TWI642731B - Photosensitive resin composition, photosensitive material, color filter and display device - Google Patents

Abstract

The present invention provides a photosensitive resin composition and a color filter comprising the same. The present specification relates to a photosensitive resin composition comprising a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, and a color filter comprising the same.

Description

Photosensitive resin composition, photosensitive material, color filter and display Display device

This specification relates to a photosensitive resin composition and a color filter comprising 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 purposes of the development of display elements is the differentiation of display element performance and the improvement of productivity in manufacturing steps due to the improvement in color purity.

Previously, the type of pigment used as a color filter of a color filter was present in a color dispersion in a particle-dispersed state, and therefore, it was difficult to adjust the brightness and the contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, it is agglomerated in a color filter, and has poor solubility and dispersibility, and causes multiple scattering of light due to large particles of aggregation. It has been pointed out that the scattering of such polarized light is the main reason for the decrease in the contrast ratio. In order to improve the brightness and the contrast ratio by ultrafine particle formation and dispersion stabilization of pigments, efforts have been made to achieve color matching of color coordinates for display devices for achieving high color purity. Limited by degree. In addition, the pigment dispersion method using the developed coloring material, especially the pigment, has reached the limit in terms of improving the color purity, brightness, and contrast ratio of the color filter using the same. Therefore, development of a coloring agent which can improve color purity and enhance color reproduction, brightness, and contrast ratio or a photosensitive resin composition containing the same is required.

[Prior Art Literature] [Patent Literature]

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

The present invention relates to a photosensitive resin composition, a color filter produced using the same.

According to an embodiment of the present invention, there is provided 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 2] [(RSiO _1.5 ) _n ] In Chemical Formula 1, L _A and L _B may be the same or different, and each independently is a direct bond or an alkyl group having a carbon number of 1 to 10, R _A to R _F They may be the same or different from each other, and are independently selected from hydrogen, a heavy hydrogen, a halogen atom, a nitro group, a substituted or unsubstituted alkyl group having a linear or branched chain of 1 to 30 carbon atoms, substituted or not. 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 Or a group consisting of polycyclic heteroaryl groups, R ₁ to R ₆ may be the same or different from each other, and are independently selected from hydrogen, dihydrogen, halogen atom, substituted or unsubstituted carbon number 1~. a straight or branched alkyl group of 6 and a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, a sulfonic acid group, a sulfonate group, a sulfonate group, a -SO ₂ NHR ₇ group, and In the group consisting of -SO ₂ NR ₈ R ₉ , R ₇ to R ₉ may be the same or different, and each independently is a linear or branched carbon group having 1 to 10 carbon atoms, X ₁ to X _{5 .} They may be the same or different from each other, and are independently selected from , heavy hydrogen, an anionic group, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and In the group consisting of 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, and R _AA and R _BB may be mutually The same or different, each independently selected from hydrogen, heavy hydrogen, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted Or unsubstituted aryl or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, halogen atom, nitro group, benzene Oxyl, carboxyl, carboxylate, carboxylate, alkoxycarbonyl, hydroxy, sulfonate, sulfonate, sulfonate, -SO ₂ NHR' and -SO ₂ NR"R' In the group formed, a and b may be the same 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 parentheses may be the same or different. R', R" and R''' may or may not be identical to each other Similarly, each is independently an alkyl group having 1 to 30 carbon atoms, and in the chemical formula 2, n is an even number of 4 or more, and R is represented by -(L ₁ ) _{n1 -} R ₇ , and a plurality of R may be the same 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. When n1 is 2 or more, L ₁ may be the same or different. R ₇ is hydrogen, heavy hydrogen, -OH, epoxide group, -SH, -NH ₂ , And -N=C=O, -C=C-, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heterocyclic group having 1 to 30 carbon atoms.

Further, an embodiment of the present invention provides a photosensitive material produced using the photosensitive resin composition and a color filter containing the same.

In the case of forming a pattern for a color filter according to an embodiment of the photosensitive resin composition of the present invention, when a hole is realized in the pattern, the sensitivity can be lowered and the brightness can be improved.

Further, in the photosensitive resin composition of one embodiment of the present invention, even if the sensitivity is low, the adhesion between the pattern and the substrate is excellent.

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

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

In the present specification, when a certain component is "included" as a component, unless otherwise stated, the case does not mean that other components are excluded, and that other components may be included.

According to an embodiment of the present specification, there is provided a photosensitive resin composition comprising the compound represented by the above Chemical Formula 1 and the compound represented by the Chemical Formula 2.

In this specification, the term "substituted or unsubstituted" means Selected from the group consisting of heavy hydrogen, halogen atom, alkyl, alkenyl, alkoxy, cycloalkyl, arylalkenyl, aryl, aryloxy, aralkyl, aralkenyl, alkylamino, aromatic Alkylamino, arylamino, heteroaryl, carbazolyl, acryl fluorenyl, acrylate, ether, nitrile, nitro, hydroxy, cyano, containing N, O, S or One or more substituents in the group of one or more heteroaryl groups and anionic groups in the P atom may or may not have any substituent.

