TW201702319A - Colored photosensitive resin composition which can be used in the manufacture of color filter in the liquid crystal display device, particularly in the manufacturing of the color filter having high coloring reproducibility - Google Patents

Abstract

According to the present invention, the colored photosensitive resin composition for color filter comprises a coloring agent with specific structure, which enables to enhance transparency and coloring ability, so as to be effectively used in the manufacture of color filter in the liquid crystal display device, particularly in the manufacturing of the color filter having high coloring reproducibility. The composition is represented by the chemical formula 1listed in the specification, where R1 to R8 are each independently a hydrogen atom or a halogen atom, and are not simultaneously a halogen atom, R9 is a hydrogen atom, a substituted or unsubstituted alkoxy group, -SO3H, -COOH and a metal salt thereof, an unsubstituted alkylammonium group, a substituted or unsubstituted phthalic imino methyl group, or a substituted or unsubstituted sulfamoyl group.

Description

Colored photosensitive resin composition

The present invention relates to a colored photosensitive resin composition capable of improving lightness and darkness, color reproducibility, and coloring power while maintaining transparency.

The color filter used in the liquid crystal display device is manufactured by forming three primary colors, that is, red, green, and blue patterns on a glass substrate. The step of producing a color pattern generally includes a step of uniformly applying a photosensitive coloring composition containing a coloring agent corresponding to each color element to a substrate, and heating the applied composition - The step of drying to form a film, the step of selectively exposing the dried film by a mask having a desired shape, and the step of heating and curing the film after development. As the coloring agent of the above-mentioned photosensitive coloring composition, a pigment is generally used.

On the other hand, with the recent development of display technology, the performance of a liquid crystal display device is required to have high transmission and high contrast characteristics, and it is required to realize high color reproduction rate. Therefore, the selection, development, and cooperation of color materials that satisfy these performances and minimize the change in physical properties during the color filter manufacturing process play an important role in display technology.

With regard to improving the transmission performance of color filters, the development of highly transparent materials suitable for the three primary colors of color filters is being actively carried out. In particular, green elements in the three primary colors, which are constituent elements of the color filter, have a high contrast ratio between light and dark, and are elements that have a decisive influence on the transmission performance of the entire color filter. how is it Research on improving the transparency of color materials forming green primitives is active.

In particular, regarding the improvement of the transparency of green color materials, recently, the development of green dye materials or yellow dye materials for coloring which can be introduced into green color materials is active, however, it is applicable to green color elements. Dye materials, which are difficult to be used in mass production due to the decrease in heat resistance, the compatibility with photosensitive materials, and the solubility reduction of solvents, etc. during heat treatment of color filter manufacturing engineering, or In most cases, it stays at a level that is difficult to affect the performance of the element.

As a conventional green pigment, a color-sensitive photosensitive resin using a Phthalocyanine-based compound has been proposed. As a specific example of the green pigment, copper chloride phthalocyanine pigment CI pigment green 7 , copper bromide phthalocyanine pigment CI pigment 36 and zinc bromide phthalocyanine pigment CI pigment 58 may be mentioned.

As the green coloring agent for coloring, Y138, Y150, Y129, Y185, Y180, Y139, etc. can be used. From the viewpoint of obtaining high transmittance, CI Pigment Yellow 138 (hereinafter, abbreviated as Y138) can be generally used. ). However, C.I. Pigment Yellow 138 is excellent in transmittance, however, it needs to be improved in terms of coloring power and the like.

Further, in the case where the particles are finely processed in order to improve the contrast of Y138, the sedimentation and dispersion stability of the colorant may be lowered, and problems such as stains may occur.

Therefore, it is required to develop a yellow coloring agent having higher transparency and coloring power.

An object of the present invention is to provide a colored photosensitive resin composition for use in a yellow coloring agent and a color filter having the yellow coloring agent, and which improves brightness and darkness contrast and coloring power, Ability to maintain transparency.

