基或碳數1～30的雜芳基，或者 R₃₀₂ 與R₃₀₃ 或者R₄₀₂ 與R₄₀₃ 彼此鍵結而形成經取代或未經取代的環， Ar₃ 及Ar₄ 可彼此相同亦可不同，分別獨立地為直接鍵結、碳數1～10的伸烷基、由-[CH(R₃₁₁ )-CH(R₃₁₂ )-O]_x -CH(R₃₁₃ )-CH(R₃₁₄ )-或-[(CH₂ )_y1 -O]_z -(CH₂ )_y2 -表示的二價連結基， R₃₁₁ ～R₃₁₄ 可彼此相同亦可不同，分別獨立地為氫或碳數1～10的烷基， x為1～18的整數，於x為2以上的情況下，括號內的結構可彼此相同亦可不同， y1及y2可彼此相同亦可不同，分別獨立地為1～5的整數， z為1～18的整數，於z為2以上的情況下，括號內的結構可彼此相同亦可不同， Q為選自由直接鍵結、碳數1～10的伸烷基、碳數6～30的伸芳基、-CONH-、-COO-及碳數1～10的醚基所組成的群組中的任一個或兩個以上連結而成的連結基。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] -quinazin-11-one; 4-diethylamino group Chalcone compounds such as ketone ketone, 4-azidobenzylidene acetophenone; 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.

[化學式2]

化學式15中，所述R₁ ～R₆ 、R_A ～R_D 、R_AA 、R_BB 及X₁ ～X₅ 的定義及化學式2的定義參照上文所提及的。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 curing the resin composition of the present specification include mercury vapor arc (arc), carbon arc, Xe arc, and the like that emit light having 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.

將5 g的A-1（8.710 mmol）、8.233 g的B-1（34.838 mmol）、4.815 g的K₂ CO₃ （34.5838 mmol）放入100 ml的NMP中，於95℃下攪拌12小時。之後，於減壓下去除溶媒，將200 ml的水放入析出物中並攪拌1小時。另外，於減壓下對析出物進行過濾，並於80℃下使其乾燥12小時。之後，藉由管柱層析法使已乾燥的析出物分離。（溶析液（Eluent）-MC：MeOH） 結果，可獲得6 g的化合物1（3.322 mmol），產率為72%。 結果如下所述。 離子化模式=：大氣壓化學遊離（Atmospheric Pressure Chemical Ionization，APCI）+：m/z=949[M+H]+，準確質量（Exact Mass）：948 所述化合物1的¹ H-NMR的測定結果如下所述。¹ H NMR(500 MHz,二甲基亞碸（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) 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]

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) were put into 100 ml of 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)

如所述反應式2般，將1.43 g的C‐1（2.732 mmol）、2.99 g的B‐1（9.490 mmol）、1.31 g的K₂ CO₃ （9.490 mmol）放入20 ml的NMP中，於95℃下攪拌12小時。之後，於減壓下去除溶媒，將200 ml的水放入析出物中並攪拌1小時。另外，於減壓下對析出物進行過濾，並於80℃下使其乾燥12小時。之後，藉由管柱層析法使已乾燥的析出物分離。（溶析液（Eluent）-MC：MeOH） 結果，可獲得1.622 g的化合物2（1.912 mmol），產率為70%。 離子化模式=：APCI+：m/z=977[M+H]+，準確質量（Exact Mass）：976[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

如所述反應式3般，將1.608 g的D-1（2.732 mmol）、2.99 g的B-1（9.490 mmol）、1.31 g的K₂ CO₃ （9.490 mmol）放入20 ml的NMP中，於95℃下攪拌12小時。之後，於減壓下去除溶媒，將200 ml的水放入析出物中並攪拌1小時。另外，於減壓下對析出物進行過濾，並於80℃下使其乾燥12小時。之後，藉由管柱層析法使已乾燥的析出物分離。（溶析液（Eluent）-MC：MeOH） 結果，可獲得1.526 g的化合物3（1.622 mmol），產率為59%。 離子化模式=：APCI+：m/z=963[M+H]+，準確質量（Exact Mass）：962[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

Experimental Example Examples 1 to 4 and Comparative Examples 1 to 3 were produced at the ratios shown in Table 1 below. The input unit of each component is gram (g).

