Red pixel with a colored photosensitive resin composition, and the use of its manufacturing color filter and display device

Abstract

The present application provides a kind of red pixel with colored photosensitive resin composition, and the color filter and display device manufactured using it, the red pixel with colored photosensitive resin composition includes (A) colorant, (B) alkali-soluble resin, (C) photopolymerizable compound, (D) photopolymerization initiator and (E) solvent, the (A) colorant includes C.I.Pigment Red 177, C.I.Pigment Orange 64 and C.I.Pigment Violet 19, the content of C.I.Pigment Violet 19 is 1.2% to 4.8% relative to the total weight of red pixel with colored photosensitive resin composition solid component.The red pixel with colored photosensitive resin composition of the present application provides excellent color strength, so as to achieve the effect of high color reproduction and excellent brightness.

Description

Technical Field

[0001] The present invention relates to a photosensitive resin composition for coloring red pixels used in the manufacturing process of display devices such as color filters, a color filter comprising the photosensitive resin composition for coloring red pixels, and a display device. Background Technology

[0002] Color filters are widely used in camera components, liquid crystal display devices, and their application scope is rapidly expanding.

[0003] Color filters used in color liquid crystal display devices or camera elements are typically manufactured as follows: On a substrate with a black matrix pattern, a coloring photosensitive resin composition containing colorants corresponding to red, green, and blue is uniformly coated by spin coating. The coating film formed by heating and drying (hereinafter sometimes referred to as pre-firing) is exposed, developed, and further heated and cured as needed (hereinafter sometimes referred to as post-firing). This operation is repeated for each color, thereby forming pixels of each color.

[0004] The color patterns of each color filter are typically formed using a coloring photosensitive resin composition comprising colorants such as pigments and / or dyes, alkali-soluble resins, photopolymerizable compounds, photopolymerization initiators, and solvents. The coloring patterns using the coloring photosensitive resin composition are typically processed using photolithography.

[0005] In conventional photosensitive resin compositions for forming red pixels, excessive amounts of coloring materials such as pigments are included in order to achieve high chromaticity and high brightness. As a result, the pigment weight concentration (PWC) increases, making it difficult to achieve color filters with low PWC and high brightness.

[0006] Korean Patent Publication No. 10-2020-0064822 discloses a red photosensitive resin composition, the contents of which are as follows: A red photosensitive resin composition comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, wherein the (A) colorant comprises one or more selected from the group consisting of CI Pigment Red 179 and CI Pigment Red 264, and the (D) photopolymerization initiator comprises one or more selected from the group consisting of carbazole-based and fluorene-oxime-based compounds, and the spectral transmittance of a film made from the red photosensitive resin composition in the 590 nm to 595 nm range is less than 10%.

[0007] However, the aforementioned red photosensitive resin composition contains only red pigments such as CI Pigment Red 179 and CI Pigment Red 264 as (A) colorants, and therefore cannot achieve the high chromaticity and high brightness of the conventional red pixel coloring photosensitive resin compositions. Furthermore, the tinting strength is reduced, which may cause problems in terms of processability. Therefore, this issue needs to be addressed.

[0008] Existing technical documents

[0009] Patent documents

[0010] Patent Document 1: Korean Patent Publication No. 10-2020-0064822 Summary of the Invention

[0011] The technical problem to be solved

[0012] The present invention addresses the problems of the prior art described above and aims to provide a coloring photosensitive resin composition for red pixels, which contains a specific combination of colorants, enabling high color reproduction through excellent tinting strength, excellent brightness, and excellent processability, thereby forming a positive cone without producing residue.

[0013] Furthermore, the present invention aims to provide a color filter and display device manufactured using the aforementioned red pixel coloring photosensitive resin composition.

[0014] Technical solution

[0015] To achieve the above objectives, the present invention provides a coloring photosensitive resin composition for red pixels, comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, wherein the colorant (A) comprises CI Pigment Red 177, CI Pigment Orange 64, and CI Pigment Violet 19, and the content of CI Pigment Violet 19 is 1.2% to 4.8% relative to the total weight of the solid components of the coloring photosensitive resin composition for red pixels.

[0016] Furthermore, the present invention provides a color filter manufactured using the aforementioned red pixel coloring photosensitive resin composition.

[0017] Furthermore, the present invention provides a display device including the color filter.

[0018] The effects of the invention

[0019] The red pixel coloring photosensitive resin composition of the present invention provides excellent coloring power, thereby achieving high color reproduction and excellent brightness.

[0020] Moreover, it offers excellent processability, forming a positive cone without producing residue. Detailed Implementation

[0021] The present invention will now be described in more detail.

[0022] The present invention relates to a coloring photosensitive resin composition for red pixels, and a color filter and display device formed therefrom, the coloring photosensitive resin composition for red pixels comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, and comprising a specific combination of pigments as the aforementioned (A) colorant.

[0023] According to the present invention, the coloring photosensitive resin composition for red pixels has excellent tinting strength, and a color filter and display device manufactured by comprising the coloring photosensitive resin composition for red pixels can be provided, which has high brightness, excellent processability, and does not produce taper or residue.

[0024] The embodiments of the present invention will now be described in more detail. However, the terminology used in this specification is for illustrative purposes and is not intended to limit the invention. In this specification, the singular form includes the plural form as well as the singular form, unless otherwise stated in the context.

[0025] The terms “comprises” and / or “comprising” as used in this specification are used to mean, without excluding, one or more other constituent elements, steps and / or ingredients besides those mentioned.