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

In the present 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 thereof include an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group, but are not limited thereto.

In the present specification, the alkoxy group may be a straight chain or a branched chain, and is not particularly limited, and the carbon number may be from 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 the present specification, examples of the halogen atom include fluorine, chlorine, bromine or iodine.

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

In the case where 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 or a phenyl group. Triphenyl or the like, but is not limited thereto.

In the case where the aryl group is a polycyclic aryl group, it is not particularly limited, and the carbon number may be 10 to 40. Specifically, examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthryl group, an anthryl group, and a fluorenyl group. Base or thiol, etc., but is not limited thereto.

In the case where the sulfhydryl group is substituted, it can become , Snail base, (9,9-dimethylindenyl) and A fluorenyl group substituted with (9,9-diphenylfluorenyl) or the like. However, it is not limited to this.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as a hetero atom, and the number of carbon atoms is not particularly limited. According to one embodiment, the heterocyclic group has a carbon number of from 1 to 30. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidinyl group, a pyridazinyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, and an isothiazolyl group. , triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxenyl , triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthene, diaza naphthyl, three Azaindolyl, fluorenyl, porphyrinyl, pyridazinyl, pyridazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl Benzimidazolyl, benzothienyl, benzofuranyl, dibenzothiophenyl, dibenzofuranyl, oxazolyl, benzoxazolyl, dibenzoxazolyl, indolocarbazole Base, indolocarbazolyl, cyanoazinyl, imidazopyridyl, Phenoxyzinyl, phenanthryl, phenanthroline, phenothiazine, imidazolinyl, benzimidazoquinazolinyl or benzimidazolidinyl, but not Only limited to these.

In an embodiment of the present specification, the number of the ring-forming elements of the heterocyclic group is from 3 to 60. In another embodiment, the number of ring-forming elements of the heterocyclic group is from 3 to 40. Further, in one embodiment, the number of ring-forming elements of the heterocyclic group is from 3 to 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 from 1 to 30. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridine. Acridyl, pyridazinyl, quinolyl, isoquinolinyl, fluorenyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzo The thienyl group, the dibenzothiophenyl group, the benzofuranyl group, the dibenzofuranyl group and the like are not limited thereto. In the present specification, the description of the heterocyclic group may be applied to the heteroaryl group in addition to the aromatic group.

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

In the present specification, the description of the aryl group may be applied to the arylene in addition to the divalent group.

In the present specification, the heteroaryl group may be applied in addition to the divalent group. Description of the heteroaryl group.

In the present specification, the 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 is formed, A substituted or unsubstituted aliphatic heterocyclic ring, a substituted or unsubstituted aromatic heterocyclic ring or a condensed ring thereof.

In the present specification, the aliphatic hydrocarbon ring is a ring which is not aromatic and means a ring containing only a carbon atom and a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, and 1,4-cyclohexadiene. Cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc., but not limited thereto.

In the present specification, the aromatic hydrocarbon ring means an aromatic ring containing only a carbon atom and a hydrogen atom. In the present specification, specific examples of the aromatic hydrocarbon ring include benzene, naphthalene, anthracene, phenanthrene, anthracene, fluoranthene, ternary triphenyl, anthracene, anthracene, and fused tetrathene. , pentacene, hydrazine, hydrazine, hydrazine, benzopyrene, snail, etc., but not limited to these.

In the present specification, the aliphatic heterocyclic ring means one or more aliphatic rings containing a hetero atom. Specific examples of the aliphatic heterocyclic ring include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, pyridine, and morpholine. And oxepan, azocane, thiocane, etc., but are not limited thereto.

In the present specification, the term "aromatic heterocyclic ring" means one of the hetero atoms. More than one aromatic ring. Specific 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, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, Quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazepine, triazaindene, anthraquinone, indolizine, benzothiazole, benzoxazole, benzimidazole, benzene And thiophene, benzofuran, dibenzothiophene, dibenzofuran, oxazole, benzoxazole, dibenzoxazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, anthracene Carbazole, etc., but not limited to these.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring, and the aromatic heterocyclic ring may be a single ring or a polycyclic ring.

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

In one embodiment, L _A and L _B are respectively a propyl group.

In an embodiment of the present specification, R _A to R _F may be the same or different from each other, and are independently selected from hydrogen, heavy hydrogen, halogen atom, nitro group, substituted or unsubstituted carbon number 1 to 30. An alkyl group, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted A group consisting of monocyclic or polycyclic heteroaryl groups having 1 to 30 carbon atoms.

In one embodiment, R _A ~ R _F are hydrogen.