[Table 1]

Experimental Example 1. Measurement of film cutting The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm) and prebake at 110 ° C. for 70 seconds to form a film. The entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm ² . After removing the film layer in the center portion of the substrate, the step was confirmed using a surface step measuring device. Thereafter, the exposed substrate was developed with a developing solution (KOH, 0.04%) at 0.1 mPa for 55 seconds, and a step was measured using a surface step measuring device. The steps before and after development were confirmed, and the degree of film cutting was determined and shown in Table 2 below.

Experimental example 2. Evaluation of peeling The photosensitive resin composition was spin-coated on glass (5 cm × 5 cm) 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 600 μm, and the entire surface of the substrate was irradiated with an exposure amount of 30 mJ / cm ² . After that, the exposed substrate was developed with a developing solution (KOH, 0.04%) at 0.2 mPa for 300 seconds, and then the pattern was observed with an Olympus optical microscope to confirm the degree of pattern peeling. The degree of spalling is shown in Figure 1 of the accompanying drawings. [Table 2] As shown in Table 2 and FIG. 1, the photosensitivity of Examples 1 to 4 using both the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 is known. When a resin composition is used to produce a color filter, the effect of reducing film cutting or peeling is exhibited.

no

FIG. 1 shows the use of a photosensitive resin composition according to an embodiment of the present invention and a photosensitive resin composition manufactured as a comparative example to form a color filter pattern. The color filter is compared with N-methylpyrrolidone. (N-Methyl Pyrrolidone, NMP) solvent was compared for chemical resistance.

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]

(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 independently independent Selected from hydrogen, deuterium, halogen atom, nitro, substituted or unsubstituted alkyl having 1 to 30 carbons, substituted or unsubstituted alkoxy having 1 to 30 carbons, substituted or unsubstituted In the group consisting of a substituted 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, R ₁ ~ R ₆ may be the same as or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, a halogen atom, a substituted or unsubstituted linear or branched alkyl group having 1 to 6 carbon atoms, In the group consisting of substituted alkoxy groups having 1 to 6 carbon atoms, sulfonic acid group, sulfonic acid ester group, sulfonate group, -SO ₂ NHR ₇ group, and -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 may be the same as or different from each other, and are independently selected from the group consisting of hydrogen, deuterium, Overcast Sex 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 substituted or unsubstituted In a group consisting of a monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, at least one of X ₁ to X ₅ is an anionic group, and R _AA and R _BB may be the same as or different from each other, 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 groups having 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms, halogen atoms, nitro, phenoxy, carboxyl groups, Composed of carboxylate, carboxylate, alkoxycarbonyl, hydroxyl, sulfonate, sulfonate, sulfonate, -SO ₂ NHR 'and -SO ₂ NR `` R''' In the group, 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 or different from each other, and R ′, R '' And R '''may be the same as each other Different, each independently alkyl having 1 to 30 carbon atoms, in the formula 2, R is alkyl of 1 to 5, M ₁ and L ₁ may be identical or different from each other, they are independently a direct bond or For alkylene groups having 1 to 10 carbon atoms, n1 and n2 may be the same as or different from each other, and are each independently an integer of 1 to 4. In the case where n1 and n2 are 2 or more, the structures in the brackets may be the same as each other. Different, n3 is 0 or 1, and n4 is an integer from 0 to 4. When n4 is 2 or more, the structures in the brackets may be the same as or different from each other. R ₁₀₀ is hydrogen, deuterium, or a carbon number of 1 to 30. alkyl). 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, -O ₂ ^- Z ⁺ , -CO ₂ R _a , -SO ₃ R _b and -SO ₃ NR _c R _d , at least one of the groups, Z ⁺ represents N (R _e ) ₄ ⁺ , Na ⁺ Or K ⁺ , R _a to R _e may be the same as or different from each other, and are each independently selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number 6 to 30 At least one of the 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 compound represented by the chemical formula 2 is any one selected from the following compounds;

. 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 based on the total weight of solid components in the photosensitive resin composition. The content of the compound represented by the chemical formula 2 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 part by weight. -20 parts by weight, and the content of the polyfunctional monomer is 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 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 patent application, wherein the anthraquinone 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 tetraazaporphyrin-based 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 triarylmethane 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 item 12 of the scope of 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.