Photosensitive resin composition, photosensitive resin film manufactured using the photosensitive resin composition, and color filter

Abstract

This invention provides a photosensitive resin composition that offers excellent reliability in terms of brightness, contrast ratio, and durability. [Solution] A photosensitive resin composition comprising (A) a colorant containing a compound represented by the following formula, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent. JPEG2026116779000088.jpg7078

Description

[Technical Field]

[0001] The present invention relates to a photosensitive resin composition, a photosensitive resin film manufactured using the photosensitive resin composition, and a color filter. [Background technology]

[0002] Liquid crystal displays (LCDs), a type of display device, have advantages such as being lightweight, thin, inexpensive, low-power, and having excellent connectivity with integrated circuits, and their range of applications is expanding to include laptops, monitors, and TV displays.

[0003] Such a liquid crystal display device comprises a lower substrate on which a black matrix, a color filter, and ITO pixel electrodes are formed, and an upper substrate on which an active circuit section consisting of a liquid crystal layer, a thin-film transistor, and an energy storage capacitor layer, and ITO pixel electrodes are formed.

[0004] A color filter has a structure in which a black matrix layer formed in a predetermined pattern on a transparent substrate to shield the boundaries between pixels, and pixel sections arranged in a predetermined order with multiple colors (usually the three primary colors of red (R), green (G), and blue (B)) to form each pixel, are sequentially stacked.

[0005] One method for realizing color filters is the pigment dispersion method, which involves coating a transparent substrate provided with a black matrix with a photopolymerizable composition containing a colorant, exposing the pattern of the desired shape to the light, and then repeating a series of steps to remove the unexposed areas with a solvent and heat-cur the mixture, thereby forming a colored thin film.

[0006] The colored photosensitive resin compositions used in the manufacture of color filters by the pigment dispersion method generally consist of alkali-soluble resins, photopolymerization monomers, photopolymerization initiators, epoxy resins, solvents, and other additives.

[0007] The pigment dispersion method having the above characteristics is actively used for manufacturing LCDs such as mobile phones, notebook computers, monitors, TVs, etc.

[0008] However, recently, in the photosensitive resin composition for color filters using a pigment dispersion method having various advantages, not only excellent pattern characteristics but also further improved performance are required. In particular, in fact, characteristics of high brightness and high contrast ratio along with a high color reproduction rate are required.

[0009] On the other hand, an image sensor refers to an imaging element component that generates an image in a mobile phone camera, a DSC (Digital Still Camera), etc., and can be largely classified into a charge coupled device (CCD) image sensor and a complementary metal oxide semiconductor (CMOS) image sensor according to its manufacturing process and application method.

[0010] Color imaging elements used in solid-state imaging devices or complementary metal oxide semiconductors, etc., generally install color filters (color filters) each provided with filter segments of additive mixing primary colors of red, green, and blue on their light-receiving elements to perform color separation.

[0011] Recently, the size of the pattern of the color filter mounted on such a color imaging element is 1 / 100 to 1 / 200 times that of the existing color filter pattern for LCDs with a size of 2 μm or less. Thereby, an increase in resolution and a reduction in residues are important items that affect the performance of the element.

[0012] Therefore, even in photosensitive resin compositions for color filters that utilize pigment dispersion methods, which have various advantages, there is a growing demand not only for excellent pattern characteristics but also for further improved performance. In particular, there is a demand for compositions that have high coloring power, contrast ratio, and residue characteristics while improving the dispersion stability of the pigments.

[0013] On the other hand, color filters manufactured from pigment-type photosensitive resin compositions have limitations in brightness and contrast ratio due to the size of the pigment particles, and in the case of color image sensors for image sensors, even smaller dispersion particle sizes are required for the formation of fine patterns. Therefore, there are attempts to realize color filters with improved brightness and contrast ratio by introducing dyes that do not form particles instead of pigments and manufacturing photosensitive resin compositions suitable for dyes.

[0014] After clearly understanding these requirements, the inventors of this invention have created a photosensitive resin composition that incorporates both dyes and pigments, resulting in a composition that not only excels in brightness and contrast ratio but also in reliability, including durability. [Overview of the project] [Problems that the invention aims to solve]

[0015] One of the objectives of the present invention is to provide a photosensitive resin composition that is excellent not only in brightness and contrast ratio, but also in reliability, such as durability.

