TW201920495A - Coloring agent compound, coloring composition, color filter and display device - Google Patents

Abstract

A coloring agent compound, a coloring composition, a color filter, and a display device are provided. More particularly, a coloring agent compound of a novel structure which has excellent color characteristics, heat resistance, and solubility, thereby being applicable for manufacturing a color filter, and a coloring composition including the same, are provided. The coloring agent compound is represented by the following Formula 1. In Formula 1, the definition of each substituents is the same as in detail description.

Description

Colorant compound and coloring composition including the same

The present invention relates to a color former compound and a colored composition comprising the same. More specifically, the present invention relates to a novel structure of a color former compound and a coloring composition comprising the same, which have excellent color characteristics, heat resistance and solubility. [Cross-Reference to Related Applications]

The present application is based on Korean Patent Application No. 10-2017-0112691 and No. 10-2018-0098142, filed on Sep. 4, 2017, and on August 22, s. The disclosure of the present invention is hereby incorporated by reference in its entirety.

A color filter in a liquid crystal display device (LCD), an organic light emitting diode (OLED), or the like is used to generate a color image in a display device, and the color filter can be used by Fabrication is accomplished using a variety of methods for coating, curing, and patterning colors onto a base substrate.

The color filter includes individual unit pixels displaying three colors of red, green, and blue, three colors are formed on a transparent substrate such as glass, and a color filter for an image display device or a solid-state imaging device usually has red (red The color patterns of the three primary colors of R), green (green), and blue (blue; B), and thus function in coloring the transmitted light or separating the light into three primary colors.

The colors showing red, green, and blue are formed by fine particles, that is, dyes or pigments. In order to obtain the color display characteristics of the desired area, these colors can be used in a mixture of similar colors instead of using a single color to display red, green, and blue.

A material used as a color generally requires a preferable absorption property in terms of color reproducibility, and good light resistance, heat resistance, and resistance to an oxidizing gas such as ozone under use conditions.

Recently, technologies for large screens and high definition liquid crystal displays are being developed. In this case, a color filter for a liquid crystal display or the like needs to have high color purity. Various colors or colorants that can be used to make color filters are known, but methods that use only known coloring materials to improve color purity, brightness, and contrast are reaching their limits.

In particular, when a color filter is produced by a pigment dispersion method, it is difficult to increase the pigment content in a photosensitive resin composition due to a pigment derivative and a dispersant added according to a pigment dispersion method, and Therefore, it is difficult to manufacture a film color filter. Therefore, in order to solve such problems, there is a demand for novel pigments. [Prior Technical Literature] [Patent Literature]

(Patent Document 0001) Korean Patent Publication No. 10-2014-01252183.

[technical problem]

In order to solve the above problems, the present invention provides a novel structure of a color former compound and a coloring composition comprising the same, wherein the colorant compound has excellent color reproducibility, color characteristics, heat resistance, solubility, etc., thereby being used as Coloring material for color filters. [Technical Solutions]

In order to solve the above problems, an embodiment of the present invention provides a color former compound represented by the following formula 1: [Formula 1] Wherein, in Formula 1, R ₁ to R ₅ are each hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, or an aromatic ring having 6 to 20 carbon atoms (aromatic) N-alkylene-piperidine dione or N-alkylene-pyrrolidine dione linked to one or more of the rings; R ₆ Is the following formula 2 or formula 3; and each of R ₇ to R ₁₀ is hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a cyclic or linear alkyl sulfide having 1 to 30 carbon atoms An alkyl thiol group, an aryl thiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms, [Formula 2] [Formula 3] Wherein, in Formula 2 and Formula 3, each of R ₁₁ to R ₂₀ is hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a cyclic or linear alkyl group having 1 to 30 carbon atoms a thiol group, an aryl thiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms, and any one or more of R ₇ to R ₂₀ having 1 to A cyclic or linear alkylthiol group of 30 carbon atoms, an arylthiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms.

Another embodiment of the present invention provides a colored composition comprising a colorant compound.

Yet another embodiment of the present invention provides a color filter comprising a colored composition.

Yet another embodiment of the present invention provides a display device including a color filter. [Effect of the present invention]

The color former compound of the present invention is a compound of a novel structure which is not yet known, and may contain a specific moiety to exhibit stable color reproducibility and excellent heat resistance and solubility. Further, the colorant compound may have excellent solubility to a solvent as compared with a color former compound of the known art, and thus, when the colorant compound is used in a pigment dispersion method, pigment derivatives and dispersants may be reduced. use.

Therefore, the color filter according to the present invention can be a high-resolution color filter which has a wider color reproduction range and higher brightness and high contrast due to excellent color reproducibility and heat resistance. In addition, the pigment content in the coloring composition can be increased due to the excellent solubility of the novel colorant compound, and thus it is possible to manufacture a film color filter.