In order to achieve the above object, the present invention provides a chemical formula 1 represented by the following formula Compound.

In the above Chemical Formula 1, R ¹ to R ⁸ are each independently a hydrogen atom or a halogen atom, and are not simultaneously a halogen atom, R ⁹ is a hydrogen atom, a substituted or unsubstituted alkoxy group, -SO ₃ H, -COOH and a metal salt, a substituted or unsubstituted alkylammonium group, a substituted or unsubstituted iminomethyl phthalate, or a substituted or unsubstituted sulfonamide group.

The present invention also provides a colored photosensitive resin composition comprising the compound of the above Chemical Formula 1.

According to one implementation, the compound of the above Chemical Formula 1 may comprise from 0.1 to 40% by mass based on the total mass of the composition.

According to one embodiment, the colored photosensitive resin composition may further contain a dispersing agent, an alkali-soluble resin, a photoinitiator, a crosslinking agent, a solvent, or a combination thereof in addition to the compound of the above Chemical Formula 1.

In addition, a coloring agent selected from the group consisting of a green colorant, a red colorant, a yellow colorant, and combinations thereof is also included.

In addition, the above dispersant may comprise an acrylic copolymer, polyurethane, polyethylene Imines and mixtures thereof.

According to an implementation, the colored photosensitive resin composition comprises: 0.1 to 40% by mass of a coloring agent containing a chemical formula 1, 0.1 to 20% by mass of a dispersing agent, and 1 to 50 mass, based on the total mass of the composition. % alkali-soluble resin, 0.1 to 5% by mass of a photoinitiator, 0.5 to 10% by mass of a crosslinking agent, and 40 to 90% by mass of a solvent.

Since the coloring agent contained in the colored photosensitive resin composition of the present invention contains the compound of Chemical Formula 1, it can maintain transparency while improving brightness and darkness contrast, color reproduction ratio, and coloring power, and therefore can be effectively used. In the manufacture of a color filter of a liquid crystal display device, etc.

The following is a detailed description of the invention. The terms or words used in the specification and the scope of the claims should not be construed as a general meaning or a meaning in a dictionary, and it should be construed that the inventor defines the concept of the term based on the adjustment in order to explain the invention in the most appropriate manner. A principle conforms to the meaning and concept of the technical idea of the present invention.

For all compounds, unless otherwise specified, they may be substituted or unsubstituted compounds. Here, "substituted" means that at least one hydrogen atom contained in the compound is a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkyl halide group, a cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 6 to 30 carbon atoms, a hydroxyl group, an alkoxy group having 1 to 10 carbon atoms, a carboxylic acid group, an aldehyde group, and an epoxy group. Group), a cyano group, a nitro group, an amino group, a sulfonic acid group, and a derivative thereof are substituted for the substituent selected.

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

The present invention provides a compound represented by the following Chemical Formula 1.

In the above Chemical Formula 1, R ¹ to R ⁸ are each independently a hydrogen atom or a halogen atom, and are not simultaneously a halogen atom, R ⁹ is a hydrogen atom, a substituted or unsubstituted alkoxy group, -SO ₃ H, -COOH and Metal salt, substituted or unsubstituted alkyl ammonium group (Alkylammonium group), substituted or unsubstituted phthalic imino methyl, or substituted or unsubstituted sulfamoyl group (Sulfamoyl) .

In the above R ⁹ , "substituted or unsubstituted" may be substituted or unsubstituted by a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, for example, a hydrogen atom or a carbon atom of 1 An alkyl group to 10.

The above alkyl group having 1 to 20 carbon atoms may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group or an isobutyl group. (isobutyl), s-butyl, t-butyl, amyl, isoamyl, t-amyl, hexyl, g. Heptyl, octyl, isooctyl, 2-ethylhexyl, t-octyl, nonyl, isodonyl , decyl, isodecyl, undecane Undccyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, cyclopentyl ), cyclohexyl, cyclohexylmethyl, lauryl group, combinations thereof, and the like.