[0016] Another object of the present invention is to provide a photosensitive resin film manufactured using a photosensitive resin composition.

[0017] Another object of the present invention is to provide a color filter comprising a photosensitive resin film. [Means for solving the problem]

[0018] According to one embodiment of the present invention, there is provided a photosensitive resin composition containing (A) a colorant, (B) a photopolymerizable compound, (C) a photoinitiator, (D) a binder resin, and (E) a solvent, wherein the colorant contains a compound represented by the following Chemical Formula 1A or Chemical Formula 1B.

Chem.

Chem.

[0019] The substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms may be represented by the following Chemical Formula 2.

Chem.

[0020] In the aforementioned chemical formula 1A or chemical formula 1B, L 1 and L 2 At least one of them is a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, R 2 R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 This may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0021] In the aforementioned chemical formula 1A or chemical formula 1B, R 1 It may also be represented by the following chemical formula 3. [ka] ...[Chemical formula 3] In the aforementioned chemical formula 3, L 1 and L 2 Each of these is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof, L 1 and L 2 It is not a single bond at the same time.

[0022] The aforementioned chemical formula 1A may be represented by the following chemical formula 4-1A or chemical formula 4-2A, and the aforementioned chemical formula 1B may be represented by the following chemical formula 4-1B or chemical formula 4-2B. [ka] ...[Chemical formula 4-1A] [ka] ...[Chemical formula 4-2A] [ka] ...[Chemical formula 4-1B] [ka] ...[Chemical formula 4-2B] In the aforementioned chemical formulas 4-1A to 4-2B, L 2 This is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof. L 4 This is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. R 2 and R 3 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0023] In the aforementioned chemical formula 1A or chemical formula 1B, R 2 and R 3 These elements may condense together to form a fused ring.

[0024] The compound represented by chemical formula 1A or chemical formula 1B may be a dye.

[0025] The compound represented by chemical formula 1A or chemical formula 1B may also be represented by any one of the following chemical formulas 1-1 to 1-8. [ka] ...[Chemical formula 1-1] [ka] ...[Chemical formula 1-2] [ka] ...[Chemical formula 1-3] [ka] ...[Chemical formula 1-4] [ka] ...[Chemical formula 1-5] [ka] ...[Chemical formula 1-6] [ka] ...[Chemical formula 1-7] [ka] ...[Chemical formula 1-8]

[0026] The compound represented by chemical formula 1A or chemical formula 1B may be included in an amount of 1% to 10% by weight relative to the total amount of the photosensitive resin composition.

[0027] The coloring agent may further contain a pigment.

[0028] The aforementioned pigment may include a red pigment, a yellow pigment, or a combination thereof.

[0029] The photosensitive resin composition may contain, with respect to the total amount of the photosensitive resin composition, 10% to 30% by weight of (A) the colorant; 0.1% to 10% by weight of (B) the photopolymerizable compound; 0.1% to 5% by weight of (C) the photopolymerization initiator; 0.5% to 10% by weight of (D) the binder resin; and the remaining amount of (E) the solvent.

[0030] According to another embodiment, a photosensitive resin film manufactured using the photosensitive resin composition is provided.

[0031] The photosensitive resin film may be a negative photoresist.

[0032] In yet another embodiment, a color filter including the photosensitive resin film is provided.

[0033] Other specific aspects of the present invention are included in the detailed description below. [Effects of the Invention]

[0034] The photosensitive resin composition according to one embodiment can realize a color filter with excellent brightness and contrast ratio, as well as superior reliability such as durability. Therefore, a superior display device can be realized by using the photosensitive resin composition according to one embodiment. In particular, compared to conventional photosensitive resin compositions containing xanthene compounds as colorants, there is no decrease in light resistance and chemical resistance, and brightness can be greatly improved. [Modes for carrying out the invention]

[0035] Embodiments of the present invention will be described in detail below. However, these are presented as examples only and do not limit the present invention, which is defined solely by the scope of the claims described later.