While the invention is susceptible to various modifications and alternatives It should be understood, however, that the invention is not intended to be

Hereinafter, the color former compound of the present invention and a colored composition containing the same will be described in more detail. [colorant compound]

A coloring agent compound according to an embodiment of the present invention is represented by the following formula 1: [Formula 1] Wherein, in Formula 1, R ₁ to R ₅ are each hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, or one or more of an aromatic ring having 6 to 20 carbon atoms a N-alkyl-piperidinone or an N-alkyl-pyrrolidone; R ₆ is a formula 2 or formula 3; and R ₇ to R ₁₀ are each hydrogen, halogen, and have 1 to An aliphatic group of 10 carbon atoms, a cyclic or linear alkylthiol group having 1 to 30 carbon atoms, an arylthiol group having 1 to 30 carbon atoms or having 1 to 30 Alkoxy group of a carbon atom, [Formula 2] [Formula 3] Wherein, in Formula 2 and Formula 3, each of R ₁₁ to R ₂₀ is hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a cyclic or linear alkyl group having 1 to 30 carbon atoms a thiol group, an aryl thiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms, and any one or more of R ₇ to R ₂₀ having 1 to A cyclic or linear alkylthiol group of 30 carbon atoms, an arylthiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms.

Also, as used in this article, Means a bond to another substituent.

A coloring agent compound according to another embodiment of the present invention is a coloring agent compound of Formula 1, wherein R ₁ , R ₂ , R ₄ and R ₅ may each be hydrogen or halogen, and R ₃ may be a functional group of the following formula 4 Or a functional group of the following formula 5: [Formula 4] [Formula 5] Wherein, in Formula 4 and Formula 5, R ₂₁ , R ₂₂ and R ₂₃ are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbons. a substituted or unsubstituted alkoxy group of an atom, a substituted or unsubstituted hydroxyalkyl group having 1 to 20 carbon atoms, a substituted or not having 6 to 30 carbon atoms Substituted aryl group, substituted or unsubstituted arylalkyl group having 7 to 30 carbon atoms or substituted or unsubstituted having 7 to 30 carbon atoms An alkylaryl group; and n, n ₁ and n ₂ may be integers satisfying 0 ≤ n ≤ ₄ , 0 ≤ n ₁ ≤ 3, and 0 ≤ n ₂ ≤ 3. Meanwhile, as used herein, n, n ₁ and n _{2 are} interpreted to mean the number of substituted functional groups in the corresponding benzene ring.

Also, as used herein, the term "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of hydrazine, halo, nitrile. , nitro, hydroxy, carbonyl, ester, oximine, amine, phosphine oxide, alkoxy, aryloxy, alkylthiol, aryl thiol, alkyl sulfonate Alkylsulfoxy group), arylsulfoxy group, decyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl group, An alkylamine group, an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphino group, and one or more of the N, O, and S atoms A heterocyclic group, or means a substituent substituted by or without a substituent obtained by linking two or more of the substituents shown above. For example, the "substituent obtained by linking two or more substituents" may be biphenyl. In other words, biphenyl can be interpreted as an aryl group or can be interpreted as a substituent obtained by linking two phenyl groups.

The alkyl group may be a linear or branched alkyl group having 1 to 20 carbon atoms, 1 to 10 carbon atoms or 1 to 5 carbon atoms. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, and t-butyl ( Sec-butyl), 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl , 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1 -methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-decyl, 2,2- Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not Limited to this.

The alkoxy group may be a straight chain, a branched chain or a cyclic group. The number of carbon atoms of the alkoxy group is preferably from 1 to 30, but is not particularly limited thereto. Specifically, the alkoxy group may include, but is not limited to, a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropyloxy group, an n-propyloxy group, a n-butoxy group, and an isopropoxy group. Butoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-di Methylbutoxy group, n-octyloxy group, n-decyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group or the like, but is not limited thereto.

The aryl group may be a monocyclic aryl group or a polycyclic aryl group having 6 to 30 carbon atoms, 6 to 20 carbon atoms or 6 to 12 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a crycenyl group, a fluorenyl group or the like, but is not limited thereto.

The aryl group in the aralkyl group and the alkaryl group is the same as the examples of the aryl group described above. The alkyl groups in the aralkyl group and the alkaryl group are the same as the examples of the alkyl group described above.

A coloring agent compound according to still another embodiment of the present invention is the coloring agent compound of Formula 1, wherein one or more of R ₇ to R ₁₀ may be a cyclic or linear alkyl group having 1 to 30 carbon atoms A thiol group or an aryl thiol group having 1 to 30 carbon atoms, and each of R ₁₁ to R ₂₀ may be hydrogen, halogen or an aliphatic group having 1 to 10 carbon atoms.