[0026] In this invention, the total weight of the solid components of the red pixel coloring photosensitive resin composition refers to the total weight of the remaining components after removing the solvent from the red pixel coloring photosensitive resin composition. More specifically, the total weight of the solid components of the red pixel coloring photosensitive resin composition of this invention can be the total weight of the remaining components after removing the solvent contained in the red pixel coloring photosensitive resin composition and the solvent contained in other components. For example, when the colorant of this invention is manufactured and contained in the form of a pigment dispersion, it can refer to the weight after the solvent contained in the pigment dispersion is also removed.

[0027] On the other hand, the solid components of the present invention may refer to the non-volatile components that actually remain in the product after removing volatile components in addition to the solvent. For example, when the colorant of the present invention is manufactured and contained in the form of a pigment dispersion, the grinding media such as zirconia beads used in the bead milling process for manufacturing the pigment dispersion are excluded from the calculation of the solid component content.

[0028] <Coloring Photosensitive Resin Composition for Red Pixels>

[0029] This invention relates to a coloring photosensitive resin composition for red pixels, comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, wherein the colorant (A) comprises CI Pigment Red 177, CI Pigment Orange 64, and CI Pigment Violet 19, and the content of CI Pigment Violet 19 is 1.2% to 4.8% relative to the total weight of the solid components of the red pixel coloring photosensitive resin composition.

[0030] The following is a detailed description of the coloring photosensitive resin composition for red pixels of the present invention, according to its constituent components.

[0031] (A) Coloring agent

[0032] Pigment (a1)

[0033] The colorant (A) included in the red pixel coloring photosensitive resin composition of the present invention is characterized in that it comprises CI pigment red 177, CI pigment orange 64 and CI pigment violet 19 as pigments (a1), and the content of CI pigment violet 19 is 1.2% to 4.8% relative to the total weight of the solid components of the red pixel coloring photosensitive resin composition.

[0034] When the colorant (A) comprises CI Pigment Red 177, CI Pigment Orange 64, and CI Pigment Violet 19 as pigments (a1), and the content of CI Pigment Violet 19 is 1.2% to 4.8%, preferably 1.4% to 4%, and more preferably 1.5% to 3.5%, relative to the total weight of the solid components of the coloring photosensitive resin composition for red pixels, the combination of these pigments offers the advantages of excellent brightness, low pigment weight concentration (PWC), excellent tinting strength, excellent processability, and the absence of taper and development residue, making it preferred. When the content of CI Pigment Violet 19 is below the above weight range, the tinting strength and processability decrease; when the content is above the above weight range, the brightness decreases sharply, making it difficult to function as a high-brightness color filter.

[0035] Furthermore, the colorant (A) may further contain other pigments.

[0036] The pigment can be any organic or inorganic pigment commonly used in the art. Furthermore, the pigment can be subjected to resin treatment, surface treatment using pigment derivatives with introduced acidic or basic groups, grafting treatment of the pigment surface using polymeric compounds, micronization treatment using sulfuric acid micronization, cleaning treatment using organic solvents or water for impurity removal, or removal of ionic impurities using ion exchange methods, etc., as needed.

[0037] The organic pigments mentioned can be used in various pigments used in printing inks, inkjet inks, etc., specifically including water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolineone pigments, isoindoline pigments, perylene pigments, perylene ketone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinone pigments, anthraquinone pigments, anthraquinone pigments, indanone pigments, flavanone pigments, pinantrone pigments, diketopyrrolopyrrole pigments, etc.

[0038] Furthermore, the inorganic pigments may be metal compounds such as metal oxides or metal complex salts, specifically including oxides or composite metal oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black, organic black pigments, titanium black, and pigments that mix red, green, and blue to produce black.

[0039] The pigment is preferably a pigment dispersion in which the pigment particles are uniformly dispersed. Examples of methods for uniformly dispersing pigment particles include methods involving dispersion treatment with a pigment dispersant (a2), according to which a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

[0040] Pigment dispersant (a2)

[0041] The pigment dispersant is added to deagglomerate the pigment and maintain its stability. Specific examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, and polyamine surfactants, which can be used individually or in combination of two or more, but are not limited to these.

[0042] Specific examples of the cationic surfactants mentioned above include stearamine hydrochloride and amine salts or quaternary ammonium salts such as lauryl trimethylammonium chloride.

[0043] Specific examples of the anionic surfactants mentioned above include: higher alcohol sulfate salts such as sodium lauryl sulfate and sodium oleyl sulfate; alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate; and alkyl aryl sulfonates such as sodium dodecylbenzene sulfonate and sodium dodecylnaphthalene sulfonate.

[0044] Specific examples of the aforementioned nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene aryl ethers, polyoxyethylene alkylaryl ethers, other polyoxyethylene derivatives, ethylene oxide / propylene oxide block copolymers, dehydrated sorbitol fatty acid esters, polyoxyethylene dehydrated sorbitol fatty acid esters, polyoxyethylene sorbitol fatty acid esters, fatty acid glycerides, polyoxyethylene fatty acid esters, and polyoxyethylene alkylamines.

[0045] In addition, examples include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitol fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, and polyethyleneimine.

[0046] Furthermore, the pigment dispersant preferably comprises an acrylate-based dispersant containing butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA) (hereinafter referred to as an acrylate-based dispersant). Commercially available examples of such acrylate-based dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150, BYK-LPN6919, BYK-LPN21116, or BYK-LPN21324, etc., and these acrylate-based dispersants can be used individually or in combination.