[0036] Unless otherwise specified herein, “substitution” means that at least one hydrogen atom in a compound is replaced by a halogen atom (F, Cl, Br, I), a hydroxyl group, a carbon-1 to carbon-20 alkoxy group, a glycidyl group, a nitro group, a cyano group, an amine group, an imino group, an azide group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamoyl group, a thiol group, an ester group, an ether group, a carboxyl group or its salt, a sulfonic acid group or its salt, phosphoric acid or its salt, This means that the molecule is substituted with substituents of an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkenyl group having 3 to 20 carbon atoms, a cycloalkynyl group having 3 to 20 carbon atoms, a heterocycloalkyl group having 2 to 20 carbon atoms, a heterocycloalkenyl group having 2 to 20 carbon atoms, a heterocycloalkynyl group having 2 to 20 carbon atoms, or a combination thereof.

[0037] Unless otherwise specified herein, “heterocycloalkyl group,” “heterocycloalkenyl group,” “heterocycloalkynyl group,” and “heterocycloalkylene group” mean the presence of at least one N, O, S, or P heteroatom within the cyclic compound of a cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkylene, respectively.

[0038] Unless otherwise specified herein, "(meth)acrylate" means that both "acrylate" and "methacrylate" are possible.

[0039] Unless otherwise defined herein, “combination” means mixing or copolymerization. “Copolymerization” means block copolymerization or random copolymerization, and “copolymer” means block copolymerization or random copolymerization.

[0040] Unless otherwise defined in the chemical formulas herein, the absence of a chemical bond at a position where one should be depicted means that a hydrogen atom is bonded to that position.

[0041] Unless otherwise defined herein, "*" means a portion that is bonded to the same or different atoms or chemical formulas.

[0042] Unless otherwise defined herein, “particle size” may mean the diameter of a particle, and such particle size may be the Z-average value of the particle diameter measured by dynamic light scattering.

[0043] [Photosensitive resin composition] According to one embodiment, a photosensitive resin composition is provided comprising (A) a colorant, (B) a photopolymerizable compound, (C) a photopolymerization initiator, (D) a binder resin, and (E) a solvent, wherein the colorant comprises a compound represented by the following chemical formula 1A or chemical formula 1B. [ka] ...[Chemical formula 1A] [ka] ...[Chemical formula 1B]

[0044] In chemical formulas 1A and 1B, L 1 and L 2 Each of these is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof, L 1 and L 2 It is not a single bond at the same time. 1 ~R 3 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a combination thereof. 1 and R 1 They may condense with each other to form a fused ring, R 2 and R 3 These elements may condense together to form a fused ring.

[0045] The compounds represented by chemical formulas 1A and 1B are xanthene compounds and have resonance structures with each other as shown below. [ka]

[0046] (A) Coloring agent As mentioned above, color filters manufactured from pigment-type photosensitive resin compositions have limitations in brightness and contrast ratio due to the size of the pigment particles. Furthermore, for applications in image sensors, resin compositions with even smaller particles are required for the formation of fine patterns. To achieve this, it is necessary to develop compounds that help disperse the pigment and prevent re-aggregation, as well as compositions using these compounds.

[0047] Therefore, the present inventors have confirmed that by including the compound represented by the above chemical formula 1A or chemical formula 1B, i.e., a dye compound, as a coloring agent, they can overcome the limitations of lightness and contrast ratio that are inherent in pigment-type photosensitive resin compositions, and furthermore, they can realize a color filter with improved reliability, including durability and chemical resistance, using a photosensitive resin composition containing the dye compound represented by the above chemical formula 1A or chemical formula 1B, thus completing the present invention.

[0048] Xanthene compounds are generally known to have excellent red spectral properties. However, the present inventors have modified the structure of xanthene compounds to realize a photosensitive resin composition for color filters that is excellent in terms of brightness and contrast, as well as durability, chemical resistance, and reliability. In particular, the above effects can be further doubled when a compound represented by chemical formula 1A or chemical formula 1B is used in combination with a pigment.

[0049] Specifically, the compounds represented by chemical formula 1A or chemical formula 1B above can easily achieve the above-mentioned effects because, in addition to the nitrogen atom bonded to the xanthene compound matrix (xanthene skeleton) not having a hydrogen atom directly bonded to it, they contain one or more epoxy groups as substituents at their ends. If even one hydrogen atom is directly bonded to the nitrogen atom bonded to the xanthene compound matrix (xanthene skeleton), or if there are no epoxy groups substituted at the ends, it is not easy to achieve the above-mentioned effects.

[0050] Furthermore, in the above chemical formula 1A or chemical formula 1B, L 1 and L 2 It may not contain cyclic linking groups such as arylene groups. In this case, it is possible to easily obtain an improvement in coloring power while minimizing the reduction in durability and other properties.