A coloring agent compound according to still another embodiment of the present invention is the coloring agent compound of Formula 1, wherein each of R ₇ to R ₁₀ may be hydrogen, halogen or an aliphatic group having 1 to 10 carbon atoms, and R ₁₁ One or more of R ₁₄ or one or more of R ₁₅ to R ₂₀ may be a cyclic or linear alkyl thiol group having 1 to 30 carbon atoms or have 1 to 30 carbons An aryl thiol group of an atom.

In Formula 1, one or more of R ₇ to R ₂₀ may be a cyclic or linear alkylthiol group having 1 to 30 carbon atoms, and an aryl sulfur having 1 to 30 carbon atoms. An alcohol group or an alkoxy group having 1 to 30 carbon atoms, and more specifically, a cyclic or linear alkylthiol group having 1 to 30 carbon atoms.

According to an embodiment of the present invention, one or more of R ₇ to R ₂₀ may be a cyclic or linear alkylthiol group having 3 to 6 carbon atoms, for example, a butyl thiol of the following formula 10. base. [Formula 10]

As described, the coloring agent compound of Formula 1 may have a structure in which a cyclic or linear alkylthiol group having 1 to 30 carbon atoms and an aromatic group having 1 to 30 carbon atoms are contained. a one or more of a thiol group or an alkoxy group having from 1 to 30 carbon atoms, and more specifically, a cyclic or linear alkyl thiol group having from 1 to 30 carbon atoms or One or more of the arylthiol groups having 1 to 30 carbon atoms are substituted at a specific position of the quinophthalone-based derivative compound.

In particular, one or more of the alkylthiol groups can be introduced into the color former compound of Formula 1 to reduce the planarity of the molecule, thereby reducing the intermolecular π-π interaction. Therefore, the molecules are easily dissolved in the organic solvent, and the solubility of the colorant compound to the organic solvent can be improved.

Therefore, the solubility of the coloring agent compound to an organic solvent (for example, DMF) is remarkably improved, and when the coloring composition containing the compound is prepared by a pigment dispersion method, the required amount of the pigment derivative and the dispersing agent is remarkably reduced. . Therefore, the content of the coloring agent compound or pigment in the coloring composition can be increased by the amount reduced as described above, whereby the film color filter can be easily manufactured.

Specific examples of the color former compound described above may include the compound represented by the following formula 6 to formula 47, but the invention is not limited thereto. [Equation 6] [Formula 7] [Equation 8] [Equation 9] [Formula 10] [Formula 11] [Formula 12] [Formula 13] [Formula 14] [Equation 15] [Formula 16] [Equation 17] [Equation 18] [Formula 19] [Formula 20] [Formula 21] [Formula 22] [Formula 23] [Expression 24] [Equation 25] [Equation 26] [Equation 27] [Formula 28] [Equation 29] [Formula 30] [Form 31] [Formula 32] [Formula 33] [Expression 34] [Expression 35] [Expression 36] [Expression 37] [Expression 38] [Formula 39] [Formula 40] [Formula 41] [Expression 42] [Formula 43] [Formula 44] [Formula 45] [Formula 46] [Expression 47]

As a method of synthesizing the color former compound of Formula 1, a known synthesis method and composition can be used without any limitation. For example, it can be selectively introduced into a yellow pigment by phthalimide or 1,8-naphthylimine and then an alkylthiol (for example, 1-butanethiol (1) -butanthiol)) reacts therewith to prepare a color former compound of formula 1. [Coloring composition]

According to one embodiment of the invention, a colored composition comprising a colorant compound is provided.

According to an embodiment of the present invention, the coloring composition may further comprise at least one of a dye and a pigment, wherein each of the dye and the pigment may comprise one or more of the compounds, the compound exhibiting being selected from the group consisting of yellow and red. And any color of green.

According to one embodiment of the invention, the compound exhibiting yellow may comprise one or more compounds selected from the group consisting of metal-complex-based compounds, azo-azos. Based on compounds, quinophthalone-based compounds, isoindoline-based compounds, and styryl-based compounds.

According to another embodiment of the present invention, the compound exhibiting red color may comprise one or more compounds selected from the group consisting of metal complex compounds, azo compounds, xanthene-based a compound, a diketopyrrolopyrrole-based compound, an anthraquinone-based compound, and a perylene-based compound.

According to still another embodiment of the present invention, the compound exhibiting green color may comprise one or more compounds selected from the group consisting of metal complex compounds, triarylmethane-based compounds, and ruthenium. Terpenoids.

