Colored photosensitive resin composition, color filter, imaging device and preparation method

Abstract

The invention provides a colored photosensitive resin composition, a color filter, imaging equipment and a preparation method, and relates to the technical field of imaging equipment. The colored photosensitive resin composition comprises a coloring agent, alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive and a solvent, the alkali-soluble resin is formed by polymerizing unsaturated monomer substances; the unsaturated monomeric substance includes a first monomeric substance represented by the following chemical formula. The colored photosensitive resin composition provided by the invention contains the carboxylated ionic liquid and the hydrophilic halide anions, so that not only is the developing property enhanced, but also the adhesion with a substrate is remarkably improved, and the colored photosensitive resin composition is of great importance for improving the production efficiency and the product performance.

Description

Technical Field

[0001] The present invention relates to the technical field of developing equipment, and in particular to a colored photosensitive resin composition, a color filter, a developing equipment and a preparation method thereof. Background Art

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

[0003] In the prior art, the preparation of colored photosensitive resin compositions usually involves the addition of colorants. In order to enhance the color performance of the filter, technicians tend to increase the concentration of the colorant. However, this practice is not without disadvantages. Studies have shown that an increase in the concentration of the colorant will lead to a slower development speed and reduce the sensitivity of the photosensitive resin composition. This is detrimental to both production efficiency and product performance.

[0004] In order to solve the problem of slow development speed, technicians tried to adjust it by increasing the amount of carboxylic acid in the alkali-soluble resin. Although this method can improve the development speed to a certain extent, it brings new problems. After increasing the amount of carboxylic acid, the colored photosensitive resin composition may have incomplete graphics during the film forming process, which directly affects the optical performance and display effect of the filter.

[0005] In summary, the prior art has a series of problems in the preparation of colored photosensitive resin compositions. First, although the increase in colorant concentration can improve color performance, it will lead to problems with development speed and sensitivity. Secondly, the increase in the amount of carboxylic acid used to solve the development speed problem will lead to the problem of incomplete graphics after film formation. These problems are interrelated and jointly restrict the improvement of color filter performance. Therefore, how to ensure the development speed and the integrity of the graphics after film formation while improving color performance has become a technical challenge that needs to be solved in this field.

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

[0007] The object of the present invention is to provide a colored photosensitive resin composition, a color filter, an imaging device and a preparation method. The colored photosensitive resin composition achieves significant improvements in developability, adhesion and color performance, and solves the balance problem between development speed and image integrity.

[0008] In order to achieve the above-mentioned purpose of the present invention, the following technical solutions are particularly adopted:

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

[0010] A colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive and a solvent; the alkali-soluble resin is polymerized from an unsaturated monomer substance; the unsaturated monomer substance includes a first monomer substance shown in 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 the alkali-soluble resin added is 10% to 70% of the total weight of the solid components in the colored photosensitive resin composition, wherein the solid components are other solid components except the solvent, for example, 10%, 20%, 30%, 50%, 60%, 70%, etc.

[0014] In an optional embodiment, the water drop angle of the colored photosensitive resin composition after being cured 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. The 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 monomer substance further includes at least one of a second monomer substance, a third monomer substance, and a fourth monomer substance.

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

[0020] In an alternative embodiment, the second monomeric substance is styrene.

[0021] In an optional embodiment, the third monomer substance includes at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3.4-epoxybutyl (meth)acrylate, 6.7-epoxyheptyl (meth)acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether and p-vinylbenzyl glycidyl ether;

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

[0023] In an optional embodiment, the fourth monomer 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 substance 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 number of functional groups of the multifunctional monomer is at least 3;

[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 photopolymerizable compound is added in an amount of 5% to 50% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

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

[0031] In an optional embodiment, the photopolymerization initiator includes at least one of 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 photopolymerization initiator is added in an amount of 0.1% to 5% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

[0033] In an optional embodiment, the solvent is a solvent that can dissolve each component in the colored photosensitive resin composition;

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

[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 of ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerol;

[0038] In an optional embodiment, the ester solvent includes at least one of 3-ethoxyethyl propionate, 3-methoxymethyl propionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol 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 gamma-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 the solvent added is 60% to 90% relative to the total weight of the solid components in the colored photosensitive resin composition;

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

[0042] In an alternative 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 vinyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxy silane, 3-glycidoxypropyl triethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl triethoxy silane and 3-mercaptopropyl trimethoxy silane;