[0047] The aforementioned pigment dispersants can also be pigment dispersants of other resin types besides acrylate-based dispersants. Examples of other resin types of pigment dispersants include well-known resin-type pigment dispersants, particularly polyurethanes, polycarboxylic acid esters (represented by polyacrylates), unsaturated polyamides, polycarboxylic acids, (partial) amine salts of polycarboxylic acids, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphates, esters of hydroxyl-containing polycarboxylic acids and their modified products, or oily dispersants such as amides or their salts formed by the reaction of polyesters with free carboxyl groups and poly(lower alkylimides); water-soluble resins or water-soluble polymer compounds such as (meth)acrylate-styrene copolymers, (meth)acrylate-(meth)acrylate copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, or polyvinylpyrrolidone; polyesters; modified polyacrylates; ethylene oxide / propylene oxide addition products; and phosphate esters, etc.

[0048] For commercially available pigment dispersants of other resin types mentioned above, examples of cationic resin dispersants include those from BYK Chemical Company under the following trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, etc. BYK-184; BASF's product names: 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-4510, EFKA-4800; Lubirzol's product names: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 / 10; Kawakami Seika's product names: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Ajinomoto's product names: AJISPUR PB-821, AJISPUR PB-822, AJISPURPB-823; Kyoei Chemical Co., Ltd.'s trade names: FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33, FLORENE DOPA-44, etc.

[0049] Other resin-type pigment dispersants besides the acrylate-based dispersants mentioned above can be used individually or in combination of two or more, or in combination with acrylate-based dispersants.

[0050] The content of the pigment dispersant is not particularly limited. For example, the content of the pigment dispersant relative to 1 part by weight of pigment can be greater than 0 and less than 1 part by weight, preferably 0.05 to 0.5 parts by weight. When the content of the pigment dispersant is greater than 0 and less than 1 part by weight, it is advantageous to obtain a uniformly dispersed pigment.

[0051] Dye (a3)

[0052] The present invention may further include dyes (a3) ​​commonly used in the art.

[0053] The dye can be used without restriction as long as it is soluble in organic solvents. It is preferred to use a dye that is soluble in organic solvents and can ensure the reliability of its solubility in alkaline developing solutions, as well as its heat resistance and solvent resistance.

[0054] The dye may be selected from acid dyes having acidic groups such as sulfonic acid or carboxylic acid, salts of acid dyes and nitrogen-containing compounds, sulfonamide forms of acid dyes, and their derivatives. Alternatively, azo, xanthine, and phthalocyanine acid dyes and their derivatives may also be selected. Preferably, compounds classified as dyes in the *Dye Index* (published by The Society of Dyers and Colourists) or well-known dyes described in the *Dyeing Handbook* (Shiki-densha). These dyes may be used individually or in combination of two or more.

[0055] The content of the colorant (A) above can be 25% to 65%, preferably 35% to 55%, and more preferably 40% to 50%, relative to the total weight of the coloring photosensitive resin composition for red pixels. When the colorant is included in the above content range, sufficient transmittance of the pixel is provided during film formation, and the effect of preventing contrast reduction is also provided, which is therefore preferred.

[0056] (B) Alkali-soluble resin

[0057] The aforementioned alkali-soluble resin (B) is a component used in the developing process to impart solubility to the alkaline developing solution. It can be used without limitation as long as it can dissolve in the alkaline developing solution. To enable the alkali-soluble resin of the present invention to dissolve in the alkaline developing solution, carboxyl groups can be introduced into the resin to impart an acid value. More specifically, it can be manufactured by copolymerizing an ethylene unsaturated monomer (b1) having carboxyl groups, or by reacting an acid anhydride with a resin copolymer (b2) having hydroxyl groups to impart an acid value. In this case, the acid value of the alkali-soluble resin (B) is preferably 30 to 200 mg KOH / g. When the acid value of the alkali-soluble resin (B) is below 30 mg KOH / g, it is difficult for the coloring photosensitive resin composition to ensure a sufficient developing speed; when it is above 200 mg KOH / g, the adhesion to the substrate decreases, easily leading to short circuits in the pattern, and compatibility with the colorant becomes problematic, resulting in colorant precipitation in the coloring photosensitive resin composition or a decrease in the storage stability of the coloring photosensitive resin composition, and an increase in viscosity.

[0058] Specific examples of the aforementioned carboxyl-containing vinyl unsaturated monomers (b1) include: monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as fumaric acid, medaconic acid, and itaconic acid; and anhydrides of these dicarboxylic acids; mono(meth)acrylates of polymers having carboxyl and hydroxyl groups at both ends, such as ω-carboxylated polycaprolactone mono(meth)acrylate, etc., preferably acrylic acid and methacrylic acid.

[0059] As a method for reacting the acid anhydride with the above-mentioned resin copolymer (b2) containing hydroxyl groups to impart an acid value, there is a method of further reacting the acid anhydride with a hydroxyl acrylate copolymer to impart an acid value, but it is not limited to this.

[0060] The hydroxyacrylates are representative of the following:

[0061] Hydroxyethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, 2-hydroxy-3-phenoxypropyl methacrylate, N-hydroxyethyl acrylamide, and other hydroxyethyl methacrylates.

[0062] The following examples illustrate unsaturated monomers (b3) that can be copolymerized when manufacturing the above-mentioned alkali-soluble resin (B), but are not necessarily limited to these.