According to an embodiment of the present invention, the pigment may comprise one or more selected from the group consisting of yellow pigment group comprising PY129, PY138, PY139, PY150 and PY185; red pigment group comprising PR48, PR 48:1, PR 48:2, PR 48:3, PR 48:4, PR 177, PR 179, PR 207, PR 254, PR 255, PR 264, and PR269; and green pigment group, including PG 7, PG 36 , PG 58 and PG 59.

The coloring composition according to one embodiment of the present invention may further comprise a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent, in addition to the colorant compound.

The detailed description of the colorant compound and specific examples thereof is the same as described above, and the coloring composition may include 20 parts by weight or more than 20 parts by weight (particularly 25 parts by weight) based on 100 parts by weight of the coloring composition. Or a colorant compound in an amount of more than 25 parts by weight and 50 parts by weight or less than 50 parts by weight, specifically 40 parts by weight or less.

When the content of the colorant compound is less than the above range, it is difficult to achieve a dark color, and when the content of the colorant compound is more than the above range, the curing reaction of the resin composition may occur abnormally. Therefore, the colorant compound is preferably included in the above range.

Meanwhile, 100 parts by weight of the coloring composition may be a sum of a color former compound, a binder resin, a polyfunctional monomer, and a photoinitiator contained in the coloring composition, and when more solvent is included as described below, The solid content including the components described above was regarded as 100 parts by weight.

In the coloring composition according to one embodiment of the present invention, the color former compound of Formula 1 may be used singly or in a mixture of two or more thereof. Further, the coloring composition according to one embodiment of the present invention may further contain any known coloring agent in addition to the coloring agent compound of Formula 1.

When the coloring composition is mixed with a known coloring agent, an effect of preventing re-aggregation of the pigment or generation of a foreign substance can be additionally obtained. Therefore, when the colored composition of the above form is applied to the color filter, an effect of improving contrast can be additionally obtained.

The binder resin is not particularly limited, but those which are generally used in the technical field of the present invention can be used, and an alkali-soluble resin can be preferably used.

Specifically, a (meth)acrylic resin, an acrylamide resin, a novolac resin or the like as an alkali-soluble resin can be used, and a weight average molecular weight (weight) of from 3,000 g/m to 150,000 g/mole can be used. The resin of average molecular weight; Mw), but the invention is not limited thereto. The weight average molecular weight was determined by using polystyrene as a standard GPC (gel permeation chromatography).

The coloring composition may include 3 parts by weight or more than 3 parts by weight (particularly 5 parts by weight or more than 5 parts by weight, and more specifically 10 parts by weight or more than 10 parts by weight, based on 100 parts by weight of the coloring composition). And an adhesive resin in an amount of 30 parts by weight or less, particularly 20 parts by weight or less, and more specifically 15 parts by weight or less.

The polyfunctional monomer is not particularly limited, but those polyfunctional monomers which are generally used in the technical field to which the present invention relates may be used. The polyfunctional monomer is a monomer used to form a photoresist phase by light. Specifically, the polyfunctional monomer may be any one selected from the group consisting of propylene glycol methacrylate, dipentaerythritol hexaacrylate, and dipentaerythritol acrylate. (dipentaerythritol acrylate), neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate , tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, tris(hydroxyethyl)isocyanurate trimethacrylate (tris(hydroxyethyl) Isocyanurate trimethacrylate), trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate Tetramethacrylate) and dipentaerythritol hexamethacrylate, or a mixture of two or more thereof.

The coloring composition may comprise 30 parts by weight or more than 30 parts by weight (specifically 40 parts by weight or more than 40 parts by weight, and more specifically 50 parts by weight or more than 50 parts by weight, based on 100 parts by weight of the coloring composition). And a polyfunctional monomer in an amount of 80 parts by weight or less, specifically 70 parts by weight or less, and more specifically 60 parts by weight or less than 60 parts by weight.

The photoinitiator may comprise one or more compounds selected from the group consisting of 2,4-trichloromethyl-(4'-methoxyphenyl)-6-triazine (2,4). -trichloromethyl-(4'-methoxyphenyl)-6-triazine), 2,4-trichloromethyl-(4'-methoxystyryl)-6-triazine (2,4-trichloromethyl-(4') -methoxystyryl)-6-triazine), 2,4-trichloromethyl-(fipronil) 6-triazine, 1-hydroxycyclohexyl phenyl ketone (1-hydroxycyclohexyl phenyl ketone), 4-(2-hydroxyethoxy)-phenyl (2-hydroxy)propyl ketone, benzophenone, Benzophenone and 2,4,6-trimethylaminobenzophenone, but are not limited thereto.

The coloring composition may include a photoinitiator in an amount of from 0.1 part by weight to 10 parts by weight based on 100% by weight of the coloring composition.

Meanwhile, the coloring composition according to an embodiment of the present invention may further contain a solvent in order to improve coating properties and workability.