According to an embodiment of the present specification, R ₁ to R ₆ may be the same or different from each other, and are independently selected from a hydrogen or a heavy hydrogen, a substituted or unsubstituted straight or branched chain having 1 to 6 carbon atoms. A group consisting of an alkyl group, a sulfonic acid group, a sulfonate group, a -SO ₂ NHR ₇ group, and -SO ₂ NR ₈ R ₉ .

R ₇ to R ₉ may be the same or different from each other, and each independently is 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 or different from each other, and are independently selected from a hydrogen or a heavy hydrogen, a substituted or unsubstituted straight or branched chain having 1 to 6 carbon atoms. A group consisting of an alkyl group and a sulfonate group.

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

In an embodiment 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 ⁺ , R _a ~R _{e is} independently an alkyl group selected from a straight or branched chain having 1 to 30 carbon atoms which may be substituted or unsubstituted, 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 embodiment of the present specification, the anionic group may be -SO ₃ ^- or -SO ₃ ^- Na ⁺ .

The anionic group may have an anion itself or may be present together with other cations in the form of a compound. Thus, the sum of the total charges of the molecules of the compound of Chemical Formula 1 can be changed depending on the number of substituted anionic groups. The compound of the present invention has a cation in one amine group, and therefore, the sum of the total charges of the molecules may have an anion to a value of 0 from the number 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 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 or different from each other, and are 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, ethyl or propyl.

In one embodiment of the present specification, R ₁ is hydrogen, hydrogen, -OH, epoxy, -SH, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, and aromatic having 6 to 30 carbon atoms. 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 an 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]

In one embodiment, the R may be represented by any one of the chemical formula 2-b and the chemical formula 2-c.

In an embodiment of the present specification, the compound represented by the chemical formula 2 may be SQ506 for 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 Co., Ltd.

In an embodiment of the present specification, the photosensitive resin composition may further comprise 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 the film produced from the resin composition.

As the binder resin, a copolymer resin which imparts mechanical strength to a polyfunctional monomer and a monomer which imparts alkali solubility can be used, and a binder which is generally used in the art can be further included.

In one embodiment, an acrylic binder resin is exemplified as the binder resin.

The polyfunctional monomer which imparts mechanical strength to the film may be selected from the group consisting of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated quinones, and acid anhydrides. Any one of them.

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, (methyl) ) dimethylaminoethyl acrylate, isobutyl (meth)acrylate, tert-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, bismuth (meth)acrylate Benzyloxy-2-hydroxypropyl ester, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy Diethylene glycol (meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (methyl) Acrylate, phenoxy diethylene glycol (meth) acrylate, p-nonyl phenoxy polyethylene glycol (meth) acrylate, p-nonyl phenoxy polypropylene glycol (meth) acrylate, Glycidyl methacrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate , heptafluorodecyl (meth)acrylate, tribromophenyl (meth)acrylate, α-hydroxymethyl methacrylate, α-hydroxyethyl methacrylate, α-hydroxypropyl methacrylate and α The group consisting of -hydroxybutyl methacrylate is, but not limited to, only those.

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, but not limited to, only those.

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

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

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

The monomer which imparts alkali solubility is not particularly limited as long as it contains an acid group. For example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, and fumar. Acid, monomethyl maleate, 5-norbornene-2-carboxylic acid, mono-2-((meth)acryloxy)ethyl phthalate, mono-2-(succinic acid) One or more of the group consisting of acryloyloxy)ethyl ester and ω-carboxypolycaprolactone mono(meth)acrylate, but not limited thereto.

According to an embodiment of the present specification, the binder 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 functions to form a photoresist image by light, and specifically may be selected from the group consisting of propylene glycol methacrylate, dipentaerythritol hexaacrylate, and dipentaerythritol acrylate. Neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanide Urea trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate One or a mixture of two or more of the groups.

The photoinitiator is not particularly limited as long as it is a starter which catalyzes crosslinking by light generation, and may be, for example, selected from the group consisting of an acetophenone-based compound, a biimidazole-based compound, and a triazine-based compound. One or more of the group consisting of a compound and a lanthanide compound.

Examples of the acetophenone-based compound include 2-hydroxy-2-methyl-1-benzene. Propane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)-phenyl-(2- Hydroxy-2-propyl)one, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone , 2-methyl-(4-methylthio)phenyl-2-morpholinyl-1-propan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholine Phenyl)butane-1-one, 2-(4-bromo)-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one or the like, but is 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'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl) -4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-linked Imidazole or the like, but is not limited thereto.

Examples of the triazine-based compound include 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2 , 4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid 1,1,1,3,3,3-hexafluoroisopropyl, 2-{4-[2 , 4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}ethyl acetate, 2-{4-[2,4-bis(trichloromethyl)-s-triazine-6 -yl]phenylthio}acetic acid 2-epoxyethyl ester, 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetic acid cyclohexyl ester , 2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}benzyl acetate, 3-{chloro-4-[2,4-bis(III Chloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio} Propylamine, 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethyl Aminophenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-pair The oxystyryl-s-triazine or the like is not limited thereto.

