JP2017173828A - Red photosensitive resin composition, color filter manufactured by using the same, and display element including the color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a red photosensitive resin composition, a color filter manufactured by using the composition, and a display element including the color filter.SOLUTION: The present invention relates to a red photosensitive resin composition described below, a color filter manufactured by using the composition, and a display element including the color filter. The red photosensitive resin composition comprises a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, the colorant (A) including a red pigment and a black pigment, where the red photosensitive resin composition has, when the composition is formed into a cured film having a thickness of 3 μm, the film shows a spectral transmittance of 20% or less at a wavelength from 430 to 590 nm and a spectral transmittance of 70% to 90% at a wavelength from 635 to 780 nm. The red photosensitive resin composition of the present invention can solve problems of insufficient high color reproducibility and processability of a conventional red photosensitive resin composition, while being used as an alternative to a polarizing plate in the display element.SELECTED DRAWING: Figure 1

Description

The present invention relates to a red photosensitive resin composition, a color filter produced using the same, and a display element including the color filter.

Recently, a flexible display element that can display an image even when bent like a paper by forming a display portion, wiring, etc. on a flexible substrate such as a flexible material plastic has recently attracted attention. Yes.

The flexible display element has a wide range of applications from a computer monitor and a television to a personal portable device. In particular, an organic light emitting display (OLED) is a liquid crystal display (Liquid Crystal Display); Unlike LCDs, no separate light source is required, so that it is possible to achieve a relatively thin thickness, and research on organic light-emitting elements has been actively conducted regarding flexible display elements.

On the other hand, in order for the flexible display element to be actually applied, it must be capable of full color, consume less power, and be easy to read outdoors even when compared with various display products.

In this sense, the organic light emitting element has the advantages of full color realization, low power consumption, and fast response speed, and is therefore the most useful resource as a light source for flexible display elements. The current organic light emitting device maintains a high contrast ratio in order to protect the organic light emitting device from oxygen and moisture and an encapsulation barrier layer, and to be outdoor readable. Thus, a polarizer is required.

However, when a polarizing plate having hard properties is applied, there may be a drawback that the flexibility of the flexible display element is reduced. On the other hand, if the polarizing plate is not applied, the external light is transmitted through the flexible display element and then reflected again, and then mixed with the light emitted from the organic light emitting element under the external light source. The light / dark ratio is greatly reduced.

As a result, research for improving this has been actively carried out recently. For example, in Patent Document 1, a colorant containing a green colorant and a yellow colorant, a binder resin, and an ink composition containing a black isocyanate group In Patent Document 2, a colorant containing a red colorant and a green colorant, a binder resin, and an ink composition containing a black isocyanate group are presented. However, in the case of the above prior art, the color material selection range is limited in realizing high color reproducibility, and various color regions are insufficiently realized. Due to lack of processability such as cutting, continuous improvement is required in the art.

Korean Published Patent No. 10-2013-0134494 Korean Published Patent No. 10-2013-0134498

Accordingly, an object of the present invention is to provide a red photosensitive resin composition for pixel formation that can solve the conventional problem of insufficient processability and can realize high color reproducibility while being able to replace a polarizing plate. And

Another object of the present invention is to provide a color filter manufactured using the red photosensitive resin composition and a display element including the color filter.

The present invention is a red photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the colorant comprises a red pigment and a black pigment, wherein the red When the photosensitive resin composition is formed into a cured film having a thickness of 3 μm, the spectral transmittance at a wavelength of 430 to 590 nm is 20% or less, and the spectral transmittance at a wavelength of 635 to 780 nm is 70% or more and less than 90%. A red photosensitive resin composition is provided.

In one embodiment, the red photosensitive resin composition has a spectral transmittance of 20% or less at a wavelength of 430 to 590 nm when formed into a cured film having a thickness of 3 μm, and the red photosensitive resin composition has a thickness of 3 μm. The spectral transmittance at a wavelength of 635 to 780 nm may be 70% or more and less than 90% at the time of forming the cured film having the thickness.

In another embodiment, when the red photosensitive resin composition is formed into a cured film having a thickness of 3 μm, the spectral transmittance at a wavelength of 635 to 780 nm may be 80% or more and less than 90%.

In still another embodiment, the red pigment is C.I. I. Pigment red 179, C.I. I. Pigment red 177, C.I. I. Pigment red 209, C.I. I. Pigment red 242, and C.I. I. It may be one or more selected from the group consisting of CI Pigment Red 254.

In another embodiment, the black pigment is a pigment in which red, blue and green are mixed, C.I. I. Pigment black 1, C.I. I. It may be one or more selected from the group consisting of pigment black 7, carbon black, organic black pigment, and titanium black.

In still another embodiment, the black pigment may be contained in an amount of 0.5 to 10% by weight based on the total solid content of the color material.

In another embodiment, the weight ratio of the red pigment to the black pigment may be 99.9 to 80:20 to 0.1.

In still another embodiment, the colorant is 10 to 80% by weight, the alkali-soluble resin is 5 to 80% by weight, and the photopolymerizable compound is 5 to 50% by weight based on the total solid content in the red photosensitive resin composition. The photopolymerization initiator is contained in an amount of 0.1 to 40 parts by weight based on 100 parts by weight of the total solid content of the alkali-soluble resin and the photopolymerizable compound, and the solvent is the total weight of the red photosensitive resin composition. It may be contained in an amount of 25 to 80% by weight.

In still other embodiments, the colorant may further include a yellow pigment.

In another embodiment, the yellow pigment may be included in an amount of 3 to 30 parts by weight based on 100 parts by weight of the total content of the red pigment and the black pigment.

In still other embodiments, the yellow pigment is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, and C.I. I. One or more selected from the group consisting of CI Pigment Yellow 150 may be used.

In still another embodiment, the acid value of the alkali-soluble resin may be 30 to 150 mgKOH / g, and the glass transition temperature may be 100 ° C. or higher.