According to one embodiment, the compound of the above Chemical Formula 1 contains a compound in which R ¹ to R ⁴ are a hydrogen atom, or a compound in which R ⁵ to R ⁸ are a hydrogen atom, or a compound in which all of R ¹ to R ⁸ are a hydrogen atom.

Specific examples of the compound of the above Chemical Formula 1 may include a compound of the following Chemical Formula 2 to Chemical Formula 4.

R ⁵ to R ⁸ of Chemical Formula 2 are a hydrogen atom or a halogen atom, and are not simultaneously a hydrogen atom, and are preferably a halogen atom.

[Chemical Formula 3] R ¹ to R ⁴ of Chemical Formula 3 are a hydrogen atom or a halogen atom, and are not simultaneously a hydrogen atom, and are preferably a halogen atom.

Since the coloring agent contained in the coloring photosensitive resin composition of the present invention contains the compound represented by the above Chemical Formula 1, the toner has a high contrast between light and dark, and the coloring power of the coloring agent can be improved, so that the color reproduction ratio can be improved.

According to one embodiment, the above chemical formula 1 can be used as the total amount of the colorant, and when the content is too low, the effects of coloring power, contrast of light and darkness, and brightness (brightness) are not good, and thus, for example, the total mass of the composition The reference may include 0.1 to 40% by mass, for example, further may include 0.1 to 20% by mass.

The composition provided by the present invention comprises the above chemical formula 1 as green and A red coloring coloring agent. The above coloring agent contains the compound of Chemical Formula 1, and usually contains a commercially available organic or inorganic pigment together with the compound of Chemical Formula 1 to be used as a coloring agent, and for example, may include a green coloring agent, a red coloring agent, a yellow coloring agent, and a combination thereof. Specifically, the above green colorant may comprise CI pigments G7, G36, G37, G58, G59 green dyes, and combinations thereof, and the red colorants may include CI pigments R176, R177, R179, R254, R264 red dyes, and combinations thereof.

In addition, the yellow coloring agent is not particularly limited as long as it is an organic pigment having high transparency, color definition, and heat resistance, and may include, for example, Y129, Y138, Y139, Y150, Y180, Y181, Y185, and Y213. , Y214 yellow dye and combinations thereof. Specific examples of the above yellow dye may be acid yellow 1, 3, 5, 7, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 134, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; solvent yellow 14, 23, 38, 62, 63, 64, 68, 78, 82, 89, 90, 91, 92, 94, 98, 99, 104, 105, 106, 126, 128, 129, 130, 132, 133, 134, 138, 139, 140, 144, 145, 156, 160, 161, 162, 163, 164, 165, 168, 169, 170, 171, and the like.

Further, the orange pigment which can be used together with the coloring agent containing the compound of the above Chemical Formula 1 may comprise CI pigment oranges 38, 43, 71, 73, and combinations thereof.

According to an implementation, the colored photosensitive resin composition for a color filter provided by the present invention may further comprise an auxiliary coloring agent, a dispersing agent, an alkali-soluble resin, a photoinitiator, a crosslinking agent in addition to those described above. , solvent or a combination thereof.

The above auxiliary coloring agent is not particularly limited as long as it is generally used in the art, and the content thereof may be from 0.1 to 20% by mass.

The dispersing agent is not particularly limited as long as it is generally used. For example, it may include an amino group or an ammonium salt group as a pigment substituent, and specifically, an acrylic copolymer (polyrylic copolymer) or a polyurethane (polyurethane) may be contained. Polyethyleneimine and mixtures thereof. In addition, commercially available dispersants may include BYK-Chemie's Disperbyk-160, Disperbyk-161, Disperbyk-165, Disperbyk-168, Disperbyk-170, Disperbyk-171, Disperbyk-2000, Disperbyk-2001. , Disperbyk-LN21116 and Disperbyk-LN6919, EFKA-4046, EFKA-4047 and EFKA-4340 from EFKA, Solsperse-5000, Solsperse-12000, Solsperse-22000, Solsperse-24000 and Solsperse-32500 from AVECIA, Ajinomoto Company (AJINOMOTO) company PB-821, PB-822, PB-824, PB-827, etc., and these can be used independently or in combination of two or more.