According to one embodiment of the invention, the solvent may comprise one or more compounds selected from the group consisting of methyl ethyl ketone, methyl cellosolve, ethyl cellosolve (ethyl). Cellosolve), ethylene glycol dimethyl ether, ethylene glycol ether, propylene glycol dimethyl ether, propylene glycol ethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ether, 2-ethoxy Propyl alcohol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol diethyl ether acetate, 3-methoxybutyl acetate ( 3-methoxybutyl acetate), ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, and dipropylene glycol Monomethyl ether, but is not limited to this.

The content of the solvent can be controlled in consideration of coating properties and workability, and the content of the solvent is not particularly limited, but may include a solvent in an amount of from 50 parts by weight to 500 parts by weight based on 100 parts by weight of the coloring composition.

According to an embodiment of the present invention, the coloring composition may further comprise an additive, which may be included in a known coloring composition for a color filter, in addition to the components described above. Additives such as a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, an ultraviolet absorber, a leveling agent, a sensitizer, a plasticizer, an adhesion promoter, a filler, a surfactant, and the like.

Examples of the curing accelerator may include one or more selected from the group consisting of 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercapto 2-mercaptobenzooxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6- 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris(3-mercaptopropionate) (pentaerythritol tris) (3-mercaptopropionate)), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate), trishydroxyl Trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylol b Trimethylolethane tris (2-mercaptoaceta) Te)) and trimethylolethane tris (3-mercaptopropionate), but are not limited thereto, and the curing accelerator may be generally known in the technical field to which the present invention relates. Their curing accelerators.

The coloring composition according to one embodiment of the present invention can be used to manufacture a color filter by a method generally known in the art to which the present invention relates, such as a printing method or photolithography.

For example, according to lithography, the transparent substrate is coated with a colored composition by spraying, spin coating, slit coating, roll coating, immersion, or the like. The coated substrate is selectively subjected to an exposure process via a mask having a predetermined pattern. The prebaking process and/or the post baking process can be further performed. After exposure, the colored composition is developed to form the desired photoresist pattern. When the developed substrate is washed and dried, a color filter on which a desired photoresist pattern is formed can be obtained. The obtained color filter can be applied to a display device or the like.

As described above, the color former compound of the present invention may be a compound of a novel structure which is not yet known, and may contain a specific portion to exhibit stable color reproducibility and excellent heat resistance and solubility. In addition, the colorant compound may have excellent solubility to a solvent as compared with known techniques, thereby reducing the amount of the pigment derivative and the dispersant used in the pigment dispersion method.

Therefore, the color filter according to the present invention can be a high-resolution color filter which has a higher color reproduction range, higher brightness, and high contrast due to excellent color reproducibility and heat resistance. In addition, due to the excellent solubility of the novel colorant compound, the pigment content in the coloring composition can be increased, and thus it is possible to manufacture a film color filter.

Hereinafter, the actions and effects of the present invention will be described in more detail with reference to specific examples of the invention. However, the examples are given for the purpose of illustration only, and are not intended to limit the scope of the invention. Preparation Example 1: Synthesis of Compound 1

Compound A was obtained according to the method described in U.S. Patent No. 6,849,116 B2. In detail, 25.5 g of phthalimide and 7.4 g of paraformaldehyde were mixed and added to 560 g of 3.6 wt% fuming sulfuric acid at 25 °C. The mixture was heated to 50 ° C and stirred for 30 minutes.

100 g of Pigment Yellow 138 (BASF) was added thereto, and then the mixture was heated to 100 ° C and stirred for 3 hours. Subsequently, this mixture was added to 3500 g of water and stirred at 60 ° C for 30 minutes. The precipitated product thus obtained was filtered and washed with water until the product became neutral, and then dried at 90 ° C in a vacuum drying cabinet to obtain a compound (A).

Subsequently, 3 g (3.417 mmol) of compound (A), 0.52 g (7.033 mmol) of 1-butanethiol and 1.94 g (14.06 mmol) of K ₂ CO _{3 were} placed in a 500 ml single neck circle. The bottom flask (1-neck RBF) was stirred at 60 ° C for 24 hours. The reaction solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the resultant was purified by a column to obtain Compound 1. The results of APCI negative MS analysis showed that Compound 1 had a molecular weight of 907. Preparation Example 2 : Synthesis of Compound 2

A compound was obtained according to the method described in U.S. Patent No. 6,849,116 B2, in the same manner as in Preparation Example 1, except that 1,8-naphthylimine was used instead of phthalimide. B.