In addition, the present invention provides a color filter manufactured using the red photosensitive resin composition, and the color filter is characterized by having high color reproducibility without using a polarizing plate.

Furthermore, the present invention provides a display device including the color filter.

One embodiment may include a red light source.

In other embodiments, the display element may be an organic light emitting element.

In still other embodiments, the display element may be a flexible display element.

The red photosensitive resin composition of the present invention can solve the problems of high color reproducibility and insufficient processability of the conventional red photosensitive resin composition for pixel formation while substituting a polarizing plate in a display element. It is. Particularly, when the red photosensitive resin composition is formed into a cured film having a thickness of 3 μm, the spectral transmittance at a wavelength of 430 to 590 nm is 20% or less, and the red photosensitive resin composition has a thickness of 3 μm. It is characterized in that the spectral transmittance at a wavelength of 635 to 780 nm is 70% or more and less than 90% at the time of forming a cured film having. When the red photosensitive resin composition is formed into a cured film having a thickness of 3 μm, if the spectral transmittance at a wavelength of 430 to 590 nm exceeds 20%, the color purity of red is lowered. When the spectral transmittance at a wavelength of 780 nm is less than 70%, the external light reflection effect is good, but the visibility due to a decrease in luminance may be poor. When it exceeds 90%, the luminance is good, but the external light reflection effect is It can be slight.

As a result of Experimental Example 2, spectral transmittance by wavelength is shown. 6 is a graph showing spectral transmittance at 430 to 590 nm according to the result of Experimental Example 2. 10 is a graph showing spectral transmittance at 635 to 775 nm according to the result of Experimental Example 2.

The present invention relates to a red photosensitive resin composition, a color filter produced using the same, and a display element including the color filter.

In the present invention, as the composition of the red photosensitive resin composition, the pigment dispersion composition contains a red pigment and a black pigment as essential components, so that a color can be realized without using a polarizing plate. It is characterized by showing the spectral transmittance of a specific range in the wavelength band of the range.

Hereinafter, the present invention will be described in detail.

Colorant (A)
The colorant may be contained in an amount of 10 to 80% by weight, preferably 20 to 60% by weight, more preferably 30 to 50% by weight based on the total solid content in the red photosensitive resin composition. Also good.

The pigment (a1) contained in the colorant essentially contains a red pigment and a black pigment. 99.9-80: 20-0.1 may be sufficient as the weight ratio of the red pigment mentioned above and a black pigment, Preferably 99.5-90: 10-0.5 may be sufficient. When the range is satisfied, the red photosensitive resin composition has a spectral transmittance of 20% or less at a wavelength of 430 to 590 nm when formed into a cured film having a thickness of 3 μm, and the red photosensitive resin composition May be advantageous in achieving a spectral transmittance of 70% or more and less than 90% at a wavelength of 635 to 780 nm when formed into a cured film having a thickness of 3 μm.

When the red photosensitive resin composition is formed into a cured film having a thickness of 3 μm, if the spectral transmittance at a wavelength of 430 to 590 nm exceeds 20%, the color purity of red is lowered. When the spectral transmittance at a wavelength of 780 nm is less than 70%, the external light reflection effect is good, but the visibility due to a decrease in luminance may be poor. When it exceeds 90%, the luminance is good, but the external light reflection effect is It can be slight.

As the black pigment that can be used in the present invention, black pigments used in the art can be used without particular limitation. For example, pigments mixed with red, blue and green, C.I. I. Pigment black 1, C.I. I. Pigment Black 7, Carbon Black, Organic Black, Titanium Black, etc. can be used alone or in combination of two or more, and preferably one selected from carbon black and organic black is used. More preferably, carbon black can be used.

In the present invention, the black pigment may be 0.5 to 10% by weight based on the total solid content of the color material, and the color material means a dye and a pigment contained in the pigment dispersion composition. When the above criteria are satisfied, it may be advantageous in terms of the effect of preventing reflection of external light and visibility.

Hereinafter, the colorant will be described in detail.

Pigment (a1)
The pigment (a1) contains a red pigment and a black pigment as essential components.

Examples of the red pigment of the present invention include C.I. I. Pigment red 177, C.I. I. Pigment red 179, C.I. I. Pigment red 202, C.I. I. Pigment red 206, C.I. I. Pigment red 207, C.I. I. Pigment red 208, C.I. I. Pigment red 209, C.I. I. Pigment red 215, C.I. I. Pigment red 216, C.I. I. Pigment red 220, C.I. I. Pigment red 224, C.I. I. Pigment red 226, C.I. I. Pigment red 242, C.I. I. Pigment red 243, C.I. I. Pigment red 245, C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 264, and C.I. I. One or more selected from the group consisting of CI Pigment Red 265 may be used. I. Pigment red 179, C.I. I. Pigment red 177, pigment red 209, C.I. I. Pigment red 242, and C.I. I. Pigment Red 254 is preferred. The red pigment is C.I. I. Pigment red 177, C.I. I. Pigment Red 179 and Pigment Red 254 are more preferable.

The black pigment of the present invention includes carbon black; organic black pigment; titanium black; and a pigment dispersion obtained by mixing red, blue and green, C.I. I. Pigment black 1, C.I. I. Pigment Black 7 or the like can be used.

More specifically, the black pigment can be used by producing a colored dispersion obtained by mixing and milling carbon black and two or more color pigments.