As the lanthanoid compound, 1,2-octanedione-1-(4-phenylthio)phenyl-2-(o-benzoyl fluorenyl) (Ciba-Geigy) can be cited. Manufactured by the company, CGI124), Ethyl Ketone-1-(9-Ethyl)-6-(2-methylbenzhydryl-3-yl)-1-(O-ethylindenyl) (CGI242), N -1919 (made by Adeka Co., Ltd.), etc., but is not limited thereto.

The solvent may be 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, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol , cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate One or more of the group consisting of ester, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto.

In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is from 0.1 part by weight to 50 parts by weight based on the total weight of the solid content in the photosensitive resin composition, from the chemical formula 2 The content of the compound represented is 0.01 parts by weight to 10 parts by weight. The content of the binder resin is from 1 part by weight to 60 parts by weight, the content of the photoinitiator is from 0.1 part by weight to 20 parts by weight, and the content of the polyfunctional monomer is from 0.1 part by weight to 50 parts by weight. Parts by weight.

The total weight of the solid component refers to the sum of the total weights of the components after the solvent is removed from the resin composition. The basis of the solid content and the weight fraction based on the solid content of each component can be measured by a usual analytical 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 comprise at least one of a dye and a pigment.

Dyes and pigments are both responsible for the wavelength of the desired range of absorption, and can be distinguished as dyes and pigments depending on the solubility of the solvent. The dye means that the solubility in the solvent is large and it is easy to dissolve, and the pigment means that the solubility is relatively low and it is difficult to dissolve.

Further, the dye may be at least one selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane dye.

Further, the lanthanide dye can be represented by the following 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 amine group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. By.

Further, according to an embodiment of the present specification, the anthraquinone dye may be any one selected from the group consisting of the following compounds.

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

Further, according to an embodiment of the present specification, the triarylmethane dye may be any one selected from the group consisting of the following compounds.

Further, in an embodiment of the present specification, the pigment is a blue pigment.

The blue pigment may be, for example, a 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, or the like.

In one embodiment, the pigment may comprise a copper indigo pigment.

Further, the blue dye may contain, for example, a methyl dye, an anthraquinone dye, an azo dye, a triarylmethane dye, an indigo dye, or the like as the blue dye.

Further, the blue pigment may be, for example, a blue lake pigment, which may be obtained by lake-forming a blue pigment as described above by a lake forming agent. The coloring agent is not particularly limited, and for example, phosphotungstic acid, phosphomolybdic acid, phosphotungstic acid, tannic acid, lauric acid, 3,4,5-trihydroxybenzoic acid, ferricyanide, or sub- Ferric cyanide and the like.

As examples of specific blue lake pigments, 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, C.I. Pigment Blue 53, C.I. Pigment Blue 56, C.I. Pigment Blue 56:1, C.I. Pigment Blue 61, C.I. Pigment Blue 61:1, C.I. Pigment Blue 62, C.I. Pigment Blue 63, C.I. Pigment Blue 78 and the like.

In one embodiment of the present specification, the photosensitive resin composition further contains a dispersing agent, and the dispersing agent may include a polymer containing a repeating unit represented by the following Chemical Formula 11 or a repeating unit represented by the following Chemical Formula 12.

In Chemical Formula 11 and Chemical Formula 12, R ₃₀₁ and R ₄₀₁ may be the same or different, and each independently is 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. Differently, they may independently be hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 1 to 30 carbon atoms, or R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R _{403 may} be mutually Bonding to form a substituted or unsubstituted ring, Ar ₃ and Ar ₄ may be the same or different, each independently being a direct bond, an alkyl group having a carbon number of 1 to 10, and consisting of -[CH(R ₃₁₁₎ )-CH(R ₃₁₂ )-O] _x -CH(R ₃₁₃ )-CH(R ₃₁₄ )- or -[(CH ₂ ) _y1 -O] _z -(CH ₂ ) _y2 - represents a divalent linking group, R ₃₁₁ to R ₃₁₄ may be the same or different from each other, and each independently is hydrogen or an alkyl group having 1 to 10 carbon atoms, and x is an integer of 1 to 18. In the case where x is 2 or more, the structures in parentheses may be mutually The same or different, y1 and y2 may be the same or different from each other, and are independently an integer of 1 to 5, and z is an integer of 1 to 18. In the case where z is 2 or more, the structures in the parentheses may be identical to each other. Differently, Q is selected from a direct bond, an alkyl group having a carbon number of 1 to 10, and a carbon number of 6 to 30. A linking group in which one or more of the group consisting of an aryl group, -CONH-, -COO-, and an ether group having 1 to 10 carbon atoms are bonded.

In one embodiment, the dispersing agent may be contained in an amount of 0.5 part by weight to 50 parts by weight based on the total mass of the solid component in the resin composition.