Subsequently, 3 g (3.32 mmol) of compound (B), 0.49 g (6.65 mmol) of 1-butanethiol, and 1.83 g (13.28 mmol) of K ₂ CO _{3 were} placed in a 500 ml single neck RBF. It was stirred at 60 ° C for 24 hours. The reaction solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the resultant was purified by a column to obtain Compound 2. The results of the APCI negative MS analysis showed that Compound 2 had a molecular weight of 957. Preparation Example 3 : Synthesis of Compound 3

Compound C was obtained according to the synthesis method described in Korean Patent Publication No. 2013-0137028, and then Compound D was obtained according to the method described in U.S. Patent No. 6,849,116 B2.

Subsequently, 3 g (3.92 mmol) of compound (D), 0.58 g (7.84 mmol) of 1-butanethiol and 2.17 g (15.69 mmol) of K ₂ CO _{3 were} placed in a 500 ml single neck RBF. It was stirred at 60 ° C for 24 hours. The reaction solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the resultant was purified by a column to obtain Compound 3. The results of the APCI negative MS analysis showed that Compound 3 had a molecular weight of 819. Preparation Example 4 : Synthesis of Compound 4

Compound C is obtained according to the synthesis method described in Korean Patent Publication No. 2013-0137028, except that 1,8-naphthylimine is used instead of phthalimide, and according to US Patent Publication Compound E was obtained by the method described in No. 6849116 B2.

Subsequently, 3 g (3.68 mmol) of compound (E), 0.54 g (7.36 mmol) of 1-butanethiol and 2.03 g (14.72 mmol) of K ₂ CO _{3 were} placed in a 500 ml single neck RBF. It was stirred at 60 ° C for 24 hours. The reaction solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the resultant was purified by column to afford compound 4. The results of APCI negative MS analysis showed that Compound 4 had a molecular weight of 869. Preparation Example 5 : Synthesis of Compound 5

Compound 5 was synthesized as in Preparation Example 1, except that Compound F was used instead of PY138 and Compound G was used instead of Compound A.

The results of APCI negative MS analysis showed that Compound 5 had a molecular weight of 753. Preparation Example 6 : Synthesis of Compound 6

Compound 6 was synthesized as in Preparation Example 1, except that Compound H was used instead of PY138 and Compound H was used instead of Compound A.

The results of the APCI negative MS analysis showed that Compound 6 had a molecular weight of 803. Preparation Example 7 : Synthesis of Compound 7

Compound 7 was synthesized as in Preparation Example 1, except that Compound J was used instead of PY138 and Compound K was used instead of Compound A.

The results of APCI negative MS analysis showed that Compound 7 had a molecular weight of 803. Preparation Example 8 : Synthesis of Compound 8

Compound 8 was synthesized as in Preparation Example 1, except that Compound L was used instead of PY138 and Compound M was used instead of Compound A.

The results of APCI negative MS analysis showed that Compound 8 had a molecular weight of 853. Preparation Example 9 : Synthesis of Compound 9

Compound O was synthesized as in Preparation Example 1, except that Compound N was used instead of PY138. Subsequently, 2.231 g (3.68 mmol) of compound (O), 0.814 g (7.36 mmol) of 1-thiophenol, and 2.03 g (14.72 mmol) of K ₂ CO _{3 were} placed at 500. Milliliter in single-necked RBF and stirred at 60 ° C for 24 hours. The reaction solution was cooled to room temperature and filtered under reduced pressure. The solvent was removed under reduced pressure, and the resultant was purified by a column to obtain compound 9. The results of the APCI negative MS analysis showed that Compound 9 had a molecular weight of 735. Preparation Example 10 : Synthesis of Compound 10

Compound O was prepared as in Preparation 9 except that cyclopentyl thiol was used instead of thiophenol, and Compound 10 was synthesized as in Preparation 9. The results of the APCI negative MS analysis showed that Compound 10 had a molecular weight of 722. Preparation 11 : Synthesis of Compound 11

Compound O was prepared as in Preparation Example 9, except that benzyl mercaptan was used instead of thiophenol, and Compound 11 was synthesized as in Preparation 9. The results of the APCI negative MS analysis showed that Compound 11 had a molecular weight of 749. Comparative preparation

Pigment Yellow 138 (PY-138) (manufactured by BASF) which is generally used as a color material in the photosensitive resin composition was prepared. Experiment 1 : Soluble Evaluation

The compounds according to Preparation Example 1 to Preparation 11 and Comparative Preparations were prepared, and their solubility in 100 g of dimethylformamide (DMF) was measured. The results are shown in Table 1 below. In particular, 1% or greater than 1% of the soluble expression is O, while less than 1% of the soluble expression is X. [Table 1] Example 1

