Coloring photosensitive resin composition, color filter, developing equipment and preparation method

Abstract

This invention provides a coloring photosensitive resin composition, a color filter, a developing device, and a preparation method, relating to the field of developing device technology. The coloring photosensitive resin composition includes a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, additives, and a solvent; the alkali-soluble resin is polymerized from unsaturated monomers; the unsaturated monomers include a first monomer represented by the following chemical formula. The coloring photosensitive resin composition provided by this invention contains carboxylated ionic liquids and hydrophilic halide anions, which not only enhances its developability but also significantly improves its adhesion to the substrate, which is crucial for improving production efficiency and product performance.

Description

Technical Field

[0001] This invention relates to the field of imaging equipment technology, and more specifically, to a coloring photosensitive resin composition, a color filter, an imaging device, and a preparation method. Background Technology

[0002] In the field of modern display technology, color filters are one of the key components for achieving color displays, and are widely used in display technologies such as liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), and quantum dot displays (QDs). The coloring photosensitive resin composition, as the core material for manufacturing color filters, directly affects the color performance and stability of the filter. The colorant, as one of the main components of the coloring photosensitive resin composition, is crucial for improving the color performance of the filter when its concentration is adjusted.

[0003] In existing technologies, the preparation of colored photosensitive resin compositions typically involves the addition of colorants. To enhance the color performance of filters, technicians tend to increase the concentration of colorants. However, this practice is not without its drawbacks. Studies have shown that increasing the colorant concentration leads to slower development speeds and reduces the sensitivity of the photosensitive resin composition. This is detrimental to both production efficiency and product performance.

[0004] To address the slow development speed, technicians attempted to adjust it by increasing the amount of carboxylic acid in the alkali-soluble resin. While this method improved the development speed to some extent, it introduced new problems. Increasing the amount of carboxylic acid could lead to incomplete patterns in the coloring photosensitive resin composition during film formation, directly affecting the optical performance and display effect of the filter.

[0005] In summary, existing technologies present a series of problems in the preparation of coloring photosensitive resin compositions. First, while increasing the colorant concentration can improve color performance, it leads to issues with development speed and sensitivity. Second, the increased amount of carboxylic acid used to address the development speed problem results in incomplete patterns after film formation. These problems are interconnected and collectively restrict the improvement of color filter performance. Therefore, how to improve color performance while ensuring development speed and the integrity of the post-film pattern has become a pressing technical challenge in this field.

[0006] In view of this, the present invention is hereby proposed. Summary of the Invention

[0007] The purpose of this invention is to provide a coloring photosensitive resin composition, a color filter, a developing device, and a preparation method. The coloring photosensitive resin composition significantly improves developability, adhesion, and color performance, and solves the balance problem between developing speed and image integrity.

[0008] In order to achieve the above-mentioned objectives of the present invention, the following technical solution is adopted:

[0009] In a first aspect, the present invention provides a coloring photosensitive resin composition comprising:

[0010] The composition includes a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, additives, and a solvent; the alkali-soluble resin is polymerized from unsaturated monomers; the unsaturated monomers include a first monomer represented by the following chemical formula:

[0011]

[0012] Wherein, R1 is independently at least one of an alkyl group having 1 to 3 carbon atoms and an aryl group having 6 to 10 carbon atoms;

[0013] In an optional embodiment, the amount of alkali-soluble resin added is 10% to 70% relative to the total weight of solid components in the coloring photosensitive resin composition. The solid components are solid components other than the solvent. For example, it can be 10%, 20%, 30%, 50%, 60%, 70%, etc.

[0014] In an optional embodiment, the water droplet angle of the coloring photosensitive resin composition after curing into a film is greater than 0° and less than 45°.

[0015] In an optional embodiment, the alkali-soluble resin has at least one of the following characteristics:

[0016] A. Weight-average molecular weight is above 10,000 and below 50,000;

[0017] B. The acid value is above 50 mg·KOH / g and below 180 mg·KOH / g.

[0018] In an optional embodiment, the unsaturated monomeric substance further includes at least one of a second monomeric substance, a third monomeric substance, and a fourth monomeric substance.

[0019] In an optional embodiment, the second monomeric substance includes at least one of styrene, α-methylstyrene, and p-methylstyrene;

[0020] In an optional embodiment, the second monomer is styrene.

[0021] In an optional embodiment, the third monomeric substance includes at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether.

[0022] In an optional embodiment, the third monomer is glycidyl methacrylate;

[0023] In an optional embodiment, the fourth monomeric substance includes at least one of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, and tert-butyl methacrylate.

[0024] In an optional embodiment, the fourth monomer is methyl methacrylate.

[0025] In an optional embodiment, the photopolymerizable compound is a multifunctional monomer containing at least two functional groups;

[0026] In an optional embodiment, the multifunctional monomer has at least three functional groups;

[0027] In an optional embodiment, the multifunctional monomer includes at least one of trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate, and dipentaerythritol hexa(meth)acrylate;

[0028] In an optional embodiment, the multifunctional monomer is dipentaerythritol hexa(meth)acrylate;

[0029] In an optional embodiment, the amount of the photopolymerizable compound added is 5% to 50% relative to the total weight of the solid components in the coloring photosensitive resin composition.

[0030] In an optional embodiment, the photopolymerization initiator is an oxime ester-based photopolymerization initiator;

[0031] In an optional embodiment, the photopolymerization initiator includes at least one selected from 1,2-octanedione, 1-[4-(phenylthio)phenyl]-2-(O-benzoyl oxime, 2-[4-(phenylthio)phenyl],2-(O-benzoyl oxime), and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]hexanone-1-(O-acetyl oxime);

[0032] In an optional embodiment, the amount of photopolymerization initiator added is 0.1% to 5% relative to the total weight of the solid components in the colored photosensitive resin composition.

[0033] In an optional embodiment, the solvent is a solvent capable of dissolving each component in the coloring photosensitive resin composition;

[0034] In an optional embodiment, the solvent includes propylene glycol monomethyl ether acetate; and at least one of aromatic hydrocarbon solvents, ketone solvents, alcohol solvents, ester solvents, and amide solvents.

[0035] In an optional embodiment, the aromatic hydrocarbon solvent includes at least one of benzene, toluene, xylene, and mesitylene;

[0036] In an optional embodiment, the ketone solvent includes at least one of methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone;

[0037] In an optional embodiment, the alcohol solvent includes at least one selected from ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol;

[0038] In optional embodiments, the ester solvent includes at least one of ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellolytic acetate, ethyl cellolytic 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 monoacetate, 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 monoethyl ether acetate, ethylene carbonate, propylene carbonate, and γ-butyrolactone.

[0039] In an optional embodiment, the amide solvent includes N,N-dimethylformamide and / or N,N-dimethylacetamide;

[0040] In an optional embodiment, the amount of solvent added is 60% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition;

[0041] In an optional embodiment, the amount of solvent added is 70% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition.

[0042] In an optional embodiment, the additive includes at least one of a surfactant and an adhesion promoter;

[0043] The surfactant includes one of F-470, F-475, F-482 and F-554;

[0044] The adhesion promoter includes at least one of vinyltrimethoxysilane, 3-glycidyl etheroxypropylmethyldimethoxysilane, 3-glycidyl etheroxypropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropyltriethoxysilane, and 3-mercaptopropyltrimethoxysilane.

[0045] In an optional embodiment, the adhesion promoter includes at least one of KBM-403, KBM-503, and KBM-803;

[0046] In an optional embodiment, the amount of additive added is 0.1% to 2% relative to the total weight of the solid components in the coloring photosensitive resin composition.