[0051] For example, a substituted or unsubstituted oxyalkylene group with 1 to 20 carbon atoms is represented by the following chemical formula 2. [ka] ...[Chemical formula 2]

[0052] In chemical formula 2, L 3 n is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, and n is an integer from 1 to 10.

[0053] For example, in the above chemical formula 1A or chemical formula 1B, L 1 and L 2 At least one of them is a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, R 2 R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, 3 This may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

[0054] For example, R 1 It is represented by the following chemical formula 3. [ka] ...[Chemical formula 3]

[0055] In chemical formula 3, L 1 and L 2 Each of these is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof, L 1 and L 2 It is not a single bond at the same time.

[0056] That is, in the above chemical formula 1A or chemical formula 1B, there may be two or more terminal epoxy substituents, and in this case, the linking group between the xanthene compound parent (xanthene skeleton) and the terminal epoxy substituent may be the same.

[0057] For example, in chemical formula 1A or chemical formula 1B, L 1 and R 1 These elements can condense together to form a condensed ring, in which case chemical formula 1A is represented by chemical formula 4-1A or chemical formula 4-2A below, and chemical formula 1B is represented by chemical formula 4-1B or chemical formula 4-2B below. [ka] ...[Chemical formula 4-1A] [ka] ...[Chemical formula 4-2A] [ka] ...[Chemical formula 4-1B] [ka] ...[Chemical formula 4-2B]

[0058] In Chemical Formula 4-1A~Chemical Formula 4-2B, L 2 L is a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof. 4 R is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. 2 and R 3 Each of these is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a combination thereof.

[0059] For example, in chemical formula 1A or chemical formula 1B, R 2 and R 3 These elements can condense together to form a condensed ring, in which case chemical formula 1A is represented by the following chemical formula 5-1A, and chemical formula 1B is represented by the following chemical formula 5-1B. [ka] ...[Chemical formula 5-1A] [ka] ...[Chemical formula 5-1B]

[0060] In chemical formulas 5-1A and 5-1B, L 1and L 2 Each of these is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof, L 1 and L 2 It is not a single bond at the same time, R 1 L is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a combination thereof. 4 and L 5 Each of these is independently a single-bonded, substituted, or unsubstituted alkylene group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, and A is a nitrogen-containing single ring or a nitrogen-containing condensed ring.

[0061] For example, if A is a nitrogen-containing single ring, A may be pyrrolidine, azetidine, aziridine, pyrrole, pyrazole, imidazole, triazole, etc., but is not necessarily limited to these.

[0062] For example, if A is a nitrogen-containing condensed ring, A may be indoline, indole, isoindole, indazole, azaindole, carbazole, purine, quinoline, etc., but is not necessarily limited to these.

[0063] For example, the compound represented by chemical formula 1A or chemical formula 1B may be a dye, such as a red dye.

[0064] For example, compounds represented by chemical formula 1A or chemical formula 1B have a maximum absorption wavelength (λ) between 480 nm and 600 nm. max ) can have.

[0065] For example, a compound represented by chemical formula 1A or chemical formula 1B can be represented by any one of the following chemical formulas 1-1 to 1-8. [ka] ...[Chemical formula 1-1] [ka] ...[Chemical formula 1-2] [ka] ...[Chemical formula 1-3] [ka] ...[Chemical formula 1-4] [ka] ...[Chemical formula 1-5] [ka] ...[Chemical formula 1-6] [ka] ...[Chemical formula 1-7] [ka] ...[Chemical formula 1-8]

[0066] For example, the compound represented by chemical formula 1A or chemical formula 1B may be included in an amount of 1% to 10% by weight, for example, 2% to 8% by weight, or for example, 3% to 7% by weight, relative to the total amount of the photosensitive resin composition. When the compound represented by chemical formula 1A or chemical formula 1B is included within the above range, brightness and contrast can be improved more easily.

[0067] Furthermore, the coloring agent may further contain a pigment. That is, the photosensitive resin composition according to one embodiment may be a hybrid composition.

[0068] For example, the above pigments may include red pigments, yellow pigments, or combinations thereof.

[0069] As red pigments, you can use CI red pigment 254, CI red pigment 255, CI red pigment 264, CI red pigment 270, CI red pigment 272, CI red pigment 177, CI red pigment 89, etc., within the Color Index, and you can use these individually or in mixtures of two or more, but you are not necessarily limited to these.