[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 additive is added in an amount of 0.1% to 2% relative to the total weight of the solid content in the colored 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 an azo dye, an anthraquinone dye, a xanthene dye and a phthalocyanine dye;

[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 xanthene 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 Sulforhodamine B;

[0053] In an optional embodiment, the phthalocyanine dye includes at least one of phthalocyanine, 2,3-naphthalocyanine, 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-naphthalocyanine, 2,3,9,10,16,17,23,24-octa(octyloxy)-29H,31H-phthalocyanine and 2,11,20,29-tetra-tert-butyl-2,3-naphthalocyanine;

[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 a yellow pigment, an orange pigment, a red pigment, a blue pigment, a purple pigment and a 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 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;

[0060] In an optional embodiment, the purple pigment includes at least one of C.1. Pigment Violet 1, C.1. Pigment Violet 19, C.1. Pigment Violet 23, 29, C.1. Pigment Violet 32, C.1. Pigment Violet 36, C.1. Pigment Violet 37 and C.1. 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] In a second aspect of the present invention, there is provided a method for preparing a colored photosensitive resin composition in any of the optional embodiments described above, comprising:

[0063] dispersing the second pigment in the colorant to obtain first colorant particles;

[0064] Mixing and dissolving a dispersant, a first pigment in the colorant, the first colorant particles and a solvent, and performing a dispersion treatment to obtain a coloring mixed dispersion;

[0065] adding an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent and an additive into the colored mixed dispersion to obtain the colored photosensitive resin composition;

[0066] In an optional embodiment, the preparation method of the alkali-soluble resin comprises:

[0067] Putting an unsaturated monomer into a reaction container; wherein the unsaturated monomer is a first monomer substance; or, the unsaturated monomer includes the first monomer substance and at least one of a second monomer substance, a third monomer substance and a fourth monomer substance;

[0068] adding 5% of azobisisobutyronitrile relative to the total weight of the unsaturated monomer, equivalent to propylene glycol monomethyl ether acetate in the total weight of azobisisobutyronitrile and the unsaturated monomer, to obtain a reaction raw material mixture;

[0069] Under a protective atmosphere, the reaction raw material mixture is reacted under heating conditions 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 preparation method of the first monomer material comprises:

[0073] A nucleophilic reagent, vinyl imidazole, is reacted with a halogenated carboxylic acid to undergo a bimolecular nucleophilic substitution reaction to obtain the first monomer substance.

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

[0075] According to a fourth aspect of the present invention, there is provided an imaging device, comprising the color filter in any of the optional embodiments described above.

[0076] Compared with the prior art, the present invention has the following beneficial effects:

[0077] The present invention provides a colored photosensitive resin composition, a color filter, an imaging device and a preparation method. The colored photosensitive resin composition comprises: a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive and a solvent; the alkali-soluble resin is polymerized from unsaturated monomers. The colored photosensitive resin composition provided by the present invention contains a carboxylated ionic liquid and a hydrophilic halide anion, 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. In addition, by increasing the concentration of the colorant, the composition effectively improves the color performance of the color filter, meeting the demand for improving the display effect in the field of display technology. At the same time, the problems of slow development speed and low sensitivity caused by increasing the concentration of the colorant are solved, ensuring the integrity of the pattern after film formation. The chemical structure diversity of the unsaturated carboxyl ionic liquid monomer, wherein R1 can be an alkyl group with 1 to 3 carbon atoms or an aryl group with 6 to 10 carbon atoms, provides great flexibility for adjusting the performance of the resin composition, allowing products with different performances to be customized according to specific application requirements.

[0078] In summary, the colored photosensitive resin composition provided in the present invention provides a solution with excellent performance and strong adaptability for display technologies such as liquid crystal displays (LCDs), organic light emitting diodes (OLEDs) and quantum dots (QDs). BRIEF DESCRIPTION OF THE DRAWINGS

[0079] In order to more clearly illustrate the specific implementation methods of the present invention or the technical solutions in the prior art, the drawings required for use in the specific implementation methods or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are some implementation methods of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0080] Figure 1 Schematic diagram of the process for preparing the colored photosensitive resin composition in the embodiment of the present application;

[0081] Figure 2 This is a bar chart of the test results of the developing time of the embodiment and the comparative example in the horizontal test experiment of this application;

[0082] Figure 3 This is a bar chart of the transmittance test results of the embodiment and the comparative example in the horizontal test experiment of this application;

[0083] Figure 4 This is a bar graph showing the water drop angle test results of the embodiments and comparative examples in the lateral test experiment of this application. DETAILED DESCRIPTION

[0084] The embodiments of the present invention will be described in detail below in conjunction with the examples, but it will be appreciated by those skilled in the art that the following examples are only used to illustrate the present invention and should not be considered as limiting the scope of the present invention. If no specific conditions are specified in the examples, the conditions are carried out according to normal conditions or the conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments used is not specified, they are all conventional products that can be obtained commercially.