When the content of the dispersing agent is too large, the photosensitive coloring composition is affected to lower the developing speed, and when the amount is too small, the dispersion stability is not good. Therefore, it may be included based on the total mass of the composition. 0.1 to 20% by mass, for example, may be included in an amount of 1 to 10% by mass.

The alkali-soluble resin is a colored resin composition generally used for a color filter, and may contain, for example, an acrylic resin which is a polymer copolymer and is soluble in an organic solvent. A specific example of a monomer which can be used for the above acrylic resin may be a monomer containing the following. These substances are Acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, maleic acid, fumaric acid. ), a compound having more than one carboxyl group in the molecule such as itaconic acid, styrene, α-methyl styrene, vinyl toluene, vinyl benzyl Vinyl benzyl methyl Ether), benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate An aromatic vinyl compound, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate a compound having a hydroxyl group such as an unsaturated carboxylate, a 2-hydroxyalkyl (meth)acrylate or a glycerol (meth)acrylate, Methyl) methamide (meth) acrylamide, secondary or tertiary alkyl acrylamide, dialkylaminoalkyl (meth) acrylate, N-vinyl pyrrolidone (N-vinylpyrrolidone), N-vinyl Hydrophilic compound such as N-vinylcaprolactam, vinylimidazole, vinyltriazole, branched or linear butyl (meth)acrylate, ethylhexyl (A) Acrylate, phenoxy hydroxypropyl (meth) acrylamide, as other hydrophilic Monomer composition, comprising tetrahydrofurfuryl acrylate group (Tetrahydrofurfuryl), phosphoric acid group, a phosphate group, a quaternary ammonium salt, ethylene chain, trimethylene chain, a sulfonic acid group or the like.

Exceptionally, the following unsaturated carboxylate compounds can be used as the acrylic resin, and these unsaturated carboxylate compounds are methyl acrylate, methyl methacrylate, propyl acrylate, methyl n-propyl acrylate, n-butyl acrylate. , n-butyl methacrylate, methyl t-butyl acrylate, 2-hydroxyethyl acrylate, methyl 2-hydroxyethyl acrylate, 3-hydroxypropyl acrylate, methyl 3-hydroxypropyl acrylate, acrylic acid Alkyl ester, methyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, biscyclopentadienyl acrylate, etc. .

The above monomers may be used singly or in combination of two or more. In order to improve the affinity with respect to the dye and the pigment, the carboxyl group may have a carboxyl group at the end of the long chain or, in order to improve the crosslinking effect. The rate may have a polymerizable group in the side chain of the resin.

The mass average molecular weight (measured by a GPC method, polystyrene equivalent value) of the above-mentioned alkali-soluble resin may be from 1,000 to 200,000, for example, from 2,000 to 50,000, and may have a polymerizable group in a side chain in order to improve crosslinking efficiency. Further, when the content of the above-mentioned alkali-soluble resin is excessive, the dispersion and impregnation of the colorant are affected. When the amount is too small, the effect is not good. Therefore, based on the total mass of the composition, it may be included. 1 to 50% by mass, for example, may be included in an amount of 1 to 10% by mass.

As the photoinitiator, various known photoinitiator compounds can be used without particular limitation, for example, an iodide compound, a sulfonate compound, an organohalogen compound, an anthraquinone compound, and a mixture thereof. Further, commercially available photoinitiators include Irgacure-907, Irgacure-369, Irgacure OXE 01, Irgacure OXE 02, etc. of Ciba Geigy Co., Ltd., and may be used singly or in combination. The above photoinitiator may, for example, comprise from 0.1 to 5% by mass based on the total mass of the composition.