[0063] Specific examples of copolymerizable unsaturated polymerizable monomers (b3) include: styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinylbenzylmethyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, and other aromatic vinyl compounds;

[0064] N-Cyclohexylmaleimide, N-Benzylmaleimide, N-Phenylomaleimide, N-o-Hydroxyphenylmaleimide, N-m-Hydroxyphenylmaleimide, N-p-Hydroxyphenylmaleimide, N-o-Methylphenylmaleimide, N-m-Methylphenylmaleimide, N-p-Methylphenylmaleimide, N-o-Methoxyphenylmaleimide, N-m-Methoxyphenylmaleimide, N-p-Methoxyphenylmaleimide, and other N-substituted maleimide compounds;

[0065] (Meth)methyl acrylate, (Meth)ethyl acrylate, (Meth)propyl acrylate, (Meth)isopropyl acrylate, (Meth)butyl acrylate, (Meth)isobutyl acrylate, (Meth)sec-butyl acrylate, (Meth)tert-butyl acrylate and other (Meth)alkyl acrylates;

[0066] Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo(meth)acrylate [5.2.1.0] 2,6 Decane-8-yl ester, 2-dicyclopentadienoxyethyl ester (meth)acrylate, isobornyl ester (meth)acrylate, and other alicyclic (meth)acrylates;

[0067] (Meth)phenyl acrylate, (meth)benzyl acrylate, and other (meth)acrylate aryl esters;

[0068] Unsaturated oxetane compounds such as 3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, and 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane.

[0069] The monomers exemplified above as copolymerizable unsaturated monomers (b3) can be used individually or in combination of two or more.

[0070] In the red pixel coloring photosensitive resin composition of the present invention, the content of the alkali-soluble resin relative to the total weight of the red pixel coloring photosensitive resin composition can be 0.1 to 30% by weight, preferably 0.5 to 20% by weight, and more preferably 1 to 10% by weight. When the content of the alkali-soluble resin meets the above range, the solubility in the developing solution is sufficient, pattern formation is easily achieved, and film thinning of the pixel portion of the exposed part is prevented during development, resulting in better peeling of the non-pixel portion, which is therefore preferred.

[0071] (C) Photopolymerizable compounds

[0072] The photopolymerizable compound, which is one of the components of the red photosensitive resin composition of the present invention, should be a compound that can polymerize under the action of the photopolymerization initiator (D) described later. The photopolymerizable compound can be a monofunctional monomer, a difunctional monomer, or a polyfunctional monomer, and is not particularly limited in the present invention.

[0073] Specific examples of the aforementioned monofunctional monomers include: nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Specific examples of the aforementioned difunctional monomers include: 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate. Specific examples of the aforementioned polyfunctional monomers include: trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate. Preferably, polyfunctional monomers with two or more functionalities are used.

[0074] In the red pixel coloring photosensitive resin composition of the present invention, the content of the photopolymerizable compound can be 0.1 to 20% by weight, preferably 0.5 to 10% by weight, and more preferably 0.5 to 7% by weight, relative to the total weight of the red pixel coloring photosensitive resin composition of the present invention. When the above-mentioned photopolymerizable compound is included within the above range, it is preferable to improve the strength or smoothness of the pixel portion.

[0075] (D) Photopolymerization initiator

[0076] The photopolymerization initiator in the red pixel coloring photosensitive resin composition of the present invention is a compound that generates free radicals capable of initiating the polymerization of polyfunctional monomers of the aforementioned photopolymerizable compound upon exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beams, and X-rays. Examples of such photopolymerization initiators include acetophenone compounds, benzophenone compounds, biimidazole compounds, triazine compounds, oxime compounds, and thioxanone compounds, but the invention is not limited to these; two or more of these compounds may be used. In the present invention, when an oxime photopolymerization initiator is included as the aforementioned photopolymerization initiator, the red pixel coloring photosensitive resin composition is highly sensitive and can maintain high resolution, which is therefore preferred. Furthermore, the strength or surface smoothness of the pixel portion formed using the red pixel coloring photosensitive resin composition of the present invention can be improved.

[0077] Examples of the aforementioned acetophenone compounds include, for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, benzoyladium dimethyl ketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-(4-methylphenylthio)-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butane-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propane-1-one, and 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butane-1-one.

[0078] Examples of the aforementioned benzophenone compounds include: benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone.

[0079] Examples of the aforementioned biimidazole compounds include: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 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 biimidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted with an alkoxycarbonyl group. More preferably, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole and / or 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole are used.

[0080] Examples of the aforementioned triazine compounds 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-piperyl-1,3,5-triazine. -[2-(5-methylfuran-2-yl)ethylene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethylene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethylene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethylene]-1,3,5-triazine, etc.

[0081] Examples of the aforementioned oxime compounds include o-ethoxycarbonyl-α-oximino-1-phenylpropane-1-one, 2-(o-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, and 1-(o-acetyl oxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethyl one; commercially available examples include BASF's OXE-01 and OXE-02.

[0082] In addition to the photopolymerization initiators exemplified above, carbazole compounds, diketone compounds, borate sulfonate compounds, diazo compounds, etc., can also be used as photopolymerization initiators.

[0083] In the red pixel coloring photosensitive resin composition of the present invention, the content of the photopolymerization initiator relative to the total weight of the red pixel coloring photosensitive resin composition of the present invention can be 0.05 to 10% by weight, preferably 0.1 to 7% by weight, and most preferably 0.1 to 5% by weight. When the content of the photopolymerization initiator is within the above-mentioned range, photopolymerization will occur sufficiently during exposure in the pattern forming process, and the decrease in transmittance due to unreacted initiator remaining after photopolymerization can be avoided, which is therefore preferred.