[0047] In an optional embodiment, the colorant includes at least one of a first pigment and a second pigment;

[0048] The first pigment includes at least one of azo dyes, anthraquinone dyes, succinate dyes, and phthalocyanine dyes;

[0049] In an optional embodiment, the azo dye is an azo dye containing a metal complex structure;

[0050] In an optional embodiment, the azo dye includes at least one of CI Solvent Yellow 13, CI Solvent Yellow 19, CI Solvent Yellow 21, CI Solvent Yellow 25, CI Solvent Yellow 25:1, CI Solvent Yellow 81, CI Solvent Yellow 82, CI Solvent Yellow 88, CI Solvent Orange:40:1, CI Solvent Orange:41, CI Solvent Orange 62, CI Solvent Orange 81, CI Solvent Orange 99, CI Solvent Orange 83:1, CI Solvent Red 84:1, CI Solvent Red 84:1, CI Solvent Red 90:1, CI Solvent Red 91:1, CI Solvent Red 118, CI Solvent Red 119, CI Solvent Red 112, CI Solvent Red 330, and CI Solvent Red 130.

[0051] In an optional embodiment, the anthraquinone dye includes at least one of Solvent Blue 35, Solvent Blue 45, Solvent Blue 58, Solvent Blue 101, Solvent Blue 122, Solvent Violet 12, Solvent Violet 13, Solvent Violet 26, and Solvent Violet 47.

[0052] In an optional embodiment, the zeolite dye includes at least one of Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123, and Sulforodamine B.

[0053] In an optional embodiment, the phthalocyanine dye comprises at least one selected from phthalocyanine, 2,3-naphthalenephthalocyanine, 2,9,16,23-tetratert-butyl-29H,31H-phthalocyanine, 1,4,8,11,15,18,22,25-octabutoxy-29H,31H-phthalocyanine, 5,9,14,18,23,27,32,36-octabutoxy-2,3-naphthalenephthalocyanine, 2,3,9,10,16,17,23,24-octa(octoxy)-29H,31H-phthalocyanine, and 2,11,20,29-tetratert-butyl-2,3-naphthalenephthalocyanine;

[0054] In an optional embodiment, the second pigment is an organic pigment;

[0055] In an optional embodiment, the second pigment includes at least one of yellow pigment, orange pigment, red pigment, blue pigment, purple pigment, and green pigment;

[0056] In an optional embodiment, the yellow pigment includes at least one of CI pigment yellow 1, CI pigment yellow 3, CI pigment yellow 12, CI pigment yellow 13, CI pigment yellow 14, CI pigment yellow 15, CI pigment yellow 16, CI pigment yellow 17, CI pigment yellow 20, CI pigment yellow 24, CI pigment yellow 31, CI pigment yellow 53, CI pigment yellow 83, CI pigment yellow 86, CI pigment yellow 93, CI pigment yellow 94, CI pigment yellow 109, CI pigment yellow 110, CI pigment yellow 117, CI pigment yellow 125, CI pigment yellow 128, CI pigment yellow 137, CI pigment yellow 138, CI pigment yellow 139, CI pigment yellow 147, CI pigment yellow 148, CI pigment yellow 150, CI pigment yellow 153, CI pigment yellow 154, CI pigment yellow 166, CI pigment yellow 173, CI pigment yellow 194, and CI pigment yellow 214.

[0057] In an optional embodiment, the orange pigment includes at least one of CI Orange 13, CI Orange 31, CI Orange 36, CI Orange 38, CI Orange 40, CI Orange 42, CI Orange 43, CI Orange 51, CI Orange 55, CI Orange 59, CI Orange 61, CI Orange 64, CI Orange 65, CI Orange 71, and CI Orange 73;

[0058] In an optional embodiment, the red pigment includes at least one of CI Pigment Red 9, CI Pigment Red 97, CI Pigment Red 105, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 180, CI Pigment Red 192, CI Pigment Red 209, CI Pigment Red 215, CI Pigment Red 216, 224, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 264, and CI Pigment Red 265.

[0059] In an optional embodiment, the blue pigment includes blue pigments such as CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, and CI Pigment Blue 80.

[0060] In an optional embodiment, the purple pigment includes at least one of C.I. Pigment Violet 1, C.I. Pigment Violet 19, C.I. Pigment Violet 23, 29, C.I. Pigment Violet 32, C.I. Pigment Violet 36, C.I. Pigment Violet 37 and C.I. Pigment Violet 38;

[0061] In an optional embodiment, the green pigment includes at least one of CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58.

[0062] A second aspect of the present invention provides a method for preparing a coloring photosensitive resin composition as described in any of the optional embodiments above, comprising:

[0063] The second pigment in the colorant is dispersed to obtain first colorant particles;

[0064] The dispersant, the first pigment in the colorant, the first colorant particles and the solvent are mixed, dissolved and dispersed to obtain a coloring mixed dispersion;

[0065] An alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and additives are added to the coloring mixed dispersion to obtain the coloring photosensitive resin composition.

[0066] In an optional embodiment, the method for preparing the alkali-soluble resin includes:

[0067] An unsaturated monomer is introduced into a reaction vessel; wherein the unsaturated monomer is a first monomer substance; or, the unsaturated monomer includes a first monomer substance and at least one of a second monomer substance, a third monomer substance and a fourth monomer substance.

[0068] Add 5% azobisisobutyronitrile relative to the total weight of the unsaturated monomers, which is equivalent to propylene glycol monomethyl ether acetate by the total weight of azobisisobutyronitrile and the unsaturated monomers, to obtain a mixture of reaction raw materials;

[0069] The reaction mixture is reacted under heating conditions in a protective atmosphere to obtain the alkali-soluble resin.

[0070] In an optional embodiment, the heating condition is 70°C;

[0071] In an optional embodiment, the reaction time under the heating conditions is not less than 6 hours;

[0072] In an optional embodiment, the method for preparing the first monomeric substance includes:

[0073] The nucleophile vinylimidazole was reacted with a halocarboxylic acid in a bimolecular nucleophilic substitution reaction to obtain the first monomer.

[0074] In a third aspect, the present invention provides a color filter prepared using a coloring photosensitive resin composition as described in any of the optional embodiments above.

[0075] In a fourth aspect, the present invention provides a developing apparatus including the color filter as described in any of the optional embodiments above.

[0076] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0077] This invention provides a coloring photosensitive resin composition, a color filter, a developing device, and a preparation method. The coloring photosensitive resin composition comprises: a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, additives, and a solvent; the alkali-soluble resin is polymerized from unsaturated monomers. The coloring photosensitive resin composition provided by this invention contains carboxylated ionic liquids and hydrophilic halide anions, which not only enhances its developability but also significantly improves its adhesion to the substrate, crucial for improving production efficiency and product performance. Furthermore, by increasing the colorant concentration, this composition effectively improves the color performance of the color filter, meeting the demands of the display technology field for enhanced display effects. It also solves the problems of slow development speed and low sensitivity caused by increasing the colorant concentration, ensuring the integrity of the pattern after film formation. The diverse chemical structures of the unsaturated carboxylated ionic liquid monomers, where R1 can be an alkyl group with 1-3 carbon atoms or an aryl group with 6-10 carbon atoms, provide great flexibility in adjusting the performance of the resin composition, allowing for the customization of products with different properties according to specific application requirements.