Carbon blacks that can be used include CHBK-17 from Gokoku Dye Co .; Seast 5HISAFHS, Seast KH, Seast 3HHAF-HS, Seast NH, Seast 3M, Seast 300HAF-LS, Seast 116HMMAF-HS, Seast 116MAF, Seest FM FEF-HS, Seest SOFEF, Seest VGPF, Seest SVHSRF-HS, and Seest SSRF; Diagram Black II, Diagram Black N339, Diagram Black SH, Diagram Black H, Diagram LH, Diagram HA, Mitsubishi Chemical Corporation Diagram SF, Diagram N550M, Diagram M, Diagram E, Diagram G, Diagram R, Diagram N760M, Gram LR, # 2700, # 2600, # 2400, # 2350, # 2300, # 2200, # 1000, # 980, # 900, MCF88, # 52, # 50, # 47, # 45, # 45L, # 25, # CF9, # 95, # 3030, # 3050, MA7, MA77, MA8, MA11, OIL7B, OIL9B, OIL11B, OIL30B, and OIL31B; 140V, PRINTEX-95, PRINTEX-85, PRINTEX-75, PRINTEX-55, PRINTEX-45, PRINTEX-300, PRINTEX-35, PRINTEX-25, PRINTEX-200, PRINTEX-40, P INTEX-30, PRINTEX-3, PRINTEX-A, SPECIAL BLACK-550, SPECIAL BLACK-350, SPECIAL BLACK-250, SPECIAL BLACK-100, and LAMP BLACK-101; Columbia Carbon Co., Ltd. Raven-1100ULTRA, Raven- 1080ULTRA, RAVEN-1060ULTRA, RAVEN-1040, RAVEN-1035, RAVEN-1020, RAVEN-1000, RAVEN-890H, RAVEN-890, RAVEN-880ULTRA, RAVEN-860ULTRA, RAVEN-850, RAVEN-820, Raven-820U RAVEN-780ULTRA, RAVEN-760 LTRA, Raven-520, Raven-500, Raven-460, Raven-450, Raven-430ULTRA, Raven-420, Raven-410, Raven-2500ULTRA, Raven-2000, Raven-1500, Raven-1255, Raven-1250, Examples include RAVEN-1200, RAVEN-1190ULTRA, and RAVEN-1170.

Coloring pigments that can be used in combination with the carbon black include Carmine 6B (C.I. 12490), phthalocyanine green (C.I. 74260), phthalocyanine blue (C.I. 74160), Mitsubishi Carbon Black MA100, Perylene Black (BASF K0084.K0086), Cyanine Black, Lionol Yellow (CI. 21090), Lionol Yellow GRO (CI. 21090), Benzidine Yellow 4T-564D, Mitsubishi Carbon Black MA-40, Victoria Pure Blue (C.I. 42595), C.I. I. PIGMENT RED97, 122, 149, 168, 177, 180, 192, 215, C.I. I. PIGMENT GREEN 7, 36, C.I. I. PIGMENT 15: 1, 15: 4, 15: 6, 22, 60, 64, C.I. I. PIGMENT 83, 139, C.I. I. PIGMENT VIOLET23 etc., and white pigments, fluorescent pigments, etc. may be used.

The carbon black is not particularly limited as long as it is a light-shielding pigment, and known carbon black can be used. Specific examples of the carbon black of the black pigment include channel black, furnace black, thermal black, lamp black, and the like.

Moreover, you may contain a yellow pigment selectively.

The yellow pigment is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, and C.I. I. May be one or more selected from the group consisting of CI Pigment Yellow 150. I. Pigment yellow 139 and C.I. I. Pigment yellow 150, and more preferably C.I. I. Pigment Yellow 139.

The yellow pigment may be contained in an amount of 3 to 30 parts by weight based on 100 parts by weight of the total content of the red pigment and the black pigment. When the yellow pigment is included in the content range, the content of the pigment in the resist based on the solid content can be reduced, which is advantageous in terms of pattern adhesion and straightness in processability.

The content of the pigment (a1) may be 10 to 90% by weight, preferably 20 to 50% by weight, based on the total solid content in the colorant (A). If the content of the pigment is in the range of 10 to 90% by weight based on the above criteria, it is preferable because the viscosity is low, the storage stability is excellent, the dispersion efficiency is high, and the light / dark ratio is effective. As the pigment, it is preferable to use a pigment dispersion in which the particle diameter is uniformly dispersed. An example of a method for uniformly dispersing the particle size of the pigment includes a method in which the pigment dispersant (a2) is contained and dispersed, and according to this method, the pigment is uniformly dispersed in the solution. A pigment dispersion can be obtained.

Pigment dispersant (a2)
The pigment dispersant (a2) is added for deagglomeration and stability maintenance of the pigment, and those generally used in the art can be used without limitation. Preferably, an acrylate dispersant (hereinafter referred to as an acrylic dispersant) containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate) may be contained. At this time, it is preferable to apply the acrylic dispersant manufactured by the living control method as disclosed in Korean Patent Publication No. 2004-0014311, but the acrylate manufactured by the living control method is used. Examples of commercially available dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150, and the like.

The acrylic dispersants exemplified above can be used alone or in combination of two or more. As the dispersant (a2), in addition to the acrylic dispersant, other resin type pigment dispersants may be used. Examples of the other resin-type pigment dispersants include known resin-type pigment dispersants, in particular, polycarboxylic acid esters represented by polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, and polycarboxylic acid (partial). A) amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate salts, esters of hydroxyl groups-containing polycarboxylic acids, and their modified products, or free (Free) Oily dispersants such as amides or salts thereof formed by the reaction of polyesters with carboxyl groups and poly (lower alkyleneimines); (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (Meth) acrylate ester copolymer, styrene Maleic acid copolymer, polyvinyl alcohol or water-soluble resin or a water-soluble polymeric compounds such as polyvinyl pyrrolidone; polyesters; modified polyacrylate; and ethylene oxide / propylene oxide addition product and phosphate esters. As a commercial product of the resin-type dispersant, as a cationic resin dispersant, for example, trade names of BYK (BIC) Chemie: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK- 163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; trade names of BASF: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA -4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4 10, EFKA-4800; trade names of Lubilzol: SOLPERS-24000, SOLSPERS-32550, NBZ-4204 / 10; trade names of Kawaken Fine Chemicals: Hinoact T-6000, Hinoact T-7000, Hinoact T- 8000; Ajinomoto's trade names: AJISPUR PB-821, Ajisper PB-822, Azisper PB-823; Kyoeisha Chemicals' trade names: FLORENE DOPA-17HF, FLOREN DOPA-15BHF, FLOREN DOPA-33 And Floren DOPA-44. In addition to the acrylic dispersant, other resin-type pigment dispersants may be used alone or in combination of two or more, and may be used in combination with an acrylic dispersant.