The above crosslinking agent may be a known crosslinking agent compound, which is not particularly limited, for example, ethylene glycol di(meth)acrylate, and the number of ethylene groups is 2 to 14 polyethylene glycol di(meth)acrylate, Trimethylolpropane di(meth)acrylate, trimethylolpropane tri (Trimethylolpropane tri(meth)acrylate), Pentaerythritol tri(meth)acrylate, Pentaerythritol tetra(meth)acrylate, 2 2-trisacryloyloxy methyl ethyl phthalic acid, Propylene glycol di (meth)acrylate, and the number of Propylene groups is 2 Polypropylene glycol di(meth)acrylate to dipentaerythritol penta(meth)acrylate (dipentaerythritol penta (meth) acrylate) and dipentaerythritol hexa (meth) acrylate, etc., may be used independently or in combination. The above crosslinking agent may include, for example, 0.5 to 10% by mass.

The solvent is not particularly limited, and for example, a water-soluble organic solvent may be contained, and a solvent having a boiling point in the range of 120 ° C to 250 ° C may be used from the viewpoint of safety. The above solvent may, for example, comprise Glycol ethers, glycol ether acetates, alkylene glycols and ketones, more specifically , Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, Propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol Diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, propylene glycol methyl ether, propylene glycol ethyl Propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether and its acetates, methyl ethyl ketone, acetone , ketones such as methyl isobutyl ketone, cyclohexanone, gamma-butyrolactone, ethyl lactate Ate), butyl lactate, ethyl pyruvate, Methyl cellosolve acetate, ethyl cellosolve acetate, etc., each independently or in combination use. The content of the above solvent can be appropriately adjusted by those skilled in the art, for example, may be 40 to 90% by mass, and more specifically 60 to 80% by mass based on the total mass of the composition.

According to one embodiment, in addition to the above compounds, one or more of the usual various additives which can be used in the art may be contained. The above additives may be surface active for example The agent may contain a generally known compound, and is not particularly limited. Specific examples may be Megafac R08 and Megafac F477 (manufactured by Nippon Ink Chemical Industry Co., Ltd.) and the like. In the case of adding these additives, the content thereof can be appropriately selected depending on the purpose of use of each additive and the like. Therefore, as a range which does not impair the effect of the present invention, for example, the total content of the additives may be in the range of 10 parts by weight or less based on 100 parts by mass of the total composition.

According to one embodiment, the coloring agent containing the compound of the above Chemical Formula 1 may be subjected to salt milling, dry milling, acid paste or the like as needed to make the particles finer, thereby serving as a color filter. The coloring agent for a sheet is not particularly limited to the above-described finening step. For example, in the case of a method of miniaturizing by salt grinding, the following steps may be employed to mill an organic pigment, a water-soluble inorganic salt, and a water-soluble organic substance containing the above coloring agent with a strong shear force by a kneader. a mixture of a solvent or the like. Thereafter, the milled mixture may be injected into water, stirred with various mixers to obtain a slurry state, and filtered to remove inorganic salts and solvents. In the above-described micronization process, the colorant contains the compound of Chemical Formula 1, and the pigment containing the colorant may further contain one or more pigments or more than one pigment mixture in addition to the compound of Chemical Formula 1. In the finening step, the water-soluble inorganic salt may include sodium chloride or potassium chloride. The inorganic salt may be contained in the range of 1 to 30 times based on the weight of the organic pigment. When the content is too small, sufficient miniaturization cannot be achieved. In the case of too much, it is difficult to remove the inorganic salt, resulting in a decrease in production efficiency.

The present invention can be variously modified and various embodiments can be carried out. The present invention will be described in detail below to enable those skilled in the art to which the present invention belongs. The following examples are intended to exemplify the invention, and the invention is not limited to the following examples, and the invention is to be construed as being limited to all modifications, equivalents and alternatives within the spirit and scope of the invention.