[0078] In summary, the coloring photosensitive resin composition provided in this invention offers a high-performance and highly adaptable solution for display technologies such as liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), and quantum dot (QDs). Attached Figure Description

[0079] To more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the specific embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained from these drawings without creative effort.

[0080] Figure 1 This is a schematic flowchart of the preparation method of the coloring photosensitive resin composition in the embodiments of this application;

[0081] Figure 2 This is a bar chart showing the development time test results of the embodiments and comparative examples in the horizontal test experiment of this application;

[0082] Figure 3 This is a bar chart showing the transmittance test results of the embodiments and comparative examples in the lateral test experiments of this application;

[0083] Figure 4 The bar chart shows the droplet angle test results of the embodiments and comparative examples in the lateral test experiments of this application. Detailed Implementation

[0084] The embodiments of the present invention will be described in detail below with reference to examples. However, those skilled in the art will understand that the following examples are for illustrative purposes only and should not be considered as limiting the scope of the invention. Unless otherwise specified in the examples, conventional conditions or conditions recommended by the manufacturer are followed. Reagents or instruments whose manufacturers are not specified are all commercially available conventional products.

[0085] In this embodiment of the application, a coloring photosensitive resin composition is provided, comprising: a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive, and a solvent; wherein the alkali-soluble resin is polymerized from an unsaturated monomer; the unsaturated monomer includes a first monomer represented by the following chemical formula:

[0086]

[0087] R1 is independently at least one of an alkyl group having 1 to 3 carbon atoms and an aryl group having 6 to 10 carbon atoms.

[0088] The aforementioned coloring photosensitive resin composition is mainly used in the manufacture of color filters and image display devices. The composition comprises six main components: a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, additives, and a solvent.

[0089] The alkali-soluble resin is one of the key components of this composition, and it is polymerized from unsaturated monomers. This design allows the resin to dissolve under alkaline conditions, which is crucial for the development step in the photolithography process.

[0090] Unsaturated monomers include the first monomer, whose chemical structure contains an R1 group, where R1 can be an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 10 carbon atoms. This design provides diversity in chemical structure, allowing for adjustments to the resin's solubility, reactivity, and final properties.

[0091] The first monomer (named L in this embodiment) is a 5-membered cyclic compound, specifically, it is an azacyclopentene derivative with a carboxylic acid group (-COOH) and contains an alkyl or aryl substituent (R1).

[0092] In the first monomeric compound, the structure contains a water-soluble halogen (such as a bromide ion Br). - The presence of halogen ions (such as Br₂) and carboxylated ions (carboxylic acid groups -COOH) in the prepared polymer will have the following effects: - Both the α group and the carboxylic acid group (-COOH) can increase the water solubility of the polymer. The carboxylic acid group can ionize under neutral or alkaline conditions to form a carboxylate ion (-COO₂). -Halogen ions themselves carry a charge, and these charged groups can increase the interaction between polymers and water molecules, thereby improving their solubility in water. Ionic groups in polymers (such as carboxylate and halide ions) can improve the electrical conductivity of polymers, making them potentially useful in electronic and optoelectronic applications, such as in battery electrolytes or electrochromic materials.

[0093] The coloring photosensitive resin composition provided in this embodiment contains carboxylated ionic liquids and hydrophilic halide anions, which not only enhances its developability but also significantly improves its adhesion to the substrate, crucial for improving production efficiency and product performance. Furthermore, by increasing the colorant concentration, the composition effectively improves the color performance of color filters, meeting the demands of the display technology field for enhanced display effects. It also solves the problems of slow development speed and low sensitivity caused by increasing the colorant concentration, ensuring the integrity of the pattern after film formation. The diverse chemical structures of the unsaturated carboxyl ionic liquid monomers, where R1 can be an alkyl group with 1-3 carbon atoms or an aryl group with 6-10 carbon atoms, provide great flexibility in adjusting the performance of the resin composition, allowing for the customization of products with different properties according to specific application requirements.

[0094] Furthermore, the amount of alkali-soluble resin added is 10% to 70% relative to the total weight of solid components in the coloring photosensitive resin composition;

[0095] Furthermore, the water droplet angle of the coloring photosensitive resin composition after curing into a film is greater than 0° and less than 45°;

[0096] Furthermore, the alkali-soluble resin has at least one of the following characteristics:

[0097] A. Weight-average molecular weight is above 10,000 and below 50,000;

[0098] B. The acid value is above 50 mg·KOH / g and below 180 mg·KOH / g.

[0099] In an optional embodiment, the alkali-soluble resin has at least one of the following characteristics:

[0100] A. Weight-average molecular weight is above 10,000 and below 50,000. This can be expressed as 50,000 ≥ Mw ≥ 10,000; for example, it can be 10,000, 20,000, 30,000, 40,000, 50,000, etc.

[0101] B. The acid value is above 50 mg·KOH / g and below 180 mg·KOH / g. This can be expressed as 180 mg·KOH / g ≥ A ≥ 50 mg·KOH / g. For example, it can be 50 mg·KOH / g, 80 mg·KOH / g, 100 mg·KOH / g, 120 mg·KOH / g, 150 mg·KOH / g, 180 mg·KOH / g, etc.

[0102] Furthermore, the unsaturated monomeric substance also includes at least one of a second monomeric substance (named B1 in this embodiment), a third monomeric substance (named B2 in this embodiment), and a fourth monomeric substance (named B3 in this embodiment).

[0103] In some embodiments, the second monomeric substance includes at least one of styrene, α-methylstyrene, and p-methylstyrene.

[0104] Furthermore, the second monomer is styrene.

[0105] In this embodiment, the alkali-soluble resin can be copolymerized from a first monomer (unsaturated carboxyl ionic liquid monomer (L), a second monomer (unsaturated monomer B1), a third monomer (unsaturated epoxy monomer B2), and a fourth monomer (acrylate B3). This allows the colored photosensitive resin composition to achieve both rapid development and preservation of the complete pattern after film formation.

[0106] The third monomeric substance mentioned above includes at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether.

[0107] Furthermore, glycidyl methacrylate has high copolymerization activity and good chemical resistance after film formation. Therefore, in a preferred embodiment, the third monomer is glycidyl methacrylate.

[0108] Furthermore, the fourth monomeric substance includes at least one of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, and tert-butyl methacrylate.

[0109] Furthermore, the fourth monomer is methyl methacrylate.

[0110] Furthermore, the photopolymerizable compound is a multifunctional monomer containing at least two functional groups.

[0111] In a preferred embodiment, the multifunctional monomer has at least three functional groups.

[0112] Furthermore, the multifunctional monomer includes at least one of trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0113] Furthermore, the multifunctional monomer is dipentaerythritol hexa(meth)acrylate.

[0114] For example, multifunctional monomers can be commercially available products, such as KAYARAD DPHA (Nippon Kayaku).

[0115] Furthermore, the amount of the photopolymerizable compound added is 5% to 50% relative to the total weight of the solid components in the coloring photosensitive resin composition. For example, it can be 5%, 10%, 20%, 30%, 40%, 50%, etc.

[0116] Furthermore, the photopolymerization initiator is an oxime ester-based photopolymerization initiator;

[0117] Furthermore, the photopolymerization initiator includes at least one selected from 1,2-octanedione, 1-[4-(phenylthio)phenyl]-2-(O-benzoyl oxime, 2-[4-(phenylthio)phenyl],2-(O-benzoyl oxime), and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]hexanone-1-(O-acetyl oxime).

[0118] Furthermore, the amount of photopolymerization initiator added is 0.1% to 5% relative to the total weight of the solid components in the colored photosensitive resin composition.