[0085] In an embodiment of the present application, a colored 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 substance; and the unsaturated monomer substance comprises a first monomer substance represented by the following chemical formula:

[0086]

[0087] Here, 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 colored photosensitive resin composition is mainly used to manufacture color filters and image display devices. The composition contains six main components: a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive, and a solvent.

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

[0090] The unsaturated monomer material includes a first monomer material, and its chemical structure contains an R1 group, and 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 the solubility, reactivity and final performance of the resin to be adjusted.

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

[0092] In the compound of the first monomer substance, the structure contains a water-soluble halogen (such as bromide ion Br - ) and carboxylated ions (carboxylic acid group -COOH), after the polymer is prepared, it will bring the following effects: halogen ions (such as Br - ) and carboxylic acid groups (-COOH) can increase the water solubility of polymers. Carboxylic acid groups can ionize under neutral or alkaline conditions to form carboxylate radicals (-COO -), and halide ions themselves carry charges, 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 carboxylates and halide ions) can increase the conductivity of polymers, making them potentially useful in electronic and optoelectronic applications, such as in battery electrolytes or electrochromic materials.

[0093] The colored 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, which is crucial for improving production efficiency and product performance. In addition, by increasing the concentration of the colorant, the composition effectively improves the color performance of the color filter, meeting the demand for improving display effects in the field of display technology. At the same time, it solves the problems of slow development speed and low sensitivity caused by increasing the concentration of the colorant, ensuring the integrity of the graphics after film formation. The chemical structure diversity of the unsaturated carboxyl ionic liquid monomer, in which R1 can be an alkyl group with 1 to 3 carbon atoms or an aromatic group with 6 to 10 carbon atoms, provides great flexibility for adjusting the performance of the resin composition, allowing products with different performance to be customized according to specific application requirements.

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

[0095] Furthermore, the water drop angle of the colored photosensitive resin composition after being cured 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. The 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. The weight average molecular weight is greater than 10,000 and less than 50,000. It 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. It 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 monomer substance also includes at least one of a second monomer substance (named B1 in this embodiment), a third monomer substance (named B2 in this embodiment) and a fourth monomer substance (named B3 in this embodiment).

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

[0104] Furthermore, the second monomer substance is styrene.

[0105] Among them, the alkali-soluble resin in this embodiment can be copolymerized by a first monomer substance (unsaturated carboxyl ionic liquid monomer (L), a second monomer substance (unsaturated monomer B1), a third monomer substance (unsaturated epoxy monomer B2) and a fourth monomer substance (acrylate substance B3). In this way, the colored photosensitive resin composition can have a faster development speed and maintain a complete pattern after film formation.

[0106] The third monomer substance comprises at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3.4-epoxybutyl (meth)acrylate, 6.7-epoxyheptyl (meth)acrylate, 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 substance is glycidyl methacrylate.

[0108] Further, the fourth monomer 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 substance is methyl methacrylate.

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

[0111] In a preferred embodiment, the number of functional groups of the multifunctional monomer is at least 3.

[0112] Further, 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, the multifunctional monomer may be a commercially available product such as KAYARAD DPHA (Nippon Kayaku) or the like.

[0115] Furthermore, the amount of the photopolymerizable compound added is 5% to 50% of the total weight of the solid content in the colored photosensitive resin composition, for example, 5%, 10%, 20%, 30%, 40%, 50%, etc.

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

[0117] Further, the photopolymerization initiator includes at least one of 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 the photopolymerization initiator added is 0.1% to 5% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

[0119] The photopolymerization initiator mentioned above may be a commercially available oxime ester photopolymerization initiator, for example, may include but not limited to Omnirad 1314 from BASF, PBG-345 from Trolly, and the like.

[0120] Furthermore, the solvent is a solvent that can dissolve each component in the colored photosensitive resin composition.

[0121] As the solvent, any solvent capable of dissolving the colored photosensitive resin composition may be additionally used.