The amount of the dispersant (a2) used is in the range of 5 to 60 parts by weight, more preferably 15 to 50 parts by weight with respect to 100 parts by weight of the solid content of the pigment (a1) used. When the content of the dispersant (a2) satisfies the above criteria, it may be advantageous in terms of viscosity and pigment atomization, and the possibility of problems such as gelation after dispersion may be reduced.

Dye (a3)
The dye (a3) may be selectively contained in a colorant. The dye (a3) may be additionally used without limitation as long as it has solubility in an organic solvent. Preferably, it is preferable to use a dye that has solubility in an organic solvent and that can ensure solubility in an alkali developer, heat resistance, solvent resistance, and the like. As the dye, an acid dye having an acid group such as sulfonic acid or carboxylic acid, a salt of an acid dye and a nitrogen-containing compound, a sulfonamide of an acid dye, or a derivative thereof can be used. In addition, azo, xanthene, and phthalocyanine acid dyes, and derivatives thereof can also be selected. Preferably, the dye may be a compound classified as a dye in a color index (published by The Society of Dyers and Colorists) or a known dye described in a dye note (color dye company).

Specific examples of the dye include C.I. I. As solvent dye,
C. I. Yellow dyes such as Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;
C. I. Among solvent dyes, C.I. excellent in solubility in organic solvents. I. Solvent Yellow 14, 16, 21, 56, 151, 79, 93 are preferable. I. Solvent Yellow 21, 79; are more preferable.

In addition, C.I. I. As an acid dye, C.I. I. Acid Yellow 1, 3, 7, 9, 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, 135, 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, etc. Is mentioned.

Among acid dyes, C.I. has excellent solubility in organic solvents. I. Acid yellow is preferred.

In addition, C.I. I. As a direct dye
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, And yellow dyes such as 136, 138, and 141.

Furthermore, C.I. I. As a modern dye,
C. I. Examples include yellow dyes such as modern yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, and 65.

These dyes can be used alone or in combination of two or more.

Dispersing solvent (a4)
The dispersion solvent (a4) may be selectively contained in the colorant, and there is no particular limitation on the type thereof, and various organic solvents used in the field can be used.

Specifically, for example, ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol Diethylene glycol dialkyl ethers such as dibutyl ether, ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether Alkylene glycol alkyl ether acetates such as acetate, methoxybutyl acetate and methoxypentyl acetate, aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene, ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone , Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin, esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone It is done. Preferably, alkylene glycol alkyl ether acetates, ketones, esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate can be used, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol Monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, or the like can be used.

The dispersion solvents can be used alone or in admixture of two or more.

Alkali-soluble resin (B)
The alkali-soluble resin (B) must be dissolved in the solvent of the present invention and reactive to the action of light or heat. Moreover, the kind can be used without a restriction | limiting in particular if it is the acrylic copolymer which fulfill | performs the function of the binder resin with respect to the said colorant, and is soluble in an alkaline developing solution.

The alkali-soluble resin may be a copolymer of a carboxyl group-containing monomer and another monomer that can be copolymerized with the monomer. The carboxyl group-containing monomer is, for example, an unsaturated polycarboxylic acid having one or more carboxyl groups in a molecule such as an unsaturated monocarboxylic acid, unsaturated dicarboxylic acid, or unsaturated tricarboxylic acid. It may be a carboxylic acid. The unsaturated monocarboxylic acid may be, for example, acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid, and the like. The unsaturated dicarboxylic acid may be, for example, maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid. The unsaturated polyvalent carboxylic acid may be an acid anhydride, and specifically may be maleic anhydride, itaconic anhydride, citraconic anhydride, and the like. Further, the unsaturated polyvalent carboxylic acid may be a mono (2-methacryloyloxyalkyl) ester, for example, succinic acid mono (2-acryloyloxyethyl), succinic acid mono (2-methacryloyloxyethyl), It may be mono (2-acryloyloxyethyl) phthalate and mono (2-methacryloyloxyethyl) phthalate. The unsaturated polyvalent carboxylic acid may be a mono (meth) acrylate of a dicarboxy polymer at both ends, such as ω-carboxypolycaprolactone monoacrylate and ω-carboxypolycaprolactone monomethacrylate. May be. The carboxyl group-containing monomers can be used alone or in combination of two or more. Specific examples of other monomers copolymerizable with the carboxyl group-containing monomer include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, aromatic vinyl compounds such as p-vinylbenzyl glycidyl ether and indene; methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, -Propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3- Hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, ants Acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxydiethylene glycol Acrylate, methoxydiethylene glycol methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate Rate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate, And unsaturated carboxylic acid esters such as glycerol monomethacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3 Unsaturated carboxylic acid aminoalkyl esters such as aminopropyl methacrylate, 3-dimethylaminopropyl acrylate, and 3-dimethylaminopropyl methacrylate; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; vinyl acetate, vinyl propionate Carboxylic acid vinyl esters such as vinyl, butyrate, and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether; acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide Vinyl cyanide compounds such as acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacryl And unsaturated amides such as N-2-hydroxyethylmethacrylamide; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; fats such as 1,3-butadiene, isoprene, and chloroprene Group conjugated dienes; polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, polysiloxane polymer molecules having a monoacryloyl group or a monomethacryloyl group at the end of the molecular chain Examples include masses. The monomers can be used alone or in combination of two or more.