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

According to an embodiment of the present specification, the solid in the resin composition is The antioxidant is contained in an amount of from 0.1 part by weight to 20 parts by weight based on the total weight of the part.

According to an embodiment of the present specification, the resin composition further comprises a photo-crosslinking sensitizer, a hardening accelerator, a adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and One or more additives in the group consisting of leveling agents.

According to an embodiment of the present specification, the additive is contained in an amount of from 0.1 part by weight to 20 parts by weight based on the total mass of the solid component in the resin composition.

As the photocrosslinking sensitizer, one or more selected from the group consisting of benzophenone, 4,4-bis(dimethylamino)benzophenone, and 4 may be used. 4-bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3,3-dimethyl-4 a benzophenone compound such as methoxybenzophenone or 3,3,4,4-tetrakis(t-butylperoxycarbonyl)benzophenone; 9-fluorenone, 2-chloro-9- Anthrone-based compounds such as anthrone and 2-methyl-9-fluorenone; thioxanthone, 2,4-diethylthiazinone, 2-chlorothiazepinone, 1-chloro-4-propanone a thioxanthone compound such as a thioxanthone, an isopropyl thioxanthone or a diisopropyl thioxanthone; a xanthone such as xanthone or 2-methylxanthone a compound; an anthraquinone compound such as hydrazine, 2-methyl hydrazine, 2-ethyl hydrazine, tert-butyl hydrazine, 2,6-dichloro-9,10-fluorene; 9-phenyl Acridine, acridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane Compound; benzyl, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrene Di-carbonyl compound; 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, bis(2,6-dimethoxybenzylidene)-2,4,4-trimethyl Oxidation of pentyl phosphine oxide Phosphine-based compound; methyl 4-(dimethylamino)benzoate, ethyl 4-(dimethylamino)benzoate, 2-n-butoxyethyl-4-(dimethylamino) a benzoate compound such as a benzoate; 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis(4-diethylaminobenzylidene) An amine-based synergist such as cyclohexanone or 2,6-bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; 3,3-carbonylvinyl-7-(diethyl Amino) coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzylidene-7-(diethylamino)coumarin , 3-benzylidene-7-methoxy-coumarin, 10,10-carbonyl bis[1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H , 5H, 11H-C1]-benzopyrano[6,7,8-ij]-quinolizin-11-one and other coumarin compounds; 4-diethylaminochalcone, 4-fold A chalcone compound such as a benzylidene acetophenone; a 2-benzylidene methylene group, a 3-methyl-b-naphthylthiazoline.

The hardening accelerator is used for the purpose of improving hardening and mechanical strength. Specifically, it can be selected from 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 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-tris(2-mercaptoacetate), and trimethylolpropane-three ( One or more of the group consisting of 3-mercaptopropionate).

As the adhesion promoter used in the present specification, methacryloxypropyltrimethoxydecane, methacryloxypropyldimethoxydecane, methacryloxypropyltricarboxylate may be selected. One or more kinds of methacryl decyl decane coupling agents such as ethoxy decane and methacryloxypropyl dimethoxy decane are used, and as the alkyl trimethoxy decane, octyl trimethoxy decane can be selected. Dodecyltrimethoxy One or more of decane, octadecyltrimethoxydecane, and the like are used.

The surfactant is a ruthenium-based surfactant or a fluorine-based surfactant. Specifically, as a ruthenium-based surfactant, BYK-Chemie (BYK-Chemie) BYK-077 can be used.克(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,克 (BYK)-375, BYK-380, BYK-390, etc. As a fluorine-based surfactant, DIC (DaiNippon Ink & Chemicals) can be used. The 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., but are not limited to these.

Examples of the antioxidant include a hindered phenol-based antioxidant, an amine-based antioxidant, a sulfur-based antioxidant, and a phosphine-based antioxidant. One or more of the groups consisting of the agents, but not limited to them.

Specific examples of the antioxidant include a phosphate-based heat stabilizer such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl- 3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[methylene-3-(3,5-di-t-butyl-4-hydroxyphenyl) Propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,5-di- Diethyl tert-butyl-4-hydroxybenzyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g, t-butylphenol 4 , 4'-butylidene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or double [3, 3-bis-(4'-hydroxy-3'-t-butylphenyl)butanoic acid]diol (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoicacid] Primary antioxidant such as Hindered phenol; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N, Amine secondary antioxidant such as N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, hydrazine a secondary anti-oxidant such as benzothiazole or tetramethylthiuram disulfide tetrakis [methylene-3-(laurylthio)propionate] methane; or triphenylphosphite, Tris(nonylphenyl)phosphite, triisodecylphosphite, bis(2,4-dibutylphenyl)pentaerythritol Diphosphite (Bis(2,4-ditbutylphenyl)Pentaerythritol Diphosphite) or 1,1'-biphenyl)-4,4'-diylbisphosphinic acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester (1,1'- Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl]ester) and other phosphite secondary antioxidants.