[0084] (E) Solvent

[0085] For the solvent, any solvent commonly used in red pixel coloring photosensitive resin compositions can be used without particular limitation, as long as it can effectively dissolve the other components contained in the red pixel coloring photosensitive resin composition. Ethers, aromatic hydrocarbons, ketones, alcohols, esters or amides are particularly preferred.

[0086] Specific examples of solvents mentioned above include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; and propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate. Alkylene glycol monopropyl ether acetate, methoxybutyl acetate, methoxypentyl acetate, and other alkylene glycol alkyl ether acetates; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl pentyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol; esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; and cyclic esters such as γ-butyrolactone.

[0087] From the perspective of coatability and drying properties, the solvents mentioned above are preferably organic solvents with a boiling point of 100°C to 200°C, and more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, etc.

[0088] The solvents exemplified above can be used individually or in combination of two or more. The content of the solvents relative to the total weight of the red pixel coloring photosensitive resin composition of the present invention can be 20 to 70% by weight, preferably 25 to 65% by weight, and most preferably 35 to 65% by weight. When the solvents are included within the above-mentioned content range, it provides the effect of improved coatability when coating using coating apparatus such as roller coaters, spin coaters, slot coaters, slot coating machines (sometimes also called die coaters), and inkjet printers, and is therefore preferred.

[0089] (F) Additives

[0090] In some embodiments, the photosensitive resin composition for the red pixel, in addition to the components described above, may further include additives for improving film properties such as coatability, adhesion, and hardness, without prejudice to the purpose of the present invention. For example, other polymeric compounds, curing agents, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers, anti-gelling agents, etc., may be added.

[0091] Other polymer compounds mentioned above can be added to improve the hardness and adhesion of the colored pattern. For example, it can include thermosetting resins such as epoxy resin and maleimide resin, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, polyurethane and other thermoplastic resins.

[0092] The curing agent may be included to increase strength through deep curing of the pattern, and examples include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.

[0093] As the aforementioned surfactants, silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms can be used. Examples include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines. In addition, the following trade names can be cited: KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (trade name, manufactured by Kyoeisha Chemical Co., Ltd.), SH-8400 (manufactured by Dow Corning Co., Ltd.), EFTOP (manufactured by Tochem Products Co., Ltd.), MEGAFAC (manufactured by Dai Nippon Ink Chemical Co., Ltd.), Flourad (manufactured by Sumitomo 3M Co., Ltd.), Asahiguard, Surflon (both manufactured by Asahi Glass Co., Ltd.), SOLSPERSE (trade name, manufactured by ZENECA Co., Ltd.), EFKA (manufactured by EFKA Chemicals Co., Ltd.), and PB 821 (manufactured by Ajinomoto Co., Ltd.).

[0094] Specific examples of the aforementioned adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanate-propyltrimethoxysilane, and 3-isocyanate-propyltriethoxysilane.

[0095] The antioxidants described above may include one or more selected from the group consisting of phenolic antioxidants, phosphorus antioxidants, and sulfur antioxidants. In one or more embodiments, the phenolic compounds, phosphorus compounds, and sulfur compounds may be used individually or in combination as phenolic-phosphorus compounds, phenolic-sulfur compounds, phosphorus-sulfur compounds, or phenolic-phosphorus-sulfur compounds.

[0096] There are no particular limitations on the types of phenolic antioxidants mentioned. Specific examples include: 3,9-bis[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethoxy]-2,4,8,10-tetraoxaspiro[5.5]undecane, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], and 1,3,5-trimethyl-2,4,6-tris(3',5'-di-tert-butyl- 4'-Hydroxybenzyl)benzene, triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 4,4'-thiobis(6-tert-butyl-3-methylphenol), tris-(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] [Ester], 2,2-thiodiethylidene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrogenated cinnamamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2,4-bis[(octylthio)methyl]-o-cresol, 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)] [Propionate], octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, 2,2'-methylenebis(4-methyl-6-tert-butylphenol), 4,4'-butylenebis(3-methyl-6-tert-butylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-tris(4-hydroxybenzyl)benzene, and tetra[methylene-3-(3,5-di-tert-butyl-4-hydroxyphenylpropionate)]methane, etc.

[0097] Among the above-mentioned phenolic antioxidants, from the perspective of heat resistance and heat-resistant discoloration prevention, the following antioxidants are preferred: 3,9-bis[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propionyloxy]-1,1-dimethylethoxy]-2,4,8,10-tetraoxaspiro[5.5]undecane, 1,3,5-trimethyl-2,4,6-tris(3',5'-di-tert-butyl-4'-hydroxybenzyl)benzene, pentaerythritol tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], 4,4'-thiobis(6-tert-butyl-3-methyl)propionate. Phenol), tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, 1,6-hexanediol-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], 2,2-thiodiethylenebis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrogenated cinnamamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene and 2,4-bis[(octylthio)methyl]-o-cresol.

[0098] Commercially available products include: Irganox 1010 (manufactured by BASF), Sumilizer BBM-S (manufactured by Sumitomo Chemical), ADK STAB AO-80 (manufactured by ADEKA), Sumilizer GP (manufactured by Sumitomo Chemical), and Irganox 1035 (manufactured by BASF).