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

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

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

[0126] Further, the ester solvent includes at least one of 3-ethoxyethyl propionate, 3-methoxymethyl propionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol 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 gamma-butyrolactone;

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

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

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

[0130] It should be noted that when the solvent content is within the above range, i.e., 70% to 90%, the coating property is improved when coating is performed using a coating device such as a roll coater, a spin coater, a slit spin coater, a slit coater, an inkjet printer, etc.

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

[0132] The surfactant may include, for example, one of F-470, F-475, F-482 and F-554 of Dainippon Ink & Chemicals Co., Ltd., which are commercially available;

[0133] The adhesion promoter includes at least one of vinyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxy silane, 3-glycidoxypropyl triethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl triethoxy silane and 3-mercaptopropyl trimethoxy silane.

[0134] In addition, the adhesion promoter may further include at least one of KBM-403, KBM-503 and KBM-803 of Shin-Etsu Corporation among commercially available products.

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

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

[0137] The first pigment includes at least one of an azo dye, an anthraquinone dye, a xanthene dye and a phthalocyanine dye;

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

[0139] Further, 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] Further, 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] Further, the xanthene 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 sulforhodamine B;

[0142] Further, the phthalocyanine dye includes at least one of phthalocyanine, 2,3-naphthalocyanine, 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-naphthalocyanine, 2,3,9,10,16,17,23,24-octa(octyloxy)-29H,31H-phthalocyanine and 2,11,20,29-tetra-tert-butyl-2,3-naphthalocyanine;

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

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

[0145] Further, 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] Further, 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] Further, 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] Further, the blue pigment includes 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] Further, the purple pigment includes at least one of C.1. Pigment Violet 1, C.1. Pigment Violet 19, C.1. Pigment Violet 23, 29, C.1. Pigment Violet 32, C.1. Pigment Violet 36, C.1. Pigment Violet 37 and C.1. 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 The present application provides a method for preparing a colored photosensitive resin composition in any of the optional embodiments described above, comprising:

[0152] Step S100, dispersing the second pigment in the colorant to obtain first colorant particles.

[0153] As mentioned above, the second pigment can be dispersed by a dispersing device. For example, the second pigment in the colorant can be dispersed by a bead mill or the like until the average particle size of the pigment reaches 0.2 μm or less to obtain first colorant particles.

[0154] Step S200 , mixing, dissolving and dispersing a dispersant, a first pigment in the colorant, the first colorant particles and a solvent to obtain a coloring mixed dispersion.

[0155] Step S300 , adding an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent and an additive into the colored mixed dispersion to obtain the colored photosensitive resin composition.

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

[0157] Step S310, adding an unsaturated monomer into a reaction container; wherein the unsaturated monomer is a first monomer substance; or, the unsaturated monomer includes the first monomer substance and at least one of a second monomer substance, a third monomer substance and a fourth monomer substance.

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

[0159] (1) First substance.

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

[0161] The reaction container may be, for example, a flask equipped with a condenser and a stirrer.

[0162] Step S320, adding 5% of azobisisobutyronitrile relative to the total weight of the unsaturated monomer, which is equivalent to propylene glycol monomethyl ether acetate of the total weight of azobisisobutyronitrile and the unsaturated monomer, to obtain a reaction raw material mixture.

[0163] Step S3310: reacting the reaction raw material mixture under heating conditions in a protective atmosphere to obtain the alkali-soluble resin.

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

[0165] Furthermore, the reaction time under the heating condition is not less than 6 hours;

[0166] Furthermore, in step S310, the preparation method of the first monomer substance includes:

[0167] Step S311, taking a nucleophilic reagent, vinyl imidazole, and a halogenated carboxylic acid to carry out a bimolecular nucleophilic substitution reaction to obtain the first monomer substance.

[0168] The halogenated carboxylic acids mentioned above may include, but are not limited to, bromoacetic acid, 3-bromopropionic acid, 4-bromo-n-butyric acid, bromomethylbenzoic acid, and the like.

[0169] As mentioned above, the amount of the halogenated carboxylic acid added may be 0.5 mol.

[0170] As mentioned above, the reaction vessel may be a reaction kettle or a reactor, for example, a four-mouth 1L reactor equipped with a thermometer, a mechanical stirrer, a cooling capacitor and a heating gantry.

[0171] In an embodiment of the present application, a color filter is provided, which is prepared by using the colored photosensitive resin composition in any of the optional embodiments described above.