Hereinafter, the present invention will be described in more detail by way of specific examples. In the present specification, "parts" or "%" are based on mass unless otherwise specified.

Production Examples 1 to 15: Synthesis of Compounds

Production Example 1: Production of Compound of Chemical Formula 4

To 200 parts of benzoic acid, 20 parts of 8-aminoquinaldine and 41 parts of phthalic anhydride were added and heated at 140 ° C for 7 hours. After completion of the above reaction, the mixture was heated at 180 ° C for 8 hours. The loss of the intermediate and the formation of the quinophthalone compound were confirmed by a MALDI-TOFF mass spectrometer. Thereafter, the mixture was cooled to room temperature, and then 4000 parts of acetone (Acetone) was added to the reaction mixture, followed by stirring at room temperature for 1 hour. After the above stirring, the product was filtered, washed with methanol and dried to obtain a quinolone compound of the following chemical formula 4.

Production Example 2: Production of Compound of Chemical Formula 5

To 200 parts of benzoic acid, 20 parts of 8-aminoquinaldine and 40 parts of tetrachlorophthalic anhydride were added and heated at 150 ° C for 10 hours. After the above reaction is completed, 20 parts of phthalic anhydride is added, and then The mixture was heated at 200 ° C for 8 hours. The loss of the intermediate and the formation of the quinophthalone compound were confirmed by a MALDI-TOFF mass spectrometer. Thereafter, the mixture was cooled to room temperature, and then 4000 parts of acetone (Acetone) was added to the reaction mixture, followed by stirring at room temperature for 1 hour. After the stirring, the product is filtered, washed with methanol, and dried to obtain a compound containing the structure of the above Chemical Formula 2, that is, a quinolone compound of the following Chemical Formula 5.

Production Example 3: Production of Compound of Chemical Formula 6

To 200 parts of benzoic acid, 20 parts of 8-aminoquinadine and 22 parts of phthalic anhydride were added and heated at 135 ° C for 7 hours. After completion of the above reaction, 40 parts of tetrafluorophthalic anhydride was charged, and the mixture was further heated at 195 ° C for 8 hours. The loss of the intermediate and the formation of the quinolone compound were confirmed by a MALDI-TOFF mass spectrometer. Thereafter, the mixture was cooled to room temperature, and then 4000 parts of acetone was added to the reaction mixture, followed by stirring at room temperature for 1 hour. After the stirring, the product is filtered, washed with methanol, and dried to obtain a quinolone compound of Chemical Formula 6 which is contained in the structure of Chemical Formula 3.

[Chemical Formula 6]

Production Example 4: Production of Acrylic Resin Solution

In a flask with a reflux condenser, a dropping funnel and a stirrer, it was replaced with a nitrogen atmosphere, and 321 parts of propylene glycol monomethyl ether acetate (PGMEA) was added and heated while stirring. 95 ° C. 50 parts of a mixture of Methacrylic acid and Acryloyloxyethyl succinate (on a molar basis of 50:50) and 64 parts of methyl methacrylate (with a molar ratio of 50:50) Methyl methacrylate), 12 parts of Butyl methacrylate, 8 parts of 2,2'-bisazo-(2,4-dimethylvaleronitrile) (2,2'-Azobis-(2,4 The mixed solution of -dimethylvaleronitrile)) was dropped into the bottle. After completion of the dropwise addition, the mixture was maintained at 95 ° C for 8 hours, and cooled to room temperature to obtain a copolymer solution. After the solution was cooled to room temperature, a sample of 1 g of the resin solution was taken out and dried by heating at 180 ° C for 90 minutes to confirm that the obtained solid portion was 23%, and the mass average molecular weight was 13,000 and the molecular weight distribution was 2.01 as measured by GPC. The acid value in terms of the solid portion was 105 mg-KOH/g.