[0099] There are no particular limitations on the types of phosphorus-based antioxidants mentioned. Specific examples include: 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, pentaerythritol diisodecyl diphosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, 2,2'-methylenebis(4,6-di-tert-butyl-1-phenoxy)(2-ethylhexoxy)phosphite, 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphazonheptenene (6-[3-(3-tert-Butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphazonheptenene ... [d,f][1,3,2]dioxaphosphepin), triphenyl phosphite, diphenyl isodecanyl phosphite, phenyl diisodecyl phosphite, 4,4'-butylenebis(3-methyl-6-tert-butyl-phenyl bis(tetrazyl)phosphite, octadecyl phosphite, tri(nonylphenyl)phosphite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-tert-butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-decoxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tri(2,4-di-tert-butylphenyl)phosphite, cyclic neopentane tetrayl bis(2,4-di- Phosphite, cyclopentanetetramethylbis(2,6-di-tert-butylphenyl)phosphite, 2,2'-methylenebis(4,6-di-tert-butylphenyl)octylphosphite, tris(2,4-di-tert-butylphenyl)phosphite, tetra(2,4-di-tert-butylphenyl)[1,1'-biphenyl]-4,4'-dimethylbisphosphite, phosphite dibis[2,4-bis(1,1-dimethylethyl)-6-methylphenyl] ethyl ester, etc.

[0100] Among the aforementioned phosphorus-based antioxidants, from the perspective of heat resistance and heat-resistant discoloration prevention, the following antioxidants are preferred: 2,2'-methylenebis(4,6-di-tert-butyl-1-phenoxy)(2-ethylhexyloxy)phosphine, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, and 6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphacycloheptenene, etc.

[0101] There are no particular limitations on the types of sulfur-based antioxidants mentioned. Specific examples include: 2,2-bis({[3-(dodecylthio)propionyl]oxy}methyl)-1,3-propadiyl-bis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, dilaurate of 3,3'-thiodipropionate, dimyristyl ester of 3,3'-thiodipropionate, distearate of 3,3'-thiodipropionate, pentaerythritol-tetra(3-laurylthiopropionate), 2-mercaptobenzimidazole, etc.

[0102] Among the above-mentioned sulfur-based antioxidants, from the perspective of heat resistance and heat-resistant discoloration prevention, the following antioxidants are preferred: 2,2-bis({[3-(dodecylthio)propionyl]oxy}methyl)-1,3-propadiyl-bis[3-(dodecylthio)propionate]; 2-mercaptobenzimidazole, etc.

[0103] Examples of anti-condensing agents include sodium polyacrylate.

[0104] The amount of the additive can be appropriately added and used by those skilled in the art without impairing the effect of the present invention.

[0105] For example, the content of the additive may be 0.01 to 10% by weight, preferably 0.01 to 5% by weight, but is not limited thereto, relative to the total weight of the coloring photosensitive resin composition for the red pixel.

[0106] <Color filters and display devices>

[0107] The present invention provides a color filter made from the above-described photosensitive resin composition for red pixels and a display device comprising the same. The color filter can be manufactured by coating the above-described photosensitive resin composition for red pixels onto a substrate, and then performing photocuring and development to form a colored pattern.

[0108] First, the red pixel is coated onto a substrate or a layer composed of the solid components of the coloring photosensitive resin composition using a coloring photosensitive resin composition. Then, it is heated and dried to remove volatile components such as solvents, thereby obtaining a smooth coating film.

[0109] As a coating method, methods such as spin coating, flexible coating, roller coating, slot spin coating, or slot coating can be implemented. After coating, the coating is dried by heating (pre-baking) or by vacuum drying, followed by heating to evaporate volatile components such as solvents. The heating temperature is 70 to 200°C, preferably 80 to 130°C. The thickness of the coating after heating and drying is approximately 0.5 to 8 μm. To form the target pattern, the coating is irradiated with ultraviolet light through a mask. At this time, parallel light should be uniformly irradiated throughout the exposed area, preferably using a mask aligner or stepper to achieve precise alignment between the mask and the substrate. When irradiated with ultraviolet light, the irradiated areas cure.

[0110] As the aforementioned ultraviolet light, g-line (wavelength: 436nm), h-line, KrF (248nm), and i-line (wavelength: 365nm) can be used. The amount of ultraviolet light irradiation can be appropriately selected as needed, and there is no limitation on it in this invention. If the cured coating is brought into contact with the developer to dissolve the non-exposed parts and develop, a cured product with the desired pattern shape can be obtained.

[0111] The above-described developing method can employ any developing method, such as the addition method, immersion method, or spray method. Furthermore, the substrate can be tilted at any angle during development. The developing solution is typically an aqueous solution containing an alkaline compound and a surfactant. Regarding the alkaline compound, both inorganic and organic alkaline compounds are acceptable. Specific examples of inorganic alkaline compounds include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium borate, potassium borate, and ammonia. Specific examples of organic alkaline compounds include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, and ethanolamine.

[0112] These inorganic and organic basic compounds can be used individually or in combination of two or more. The concentration of the basic compound in the alkaline developer is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass.

[0113] The surfactant in the above-mentioned alkaline developing solution may be at least one selected from the group consisting of nonionic surfactants, anionic surfactants, or cationic surfactants.