[0172] It should be noted that color filters are a key optical component that can selectively transmit specific wavelengths of light while absorbing or reflecting other wavelengths, thus playing an important role in many fields such as photography, display technology, scientific instruments, optical communications, lighting, medical imaging, and industrial detection. In display technologies such as liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), and quantum dot (QD) displays, color filters are used to separate and control the three basic colors of red, green, and blue to create colorful images. In addition, color filters are also indispensable in spectral analysis, fiber-optic communications, and professional lighting design. They enhance image quality, convey information, or create specific visual effects by precisely controlling the wavelength of light.

[0173] An embodiment of the present application provides an imaging device, comprising the color filter in any of the optional implementations described above.

[0174] The colored photosensitive resin composition in this embodiment can be widely used in a variety of imaging devices, including but not limited to liquid crystal displays (LCDs), organic light-emitting diodes (OLEDs), quantum dot (QD) displays, electronic paper (E-Paper), microdisplays (Microdisplay), touch screens (Touch Screen), automotive displays, and medical imaging devices, etc. These devices all rely on high-quality color filters to achieve accurate color reproduction and high-contrast image display, and the colored photosensitive resin composition provided by the present invention is intended to provide technical support for these imaging technologies through its excellent performance, and improve their color performance and stability.

[0175] In addition, the preparation method of the second pigment in the colorant may include:

[0176] 9.0 parts by weight of CI Pigment Red 254 and 1.0 parts by weight of CI Pigment Yellow 150 were used as colorants, 7.0 parts by weight of DISPERBYK 2001 (manufactured by BYK) was used as a colorant dispersant, and 83.0 parts by weight of propylene glycol methyl ether acetate was used as a solvent. The pigment dispersion composition M1 was prepared after mixing and dispersing in a bead mill for 12 hours.

[0177] Example 1

[0178] In this example, the first monomer substance was prepared. Specifically, the first monomer substance can be synthesized by the following four methods (Synthesis Examples 1 to 4):

[0179] (1) Synthesis Example 1: In a four-mouth 1L reactor equipped with a thermometer, a mechanical stirrer, a cooling capacitor and a heating gantry, 37.65 parts by weight of vinyl imidazole (0.4 mol) and 69.48 parts by weight of bromoacetic acid (0.5 mol) were added, and the mixture was stirred at 55°C for 12 h. The product was then dissolved in acetonitrile and purified with ether to obtain 1-carboxymethyl-3-vinyl imidazole 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 that of Synthesis Example 1, and finally 1-carboxyethyl-3-vinyl imidazole bromide (L2) was obtained. The chemical reaction formula is as follows:

[0182]

[0183] (3) Synthesis Example 3: Except that the amount of 4-bromo-n-butyric acid added was 86.51 parts by weight (0.5 mol), the preparation was the same as that of Synthesis Example 1, and finally 1-carboxypropyl-3-vinyl imidazole bromide (L3) was obtained. 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 that of Synthesis Example 1, and finally 1-p-toluobenzoic acid-3-vinyl imidazolium bromide (L4) was obtained. The chemical reaction formula is as follows:

[0186]

[0187] Example 2

[0188] In this embodiment, L1, L2, L3 and L4 prepared in Example 1 were used to prepare fat-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, the monomers of this example are added according to the composition of the following Table 1, and 5% by weight of azobisisobutyronitrile relative to the total weight of the above monomers; propylene glycol monomethyl ether acetate equivalent to the total weight of the above initiator (azobisisobutyronitrile) and the first monomer substance is added. Referring to the data in Table 1, the mixture is stirred under a nitrogen atmosphere and the temperature is raised to 70°C for reaction for 6 hours to obtain various alkali-soluble resins.

[0191] (2) Polymerization Example 2: This example is basically the same as the method of Polymerization Example 1. Please refer to Table 1 for the differences.

[0192] (3) Polymerization Example 3: This example is basically the same as the method of Polymerization Example 1. Please refer to Table 1 for the differences.

[0193] (4) Polymerization Example 4: This example is basically the same as the method of Polymerization Example 1. Please refer to Table 1 for the differences.

[0194] (5) Polymerization Example 5: This example is basically the same as the method of Polymerization Example 1. Please refer to Table 1 for the differences.

[0195] (6) Polymerization Example 6: This example is basically the same as the method of Polymerization Example 1. Please refer to Table 1 for the differences.