Production Example 5: Processing of Colorant 1

36 g of the compound of Chemical Formula 4 produced in the above Production Example 1, 360 g of sodium chloride, and 46 g of diethylene glycol were placed in a 1 L kneader (manufactured by Kyojin Precision Co., Ltd.), and then ground at 30 ° C for 7 hours. After the above-mentioned ground mixture was poured into 10 L of warm water of 70 ° C, the mixture was stirred for 1 hour, and repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C for 24 hours. At this time, 34 g of the coloring agent 1 was obtained.

Production Examples 6 to 13: Processing of Colorants 2 to 9

The colorant was processed in the same manner as in Production Example 5 except that the composition of the colorant was as shown in Table 1 below.

Production Example 14: Processing of Colorant 10

36 g of BA Pigment Yellow 138 (trade name: K-0961HD) sold by BASF, 360 g of sodium chloride and 46 g of diethylene glycol were placed in a 1 L kneader (manufactured by Kyojin Precision Co., Ltd.) at 30 ° C. Grind for 7 hours. The mixture after the above-mentioned polishing was placed in 10 L of warm water at 70 ° C, and the mixture was stirred for 1 hour. The mixture was repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C for 24 hours to obtain 34 g of a color former 10 .

Pigment Yellow 138 (Pigment Yellow 138)

The compositions of the coloring agents 1 to 10 according to the above Production Examples 5 to 14 are shown in Table 1 below.

Production Example 15: Production of Green Colored Dispersion Composition

14% by mass of CI Pigment Green 58 (A110 manufactured by DIC Corporation), 12.5% by mass of DISPERBYK-LN21116 (40% solid content, manufactured by BYK Chemical Co., Ltd.), and 25% by mass of acrylic resin (20% solid content, manufactured) Example 4) and 48.5 mass% of propylene glycol monomethyl ether acetate (PGMEA) were combined and stirred, and then dispersed by a vertical bead mill to obtain a green colored dispersion composition (G-1).

Examples 1 to 9 and Comparative Example 1: Production of photosensitive resin composition

Example 1

10% by mass of the coloring agent manufactured in the above Production Example 5, 12.2% by mass of DISPERBYK-LN21116 (40% solid content, manufactured by BYK Chemical Co., Ltd.), and 25% by mass of acrylic resin (20% solid content, production example) 4) and 52.5 mass% of propylene glycol monomethyl ether acetate (PGMEA) were combined and stirred, and then dispersed by a vertical bead mill to obtain a yellow colored dispersion composition (Y-1).

Using the obtained yellow colored dispersion composition Y-1 and the production example 15 The green colored dispersion composition G-1 was subjected to coloring in a C light source to satisfy chromaticities of x=0.281 and y=0.565. 45 mass% of the above-mentioned toned dispersion composition, 2.5% by mass of photoinitiator Irgacure-907, 15% by mass of dipentaerythritol hexa(meth)acrylate as a crosslinking agent, and 0.01% by mass as a surface Agafac R08 (manufactured by Nippon Ink Chemical Industry Co., Ltd.) and 37.49 mass% of propylene glycol monomethyl ether acetate (PGMEA) as a solvent were added and stirred to obtain a green colored photosensitive resin.

Examples 2 to 9

The same procedure as in Example 1 was carried out except that the composition of Table 2 below, and the coloring agents 2 to 9 and the yellow colored dispersion compositions Y-2 to Y-9 provided in the above Production Examples 6 to 13 were used. A green colored photosensitive resin was obtained.

Comparative example 1

A green colored photosensitive resin was obtained in the same manner as in Example 1 except that the composition of the following Table 2 and the coloring agent 10 and the yellow colored dispersion composition Y-10 provided in the above Production Example 14 were used.

Experimental Example 1: Evaluation of Green Colored Photosensitive Resin

The film of each of the green colored photosensitive resins provided in Examples 1 to 9 and Comparative Example 1 was formed by a spin coater, and then dried in an oven at 80 ° C for 10 minutes to obtain a coating film. The coated film was exposed to light at a light amount of 100 mJ/cm ² using an ultrahigh pressure mercury lamp, and developed with an alkaline developing solution, followed by washing with ultrapure water. The developed coated film was post-baked in an oven at 230 ° C for 20 minutes to form a pattern for the color filter.