[0114] Specific examples of the aforementioned nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene aryl ethers, polyoxyethylene alkylaryl ethers, other polyoxyethylene derivatives, ethylene oxide / propylene oxide block copolymers, dehydrated sorbitol fatty acid esters, polyoxyethylene dehydrated sorbitol fatty acid esters, polyoxyethylene sorbitol fatty acid esters, fatty acid glycerides, polyoxyethylene fatty acid esters, and polyoxyethylene alkylamines.

[0115] Specific examples of the aforementioned anionic surfactants include higher alcohol sulfates such as sodium lauryl sulfate or sodium oleyl sulfate, alkyl sulfates such as sodium lauryl sulfate or ammonium lauryl sulfate, and alkyl aryl sulfonates such as sodium dodecylbenzene sulfonate or sodium dodecylnaphthalene sulfonate.

[0116] Specific examples of the aforementioned cationic surfactants include stearamine hydrochloride or lauryltrimethylammonium chloride, as well as amine salts and quaternary ammonium salts. These surfactants can be used individually or in combination of two or more.

[0117] The concentration of the surfactant in the developer is typically 0.01 to 10% by mass, preferably 0.05 to 8% by mass, and more preferably 0.1 to 5% by mass. After development, the product is washed with water. Alternatively, a post-drying at 50 to 250°C for 10 to 60 minutes may be performed if necessary.

[0118] Furthermore, the present invention includes a display device comprising the color filter. In addition to the color filter, the display device includes configurations known to those skilled in the art to which this invention pertains; that is, the present invention includes a display device to which the color filter of the present invention can be applied.

[0119] The present invention will now be described in more detail through embodiments. However, the following embodiments are used to illustrate the present invention more specifically, and the scope of the present invention is not limited by the following embodiments.

[0120] Synthesis Example 1: Synthesis of Alkali-Soluble Resins

[0121] 120 parts by weight of propylene glycol monomethyl ether acetate and 80 parts by weight of propylene glycol monomethyl ether were added to a flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel and nitrogen inlet tube, and the inside of the flask was purged with nitrogen.

[0122] Next, 15 parts by weight of acrylic acid and 3,4-epoxy tricyclic acrylic acid [5.2.1.0] were added. 2.6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2.6A mixture of decane-9-yl esters (containing 70 parts by weight of E-DCPA, trade name "E-DCPA", Daicel) and 15 parts by weight of 2,2'-azobisisobutyronitrile (Wako) was stirred.

[0123] The reaction solution was then heated to 85°C and reacted for 6 hours. The resulting alkali-soluble resin had an acid value of 100 mg KOH / g and a weight-average molecular weight (Mw) of approximately 8,200 as determined by GPC.

[0124] Manufacturing Example 1: Manufacturing of Pigment Dispersion (A-1)

[0125] 16 parts by weight of CI pigment red 177 as a colorant, 5 parts by weight of dispersant (BYK LPN-6919, BYK) (solid component conversion), and 79 parts by weight of propylene glycol monomethyl ether acetate were mixed and then added to 300 parts by weight of 0.2 mm zirconia beads for mixing and dispersion to obtain pigment dispersion A-1.

[0126] Manufacturing Examples 2 to 6: Manufacturing of Pigment Dispersions (A-2 to A-6)

[0127] Except for replacing CI Pigment Red 177 with CI Pigment Orange 64, CI Pigment Violet 19, CI Pigment Violet 29, CI Pigment Violet 3 and CI Pigment Orange 38 respectively, the pigment dispersions A-2 to A-6 were manufactured in the same manner as in Manufacturing Example 1.

[0128] Examples 1 to 5 and Comparative Examples 1 to 6: Preparation of a coloring photosensitive resin composition for red pixels

[0129] The coloring photosensitive resin compositions for red pixels of Examples 1 to 5 and Comparative Examples 1 to 6 were prepared by mixing the components indicated in Tables 1 and 2 below in their respective amounts.

[0130] [Table 1]

[0131]

[0132] [Table 2]

[0133]

[0134] The components used in the above embodiments and comparative examples are as follows:

[0135] (A)A-1: Pigment dispersion of CI pigment red 177 as described in Example 1

[0136] (A)A-2: Pigment dispersion of CI pigment orange 64 produced in Example 2

[0137] (A)A-3: Pigment dispersion of CI pigment Violet 19 from Example 3

[0138] (A)A-4: Pigment dispersion of CI pigment Violet 29 from Example 4

[0139] (A)A-5: Pigment dispersion of CI pigment Violet 3 from Example 5

[0140] (A)A-6: Pigment dispersion of CI pigment orange 38 as described in Example 6

[0141] (B) Alkali-soluble resin: The alkali-soluble resin of Synthetic Example 1

[0142] (C) Photopolymerizable compound: A9550 (Shinnakamura Co., Ltd.)

[0143] (D) Photopolymerization initiator: OXE-02 (BASF)

[0144] (E) Solvent: Propylene glycol monomethyl ether acetate

[0145] (F) Additive 1: Organosilicon surfactant (SH-8400, Dow Corning, Korea)

[0146] (F) Additive 2: Adhesion accelerator (3-methacryloyloxypropyltrimethoxysilane)

[0147] Experimental Example

[0148] <Color Filter Manufacturing>

[0149] A color filter was manufactured using the red pixel coloring photosensitive resin composition prepared in Examples 1 to 5 and Comparative Examples 1 to 6 above. Specifically, the above-mentioned red pixel coloring photosensitive resin composition was coated onto a 5mm × 5mm glass substrate by spin coating, and then a thin film was formed by maintaining the coating in a heating oven at 100°C for 1 minute and 30 seconds. The formed coloring photosensitive composition layer was then exposed. At this time, a 1kW high-pressure mercury lamp containing gamma, h, and i rays was used as the ultraviolet light source at 150mJ / cm². 2 The film was irradiated with ultraviolet light without using a special optical filter. The film irradiated with ultraviolet light was then heated in a heating oven at 230°C for 20 minutes to obtain a color filter. The film thickness of the color filters of the red photosensitive resin compositions of Examples 1 to 5 and Comparative Examples 1 to 6 obtained therefrom was 2.5 μm.