[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 to 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 above table, the weight average molecular weight is the polystyrene-converted average molecular weight measured by gel permeation chromatography (GPC); and the acid value is measured by acid-base titration.

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

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

[0203] Example 3

[0204] In this example, a colored photosensitive resin composition was prepared.

[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 in 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] In this example, a colored photosensitive resin composition was prepared.

[0209] Preparation method:

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

[0211] Example 5

[0212] In this example, a colored photosensitive resin composition was prepared.

[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 Polymerization Example 3 in Example 2 is used.

[0215] Example 6

[0216] In this example, a colored photosensitive resin composition was prepared.

[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 Polymerization Example 4 in Example 2 is used.

[0219] Example 7

[0220] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 1 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0223] Example 8

[0224] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 1 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.11.

[0227] Example 9

[0228] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 2 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0231] Example 10

[0232] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 2 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.71.

[0235] Embodiment 11

[0236] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 3 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0239] Example 12

[0240] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 3 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.11.

[0243] Example 13

[0244] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 3 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0247] Embodiment 14

[0248] In this example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 4 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.11.

[0251] Comparative Example 1

[0252] In this comparative example, a colored photosensitive resin composition was prepared.

[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 of Polymerization Example 5 in Example 2 is used.

[0255] Comparative Example 2

[0256] In this comparative example, a colored photosensitive resin composition was prepared.

[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 of Polymerization Example 6 in Example 2 is used.

[0259] Comparative Example 3

[0260] In this comparative example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 5 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0263] Comparative Example 4

[0264] In this comparative example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 5 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.11.

[0267] Comparative Example 5

[0268] In this comparative example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 6 in Example 2 is 9.94; the weight fraction of propylene glycol monomethyl ether acetate is 47.39.

[0271] Comparative Example 6

[0272] In this comparative example, a colored photosensitive resin composition was prepared.

[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 fraction of the alkali-soluble resin in Polymerization Example 6 in Example 2 is 11.22; the weight fraction of propylene glycol monomethyl ether acetate is 46.11.

[0275] Horizontal test experiment:

[0276] Experimental methods:

[0277] (1) The colored photosensitive resin compositions prepared in the above-mentioned Examples 3 to 14 and Comparative Examples 1 to 6 were respectively coated on a 500 mm×500 mm glass substrate (Corning Incorporated, EAGLEXG) using a spin coater in such a way that the film thickness after drying reached 2.2 μm. The substrate with the coating film formed after coating was moved to a vacuum drying chamber (VCD) and vacuum drying was carried out in such a way that the pressure reached 55 Pa for 17 seconds. After vacuum drying, the above-mentioned film was placed in an oven at 100°C for pre-baking for 3 minutes. Next, a test photomask with a line / space pattern of 1 μm to 100 μm was placed on the above-mentioned film, and the interval of the test photomask was set to 300 μm and irradiated with ultraviolet rays. At this time, the ultraviolet light source used a 1KW high-pressure mercury lamp containing all g, h, and i lines, and irradiated at an illumination of 40 mJ / cm2. In addition, for the entire substrate, no photomask was used, and it was produced by full-surface exposure. The film after ultraviolet irradiation was then immersed in a developer of KOH aqueous solution with a pH value of 10.5 for 2 minutes. The glass plate coated with the film was washed with distilled water, dried with nitrogen gas, and heated in an oven at 230°C for 25 minutes to produce a red color filter with a pattern and a full surface.

[0278] (2) Test Experiment 1: Evaluation of Development Rate: The time required for a portion of the coated photosensitive resin composition not irradiated with ultraviolet rays to dissolve in the developer was measured when the coated film was developed in a KOH aqueous solution. The results are shown in Table 2 below.

[0279] (3) Test experiment 2 (adhesion evaluation): The pattern of the color filter was observed with an optical microscope (LV100ND, NIKON), and 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: √: the pattern is intact; △: the pattern has 1-4 peelings; ×: the pattern has 5 or more peelings.

[0280] (4) Test experiment 3 (transmittance evaluation): The transmittance of the prepared filter glass portion was measured using a spectrophotometer (OSP-SP200, OLYMPUS). When the transmittance is close to 100%, there is no residue of the color photosensitive resin composition in the part not irradiated with ultraviolet rays, so it can be judged that there is no residue. The results are shown in Table 2 below.