The copolymer of 5.554 g of compound 1, 10.376 g of benzyl methacrylate and methacrylate synthesized according to Preparation Example 1 was mixed (molar ratio: 70:30, acid value: 113 KOH mg/g, weight The average molecular weight is 20,000, as measured by GPC, the molecular weight distribution (PDI) is 2.0 g, the solid content (SC) is 25%, including the PGMEA solvent), and the photoinitiator 2.018 g I- 369 (manufactured by BASF), 12.443 g of DPHA (manufactured by Nippon Kayaku) as a photopolymerizable compound, and 68.593 g of polypropylene glycol monomethyl ether acetate (PGMEA) as a solvent And 1.016 g of F-475 (manufactured by DIC) as an additive to prepare a photosensitive resin composition. Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 2 synthesized according to Preparation Example 2 was used. Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 3 synthesized according to Preparation Example 3 was used. Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 4 synthesized according to Preparation Example 4 was used. Example 5

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 5 synthesized according to Preparation Example 5 was used. Example 6

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 6 synthesized according to Preparation Example 6 was used. Example 7

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 7 synthesized according to Preparation Example 7 was used. Example 8

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 8 synthesized according to Preparation Example 8 was used. Example 9

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 9 synthesized according to Preparation Example 9 was used. Example 10

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 10 synthesized according to Preparation Example 10 was used. Example 11

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound 11 synthesized according to Preparation Example 11 was used. Comparative example 1

A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of the comparative preparation was used. Manufacturing substrate

The substrate was produced using each of the photosensitive resin compositions according to Examples 1 to 11 and Comparative Example 1. In detail, each of the photosensitive resin compositions according to the examples and the comparative examples was applied onto a glass substrate (5 × 5 cm) by spin coating, and prebaked at 100 ° C for 100 seconds to form membrane.

The gap between the substrate on which the film was formed and the photomask was set to 250 μm, and the entire surface of the substrate was irradiated with an exposure amount of 40 mJ/cm 2 using an exposure device. The exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-baked at 230 ° C for 20 minutes to fabricate a substrate. Experiment 2 : Heat resistance evaluation

The transmission spectrum of the substrate produced according to the above method for producing a substrate was obtained using a spectrophotometer (MCPD, Otsuka Co., Ltd.) in the visible light range of 380 nm to 780 nm. In addition, the prebaked substrate was post-baked at 230 ° C for 20 minutes to obtain a transmission spectrum in the same measurement range using the same equipment.

The obtained transmission spectrum and the C light source backlight and the obtained values E (L*, a*, b*) were used to calculate the color difference (hereinafter, referred to as ΔEab), and the results are shown in Table 2 below.

Specifically, ΔEab is calculated by the following equation: ΔE(L*, a*, b*) = {(ΔL*)2 + (Δa*)2 + (Δb*)2}1/2

In the above equation, the smaller the ΔE value indicates the better the color heat resistance. In general, when the ΔEab < 3 of the coloring material, it is indicated that the coloring material has excellent heat resistance. [Table 2]

In Table 2, it was confirmed that the color former compound of Comparative Example 1 was a commercially available material having a small color difference (ΔEab) of 0.29. It was also confirmed that each of the color former compounds used in Examples 1 to 11 had a color difference (ΔEab) of less than 3, and had excellent color heat resistance to achieve color heat resistance with the color former compound of Comparative Example 1. To a similar extent, and thus the color former compounds of Examples 1 to 11 can be used as color formers for color filters. Experiment 3 : Contrast evaluation

The photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 were prepared by mixing the components in the composition ratio (unit: gram) shown in Table 3 below. The prepared photosensitive resin composition was used to manufacture a substrate in accordance with the method of manufacturing a substrate described above.

When the upper and lower polarizing plates of the substrate were parallel and orthogonal to each other, the contrast tester (Tsubosaka) was used to measure the brightness of the substrate thus manufactured, and then the contrast was calculated by the following equation.

Contrast ratio (CR) = brightness when the upper and lower polarizing plates of the substrate are parallel to each other / brightness when the upper and lower polarizing plates of the substrate are orthogonal to each other [Table 3]

The contrast of the substrates produced using the photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 is shown in Table 4 below. [Table 4]

Referring to the results of Table 4, it was confirmed that the present invention was used in comparison with a substrate (Comparative Example 2) produced using a photosensitive resin composition containing a low-soluble pigment (PY138) having an organic solvent based on reduced light scattering. The substrates produced by the photosensitive resin compositions of Examples 12 to 22 had improved contrast.

no

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Claims (16)