As the ultraviolet absorber, 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, or the like can be used, but The present invention is not limited thereto, and can be used if it is generally used by users in the art.

As the thermal polymerization preventing agent, for example, it may be selected from the group consisting of para-anisole, hydroquinone, pyrocatechol, t-butyl catechol, and N-nitroso Phenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-tert-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 group formed, but not limited thereto, may also include those generally known in the art.

The dispersant can be used by a method of adding a pigment to the pigment in a form of surface treatment of the pigment in advance, or a method of externally adding it to the pigment. As the dispersing agent, a compound type, a nonionic, an anionic or a cationic dispersing agent can be used, and examples thereof include a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactant. These may be used separately or in combination of two or more.

Specifically, examples of the dispersant include a polyalkylene glycol and an ester thereof, a polyoxyalkylene polyol, an ester alkylene oxide adduct, an alcohol alkylene oxide adduct, a sulfonate, and the like. One or more of the group consisting of a sulfonate, a carboxylic acid ester, a carboxylate, an alkylguanamine alkylene oxide adduct, and an alkylamine, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. As a poly Specific examples of the compound leveling agent include polyethyleneimine, polyamidamine, a reaction product of an amine and an epoxide, and specific examples of a non-polymeric leveling agent, including a non-polymer sulfur-containing compound. The non-polymer nitrogen-containing compound is not limited thereto, and can be used as long as it is generally used in the art.

One embodiment of the present specification provides 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 dispersing agent, and the dye is a triarylmethane-based dye.

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 as referred to above.

One embodiment of the present specification provides a photosensitive material produced using the resin composition.

More specifically, a photosensitive material in the form of a film or a pattern in which a resin composition according to an embodiment of the present invention is applied onto 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, and a spin coating method can be widely used. Further, after the coating film is formed, a part of the residual solvent may be removed under reduced pressure as the case may be.

Examples of the light source for curing the resin composition of the present specification include a light mercury vapor arc (arc) having a wavelength of 250 nm to 450 nm, a carbon arc, a Xe arc, and the like, but are not necessarily limited thereto.

The resin composition of the present specification can be used for a pigment dispersion type photosensitive material for producing a Thin Film Transistor Liquid Crystal Display (TFT LCD) color filter, a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode. Photosensitive material for forming a black matrix of a polar body, a photosensitive material for forming an overcoat layer, a photosensitive spacer material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, and a printed wiring The photosensitive material for a sheet, a photosensitive material for a plasma display panel (PDP), and the like are not particularly limited.

According to an embodiment of the present specification, a color filter comprising the photosensitive material is provided.

The color filter includes the photosensitive resin composition. The photosensitive resin The composition is applied onto a substrate to form a coating film, and the coating film is exposed, developed, and cured, whereby a color filter can be formed.

The resin composition of an embodiment of the present specification can provide a color filter which reduces sensitivity and enables high luminance when a hole is realized in a pattern.

The substrate may be a glass plate, a ruthenium wafer, a plate of a plastic substrate such as polyether sulfone (PES) or polycarbonate (PC), and the like, and the kind thereof is not particularly limited.

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

Additionally, according to an embodiment, the color filter may further comprise an overcoat layer.

Between the color pixels of the color filter, a lattice-like black pattern called a black matrix can be arranged for the purpose of enhancing the contrast ratio. As a material of the black matrix, chromium can be used. In this case, the chromium can be vapor-deposited on the entire glass substrate, and a pattern can be formed by an etching process. However, in consideration of the high cost in the step, the high reflectance of chromium, and the environmental pollution caused by the chromium waste liquid, a resin black matrix using a pigment dispersion method capable of microfabrication can be used.

A black matrix of an embodiment of the present specification may use a black pigment or a black dye as a colorant. For example, carbon black may be used alone, or carbon black may be used in combination with a color pigment. In this case, since the coloring pigment having insufficient light shielding property is mixed, there is an advantage that even if the amount of the coloring agent is relatively increased, the strength or the film strength base The adhesion of the board will 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 (LED), an organic light emitting diode (OLED), or a 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 the present specification, an embodiment will be described in detail. However, the embodiments of the present specification can be modified into various other forms, and the scope of the present specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are intended to provide a more complete description of the present specification to those of ordinary skill in the art.

Synthesis of compounds

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.

5 g of A-1 (8.710 mmol), 8.233 g of B-1 (34.838 mmol), 4.815 g of K ₂ CO ₃ (34.5838 mmol) were placed in 100 ml of N-Methyl Pyrrolidone (N-Methyl Pyrrolidone, In NMP), it was stirred at 95 ° C for 12 hours. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was placed in the precipitate and stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. Thereafter, the dried precipitates are separated by column chromatography. (Eluent-MC: MeOH)

As a result, 6 g of Compound 1 (3.322 mmol) was obtained in a yield of 72%.