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

[0282] Experimental results and analysis:

[0283] Table 2. Experimental results of horizontal comparison tests

[0284] example Development time Adhesion Transmittance% Water drop angle° example Development time Adhesion Transmittance% Water drop angle° Reality 3 12 √ 99.9 23 Real 12 15 √ 99.9 24 Reality 4 14 √ 99.9 25 Reality 13 26 √ 99.8 41 Reality 5 16 √ 99.9 28 Reality 14 22 √ 99.9 31 Actual 6 23 √ 99.9 34 1 32 △ 95.4 49 Real 7 13 √ 99.9 27 2 35 √ 94.9 58 Actual 8 11 √ 99.9 18 3 36 √ 92.7 53 Real 9 15 √ 99.9 29 4 29 × 99.7 46 Actual 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, "Shi" represents "Example", for example, Shi 3 represents Example 3; "Dui" represents Comparative Example, for example, Dui 1 represents Comparative Example 1.

[0286] Referring to the results in Table 2 above and Figures 2 to 4 , in the case of Examples 3 to 14 containing unsaturated carboxyl ionic liquid, it can be confirmed that excellent effects are shown in terms of development rate, adhesion, transparency, and water contact angle.

[0287] On the other hand, in the case of Comparative Examples 1 to 6 that do not contain unsaturated carboxyl ionic liquid, it can be confirmed that the development rate decreases, the adhesion becomes poor, the transparency decreases, and the water contact angle increases.

[0288] From the above results, it can be seen that the colored photosensitive resin composition of the present invention can provide the following effects: it can achieve excellent pattern integrity while having a relatively fast development rate of the coating film.

[0289] Finally, it should be noted that: the above embodiments are only used to illustrate the technical solutions of the present invention, and are not intended to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that: they can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements on some or all of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A colored photosensitive resin composition, characterized in that include: A colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, an additive and a solvent; the alkali-soluble resin is polymerized from an unsaturated monomer substance; the unsaturated monomer substance includes a first monomer substance shown in the following chemical formula: 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; Preferably, the alkali-soluble resin is added in an amount of 10% to 70% relative to the total weight of the solid components in the colored photosensitive resin composition; Preferably, the water drop angle of the colored photosensitive resin composition after being cured into a film is greater than 0° and less than 45°; Preferably, the alkali-soluble resin has at least one of the following characteristics: A. The 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.

2. The colored photosensitive resin composition according to claim 1, wherein The unsaturated monomer substance further comprises at least one of a second monomer substance, a third monomer substance and a fourth monomer substance; Preferably, the second monomer substance comprises at least one of styrene, α-methylstyrene and p-methylstyrene; Preferably, the second monomer substance is styrene; Preferably, the third monomer substance includes at least one of glycidyl methacrylate, 2-methylglycidyl methacrylate, 3.4-epoxybutyl (meth)acrylate, 6.7-epoxyheptyl (meth)acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether and p-vinylbenzyl glycidyl ether; Preferably, the third monomer substance is glycidyl methacrylate; Preferably, the fourth monomer substance comprises at least one of methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate and tert-butyl methacrylate; Preferably, the fourth monomer substance is methyl methacrylate.

3. The colored photosensitive resin composition according to claim 1, wherein The photopolymerizable compound is a multifunctional monomer containing at least two functional groups; Preferably, the number of functional groups of the multifunctional monomer is at least 3; Preferably, 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; Preferably, the multifunctional monomer is dipentaerythritol hexa(meth)acrylate; Preferably, the photopolymerizable compound is added in an amount of 5% to 50% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

4. The colored photosensitive resin composition according to claim 1, wherein The photopolymerization initiator is an oxime ester photopolymerization initiator; Preferably, the photopolymerization initiator includes at least one of 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); Preferably, the photopolymerization initiator is added in an amount of 0.1% to 5% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

5. The colored photosensitive resin composition according to claim 1, wherein The solvent is a solvent that can dissolve the components in the colored photosensitive resin composition; Preferably, the solvent includes propylene glycol monomethyl ether acetate; and at least one of an aromatic hydrocarbon solvent, a ketone solvent, an alcohol solvent, an ester solvent and an amide solvent; Preferably, the aromatic hydrocarbon solvent includes at least one of benzene, toluene, xylene and mesitylene; Preferably, the ketone solvent includes at least one of methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone; Preferably, the alcohol solvent includes at least one of ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerol; Preferably, the ester solvent includes at least one of 3-ethoxyethyl propionate, 3-methoxymethyl propionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol 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 gamma-butyrolactone; Preferably, the amide solvent includes N,N-dimethylformamide and / or N,N-dimethylacetamide; Preferably, the amount of the solvent added is 60% to 90% relative to the total weight of the solid content in the colored photosensitive resin composition; Preferably, the amount of the solvent added is 70% to 90% by weight of the total solid content in the colored photosensitive resin composition.