Therefore, the alkali-soluble resin is, for example, (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / 2-hydroxyethyl. (Meth) acrylate / benzyl (meth) acrylate copolymer, (meth) acrylic acid / methyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / methyl (meth) acrylate / polymethyl (meta ) Acrylate macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polymethyl (meth) acrylate giant single Copolymer, (meth) acrylic acid / 2-hydroxyethyl (meta Acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polymethyl (meth) acrylate macromonomer copolymer , (Meth) acrylic acid / styrene / benzyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / succinic acid mono (2-acryloyloxy) / styrene / benzyl (meth) acrylate / N-phenyl Maleimide copolymer, (meth) acrylic acid / succinic acid mono (2-acryloyloxyethyl) / styrene / allyl (meth) acrylate / N-phenylmaleimide copolymer, and (meth) acrylic acid / benzyl (meth) acrylate / N-phenylmaleimide / styre / Glycerol mono (meth), or the like acrylate copolymer. The (meth) acrylate means acrylate or methacrylate.

Among the alkali-soluble resins, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate / styrene copolymer, (meth) acrylic acid / methyl (meth) acrylate Copolymers and (meth) acrylic acid / methyl (meth) acrylate / styrene copolymers are preferably used.

The alkali-soluble resin should have a polystyrene-reduced weight average molecular weight of 5,000 to 50,000, preferably 8,000 to 40, as measured by gel permeation chromatography (GPC) using tetrahydrofuran as an elution solvent. 1,000, more preferably 10,000 to 30,000. When the weight average molecular weight of the alkali-soluble resin is in the range of 5,000 to 50,000, the coating film hardness is improved, an excellent residual film ratio is exhibited, and good solubility and improvement in the unexposed portion of the developer are exhibited. Resolution can be shown. Moreover, an acid value is 50-150 (mgKOH / g), Preferably it is 60-140, More preferably, it is 80-130. Within the range of the acid value, the alkali-soluble resin has improved solubility in the developer, and the unexposed area is easily dissolved and highly sensitive, and the pattern of the exposed area remains at the time of development. Can be improved.

The alkali-soluble resin may be contained in an amount of 5 to 80% by weight, preferably 10 to 60% by weight, based on the total solid content in the red photosensitive resin composition. When the above range is satisfied, there is a low possibility that problems of remaining film ratio reduction and reliability reduction will occur, and pattern formation may be easy.

Photopolymerizable compound (C)
The photopolymerizable compound is a compound that can be polymerized by an active radical, an acid, or the like generated from a photopolymerization initiator by light irradiation, and is a monofunctional or polyfunctional polymerizable compound depending on the number of functional groups. May be. Examples of the monofunctional polymerizable compound may include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinyl pyrrolidone. Examples of the bifunctional polymerizable compound include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and bisphenol A. Bis (acryloyloxyethyl) ether, 3-methylpentanediol di (meth) acrylate, butylene glycol dimethacrylate, hexanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetra Ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, Carboxylate neopentyl glycol diacrylate, and it may be a propoxylated neopentyl glycol diacrylate. Examples of the trifunctional polymerizable compound include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethoxylate trimethylolpropane tri (meth) acrylate, propoxylate trimethylolpropane tri (meth) acrylate, and glycerylpropoxy. It may be a rate triacrylate, an isocyanurate triacrylate, or the like. Examples of the tetrafunctional polymerizable compound include pentaerythritol tetra (meth) acrylate and dimethylolpropane tetra (methyl) acrylate. In addition, the pentafunctional polymerizable compound may be dipentaerythritol penta (meth) acrylate, and the hexafunctional photopolymerizable compound may be dipentaerythritol hexa (meth) acrylate. Among these, as the photopolymerizable compound, a polyfunctional polymerizable compound having two or more functional groups can be preferably used, and in particular, a polyfunctional polymerizable compound having five or more functional groups can be preferably used.

Further, the photopolymerizable compound is contained in an amount of 5 to 50% by weight, more preferably 7 to 45% by weight, based on the total solid content in the red photosensitive resin composition. When the said photopolymerizable compound is contained in the said range, the intensity | strength and smoothness of a pixel part can become favorable.

Photopolymerization initiator (D)
The photopolymerization initiator in the present invention generates a radical capable of initiating polymerization of the polyfunctional monomer of the photopolymerizable compound by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray. A compound. Such photopolymerization initiators typically include acetophenone compounds, benzophenone compounds, biimidazole compounds, triazine compounds, oxime ester compounds, and thioxanthone compounds. In this invention, a photoinitiator can be used individually or in mixture of 2 or more types, It is preferable to use 1 or more types of oxime ester type compounds.

Specific examples of the acetophenone compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 2-hydroxy-1- [4- (2-hydroxyethoxy). Phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino- 1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one, 2- (4-methylbenzyl)- 2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one and the like can be mentioned.

Examples of the benzophenone compounds include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxide). Oxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Specific examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2′-bis (2,3-dichlorophenyl). ) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetra (alkoxyphenyl) biimidazole, 2,2 '-Bis (2-chlorophenyl) -4,4', 5,5'-tetra (trialkoxyphenyl) biimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4 ', 5,5' -Tetraphenyl-1,2'-biimidazole, or an imidazole compound in which the phenyl group at the 4,4 ', 5,5' position is substituted with a carboalkoxy group. Of these, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole and 2,2-bis (2,6-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole are preferably used.

Specific examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- ( 4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4 -Methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2 , 4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4- Diethylamino-2-methylphenol Nyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine and the like. .

Examples of the oxime ester compounds include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), 1- [9-Ethyl-6- (2-methylbenzoyl) -9H. -Carbazol-3-yl] ethaneone1- (O-acetyloxymeme).

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

The photopolymerization initiator (D) may further contain a photopolymerization initiation auxiliary agent (d1) in order to improve the sensitivity of the red photosensitive resin composition of the present invention. When the red photosensitive resin composition according to the present invention contains the photopolymerization initiation auxiliary agent (d1), the sensitivity is further increased and the productivity can be improved.