[0070] As yellow pigments, you can use isoindoline pigments such as CI yellow pigment 185 and CI yellow pigment 139 within the Color Index, quinophthalone pigments such as CI yellow pigment 138, and nickel complex pigments such as CI yellow pigment 150. These can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0071] For example, the above pigments may further include purple pigments, green pigments, blue pigments, black pigments, and so on.

[0072] As purple pigments, you can use CI Violet Pigment 23 (V.23), CI Violet Pigment 29, Dioxazine Violet, First Violet B, Methyl Violet Lake, Indantrene Brilliant Violet, etc., within the Color Index. These can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0073] As for green pigments, CI green pigment 7, CI green pigment 36, CI green pigment 58, CI green pigment 59, etc., can be used within the Color Index, and these can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0074] As blue pigments, copper phthalocyanine pigments such as CI blue pigment 15:6, CI blue pigment 15, CI blue pigment 15:1, CI blue pigment 15:2, CI blue pigment 15:3, CI blue pigment 15:4, CI blue pigment 15:5, CI blue pigment 15:6, and CI blue pigment 16 can be used within the Color Index. These can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0075] As black pigments, aniline black, perylene black, titanium black, and carbon black can be used within the Color Index, and these can be used individually or in mixtures of two or more, but are not necessarily limited to these.

[0076] Pigments can be used in combination with dispersants and in the form of pigment dispersions. For example, dispersants help to uniformly disperse the pigment in the dispersion, and nonionic, anionic, or cationic dispersants can be used, respectively. Specifically, polyalkylene glycols or their esters, polyoxyalkylenes, polyhydric alcohol ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonates, carboxylic acid esters, carboxylic acid salts, alkylamide alkylene oxide adducts, alkylamines, etc., can be used individually or in combination of two or more.

[0077] The pigment dispersion may further contain, in addition to the pigment and dispersant, a dispersion aid, a dispersion solvent, a dispersion resin, and the like. The solid pigment may be present in an amount of 5% to 20% by weight, for example, 8% to 15% by weight, relative to the total amount of the pigment dispersion.

[0078] As the dispersion solvent for the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc., can be used, and of these, propylene glycol methyl ether acetate can be used.

[0079] The dispersion resin can be an acrylic resin containing carboxyl groups, which can not only improve the stability of the pigment dispersion but also improve the patternability of the pixels.

[0080] For example, the coloring agent may further include metal complex dyes in addition to the compounds represented by the above chemical formulas 1A or 1B.

[0081] Metal complex dyes can use compounds that have maximum absorbance in the wavelength range of 200 nm to 650 nm. To match the color coordinates of the dye combination, any metal complex dye of any color that is soluble in organic solvents and has absorbance within the above range can be used.

[0082] Specifically, the metal complex dyes used may be a green dye having maximum absorbance in the wavelength range of 530 nm to 680 nm, a yellow dye having maximum absorbance in the wavelength range of 200 nm to 400 nm, an orange dye having maximum absorbance in the wavelength range of 300 nm to 500 nm, a red dye having maximum absorbance in the wavelength range of 500 nm to 650 nm, or a combination thereof.

[0083] Metal complex dyes can be direct dyes, acid dyes, basic dyes, acid mordant dyes, sulfur dyes, reductive dyes, azoic fuels, disperse dyes, reactive dyes, oxidation dyes, oil-soluble fuels, azo dyes, anthraquinone dyes, indigoid dyes, carbonium ion dyes, phthalocyanine dyes, nitro dyes, quinoline dyes, cyanine dyes, polymethine dyes, or combinations thereof.

[0084] Metal complex dyes may contain at least one metal ion selected from the group consisting of Mg, Ni, Cu, Co, Zn, Cr, Pt, Pd, and Fe.

[0085] Metal complex dyes include CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; and CI acid dyes such as CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109. Dyes; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI Direct dyes; CI Basic Green 1 and other CI Basic dyes; CI Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 4 A complex of the above metal ions can be used with at least one selected from the group consisting of CI mordant dyes such as 3 and 53, green pigments such as CI pigment greens 7, 36, and 58; solvent yellow 19, solvent yellow 21, solvent yellow 25, solvent yellow 79, solvent yellow 82, solvent yellow 88, solvent orange 45, solvent orange 54, solvent orange 62, solvent orange 99, solvent red 8, solvent red 32, solvent red 109, solvent red 112, solvent red 119, solvent red 124, solvent red 160, solvent red 132, and solvent red 218.