[0119] The aforementioned photopolymerization initiator can be a commercially available oxime ester-based photopolymerization initiator, such as, but not limited to, BASF's Omnirad 1314 and Tronly's PBG-345.

[0120] Furthermore, the solvent is a solvent capable of dissolving each component in the coloring photosensitive resin composition.

[0121] The solvent mentioned above can be any solvent capable of dissolving the above-mentioned coloring photosensitive resin composition.

[0122] Furthermore, the solvent includes propylene glycol monomethyl ether acetate; and at least one of aromatic hydrocarbon solvents, ketone solvents, alcohol solvents, ester solvents and amide solvents.

[0123] Furthermore, the aromatic hydrocarbon solvent includes at least one of benzene, toluene, xylene, and mesitylene;

[0124] Furthermore, the ketone solvent includes at least one of methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone;

[0125] Furthermore, the alcohol solvent includes at least one selected from ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol;

[0126] Furthermore, the ester solvent includes at least one of ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellolytic acetate, ethyl cellolytic 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 monoacetate, 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 monoethyl ether acetate, ethylene carbonate, propylene carbonate, and γ-butyrolactone.

[0127] Furthermore, the amide solvent includes N,N-dimethylformamide and / or N,N-dimethylacetamide;

[0128] Furthermore, the amount of solvent added is 60% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition;

[0129] Furthermore, the amount of solvent added is 70% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition.

[0130] It should be noted that when the solvent content is within the above-mentioned range, i.e., 70% to 90%, the coating properties are improved when using coating devices such as roller coaters, spin coaters, slot coaters, slot coating machines, and inkjet printers.

[0131] Furthermore, the additive includes at least one of a surfactant and an adhesion promoter;

[0132] The surfactant may include, for example, one of the commercially available products from Dai Nippon Ink Chemical Industry Co., Ltd.: F-470, F-475, F-482, and F-554.

[0133] The adhesion promoter includes at least one of vinyltrimethoxysilane, 3-glycidyl etheroxypropylmethyldimethoxysilane, 3-glycidyl etheroxypropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropyltriethoxysilane, and 3-mercaptopropyltrimethoxysilane.

[0134] In addition, the adhesion promoter may also include at least one of the commercially available Shin-Etsu Group's KBM-403, KBM-503, and KBM-803.

[0135] Furthermore, the amount of the additive added is 0.1% to 2% relative to the total weight of the solid components in the coloring photosensitive resin composition.

[0136] Furthermore, the colorant includes at least one of a first pigment and a second pigment;

[0137] The first pigment includes at least one of azo dyes, anthraquinone dyes, succinate dyes, and phthalocyanine dyes;

[0138] Furthermore, the azo dye is an azo dye containing a metal complex structure;

[0139] Furthermore, the azo dye includes at least one of CI Solvent Yellow 13, CI Solvent Yellow 19, CI Solvent Yellow 21, CI Solvent Yellow 25, CI Solvent Yellow 25:1, CI Solvent Yellow 81, CI Solvent Yellow 82, CI Solvent Yellow 88, CI Solvent Orange:40:1, CI Solvent Orange:41, CI Solvent Orange 62, CI Solvent Orange 81, CI Solvent Orange 99, CI Solvent Orange 83:1, CI Solvent Red 84:1, CI Solvent Red 84:1, CI Solvent Red 90:1, CI Solvent Red 91:1, CI Solvent Red 118, CI Solvent Red 119, CI Solvent Red 112, CI Solvent Red 330, and CI Solvent Red 130;

[0140] Furthermore, the anthraquinone dye includes at least one of Solvent Blue 35, Solvent Blue 45, Solvent Blue 58, Solvent Blue 101, Solvent Blue 122, Solvent Violet 12, Solvent Violet 13, Solvent Violet 26, and Solvent Violet 47;

[0141] Furthermore, the zeolite dye includes at least one of Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123, and Sulforodamine B.

[0142] Furthermore, the phthalocyanine dye includes at least one selected from phthalocyanine, 2,3-naphthalenephthalocyanine, 2,9,16,23-tetratert-butyl-29H,31H-phthalocyanine, 1,4,8,11,15,18,22,25-octabutoxy-29H,31H-phthalocyanine, 5,9,14,18,23,27,32,36-octabutoxy-2,3-naphthalenephthalocyanine, 2,3,9,10,16,17,23,24-octa(octoxy)-29H,31H-phthalocyanine, and 2,11,20,29-tetratert-butyl-2,3-naphthalenephthalocyanine;

[0143] Furthermore, the second pigment is an organic pigment;

[0144] Furthermore, the second pigment includes at least one of the following: yellow pigment, orange pigment, red pigment, blue pigment, purple pigment, and green pigment;

[0145] Furthermore, the yellow pigment includes at least one of CI pigment yellow 1, CI pigment yellow 3, CI pigment yellow 12, CI pigment yellow 13, CI pigment yellow 14, CI pigment yellow 15, CI pigment yellow 16, CI pigment yellow 17, CI pigment yellow 20, CI pigment yellow 24, CI pigment yellow 31, CI pigment yellow 53, CI pigment yellow 83, CI pigment yellow 86, CI pigment yellow 93, CI pigment yellow 94, CI pigment yellow 109, CI pigment yellow 110, CI pigment yellow 117, CI pigment yellow 125, CI pigment yellow 128, CI pigment yellow 137, CI pigment yellow 138, CI pigment yellow 139, CI pigment yellow 147, CI pigment yellow 148, CI pigment yellow 150, CI pigment yellow 153, CI pigment yellow 154, CI pigment yellow 166, CI pigment yellow 173, CI pigment yellow 194, and CI pigment yellow 214;

[0146] Furthermore, the orange pigment includes at least one of CI Orange 13, CI Orange 31, CI Orange 36, CI Orange 38, CI Orange 40, CI Orange 42, CI Orange 43, CI Orange 51, CI Orange 55, CI Orange 59, CI Orange 61, CI Orange 64, CI Orange 65, CI Orange 71 and CI Orange 73;

[0147] Furthermore, the red pigment includes at least one of CI Pigment Red 9, CI Pigment Red 97, CI Pigment Red 105, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 180, CI Pigment Red 192, CI Pigment Red 209, CI Pigment Red 215, CI Pigment Red 216, 224, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 264, and CI Pigment Red 265;

[0148] Furthermore, the blue pigments include CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, CI Pigment Blue 80, and other blue pigments.

[0149] Furthermore, the purple pigment includes at least one of C.I. Pigment Violet 1, C.I. Pigment Violet 19, C.I. Pigment Violet 23, 29, C.I. Pigment Violet 32, C.I. Pigment Violet 36, C.I. Pigment Violet 37 and C.I. Pigment Violet 38;

[0150] Furthermore, the green pigment includes at least one of CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58.

[0151] refer to Figure 1 This application provides a method for preparing a coloring photosensitive resin composition as described in any of the optional embodiments above, comprising:

[0152] Step S100: Disperse the second pigment in the colorant to obtain first colorant particles.

[0153] The second pigment can be dispersed using a dispersion device. For example, the second pigment in the colorant can be dispersed using a bead mill or similar device until the average particle size of the pigment reaches below 0.2 μm, thus obtaining the first colorant particles.

[0154] Step S200: The dispersant, the first pigment in the colorant, the first colorant particles and the solvent are mixed, dissolved and dispersed to obtain a colored mixed dispersion.

[0155] In step S300, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and additives are added to the coloring mixed dispersion to obtain the coloring photosensitive resin composition.