The results are as follows.

Ionization mode =: Atmospheric Pressure Chemical Ionization (APCI) +: m / z = 949 [M + H] +, accurate mass (Exact Mass): 948

The measurement results of the ¹ H-NMR of the compound 1 are as follows.

¹ H NMR (500 MHz, dimethyl sulfoxide (DMSO), ppm): 8.03 (m, 11H), 7.69 to 7.18 (m, 10H), 6.99 to 6.95 (t, 1H), 6.80 to 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 in the above 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. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was placed in the precipitate and stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. Thereafter, the dried precipitates are separated by column chromatography. (Eluent-MC: MeOH)

As a result, 1.622 g of Compound 2 (1.912 mmol) was obtained in a yield of 70%.

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

As in the above 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. Thereafter, the solvent was removed under reduced pressure, and 200 ml of water was placed in the precipitate and stirred for 1 hour. Further, the precipitate was filtered under reduced pressure and dried at 80 ° C for 12 hours. Thereafter, the dried precipitates are separated by column chromatography. (Eluent-MC: MeOH)

As a result, 1.526 g of Compound 3 (1.622 mmol) was obtained in a yield of 59%.

Ionization mode =: APCI +: m / z = 963 [M + H] +, accurate mass (Exact Mass): 962

As in the above Reaction Scheme 4, 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) were placed in 100 ml of NMP. The mixture was stirred at 95 ° C for 12 hours. Thereafter, the solvent was removed under reduced pressure, and 100 ml of brine 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 coloring agent (6.945 mmol) based on Compound 4 as a main product was obtained in a yield of 94%.

Experimental example

Examples 1 to 4 and Comparative Examples 1 to 4 were produced at a ratio similar to the following Table 1. The input unit of each configuration is gram (g).

[Table 1]

Substrate production

The produced compound was spin-coated on a glass (5 cm × 5 cm) on which SiN _x was deposited, and prebaked 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 exposer.

Thereafter, the exposed substrate was developed with a developing solution (KOH, 0.04%) for 55 seconds, and post-bake at 230 ° C for 20 minutes to prepare a substrate.

Hole size determination

The inner length of the pores was measured for a substrate produced under the above-described conditions by a microscopic spectrophotometer (manufactured by Olympus Optical Industries Co., Ltd., OSPSP200) at a magnification of 1000 times.

Determination of adhesion

The substrate produced under the above-described conditions was measured by a microscopic spectrophotometer (manufactured by Olympus Optical Industries Co., Ltd., OSPSP200).

As shown in the above Table 1, it is understood that the photosensitive resin composition of Examples 1 to 4 containing both the compound represented by the above Chemical Formula 1 and the compound represented by Chemical Formula 2 is used to produce color filter. In the case of a sheet, the fine pattern has excellent adhesion.

The results obtained by measuring the adhesion of the fine pattern are shown in Fig. 1 .