A coloring agent compound represented by the following formula 1: [Formula 1] Wherein, in Formula 1, R ₁ to R ₅ are each hydrogen, a halogen, an aliphatic group having 1 to 10 carbon atoms or a one or more of an aromatic ring having 6 to 20 carbon atoms; N-alkyl-piperidinone or N-alkyl-pyrrolidone; R ₆ is the following formula 2 or the following formula 3; and R ₇ to R ₁₀ are each hydrogen, halogen, having 1 to An aliphatic group of 10 carbon atoms, a cyclic or linear alkylthiol group having 1 to 30 carbon atoms, an arylthiol group having 1 to 30 carbon atoms or having 1 to 30 Alkoxy group of a carbon atom, [Formula 2] [Formula 3] Wherein, in Formula 2 and Formula 3, each of R ₁₁ to R ₂₀ is hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a cyclic or linear alkyl group having 1 to 30 carbon atoms a thiol group, an aryl thiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms, and any one or more of R ₇ to R ₂₀ having 1 to A cyclic or linear alkylthiol group of 30 carbon atoms, an arylthiol group having 1 to 30 carbon atoms or an alkoxy group having 1 to 30 carbon atoms. The coloring agent compound according to claim 1, wherein R ₁ , R ₂ , R ₄ and R _{5 of the} formula 1 are each hydrogen or halogen; and R ₃ is a functional group of the following formula 4 or Functional group: [Formula 4] [Formula 5] Wherein, in Formula 4 and Formula 5, R ₂₁ , R ₂₂ and R ₂₃ are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and 1 to 20 carbons. a substituted or unsubstituted alkoxy group of an atom, a substituted or unsubstituted hydroxyalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms or a substituted or unsubstituted alkylaryl group having 7 to 30 carbon atoms; and n, n ₁ and n ₂ To satisfy an integer of 0 ≤ n ≤ ₄ , 0 ≤ n ₁ ≤ 3, and 0 ≤ n ₂ ≤ 3. The color former compound according to claim 1, wherein one or more of R ₇ to R ₁₀ is a cyclic or linear alkylthiol group having 1 to 30 carbon atoms or has 1 An arylthiol group to 30 carbon atoms, and each of R ₁₁ to R ₂₀ is hydrogen, halogen or an aliphatic group having 1 to 10 carbon atoms. The coloring agent compound according to claim 1, wherein each of R ₇ to R ₁₀ is hydrogen, halogen or an aliphatic group having 1 to 10 carbon atoms, and any one of R ₁₁ to R ₁₄ or Many or any one or more of R ₁₅ to R ₂₀ are a cyclic or linear alkyl thiol group having 1 to 30 carbon atoms or an aryl thiol group having 1 to 30 carbon atoms. . The color former compound according to claim 1, wherein any one or more of R ₇ to R ₂₀ is a cyclic or linear alkylthiol group having 3 to 6 carbon atoms. The coloring agent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the compounds represented by the following Formula 6 to Formula 47: [Formula 6] [Formula 7] [Equation 8] [Equation 9] [Formula 10] [Formula 11] [Formula 12] [Formula 13] [Formula 14] [Equation 15] [Formula 16] [Equation 17] [Equation 18] [Formula 19] [Formula 20] [Formula 21] [Formula 22] [Formula 23] [Expression 24] [Equation 25] [Equation 26] [Equation 27] [Formula 28] [Equation 29] [Formula 30] [Form 31] [Formula 32] [Formula 33] [Expression 34] [Expression 35] [Expression 36] [Expression 37] [Expression 38] [Formula 39] [Formula 40] [Formula 41] [Expression 42] [Formula 43] [Formula 44] [Formula 45] [Formula 46] [Expression 47] . A colored composition comprising the color former compound according to any one of claims 1 to 6. The coloring composition of claim 7, further comprising at least one of a dye and a pigment. The coloring composition of claim 8, wherein each of the dye and the pigment comprises one or more of a compound exhibiting any one of yellow, red, and green. The coloring composition according to claim 9, wherein the compound exhibiting the yellow color comprises one or more compounds selected from the group consisting of metal complex compounds, azo compounds , quinoline yellow compounds, isoporphyrin compounds, and styryl compounds. The coloring composition according to claim 9, wherein the compound exhibiting the red color comprises one or more compounds selected from the group consisting of metal complex compounds, azo compounds , xanthene compounds, diketopyrrolopyrrole compounds, terpenoids and terpenoids. The colored composition according to claim 9, wherein the compound exhibiting the green color comprises one or more compounds selected from the group consisting of metal complex compounds, triaryl methanes Compounds and terpenoids. The colored composition according to claim 9, wherein the pigment comprises one or more selected from the group consisting of yellow pigment group, including PY129, PY138, PY139, PY150, and PY185; Group, including PR48, PR 48:1, PR 48:2, PR 48:3, PR 48:4, PR 177, PR 179, PR 207, PR 254, PR 255, PR 264, and PR269; and green pigment group Contains PG 7, PG 36, PG 58 and PG 59. The coloring composition as described in claim 7, further comprising a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. A color filter comprising the coloring composition as described in claim 7 of the patent application. A display device comprising the color filter of claim 15 of the patent application.