The CIE chromaticity distribution (x, y, Y) of the coating film which was thermosetting was measured by a colorimeter MCPD-3000 (manufactured by Otsuka Co., Ltd.).

In addition, the relative luminance values of the green colored photosensitive resins of Examples 1 to 9 were compared based on the green colored photosensitive resin of Comparative Example 1, and the difference value was 1.0% or less and was judged to be higher than Comparative Example 1. ◎ When the difference value is less than 0.75%, it is judged as Δ.

The thickness of the film was determined to be ◎ when the difference value was 0.1 μm or more and the value smaller than Comparative Example 1 was ◎, and the film thickness was determined to be Δ when the difference value of the film thickness was less than 0.1 μm. The results are shown in Table 3 below. .

As shown in the above Table 3, in the colored photosensitive resin composition according to the first to ninth embodiments of the present invention, the Y value and the luminance are increased as compared with the colored photosensitive resin composition of Comparative Example 1, and the film thickness is increased. Reduced.

From this, it is understood that the colored photosensitive resin composition provided by the present invention can increase the luminance (Y value) and the coloring power (film thickness), and can reproduce a bright and vivid color in accordance with an increase in the luminance value.

The detailed description of the specific portions of the present invention as described above is intended to be a preferred embodiment of the present invention, and the scope of the present invention is not limited thereto. Therefore, the actual scope of protection of the present invention should be defined by the scope of the claims and their equivalents.

Claims (10)

A compound represented by the following Chemical Formula 1: In Chemical Formula 1, R ¹ to R ⁸ are each independently a hydrogen atom or a halogen atom, and are not simultaneously a halogen atom, R ⁹ is a hydrogen atom, a substituted or unsubstituted alkoxy group, -SO 3 H, -COOH, and a metal salt thereof, A substituted or unsubstituted alkylammonium group, a substituted or unsubstituted iminomethylene phthalate, or a substituted or unsubstituted sulfonamide group. The compound according to claim 1, wherein R ¹ to R ⁴ of Chemical Formula 1 are a hydrogen atom, or R ⁵ to R ⁸ are a hydrogen atom, or R ¹ to R ^{8 are} all a hydrogen atom. The compound of claim 1, wherein R ⁹ is a hydrogen atom. The compound according to claim 1, wherein the compound is represented by the following Chemical Formulas 2 to 4: [Chemical Formula 2] In the above Chemical Formula 2 or 3, R ¹ to R ⁸ are a hydrogen atom or a halogen atom, and are not simultaneously a hydrogen atom. A coloring photosensitive resin composition comprising the compound according to any one of claims 1 to 4, which is a coloring agent. The colored photosensitive resin composition according to claim 5, wherein the coloring agent is contained in an amount of 0.1 to 40% by mass based on the total mass of the composition. The colored photosensitive resin composition according to claim 5, further comprising a dispersing agent, an alkali-soluble resin, a photoinitiator, a crosslinking agent, a solvent, or a combination thereof. The colored photosensitive resin composition according to claim 5, further comprising a coloring agent selected from the group consisting of a green coloring agent, a red coloring agent, a yellow coloring agent, and a combination thereof. The colored photosensitive resin composition according to claim 5, wherein the dispersing agent comprises an acrylic copolymer, a polyurethane, a polyethyleneimine, and a mixture thereof. The colored photosensitive resin composition according to claim 6, wherein the coloring agent containing the compound of the chemical formula 1 and the coloring agent of the chemical formula 1 are contained in an amount of from 0.1 to 40% by mass based on the total mass of the composition. A dispersant, 1 to 50% by mass of an alkali-soluble resin, 0.1 to 5% by mass of a photoinitiator, 0.5 to 10% by mass of a crosslinking agent, and 40 to 90% by mass of a solvent.