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 2] [(RSiO _1.5 ) _n ] (In Chemical Formula 1, L _A and L _B may be the same or different, and each independently is a direct bond or an alkyl group having a carbon number of 1 to 10, R _A to R _F may be the same or different from each other, and are independently selected from hydrogen, dihydrogen, halogen atom, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number 1 ~30 alkoxy, substituted or unsubstituted hexacyclic or polycyclic aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 1 to 30 carbon atoms In the group consisting of aryl groups, R ₁ to R ₆ may be the same or different from each other, and are independently selected from a hydrogen group, a hydrogen atom, a halogen atom, a substituted or unsubstituted carbon number of 1 to 6 or a straight chain or Branched chain alkyl, substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, sulfonic acid group, sulfonate group, sulfonate group, -SO ₂ NHR ₇ group and -SO ₂ NR ₈ R _In the group of ₉ constituents, R ₇ to R ₉ may be the same or different from each other, and are independently a linear or branched alkyl group having 1 to 10 carbon atoms, and X ₁ to X ₅ may be the same or different from each other. , independently selected from hydrogen, heavy hydrogen, anion a hydroxy group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted In the group consisting of monocyclic or polycyclic heteroaryl groups 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 or different, respectively. Independently selected from hydrogen, heavy hydrogen, substituted or unsubstituted alkyl having from 1 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having from 1 to 30 carbon atoms, substituted or unsubstituted carbon a 6- to 30-membered monocyclic or polycyclic aryl group, a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 1 to 30 carbon atoms, a halogen atom, a nitro group, a phenoxy group, a carboxyl group, and a carboxy group. a group consisting of an acid ester group, a carboxylate group, an alkoxycarbonyl group, a hydroxyl group, a sulfonic acid group, a sulfonate group, a sulfonate group, -SO ₂ NHR', and -SO ₂ NR"R'" a and b may be the same 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 parentheses may be the same or different, R', R" and R''' may be the same or different from each other, independently An alkyl group having 1 to 30 carbon atoms, and in Chemical Formula 2, n is an even number of 4 or more, the R - _n1 -R ₇ represents ₍₁ L), the plurality of R may be the same or different from one another, 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. When n1 is 2 or more, L ₁ may be the same or different, and R ₇ is hydrogen and heavy. Hydrogen, -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), "Substituted or unsubstituted" means selected from the group consisting of heavy hydrogen, halogen atom, alkyl, alkenyl, alkoxy, cycloalkyl, arylalkenyl, aryl, aryloxy, aralkyl. Alkyl, aralkenyl, alkylamino, aralkylamino, arylamino, heteroaryl, carbazolyl, acryl oxime, acrylate, ether, nitrile, nitro, hydroxy, cyanide One or more substituents in the group containing one or more heteroaryl groups and anionic groups of an N atom, an O atom, an S atom or a P atom are substituted with or without any substituent. The photosensitive resin composition according to claim 1, wherein the 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 ⁺ , R _a ~R _e may be the same or different from each other, and are independently selected from a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number of 6 to 30. At least one of a monocyclic or polycyclic aryl group and a substituted or unsubstituted mono- or polycyclic heteroaryl group having 1 to 30 carbon atoms. The photosensitive resin composition according to claim 1, wherein the R is represented by any one of the following Chemical Formulas 2-a to 2-e; [Chemical Formula 2-d] The photosensitive resin composition according to claim 1, further comprising: a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The photosensitive resin composition according to claim 4, wherein the content of the compound represented by the chemical formula 1 is from 0.1 part by weight to 50% by weight based on the total weight of the solid component in the photosensitive resin composition. 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 part by weight. The content of the polyfunctional monomer is from 0.1 part by weight to 50 parts by weight per 20 parts by weight. The photosensitive resin composition according to claim 4, which further comprises at least one of a dye and a pigment. The photosensitive resin composition according to claim 6, wherein the dye is selected from the group consisting of an anthraquinone dye, a tetraazaporphyrin dye, and a triarylmethane. At least one of the group of dyes. The photosensitive resin composition according to claim 7, wherein the lanthanide dye is represented by the following Chemical Formula 3; (In the chemical formula 3, R ₁₁ and R ₁₂ are each independently at least selected from the group consisting of an amine group, an alkylamino group, a dialkylamino group, a phenylamino group, and a diphenylamino group. One). The photosensitive resin composition according to claim 7, wherein the lanthanide dye is any one selected from the group consisting of the following compounds; The photosensitive resin composition according to claim 7, wherein the porphyrazine-based dye is any one selected from the group consisting of the following compounds; The photosensitive resin composition according to claim 7, wherein the triarylmethane dye is any one selected from the group consisting of: The photosensitive resin composition according to claim 4, further comprising a dispersing agent which is a polymer comprising a repeating unit represented by the following Chemical Formula 11 or a repeating unit represented by Chemical Formula 12; (In Chemical Formula 11 and Chemical Formula 12, R ₃₀₁ and R ₄₀₁ may be the same or different, and each independently is 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. Differently, each independently is hydrogen, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 1 to 30 carbon atoms, or R ₃₀₂ and R ₃₀₃ or R ₄₀₂ and R ₄₀₃ are mutually Bonding to form a substituted or unsubstituted ring, Ar ₃ and Ar ₄ may be the same or different, each independently being a direct bond, an alkyl group having a carbon number of 1 to 10, and consisting of -[CH(R ₃₁₁₎ -CH(R ₃₁₂ )-O] _x -CH(R ₃₁₃ )-CH(R ₃₁₄ )- or -[(CH ₂ ) _y -O] _z -(CH ₂ ) _y - represents a divalent linking group, R ₃₁₁ to R ₃₁₄ may be the same or different from each other, and each independently is hydrogen or an alkyl group having 1 to 10 carbon atoms, and x is an integer of 1 to 18. In the case where x is 2 or more, the structures in parentheses may be mutually 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 parentheses may be the same or different, and Q is selected from carbon numbers 1 to 10. a group consisting of an alkyl group, an alkyl group having 6 to 30 carbon atoms, a -CONH-, -COO-, and an ether group having 1 to 10 carbon atoms Two or more of any of a linking group formed by coupling). 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 dispersing agent, wherein the dye is a triarylmethane-based dye; [Chemical Formula 15] (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 the first item of the patent application scope). The photosensitive resin composition according to claim 13, wherein the triarylmethane dye is any one selected from the group consisting of the following compounds; The photosensitive resin composition according to claim 13, wherein the dispersing agent is a polymer comprising a repeating unit represented by the following Chemical Formula 11 or a repeating unit represented by Chemical Formula 12; [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 item of the patent application scope. Definition in ). A photosensitive material produced by using the resin composition according to any one of claims 1 to 15. A color filter comprising the photosensitive material of claim 16 of the patent application. A display device comprising the color filter of claim 17 of the patent application.