As the photopolymerization initiation auxiliary agent (d1), for example, one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds, and organic sulfur compounds having a thiol group can be preferably used.

As the amine compound, an aromatic amine compound is preferably used. Specifically, aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine, methyl 4-dimethylaminobenzoate, 4-dimethyl Ethyl aminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (Common name: Michler's ketone), 4,4′-bis (diethylamino) benzophenone, and the like can be used.

The carboxylic acid compound is preferably an aromatic heteroacetic acid, specifically, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid. , Dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyloxyethyl). -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptobutyrate), pentaerythritol Examples include tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), and tetraethylene glycol bis (3-mercaptopropionate).

The photopolymerization initiator (D) is added to the content of the alkali-soluble resin (B) and the photopolymerizable compound (C) based on the total solid weight of the red photosensitive resin composition of the present invention. It may be contained in an amount of 1 to 40% by weight, preferably 1 to 30% by weight. That is, the photopolymerization initiator may be contained in an amount of 0.1 to 40 parts by weight based on 100 parts by weight of the total solid content of the alkali-soluble resin and the photopolymerizable compound. If the photopolymerization initiator (D) is in the range of 0.1 to 40% by weight, the sensitivity of the red photosensitive resin composition is increased and the exposure time is shortened. This is preferable because a high resolution can be maintained. Further, the strength of the pixel portion formed using the composition under the above-described conditions and the smoothness on the surface of the pixel portion can be improved.

Further, in the case of the photopolymerization initiation auxiliary agent (d1), the total photopolymerization initiator may contain 10 to 100% by weight, preferably 20 to 100% by weight. When the content of the photopolymerization initiation auxiliary (d1) in the total photopolymerization initiator satisfies the above range, the sensitivity to the dye can be reduced, and the possibility of pattern short-circuiting during the development process can be reduced. .

Further, when the photopolymerization initiation auxiliary agent (d1) is further used, the photopolymerization initiation auxiliary agent (d1) is an alkali-soluble resin (based on the total solid weight of the red photosensitive resin composition of the present invention). The content of B) and the photopolymerizable compound (C) may be 0.1 to 40% by weight, preferably 1 to 30% by weight. If the amount of the photopolymerization initiation auxiliary (d1) used is in the range of 0.1 to 40% by weight, the sensitivity of the red photosensitive resin composition is further increased and formed using the composition. The effect of improving the productivity of the color filter is provided.

Solvent (E)
The solvent is not particularly limited as long as it dissolves the red photosensitive resin composition, and ethers, aromatic hydrocarbons, ketones, alcohols, esters, amides, and the like are particularly preferable. Specifically, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, propylene glycol Ethers such as monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dipropyl ether, and dipropylene glycol dibutyl ether; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and Alcohols such as glycerin; ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl Acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol mono Cetate, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoacetate, diethylene glycol diacetate, diethylene glycol monobutyl ether acetate, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene Examples include glycol monoethyl ether acetate, ethylene carbonate, propylene carbonate, and esters such as γ-butyrolactone. The said solvent can be used in mixture of 1 type, or 2 or more types selected from the group which consists of the illustrated solvent. Further, in terms of coating properties and drying properties, the boiling point must be 100 to 200 ° C., and propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate And methyl 3-methoxypropionate are preferred.

The solvent may be contained in an amount of 25 to 80% by weight, preferably 30 to 70% by weight, based on the total weight of the red photosensitive resin composition. In the said range, when apply | coating with application | coating apparatuses, such as a roll coater, a spin coater, a slit and spin coater, a slit coater (or die coater), and an inkjet, favorable applicability | paintability can be shown.

Additive (F)
The red photosensitive resin composition of the present invention is a filler, other polymer compound, a curing agent, an adhesion promoter, as required by those skilled in the art, in addition to the above-described components, as long as the purpose of the present invention is not impaired. It is also possible to use an additive (F) such as an ultraviolet absorber or an aggregation inhibitor in combination.

Specific examples of the filler include glass, silica, alumina, and the like, but are not limited thereto.

Specific examples of the other polymer compounds include curable resins such as epoxy resins and maleimide resins, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane. However, it is not limited to these.

The curing agent is used to increase deep curing and mechanical strength. Specifically, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, and the like can be used, but are not limited thereto. It is not a thing. Specific examples of the epoxy compound include bisphenol A-based epoxy resins, hydrogenated bisphenol A-based epoxy resins, bisphenol F-based epoxy resins, hydrogenated bisphenol F-based epoxy resins, novolac-type epoxy resins, and other aromatic epoxy resins. , Alicyclic epoxy resins, glycidyl ester resins, glycidyl amine resins, or brominated derivatives of such epoxy resins, epoxy resins, and aliphatic, alicyclic or aromatic epoxy compounds other than brominated derivatives thereof , Butadiene (co) polymer epoxidized product, isoprene (co) polymer epoxidized product, glycidyl (meth) acrylate (co) polymer, triglycidyl isocyanurate, etc. can be used. Absent. Specific examples of the oxetane compound include carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and bisoxetane cyclohexanedicarboxylate, but are not limited thereto.

The said hardening | curing agent can use together the hardening auxiliary compound which makes ring opening polymerization possible the epoxy group of an epoxy compound, and the oxetane skeleton of an oxetane compound with a hardening | curing agent. Specifically, polyhydric carboxylic acids, polyhydric carboxylic acid anhydrides, acid generators, and the like can be used as the curing auxiliary compound. As the carboxylic acid anhydrides, commercially available epoxy resin curing agents can be used. As the commercially available epoxy resin curing agent, for example, trade name (ADEKA HARDNER EH-700) (manufactured by ADEKA INDUSTRY CO., LTD.), Trade name (RIKACID HH) (manufactured by Shin Nippon Rika Co., Ltd.), trade name (MH -700) (manufactured by Shin Nippon Rika Co., Ltd.).