6. The colored photosensitive resin composition according to claim 1, wherein The additive includes at least one of a surfactant and an adhesion promoter; The surfactant includes one of F-470, F-475, F-482 and F-554; The adhesion promoter includes at least one of vinyl trimethoxysilane, 3-glycidoxypropyl methyl dimethoxy silane, 3-glycidoxypropyl triethoxy silane, 3-methacryloxypropyl trimethoxy silane, 3-methacryloxypropyl triethoxy silane and 3-mercaptopropyl trimethoxy silane; Preferably, the adhesion promoter includes at least one of KBM-403, KBM-503 and KBM-803; Preferably, the additive is added in an amount of 0.1% to 2% by weight relative to the total weight of the solid content in the colored photosensitive resin composition.

7. The colored photosensitive resin composition according to claim 1, wherein The colorant includes at least one of a first pigment and a second pigment; The first pigment includes at least one of an azo dye, an anthraquinone dye, a xanthene dye and a phthalocyanine dye; Preferably, the azo dye is an azo dye containing a metal complex structure; Preferably, the azo dye comprises 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; Preferably, the anthraquinone dye comprises 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; Preferably, the xanthene dye comprises at least one of acid red 52, basic red 1, basic violet 10, basic violet 11, rhodamine B, rhodamine 6G, rhodamine 123 and sulforhodamine B; Preferably, the phthalocyanine dye comprises at least one of phthalocyanine, 2,3-naphthalocyanine, 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-naphthalocyanine, 2,3,9,10,16,17,23,24-octa(octyloxy)-29H,31H-phthalocyanine and 2,11,20,29-tetra-tert-butyl-2,3-naphthalocyanine; Preferably, the second pigment is an organic pigment; Preferably, the second pigment includes at least one of a yellow pigment, an orange pigment, a red pigment, a blue pigment, a purple pigment and a green pigment; Preferably, 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; Preferably, 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; Preferably, 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; Preferably, the blue pigment includes 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 the like; Preferably, the purple pigment includes at least one of C.

1. Pigment Violet 1, C.

1. Pigment Violet 19, C.

1. Pigment Violet 23, 29, C.

1. Pigment Violet 32, C.

1. Pigment Violet 36, C.

1. Pigment Violet 37 and C.

1. Pigment Violet 38; Preferably, the green pigment includes at least one of CI Pigment Green 7, CI Pigment Green 36 and CI Pigment Green 58.

8. A method for preparing a colored photosensitive resin composition according to any one of claims 1 to 7, characterized in that: include: dispersing the second pigment in the colorant to obtain first colorant particles; Mixing and dissolving a dispersant, a first pigment in the colorant, the first colorant particles and a solvent, and performing a dispersion treatment to obtain a coloring mixed dispersion; adding an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent and an additive into the colored mixed dispersion to obtain the colored photosensitive resin composition; Preferably, the preparation method of the alkali-soluble resin comprises: Putting an unsaturated monomer into a reaction container; wherein the unsaturated monomer is a first monomer substance; or, the unsaturated monomer includes the first monomer substance and at least one of a second monomer substance, a third monomer substance and a fourth monomer substance; adding 5% of azobisisobutyronitrile relative to the total weight of the unsaturated monomer, equivalent to propylene glycol monomethyl ether acetate in the total weight of azobisisobutyronitrile and the unsaturated monomer, to obtain a reaction raw material mixture; Under a protective atmosphere, reacting the reaction raw material mixture under heating conditions to obtain the alkali-soluble resin; Preferably, the heating condition is 70°C; Preferably, the reaction time under the heating conditions is not less than 6 hours; Preferably, the preparation method of the first monomer substance comprises: A nucleophilic reagent, vinyl imidazole, is reacted with a halogenated carboxylic acid to undergo a bimolecular nucleophilic substitution reaction to obtain the first monomer substance.

9. A color filter, characterized in that: The colored photosensitive resin composition is prepared according to any one of claims 1 to 7.

10. A display device, characterized in that: Comprising the color filter as claimed in claim 9.

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