[0156] Furthermore, the method for preparing the alkali-soluble resin in step S300 includes:

[0157] Step S310: An unsaturated monomer is added to a reaction vessel; wherein the unsaturated monomer is a first monomer substance; or, the unsaturated monomer includes a first monomer substance and at least one of a second monomer substance, a third monomer substance and a fourth monomer substance.

[0158] The unsaturated monomers fed into the reaction vessel can be in the following two cases:

[0159] (1) First substance.

[0160] (2) First substance + (at least one of second monomer substance, third monomer substance and fourth monomer substance).

[0161] The reaction vessel described above can be, for example, a flask equipped with a condenser and a stirrer.

[0162] In step S320, 5% of azobisisobutyronitrile (AIBN) relative to the total weight of the unsaturated monomers is added, which is equivalent to propylene glycol monomethyl ether acetate by the total weight of the AIBN and the unsaturated monomers, to obtain a reaction mixture.

[0163] Step S3310: Under a protective atmosphere, the mixture of reaction raw materials is reacted under heating conditions to obtain the alkali-soluble resin.

[0164] Furthermore, the heating condition is 70°C;

[0165] Furthermore, the reaction time under the heating conditions is no less than 6 hours;

[0166] Furthermore, in step S310, the method for preparing the first monomer substance includes:

[0167] Step S311: The nucleophile vinylimidazole is reacted with a halocarboxylic acid to undergo a bimolecular nucleophilic substitution reaction to obtain the first monomer.

[0168] The aforementioned halogenated carboxylic acids may include, but are not limited to, bromoacetic acid, 3-bromopropionic acid, 4-bromobutyric acid, bromomethylbenzoic acid, etc.

[0169] The amount of halocarboxylic acid added can be 0.5 mol.

[0170] The reaction vessel can be a reaction vessel or a reactor, such as a four-port 1L reactor equipped with a thermometer, a mechanical stirrer, a cooling capacitor and a heating gate.

[0171] This application provides a color filter prepared using a coloring photosensitive resin composition as described in any of the optional embodiments above.

[0172] It's important to note that color filters are crucial optical components that selectively transmit light of specific wavelengths while absorbing or reflecting others. This makes them vital in various fields, including photography, display technology, scientific instruments, optical communications, lighting, medical imaging, and industrial inspection. In display technologies such as liquid crystal displays (LCDs), organic light-emitting diode (OLEDs), and quantum dot (QD) displays, color filters are used to separate and control the three primary colors of light—red, green, and blue—to create rich and vibrant images. Furthermore, color filters are indispensable in spectral analysis, fiber optic communications, and professional lighting design, where they enhance image quality, convey information, or create specific visual effects by precisely controlling the wavelength of light.

[0173] This application provides a developing device, including the color filter as described in any of the optional embodiments above.

[0174] The coloring photosensitive resin composition in this embodiment can be widely used in various display devices, including but not limited to liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), quantum dot (QD) displays, electronic paper (E-Paper), microdisplays, touch screens, automotive displays, and medical imaging equipment. These devices all rely on high-quality color filters to achieve accurate color reproduction and high-contrast image display. The coloring photosensitive resin composition provided by this invention aims to provide technical support for these display technologies through its superior performance, improving their color performance and stability.

[0175] Furthermore, the method for preparing the second pigment in the colorant may include:

[0176] Pigment dispersion composition M1 was prepared by mixing and dispersing 9.0 parts by weight of CI pigment red 254 and 1.0 parts by weight of CI pigment yellow 150 as pigments, 7.0 parts by weight of DISPERBYK2001 (manufactured by BYK) as pigment dispersant, and 83.0 parts by weight of propylene glycol methyl ether acetate as solvent in a bead mill for 12 hours.

[0177] Example 1

[0178] In this embodiment, the first monomer substance was prepared. Specifically, it can be synthesized using the following four methods (Synthesis Examples 1-4):

[0179] (1) Synthesis Example 1: In a 1L four-necked reactor equipped with a thermometer, mechanical stirrer, cooling capacitor, and heating gate, 37.65 parts by weight of vinylimidazole (0.4 mol) and 69.48 parts by weight of bromoacetic acid (0.5 mol) were added. The mixture was stirred at 55°C for 12 h. The product was then dissolved in acetonitrile and purified with diethyl ether to obtain 1-carboxymethyl-3-vinylimidazole bromide (L1). The chemical reaction formula is as follows:

[0180]

[0181] (2) Synthesis Example 2: Except that the amount of 3-bromopropionic acid added was 76.49 parts by weight (0.5 mol), the preparation was the same as in Synthesis Example 1, and 1-carboxyethyl-3-vinylimidazolium bromide (L2) was finally obtained. The chemical reaction formula is as follows:

[0182]

[0183] (3) Synthesis Example 3: Except for the amount of 4-bromobutyric acid added (86.51 parts by weight, 0.5 mol), the preparation was the same as in Synthesis Example 1, finally yielding 1-carboxypropyl-3-vinylimidazolium bromide (L3). The chemical reaction formula is as follows:

[0184]

[0185] (4) Synthesis Example 4: Except that the amount of p-bromomethylbenzoic acid added was 107.52 parts by weight (0.5 mol), the preparation was the same as in Synthesis Example 1, and finally 1-p-methylbenzoic acid-3-vinylimidazolium bromide (L4) was obtained. The chemical reaction formula is as follows:

[0186]

[0187] Example 2

[0188] In this embodiment, L1, L2, L3, and L4 obtained in Example 1 were used to prepare lipid-soluble resins in different examples. Specifically, they can be prepared through the following 6 polymerization examples.

[0189] Experimental methods:

[0190] (1) Polymerization Example 1: In a flask equipped with a condenser and a stirrer, each monomer in this example was added according to the composition in Table 1 below, and 5% by weight of azobisisobutyronitrile (AIBN) was added relative to the total weight of the monomers above; propylene glycol monomethyl ether acetate was added equivalent to the total weight of the initiator (AIBN) and the first monomer substance above. Referring to the data in Table 1, the mixture was stirred under a nitrogen atmosphere and the temperature was raised to 70°C for 6 hours to obtain each alkali-soluble resin.

[0191] (2) Aggregation Example 2: This example is basically the same as Aggregation Example 1. The differences are shown in Table 1.

[0192] (3) Aggregation Example 3: This example is basically the same as Aggregation Example 1. The differences are shown in Table 1.

[0193] (4) Aggregation Example 4: This example is basically the same as Aggregation Example 1. The differences are shown in Table 1.

[0194] (5) Aggregation Example 5: This example is basically the same as Aggregation Example 1. The differences are shown in Table 1.

[0195] (6) Aggregation Example 6: This example is basically the same as Aggregation Example 1. The differences are shown in Table 1.

[0196] Experimental results:

[0197] The weight-average molecular weight (Mw) is shown in Table 1 below. The acid value (mg·KOH / g) is shown in Table 1 below.

[0198] Table 1. Preparation components and test results of polymerization examples 1-6 in Example 2

[0199] Aggregation example 1 2 3 4 5 6 L1 14 0 0 0 0 0 L2 0 14 0 0 0 0 L3 0 0 14 0 0 0 L4 0 0 0 14 0 0 acrylic acid 0 0 0 0 14 0 methacrylic acid 0 0 0 0 0 14 B1 30 30 30 30 30 30 B2 32 32 32 32 32 32 B3 24 24 24 24 24 24 Molecular weight (Mw) 11100 10900 10600 10200 12200 11800 Acid value (mg·KOH / g) 96 92 86 79 107 101

[0200] It should be noted that in the table above, the weight-average molecular weight is the converted average molecular weight of polystyrene determined using gel permeation chromatography (GPC); the acid value is determined using acid-base titration.