The exemplified curing agents and curing auxiliary compounds can be used alone or in admixture of two or more.

Specific examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- ( 2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxy (Cyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane And 3-isocyanate propyl triethoxysilane is selected from the group consisting of singly or may be a mixture thereof.

The adhesion promoter may be contained in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 2 parts by weight, based on the solid content of the composition.

Specifically, 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzotriazole, alkoxybenzophenone, and the like can be used as the ultraviolet absorber, but there are limitations thereto. It is not done.

Specific examples of the anti-aggregation agent include sodium polyacrylate, but are not limited thereto.

The present invention provides a color filter produced from the red photosensitive resin composition. The red photosensitive resin composition can be applied on a substrate, photocured and developed to form a pattern.

First, after apply | coating the said red photosensitive resin composition on the board | substrate or the layer which consists of solid content of the photosensitive resin composition, it heat-drys and removes volatile components, such as a solvent, and obtains a smooth coating film.

As the coating method, spin coating, casting coating, roll coating, slit and spin coating, slit coating, or the like is performed. After application, heat drying (pre-baking) or drying after reduced pressure heats to volatilize volatile components such as a solvent. The heating temperature is 70 to 200 ° C, preferably 80 to 130 ° C. The coating thickness after heat drying is about 1 to 8 μm. The coating film is irradiated with ultraviolet rays through a mask in order to form a target pattern. At this time, it is preferable to use a device such as a mask aligner or a stepper so that the entire exposed portion is uniformly irradiated with parallel light beams and accurate alignment between the mask and the substrate can be performed. When the ultraviolet ray is irradiated, the portion irradiated with the ultraviolet ray is cured. As the ultraviolet rays, g-line (wavelength: 436 nm), h-line, i-line (wavelength: 365 nm), and the like can be used. The irradiation amount of ultraviolet rays can be appropriately selected as necessary, and is not limited in the present invention. When the cured coating film is brought into contact with a developer to dissolve the non-exposed portion and developed, a cured product having a desired pattern shape can be obtained.

The present invention also provides a display device including the color filter.

Hereinafter, preferred examples, comparative examples, and experimental examples will be presented for the understanding of the present invention. However, these examples, comparative examples, and experimental examples are merely illustrative of the present invention, and the appended claims It will be apparent to those skilled in the art that various changes and modifications can be made to the examples, comparative examples, and experimental examples within the scope and technical idea of the present invention without limiting the scope. Naturally, the modifications also belong to the appended claims.

<Production of pigment dispersion composition>
Production Example 1 Pigment dispersion composition A-1
As a pigment, C.I. I. Pigment Red 177 12.0 parts by weight, as a pigment dispersant, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK), as a solvent, 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone, propylene glycol 70.0 parts by weight of methyl ether acetate was mixed / dispersed by a bead mill for 12 hours to produce a pigment dispersion composition A-1.

Production Example 2 Pigment dispersion composition A-2
As a pigment, C.I. I. Pigment Red 179 12.0 parts by weight, as a pigment dispersant, DISPERBYK-2001 (manufactured by BYK) 5.0 parts by weight, as a solvent 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone, propylene glycol A pigment dispersion composition A-2 was produced by mixing / dispersing 70.0 parts by weight of methyl ether acetate with a bead mill for 12 hours.

Production Example 3 Pigment dispersion composition A-3
As a pigment, C.I. I. Pigment Red 254 12.0 parts by weight, as a pigment dispersant, 5.0 parts by weight DISPERBYK-2001 (manufactured by BYK), as a solvent, 13.0 parts by weight of 4-hydroxy-4-methyl-2-pentanone, propylene glycol A pigment dispersion composition A-3 was produced by mixing / dispersing 70.0 parts by weight of methyl ether acetate with a bead mill for 12 hours.

Production Example 4 Pigment dispersion composition A-4
20.0 parts by weight of carbon black PBk7, 6 parts by weight of Ajisper PB821 (Ajinomoto Fine Techno Co., Ltd.) as a dispersant, and 74 parts by weight of propylene glycol monomethyl ether acetate as a solvent are mixed / dispersed in a bead mill for 12 hours to disperse the pigment. Composition A-4 was produced.

Production Example 5 Pigment dispersion composition A-5
As a pigment, C.I. I. Pigment Yellow 139 12.0 parts by weight, DISPERBYK-2001 (manufactured by BYK) 5.0 parts by weight as a pigment dispersant, and 70 parts by weight of propylene glycol methyl ether acetate and 13 parts by weight of propylene glycol methyl ether by a bead mill. By mixing / dispersing for 12 hours, a pigment dispersion composition A-5 was produced.

Synthesis Example 1 Synthesis of alkali-soluble resin In a flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel and nitrogen inlet tube, 120 parts by weight of propylene glycol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN Parts, 13.0 parts by weight of acrylic acid, 10 parts by weight of benzyl methacrylate, 57.0 parts by weight of styrene, 20 parts by weight of methyl methacrylate, and 3 parts by weight of n-dodecyl mercapto were charged with nitrogen. Then, it stirred, the temperature of the reaction liquid was raised to 110 degreeC, and it reacted for 6 hours. The solid content acid value of the alkali-soluble resin thus synthesized was 100.2 mgKOH / g, and the weight average molecular weight Mw measured by GPC was about 15110.

Examples 1-3 and Comparative Examples 1-4. Production of red photosensitive resin composition A red photosensitive resin composition was produced with the composition and content (unit: parts by weight) shown in Table 1 below.