[0086] The metal complex dye may have a solubility of 5 or higher in the solvent used in the photosensitive resin composition according to one embodiment, i.e., the solvent described later, and specifically may be 5 to 10. Solubility can be obtained as the amount (g) of dye that dissolves in 100g of solvent. When the solubility of the metal complex dye is within the above range, compatibility with other components of the photosensitive resin composition according to one embodiment and coloring ability can be ensured, and precipitation of the dye can be prevented.

[0087] Suitable solvents include, for example, propylene glycol monomethyl ether acetate (PGMEA), ethyl lactate (EL), ethylene glycol ethyl acetate (EGA), cyclohexanone, 3-methoxy-1-butanol, or combinations thereof.

[0088] Having the above-mentioned specific range, it can be usefully used in color filters for LCDs, LEDs, etc., that exhibit high brightness and high contrast ratio at desired color coordinates.

[0089] The above-mentioned metal complex dye may be included in an amount of 0.01% to 1% by weight, for example, 0.01% to 0.5% by weight, relative to the total amount of the photosensitive resin composition. When the metal complex dye is used within the above range, high brightness and contrast ratio can be achieved at the desired color coordinates.

[0090] When the above dyes and pigments are mixed and used, they can be mixed in a weight ratio of 0.1:99.9 to 99.9:0.1, specifically in a weight ratio of 1:9 to 9:1. When mixed within this weight ratio range, chemical resistance and maximum absorption wavelength can be controlled to an appropriate range, and high brightness and contrast ratio can be achieved in the desired color coordinates.

[0091] The coloring agent may be included in an amount of 10% to 30% by weight, specifically 15% to 25% by weight, relative to the total amount of the photosensitive resin composition. Alternatively, the coloring agent may be included in an amount of 5% to 25% by weight, specifically 6% to 20% by weight, relative to the total amount of the photosensitive resin composition, based on solid content. When the coloring agent is included within the above ranges, the coloring effect and developability are excellent.

[0092] (B) Photopolymerizable compound The photopolymerizable compound can be a monofunctional or polyfunctional ester of (meth)acrylic acid having at least one ethylenically unsaturated double bond.

[0093] Photopolymerizable compounds, by possessing ethylenically unsaturated double bonds, can undergo sufficient polymerization during exposure in the pattern formation process, thereby forming patterns with excellent heat resistance, light resistance, and chemical resistance.

[0094] Specific examples of photopolymerizable compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, bisphenol A di(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate. Examples include acrylates, pentaerythritol hexa(meth)acrylate, dipentaerythritol di(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol A epoxy(meth)acrylate, ethylene glycol monomethyl ether(meth)acrylate, trimethylolpropane tri(meth)acrylate, tris(meth)acryloyloxyethyl phosphate, and novolac epoxy(meth)acrylate.

[0095] Examples of commercially available photopolymerizable compounds include the following: Examples of monofunctional esters of (meth)acrylic acid include Aronix M-101 (registered trademark), M-111 (registered trademark), and M-114 (registered trademark) from Toagosei Chemical Industry Co., Ltd.; KAYARAD TC-110S (registered trademark) and TC-120S (registered trademark) from Nippon Kayaku Co., Ltd.; and V-158 (registered trademark) and V-2311 (registered trademark) from Osaka Organic Chemical Industry Co., Ltd. Examples of the aforementioned (meth)acrylic acid difunctional esters include Aronix M-210 (registered trademark), M-240 (registered trademark), and M-6200 (registered trademark) from Toagosei Chemical Industry Co., Ltd.; KAYARAD HDDA (registered trademark), HX-220 (registered trademark), and R-604 (registered trademark) from Nippon Kayaku Co., Ltd.; and V-260 (registered trademark), V-312 (registered trademark), and V-335 HP (registered trademark) from Osaka Organic Chemical Industry Co., Ltd. Examples of the aforementioned trifunctional esters of (meth)acrylic acid include Aronix M-309 (registered trademark), M-400 (registered trademark), M-405 (registered trademark), M-450 (registered trademark), M-710 (registered trademark), M-8030 (registered trademark), M-8060 (registered trademark), etc. from Toagosei Chemical Industry Co., Ltd.; KAYARAD TMPTA (registered trademark), DPCA-20 (registered trademark), -30 (registered trademark), -60 (registered trademark), -120 (registered trademark), etc. from Nippon Kayaku Co., Ltd.; and V-295 (registered trademark), -300 (registered trademark), -360 (registered trademark), -GPT (registered trademark), -3PA (registered trademark), -400 (registered trademark), etc. from Osaka Organic Chemical Industry Co., Ltd. The above products can be used individually or in combination of two or more.