[0201] L1, L2, L3, and L4 represent the four first monomer substances among the unsaturated monomer substances prepared in Example 1, namely: 1-carboxymethyl-3-vinylimidazolium bromide (L1), 1-carboxyethyl-3-vinylimidazolium bromide (L2), 1-carboxypropyl-3-vinylimidazolium bromide (L3), and 1-p-methylbenzoic acid-3-vinylimidazolium bromide (L4).

[0202] B1 represents the second unsaturated monomer: styrene; B2 represents the third unsaturated monomer: glycidyl methacrylate; B3 represents the fourth unsaturated monomer: methyl methacrylate.

[0203] Example 3

[0204] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0205] Preparation method:

[0206] A red photosensitive resin composition was prepared by mixing 38.27 parts by weight of the aforementioned pigment dispersion composition M1, 10.62 parts by weight of the alkali-soluble resin prepared in polymerization example 1 of Example 2, 3.52 parts by weight of KAYARAD DPHA (Nippon Kayaku) as a photopolymerizable compound, 0.71 parts by weight of Omnirad 1314 (manufactured by BASF) as a photopolymerization initiator, 0.15 parts by weight of additive F-554 (manufactured by DIC Corporation of Japan), 0.02 parts by weight of additive KBM-503M (manufactured by Shin-Etsu Corporation), and 46.71 parts by weight of propylene glycol monomethyl ether acetate.

[0207] Example 4

[0208] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0209] Preparation method:

[0210] The method used in this example is basically the same as that in Example 3. The difference is that the alkali-soluble resin used in Example 2 is the same as that used in Example 2.

[0211] Example 5

[0212] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0213] Preparation method:

[0214] The method used in this example is basically the same as that in Example 3. The difference is that the alkali-soluble resin used in Example 2 for polymerizing Example 3 is employed.

[0215] Example 6

[0216] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0217] Preparation method:

[0218] The method used in this example is basically the same as that in Example 3. The difference is that the alkali-soluble resin used in Example 2, which was polymerized in Example 4, is employed.

[0219] Example 7

[0220] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0221] Preparation method:

[0222] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Example 2 (polymerization example 1) is 9.94, and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0223] Example 8

[0224] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0225] Preparation method:

[0226] The method used in this example is basically the same as that in Example 3. The difference is that the weight parts of the alkali-soluble resin used in Example 2 (polymerization example 1) are 11.22, and the weight parts of propylene glycol monomethyl ether acetate are 46.11.

[0227] Example 9

[0228] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0229] Preparation method:

[0230] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Example 2 of Polymerization Example 2 is 9.94; and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0231] Example 10

[0232] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0233] Preparation method:

[0234] The method used in this example is basically the same as that in Example 3. The difference is that the weight parts of the alkali-soluble resin used in Example 2 of Polymerization Example 2 are 11.22, and the weight parts of propylene glycol monomethyl ether acetate are 46.71.

[0235] Example 11

[0236] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0237] Preparation method:

[0238] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Example 2 (polymerization example 3) is 9.94, and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0239] Example 12

[0240] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0241] Preparation method:

[0242] The method used in this example is basically the same as that in Example 3. The difference is that the weight parts of the alkali-soluble resin used in Example 2 to polymerize Example 3 are 11.22, and the weight parts of propylene glycol monomethyl ether acetate are 46.11.

[0243] Example 13

[0244] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0245] Preparation method:

[0246] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Example 2 (polymerization example 3) is 9.94, and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0247] Example 14

[0248] This embodiment describes the preparation of a coloring photosensitive resin composition.

[0249] Preparation method:

[0250] The method used in this example is basically the same as that in Example 3. The difference is that the weight parts of the alkali-soluble resin used in Polymerization Example 4 of Example 2 are 11.22, and the weight parts of propylene glycol monomethyl ether acetate are 46.11.

[0251] Comparative Example 1

[0252] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0253] Preparation method:

[0254] The method used in this example is basically the same as that in Example 3. The difference is that the alkali-soluble resin used in Example 2 for polymerizing Example 5 is employed.

[0255] Comparative Example 2

[0256] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0257] Preparation method:

[0258] The method used in this example is basically the same as that in Example 3. The difference is that the alkali-soluble resin used in Example 2 for polymerizing Example 6 is employed.

[0259] Comparative Example 3

[0260] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0261] Preparation method:

[0262] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Polymerization Example 5 of Example 2 is 9.94, and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0263] Comparative Example 4

[0264] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0265] Preparation method:

[0266] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Polymerization Example 5 of Example 2 is 11.22, and the weight percentage of propylene glycol monomethyl ether acetate is 46.11.

[0267] Comparative Example 5

[0268] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0269] Preparation method:

[0270] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Polymerization Example 6 of Example 2 is 9.94, and the weight percentage of propylene glycol monomethyl ether acetate is 47.39.

[0271] Comparative Example 6

[0272] This comparative example demonstrates the preparation of a colored photosensitive resin composition.

[0273] Preparation method:

[0274] The method used in this example is basically the same as that in Example 3. The difference is that the weight percentage of the alkali-soluble resin used in Example 2 (polymerization example 6) is 11.22, and the weight percentage of propylene glycol monomethyl ether acetate is 46.11.

[0275] Lateral testing experiment:

[0276] Experimental methods:

[0277] (1) The coloring photosensitive resin compositions prepared in Examples 3-14 and Comparative Examples 1-6 were coated onto a 500mm × 500mm glass substrate (Corning Corporation, EAGLEXG) using a spin coater to achieve a film thickness of 2.2μm after drying. The substrate with the coated film was moved to a vacuum drying chamber (VCD) and vacuum dried at a pressure of 55Pa for 17 seconds. After vacuum drying, the film was pre-baked in an oven at 100°C for 3 minutes. Next, a test photomask with a line / gap pattern of 1μm to 100μm was placed on the film, and ultraviolet light was irradiated with a spacing of 300μm. At this time, a 1KW high-pressure mercury lamp containing all g, h, and i lines was used as the ultraviolet light source, and the irradiation was 40mJ / cm2. Furthermore, no photomask was used on the entire substrate; the entire substrate was exposed. The film, after being irradiated with ultraviolet light, was then immersed in a developing solution of KOH aqueous solution with a pH of 10.5 for 2 minutes. The glass plate coated with the film was then washed with distilled water, dried by blowing nitrogen gas, and heated in an oven at 230°C for 25 minutes to produce a red filter with a pattern and a full-face design.

[0278] (2) Test Experiment 1: Evaluation of Development Rate: When the coated film was developed in KOH aqueous solution, the time required for a portion of the unexposed ultraviolet-irradiated coated photosensitive resin composition to dissolve in the developing solution was measured. The results are shown in Table 2 below.

[0279] (3) Test Experiment 2 (Adhesion Evaluation): The pattern of the color filter was observed using an optical microscope (LV100ND, Nikon). The adhesion of the colored photosensitive resin was evaluated according to the following evaluation criteria. The results are shown in Table 2 below. The evaluation criteria include: √: pattern intact; △: pattern has 1-4 peelings; ×: pattern has 5 or more peelings.

[0280] (4) Test Experiment 3 (Transmittance Evaluation): The transmittance of the prepared color filter glass portion was measured using a spectrophotometer (OSP-SP200, Olympus). When the transmittance was close to 100%, there was no residue of the colored photosensitive resin composition in the unirradiated area, therefore it could be judged that there was no residue. The results are shown in Table 2 below.