[0150] 1. Brightness Measurement

[0151] The manufactured color filter was placed on a spectrophotometer (CM-3700d, Konica Minolta Sensors Co., Ltd.) to measure the transmittance chromaticity on the X, Y, and Z axes at 2° of light source C, and the Y value at this time was used as the luminance. The luminance of the example and the comparative example was evaluated using the luminance of the color filter made with the coloring photosensitive resin composition for the red pixel of Comparative Example 1 as the standard (100%), and the relative values ​​are shown in Table 3 below.

[0152] 2. Tinting strength (PwC) evaluation

[0153] Tinting strength is the weight concentration (PWC) of the colorant, i.e., the pigment, contained in the coloring photosensitive resin composition for red pixels under the same chromaticity and film thickness. The tinting strength of each embodiment and comparative example is shown in percentage (%) in Table 3 below.

[0154] 3. Cone shape (confirmation and evaluation of the presence or absence of an inverted cone)

[0155] The angles were measured by confirming the cross-section of the line width / space pattern of the color filter prepared above using SEM images. The results were evaluated as tapered characteristics according to the following criteria and are shown in Table 3 below.

[0156] <Evaluation Criteria>

[0157] ○: Cone angle greater than 45° and less than 80° (positive cone)

[0158] △: Cone angle is 80° or higher but less than 90° (right-angled cone)

[0159] Х: Cone angle greater than 90° (inverted cone)

[0160] 4. Developing residue

[0161] The coloring photosensitive resin compositions of the examples and comparative examples were spin-coated onto a 2-inch × 2-inch glass substrate (manufactured by Corning Incorporated, "EAGLE XG"), placed on a heated plate, and maintained at 100°C for 3 minutes to form a film. The film was then developed by immersing it in a KOH aqueous solution at pH 10.5 for 80 seconds. After rinsing the glass substrate with distilled water and drying it under nitrogen, the transmittance of the glass substrate was measured using a colorimeter (manufactured by Olympus, OSP-200), and the residue was evaluated according to the following evaluation criteria. The results are shown in Table 3 below.

[0162] <Evaluation Criteria>

[0163] ○: 99.7% or more

[0164] △: Above 99.5% but below 99.7%

[0165] ×: Below 99.5%

[0166] [Table 3]

[0167]

[0168] Based on the experimental results of the above embodiments and comparative examples, it was confirmed that in the case of the color filter formed by the color-sensitive resin composition for the red pixel of the present invention, the brightness value is above 99%, and the difference from Comparative Example 1 corresponding to the benchmark is within 1%, demonstrating excellent brightness and excellent tinting strength, thus achieving high color reproduction. Furthermore, it was also confirmed that the processability is excellent, forming a positive cone without producing residue.

[0169] On the other hand, it was confirmed that in the cases of Comparative Examples 1, 2, 5 and 6, although the brightness was excellent, the tinting strength was low, high color reproduction could not be achieved, and inverted cones and residues appeared, making them unsuitable for use as color filters.

[0170] In terms of brightness, Comparative Examples 3 and 4 showed differences of approximately 5% and 13% respectively compared to Comparative Example 1, which served as the baseline, confirming that they exhibited brightness levels unsuitable for use with high-brightness color filters.

Claims

1. A coloring photosensitive resin composition for red pixels, comprising (A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, and (E) a solvent, wherein, The colorant (A) comprises CI Pigment Red 177, CI Pigment Orange 64, and CI Pigment Violet 19. The content of CI pigment violet 19 is 1.2% to 4.8% relative to the total weight of the solid components of the coloring photosensitive resin composition for red pixels.

2. The coloring photosensitive resin composition for red pixels according to claim 1, wherein, The content of the colorant (A) is 25% to 65% relative to the total weight of the coloring photosensitive resin composition for the red pixel.

3. The coloring photosensitive resin composition for red pixels according to claim 1, characterized in that, The acid value of the alkali-soluble resin (B) is 30 to 200 mgKOH / g.

4. The coloring photosensitive resin composition for red pixels according to claim 1, wherein, The (D) photopolymerization initiator comprises an oxime-based photopolymerization initiator.

5. The coloring photosensitive resin composition for red pixels according to claim 1, wherein, Relative to the total weight of the coloring photosensitive resin composition for the red pixel, it comprises: (A) Colorant 25 to 65% by weight; (B) Alkali-soluble resin 0.1 to 30% by weight; (C) Photopolymerizable compounds 0.1 to 20% by weight; (D) Photopolymerization initiator 0.05 to 10% by weight; and (E) Solvent 20 to 70 by weight.

6. The coloring photosensitive resin composition for red pixels according to claim 1, wherein, The coloring photosensitive resin composition for the red pixel also contains (F) additives.

7. A color filter comprising a colored pattern made of a coloring photosensitive resin composition for red pixels according to any one of claims 1 to 6.

8. A display device comprising the color filter according to claim 7.

Images