アルカリ可溶性樹脂（Ｂ）：合成例１
光重合性化合物（Ｃ）：ジペンタエリスリトールヘキサアクリレート（ＫＡＹＡＲＤ ＤＰＨＡ；日本化薬（株）製）
光重合開始剤（Ｄ）：２−Ｏ−ベンゾイルオキシム−１−［４−（フェニルチオ）フェニル］−１，２−オクタンジオン（ＯＸＥ−０１；ＢＡＳＦ製）
溶剤（Ｅ）：プロピレングリコールモノメチルエーテルアセテート

Alkali-soluble resin (B): Synthesis example 1
Photopolymerizable compound (C): dipentaerythritol hexaacrylate (KAYARD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
Photopolymerization initiator (D): 2-O-benzoyloxime-1- [4- (phenylthio) phenyl] -1,2-octanedione (OXE-01; manufactured by BASF)
Solvent (E): Propylene glycol monomethyl ether acetate

Experimental Example 1 Production of color filter Color filters were produced using the red photosensitive resin compositions produced in Examples 1-3 and Comparative Examples 1-4.

Specifically, each of the red photosensitive resin compositions was applied onto a 2-inch square glass substrate (Corning, “EAGLE XG”) by spin coating, and then placed on a heating plate at 100 ° C. A thin film was formed by maintaining at a temperature of 3 minutes. Next, a test photomask having a pattern in which the transmittance is changed stepwise in the range of 1 to 100% and an exposed portion pattern of 3 × 3 cm is placed on the thin film, and the distance from the test photomask is set to 100 μm. Irradiated with ultraviolet rays. At this time, the ultraviolet light source was irradiated with an illuminance of 100 mJ / cm ² using a 1 KW high-pressure mercury lamp containing all of g, h, and i rays, and no special optical filter was used. The thin film irradiated with the ultraviolet rays was developed by immersing in a KOH aqueous solution developing solution having a pH of 10.5 for 2 minutes. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 200 ° C. for 25 minutes to produce a color filter. The thickness of the obtained film was 3 μm. The thickness of the film was measured using a film thickness measuring device (DEKTAK6M; manufactured by Veeco).

Experimental Example 2. Spectroscopic measurement The spectroscopic measurement was performed in the same manner as in Experimental Example 1 except that the test photomask was not used, and then a color filter was manufactured, and then a chromaticity meter (manufactured by Olympus, OSP-200) was used. The spectral transmittance in the visible light region in the range of 780 nm was measured, and the results are shown in Tables 2 and 3 and FIGS.

Tables 2 and 3 and FIGS. 1 to 3 show spectral transmittances according to wavelengths according to the results of the experiment.

As shown in Tables 2 and 3 and FIGS. 1 to 3, in the examples of the present invention, the red photosensitive resin composition has a wavelength of 430 to 590 nm when formed on a cured film having a thickness of 3 μm. The spectral transmittance at 20 was not more than 20%, and the spectral transmittance at a wavelength of 635 to 780 nm was 70% or more and less than 90%.

As shown in FIG. 1, in Comparative Examples 1 and 2 containing no black pigment, 90% at a wavelength of 635 nm or more was formed when the red photosensitive resin composition was formed on a cured film having a thickness of 3 μm. Although the above spectral transmittance was shown, the Example containing a black pigment showed a spectral transmittance of 70% or more and less than 90% at a wavelength of 635 nm or more.

Moreover, the Example containing a black pigment showed a transmittance of 20% or less at a wavelength of 430 nm to 590 nm when the red photosensitive resin composition was formed on a cured film having a thickness of 3 μm.

On the other hand, in Comparative Examples 3 and 4 where the black pigment is less than 0.5% by weight or more than 10% by weight based on the solid content of the color material, the surface is insufficient in terms of the antireflection effect and visibility. It was.

Claims (13)

A colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent;
The colorant is a red photosensitive resin composition containing a red pigment and a black pigment,
When the red photosensitive resin composition is formed into a cured film having a thickness of 3 μm, the spectral transmittance at a wavelength of 430 to 590 nm is 20% or less, and the spectral transmittance at a wavelength of 635 to 780 nm is 70% to 90%. % Red photosensitive resin composition characterized by being less than%. The red photosensitive resin composition according to claim 1, wherein the black pigment is 0.5 to 10% by weight based on a solid content of a coloring material. The red photosensitive resin composition according to claim 1, wherein a weight ratio of the red pigment to the black pigment is 99.9 to 80:20 to 0.1. With respect to the total solid content weight in the red photosensitive resin composition,
10-80% by weight of colorant,
5-80% by weight of alkali-soluble resin,
Containing 5 to 50% by weight of the photopolymerizable compound,
The photopolymerization initiator is contained in an amount of 0.1 to 40 parts by weight based on 100 parts by weight of the total solid content of the alkali-soluble resin and the photopolymerizable compound,
The red photosensitive resin composition according to claim 1, wherein the solvent is contained in an amount of 25 to 80% by weight based on the total weight of the red photosensitive resin composition. The red photosensitive resin composition according to claim 1, wherein the colorant further contains a yellow pigment. The red photosensitive resin composition according to claim 5, wherein the yellow pigment is contained in an amount of 3 to 30 parts by weight based on 100 parts by weight of the total content of the red pigment and the black pigment. The red pigment is C.I. I. Pigment red 179, C.I. I. Pigment red 177, C.I. I. Pigment red 209, C.I. I. Pigment red 242, and C.I. I. The red photosensitive resin composition according to claim 1, comprising at least one selected from the group consisting of CI Pigment Red 254. The black pigment is a pigment in which red, blue and green are mixed, C.I. I. Pigment black 1, C.I. I. The red photosensitive resin composition according to claim 1, comprising at least one selected from the group consisting of pigment black 7, carbon black, organic black, and titanium black. The yellow pigment is C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, and C.I. I. The red photosensitive resin composition according to claim 5, comprising at least one selected from the group consisting of CI Pigment Yellow 150. The color filter manufactured using the red photosensitive resin composition of any one of Claims 1-9. A display element comprising the color filter according to claim 10. The display element according to claim 11, wherein the display element is a flexible display element. The display element according to claim 11, wherein the display element is an organic light emitting element.

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