[0281] (5) Test Experiment 4 (Water Droplet Angle Evaluation): The contact angle of a water droplet on the entire surface of the red filter was measured using a contact angle meter (CAST-KR, HARKE). When the water droplet angle was greater than 0° and less than 45°, the coloring photosensitive resin composition exhibited good adhesion to the glass substrate; when the water droplet angle was greater than 45°, the adhesion of the coloring photosensitive resin composition to the glass substrate was poor. The results are shown in Table 2 below.

[0282] Experimental results and analysis:

[0283] Table 2. Results of the horizontal comparison test

[0284] example Development time s Adhesion Transmission % Water droplet angle ° example Development time s Adhesion Transmission % Water droplet angle ° Real 3 12 √ 99.9 23 12 15 √ 99.9 24 Real 4 14 √ 99.9 25 13 26 √ 99.8 41 Real 5 16 √ 99.9 28 14 22 √ 99.9 31 Real 6 23 √ 99.9 34 For 1 32 △ 95.4 49 Real 7 13 √ 99.9 27 2 35 √ 94.9 58 Real 8 11 √ 99.9 18 3 36 √ 92.7 53 Real 9 15 √ 99.9 29 4 29 × 99.7 46 10 12 √ 99.9 20 5 39 √ 91.2 63 Real 11 18 √ 99.9 35 6 31 △ 98.5 55

[0285] In the table, "real" represents "example", such as real 3 representing example 3; "compare" represents comparative example, such as compare 1 representing comparative example 1.

[0286] Referring to the results in Table 2 above and Figures 2-4 In Examples 3 to 14, which contain unsaturated carboxyl ionic liquids, it was confirmed that excellent effects were observed in terms of development rate, adhesion, transmittance, and droplet angle.

[0287] On the other hand, in the case of Comparative Examples 1 to 6 which do not contain unsaturated carboxyl ionic liquids, it can be confirmed that the development rate decreases, the adhesion deteriorates, the transmittance decreases, and the droplet angle increases.

[0288] As can be seen from the above results, the coloring photosensitive resin composition of the present invention can provide the following effects: it can achieve excellent pattern integrity while enabling the coating to have a fast development rate.

[0289] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, and not to limit them. Although the present invention has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein. Such modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A coloring photosensitive resin composition, characterized in that, include: The mixture comprises a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, additives, and a solvent; the alkali-soluble resin is polymerized from unsaturated monomers; the unsaturated monomers include a first monomer, a second monomer, a third monomer, and a fourth monomer; the chemical formula of the first monomer is as follows: ； Wherein, R1 is independently at least one of an alkyl group having 1 to 3 carbon atoms and an aryl group having 6 to 10 carbon atoms; The second monomeric substance includes at least one of styrene, α-methylstyrene, and p-methylstyrene; The third monomeric substance includes at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl methacrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether. The fourth monomeric substance includes at least one of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, and tert-butyl methacrylate.

2. The coloring photosensitive resin composition according to claim 1, characterized in that, The amount of alkali-soluble resin added is 10% to 70% relative to the total weight of solid components in the coloring photosensitive resin composition.

3. The coloring photosensitive resin composition according to claim 1, characterized in that, The coloring photosensitive resin composition has a water droplet angle greater than 0° and less than 45° after curing into a film.

4. The coloring photosensitive resin composition according to claim 1, characterized in that, The alkali-soluble resin has at least one of the following characteristics: A. Weight-average molecular weight is above 10,000 and below 50,000; B. The acid value is above 50 mg·KOH / g and below 180 mg·KOH / g.

5. The coloring photosensitive resin composition according to claim 1, characterized in that, The second monomer is styrene.

6. The coloring photosensitive resin composition according to claim 1, characterized in that, The third monomer is glycidyl methacrylate.

7. The coloring photosensitive resin composition according to claim 1, characterized in that, The fourth monomer is methyl methacrylate.

8. The coloring photosensitive resin composition according to claim 1, characterized in that, The photopolymerizable compound is a multifunctional monomer containing at least two functional groups.

9. The coloring photosensitive resin composition according to claim 8, characterized in that, The number of functional groups in the multifunctional monomer is at least three.

10. The coloring photosensitive resin composition according to claim 8, characterized in that, The multifunctional monomers include at least one of the following: trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, propoxylated dipentaerythritol hexa(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

11. The coloring photosensitive resin composition according to claim 8, characterized in that, The multifunctional monomer is dipentaerythritol hexa(meth)acrylate.

12. The coloring photosensitive resin composition according to claim 8, characterized in that, The amount of the photopolymerizable compound added is 5% to 50% relative to the total weight of the solid components in the coloring photosensitive resin composition.

13. The coloring photosensitive resin composition according to claim 1, characterized in that, The photopolymerization initiator is an oxime ester-based photopolymerization initiator.

14. The coloring photosensitive resin composition according to claim 13, characterized in that, The photopolymerization initiator includes at least one selected from 1,2-octanedione, 1-[4-(phenylthio)phenyl]-2-(O-benzoyl oxime, 2-[4-(phenylthio)phenyl],2-(O-benzoyl oxime), and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]hexanone-1-(O-acetyl oxime).

15. The coloring photosensitive resin composition according to claim 13, characterized in that, The amount of photopolymerization initiator added is 0.1% to 5% relative to the total weight of the solid components in the coloring photosensitive resin composition.

16. The coloring photosensitive resin composition according to claim 1, characterized in that, The solvent is a solvent capable of dissolving each component in the coloring photosensitive resin composition.

17. The coloring photosensitive resin composition according to claim 16, characterized in that, The solvent includes propylene glycol monomethyl ether acetate; and at least one of aromatic hydrocarbon solvents, ketone solvents, alcohol solvents, ester solvents and amide solvents.

18. The coloring photosensitive resin composition according to claim 17, characterized in that, The aromatic hydrocarbon solvent includes at least one of benzene, toluene, xylene, and mesitylene.

19. The coloring photosensitive resin composition according to claim 17, characterized in that, The ketone solvents include at least one of methyl ethyl ketone, acetone, methyl pentyl ketone, methyl isobutyl ketone, and cyclohexanone.

20. The coloring photosensitive resin composition according to claim 17, characterized in that, The alcohol solvents include at least one of ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol.

21. The coloring photosensitive resin composition according to claim 17, characterized in that, The ester solvents include at least one of the following: ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellosol acetate, ethyl cellosol 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 monoacetate, 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 monoethyl ether acetate, ethylene carbonate, propylene carbonate, and γ-butyrolactone.

22. The coloring photosensitive resin composition according to claim 17, characterized in that, The amide solvents include N,N-dimethylformamide and / or N,N-dimethylacetamide.

23. The coloring photosensitive resin composition according to claim 16, characterized in that, The amount of solvent added is 60% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition.

24. The coloring photosensitive resin composition according to claim 16, characterized in that, Preferably, the amount of solvent added is 70% to 90% relative to the total weight of the solid components in the coloring photosensitive resin composition.

25. The coloring photosensitive resin composition according to claim 1, characterized in that, The additives include at least one of surfactants and adhesion promoters.

26. The coloring photosensitive resin composition according to claim 25, characterized in that, The adhesion promoter includes at least one of vinyltrimethoxysilane, 3-glycidyl etheroxypropylmethyldimethoxysilane, 3-glycidyl etheroxypropyltriethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropyltriethoxysilane, and 3-mercaptopropyltrimethoxysilane.