[0096] Photopolymerizable compounds can also be treated with acid anhydrides before use to impart better developability.

[0097] The photopolymerizable compound may be included in an amount of 0.1% to 10% by weight, specifically 1% to 10% by weight, for example, 3% to 9% by weight, relative to the total amount of the photosensitive resin composition. When the photopolymerizable compound is included within the above range, sufficient curing occurs during exposure in the pattern formation process, resulting in excellent reliability and excellent developability in alkaline developers.

[0098] (C) Photopolymerization initiator The photopolymerization initiator is an initiator commonly used in photosensitive resin compositions, and may include, for example, acetophenone compounds, benzophenone compounds, thioxanthone compounds, benzoin compounds, triazine compounds, oxime compounds, or combinations thereof.

[0099] Examples of acetophenone compounds include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinopropan-1-one, and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan-1-one.

[0100] Examples of benzophenone compounds include benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylic benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.

[0101] Examples of thioxanthone compounds include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and 2-chlorothioxanthone.

[0102] Examples of benzoin compounds include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0103] Examples of triazine compounds include 2,4,6-trichloro-s-triazine, 2-phenyl4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine. Examples include din, 2-biphenyl 4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-4-bis(trichloromethyl)-6-piperonyl-s-triazine, and 2-4-bis(trichloromethyl)-6-(4-methoxystyryl)-s-triazine.

[0104] Examples of oxime compounds include O-acyl oxime compounds, 2-(o-benzoyl oxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyl oxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethanone, and O-ethoxycarbonyl-α-oxyamino-1-phenylpropane-1-one. Specific examples of the O-acyloxime compounds include 1,2-octanedione, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholine-4-ylphenyl)-butan-1-one, 1-(4-phenylsulfanylphenyl)-butan-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1,2-dione 2-oxime-O-benzoate, 1-(4-phenylsulfanylphenyl)-octan-1-one oxime-O-acetate, and 1-(4-phenylsulfanylphenyl)-butan-1-one oxime-O-acetate.

[0105] In addition to the compounds mentioned above, other photopolymerization initiators that can be used include carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, biimidazole compounds, and fluorene compounds.

[0106] Photopolymerization initiators can also be used in conjunction with photosensitizers, which induce a chemical reaction by absorbing light, becoming excited, and then transferring that energy.

[0107] Examples of photosensitizers include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, and dipentaerythritol tetrakis-3-mercaptopropionate.

[0108] The photopolymerization initiator may be included in an amount of 0.1% to 5% by weight, for example, 1% to 3% by weight, relative to the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the above range, sufficient curing occurs during exposure in the pattern formation process, resulting in excellent reliability, excellent heat resistance, light resistance, and chemical resistance of the pattern, excellent resolution and adhesion, and prevention of a decrease in transmittance due to unreacted initiators.

[0109] (D) Binder resin The binder resin may include acrylic resins.

[0110] The acrylic resin is a copolymer of a primary ethylenically unsaturated monomer and a secondary ethylenically unsaturated monomer copolymerizable therewith, and is a resin containing one or more acrylic repeating units.

[0111] The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing one or more carboxyl groups, and specific examples include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, or combinations thereof.

[0112] The first ethylenically unsaturated monomer may be included in an amount of 5% to 50% by weight, for example, 10% to 40% by weight, relative to the total amount of the acrylic binder resin.

[0113] Examples of secondary ethylenically unsaturated monomers include aromatic vinyl compounds such as styrene, α-methylstyrene, vinyltoluene, and vinylbenzyl methyl ether; unsaturated carboxylic acid ester compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, and phenyl (meth)acrylate; unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth)acrylate and 2-dimethylaminoethyl (meth)acrylate; vinyl carboxylic acid ester compounds such as vinyl acetate and vinyl benzoate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate; vinyl cyanide compounds such as (meth)acrylonitrile; and unsaturated amide compounds such as (meth)acrylamide. These can be used individually or in combination of two or more.