27. The coloring photosensitive resin composition according to claim 25, characterized in that, The amount of additive added is 0.1% to 2% of the total weight of the solid components in the coloring photosensitive resin composition.

28. The coloring photosensitive resin composition according to claim 1, characterized in that, The colorant includes at least one of a first pigment and a second pigment; The first pigment includes at least one of azo dyes, anthraquinone dyes, succinate dyes, and phthalocyanine dyes.

29. The coloring photosensitive resin composition according to claim 28, characterized in that, The azo dye is an azo dye containing a metal complex structure.

30. The coloring photosensitive resin composition according to claim 28, characterized in that, The azo dyes include at least one of CI Solvent Yellow 13, CI Solvent Yellow 19, CI Solvent Yellow 21, CI Solvent Yellow 25, CI Solvent Yellow 25:1, CI Solvent Yellow 81, CI Solvent Yellow 82, CI Solvent Yellow 88, CI Solvent Orange 40:1, CI Solvent Orange 41, CI Solvent Orange 62, CI Solvent Orange 81, CI Solvent Orange 99, CI Solvent Orange 83:1, CI Solvent Red 84:1, CI Solvent Red 90:1, CI Solvent Red 91:1, CI Solvent Red 118, CI Solvent Red 119, CI Solvent Red 112, CI Solvent Red 330, and CI Solvent Red 130.

31. The coloring photosensitive resin composition according to claim 28, characterized in that, The anthraquinone dyes include at least one of Solvent Blue 35, Solvent Blue 45, Solvent Blue 58, Solvent Blue 101, Solvent Blue 122, Solvent Violet 12, Solvent Violet 13, Solvent Violet 26, and Solvent Violet 47.

32. The coloring photosensitive resin composition according to claim 28, characterized in that, The zeatane dyes include at least one of Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123, and Sulforodamine B.

33. The coloring photosensitive resin composition according to claim 28, characterized in that, The phthalocyanine dyes include at least one selected from phthalocyanine, 2,3-naphthalenephthalocyanine, 2,9,16,23-tetra-tert-butyl-29H,31H-phthalocyanine, 1,4,8,11,15,18,22,25-octabutoxy-29H,31H-phthalocyanine, 5,9,14,18,23,27,32,36-octabutoxy-2,3-naphthalenephthalocyanine, 2,3,9,10,16,17,23,24-octaoctyloxy-29H,31H-phthalocyanine, and 2,11,20,29-tetra-tert-butyl-2,3-naphthalenephthalocyanine.

34. The coloring photosensitive resin composition according to claim 28, characterized in that, The second pigment is an organic pigment.

35. The coloring photosensitive resin composition according to claim 28, characterized in that, Preferably, the second pigment includes at least one of yellow pigment, orange pigment, red pigment, blue pigment, purple pigment, and green pigment.

36. The coloring photosensitive resin composition according to claim 35, characterized in that, The yellow pigment includes at least one of CI pigment yellow 1, CI pigment yellow 3, CI pigment yellow 12, CI pigment yellow 13, CI pigment yellow 14, CI pigment yellow 15, CI pigment yellow 16, CI pigment yellow 17, CI pigment yellow 20, CI pigment yellow 24, CI pigment yellow 31, CI pigment yellow 53, CI pigment yellow 83, CI pigment yellow 86, CI pigment yellow 93, CI pigment yellow 94, CI pigment yellow 109, CI pigment yellow 110, CI pigment yellow 117, CI pigment yellow 125, CI pigment yellow 128, CI pigment yellow 137, CI pigment yellow 138, CI pigment yellow 139, CI pigment yellow 147, CI pigment yellow 148, CI pigment yellow 150, CI pigment yellow 153, CI pigment yellow 154, CI pigment yellow 166, CI pigment yellow 173, CI pigment yellow 194, and CI pigment yellow 214.

37. The coloring photosensitive resin composition according to claim 35, characterized in that, The orange pigment includes at least one of CI Pigment Orange 13, CI Pigment Orange 31, CI Pigment Orange 36, CI Pigment Orange 38, CI Pigment Orange 40, CI Pigment Orange 42, CI Pigment Orange 43, CI Pigment Orange 51, CI Pigment Orange 55, CI Pigment Orange 59, CI Pigment Orange 61, CI Pigment Orange 64, CI Pigment Orange 65, CI Pigment Orange 71, and CI Pigment Orange 73.

38. The coloring photosensitive resin composition according to claim 35, characterized in that, The red pigment includes at least one of CI Pigment Red 9, CI Pigment Red 97, CI Pigment Red 105, CI Pigment Red 122, CI Pigment Red 123, CI Pigment Red 144, CI Pigment Red 149, CI Pigment Red 166, CI Pigment Red 168, CI Pigment Red 175, CI Pigment Red 176, CI Pigment Red 177, CI Pigment Red 180, CI Pigment Red 192, CI Pigment Red 209, CI Pigment Red 215, CI Pigment Red 216, CI Pigment Red 224, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Red 264, and CI Pigment Red 265.

39. The coloring photosensitive resin composition according to claim 35, characterized in that, The blue pigment includes at least one of CI Pigment Blue 15, CI Pigment Blue 15:3, CI Pigment Blue 15:4, CI Pigment Blue 15:6, CI Pigment Blue 60, and CI Pigment Blue 80.

40. The coloring photosensitive resin composition according to claim 35, characterized in that, The purple pigment includes at least one of CI pigment purple 1, CI pigment purple 19, CI pigment purple 23, 29, CI pigment purple 32, CI pigment purple 36, CI pigment purple 37 and CI pigment purple 38.

41. The coloring photosensitive resin composition according to claim 35, characterized in that, The green pigment includes at least one of CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58.

42. A method for preparing a coloring photosensitive resin composition according to any one of claims 1-41, characterized in that, include: The second pigment in the colorant is dispersed to obtain first colorant particles; The dispersant, the first pigment in the colorant, the first colorant particles and the solvent are mixed, dissolved and dispersed to obtain a coloring mixed dispersion; An alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and additives are added to the coloring mixed dispersion to obtain the coloring photosensitive resin composition.

43. The method for preparing the coloring photosensitive resin composition according to claim 41, characterized in that, The method for preparing the alkali-soluble resin includes: An unsaturated monomer is introduced into a reaction vessel; wherein the unsaturated monomer includes a first monomer substance, as well as a second monomer substance, a third monomer substance, and a fourth monomer substance; Add 5% azobisisobutyronitrile relative to the total weight of the unsaturated monomers, which is equivalent to propylene glycol monomethyl ether acetate by the total weight of azobisisobutyronitrile and the unsaturated monomers, to obtain a mixture of reaction raw materials; The reaction mixture is reacted under heating conditions in a protective atmosphere to obtain the alkali-soluble resin.

44. The method for preparing the coloring photosensitive resin composition according to claim 43, characterized in that, The heating condition is 70°C.

45. The method for preparing the coloring photosensitive resin composition according to claim 43, characterized in that, The reaction time under the heating conditions is no less than 6 hours.

46. ​​The method for preparing the coloring photosensitive resin composition according to claim 43, characterized in that, The preparation method of the first monomeric substance includes: The nucleophile vinylimidazole was reacted with a halocarboxylic acid in a bimolecular nucleophilic substitution reaction to obtain the first monomer.

47. A color filter, characterized in that, It is prepared using the coloring photosensitive resin composition as described in any one of claims 1-41.

48. A display device, characterized in that, Includes the color filter as described in claim 47.

Images