[0114] Specific examples of acrylic resins include (meth)acrylic acid / benzyl methacrylate copolymer, (meth)acrylic acid / benzyl methacrylate / styrene copolymer, (meth)acrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer, and (meth)acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, but are not limited to these, and can be used individually or in combination of two or more.

[0115] Acrylic resins can have a weight-average molecular weight ranging from 5,000 g / mol to 30,000 g / mol. When acrylic resins have a weight-average molecular weight within this range, it can help improve durability and chemical resistance.

[0116] The binder resin may further contain epoxy-based binder resin.

[0117] The heat resistance of the binder resin can be improved by further including an epoxy binder resin. Examples of epoxy binder resins include, but are not limited to, phenol novolac epoxy resins, tetramethylbiphenyl epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, alicyclic epoxy resins, or combinations thereof.

[0118] Furthermore, binder resins containing epoxy-based binder resins ensure the dispersion stability of colorants such as pigments, as described later, while simultaneously helping to form pixels of the desired resolution during the development process.

[0119] The epoxy binder resin may be included in an amount of 1% to 10% by weight, for example, 5% to 10% by weight, relative to the total amount of binder resin. When the epoxy binder resin is included within the above range, the residual film rate and chemical resistance can be greatly improved.

[0120] The epoxy equivalent weight of the epoxy binder resin may be between 150 g / eq and 200 g / eq. When an epoxy binder resin having an epoxy equivalent weight within the above range is included in the binder resin, it has a favorable effect on improving the degree of curing of the formed pattern and on the adhesion of the colorant within the structure in which the pattern is formed.

[0121] The binder resin can be dissolved in a solvent described later in solid form to form a photosensitive resin composition. In this case, the amount of the binder resin in solid form may be about 0.5% to 10% by weight, for example, 1% to 4% by weight, relative to the total amount of the binder resin solution dissolved in the solvent.

[0122] Furthermore, the binder resin may be included in an amount of 0.5% to 10% by weight, specifically 1% to 5% by weight, relative to the total amount of the photosensitive resin composition. When the binder resin is included within the above range, excellent developability, improved crosslinking properties, and superior surface smoothness can be obtained during the manufacture of the color filter.

[0123] (E) Solvent The solvent can be a substance that is compatible with and does not react with the colorant, binder resin, photopolymerizable compound, and photopolymerization initiator.

[0124] Examples of solvents include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; methyl ethyl ketone, cyclohexanone, 4-hydroxy-4- Ketones such as methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylate alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactate esters such as methyl lactate and ethyl lactate; alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; alkyl 3-oxypropionates such as methyl 3-oxypropionate and ethyl 3-oxypropionate; alkyl 3-alkoxypropionates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, and methyl 3-ethoxypropionate; alkyl 2-oxypropionates such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate;Alkyl 2-alkoxypropionate esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate, and methyl 2-ethoxypropionate; 2-oxy-2-methylpropionate esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; Alkyl monooxymonocarboxylate esters of alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyethyl acetate, 2-hydroxy Examples include esters such as methyl xy-3-methylbutanoate; ketonic acid esters such as ethyl pyruvate; and high-boiling point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.

[0125] Of these, considering compatibility and reactivity, the solvents that can be used are propylene glycol monomethyl ether acetate (PGMEA), n-butyl acetate (n-BA), ethylene glycol dimethyl ether, cyclohexanone, or a combination thereof.

[0126] The solvent may be included in the remaining amount relative to the total amount of the photosensitive resin composition, for example, 40% to 90% by weight, or for example, 45% to 70% by weight. When the solvent is included within the above range, a coating film with excellent coatability and flatness can be obtained for the photosensitive resin composition.

[0127] (F) Other additives The photosensitive resin composition may further contain at least one additive selected from malonic acid; 3-amino-1,2-propanediol; a coupling agent containing a vinyl group or (meth)acrylooxy group; a leveling agent; a surfactant; and a radical polymerization initiator, in order to prevent stains and spots during application, improve leveling performance, and prevent the formation of residue due to undeveloped material.

[0128] The additives can be easily adjusted according to the desired physical properties.

[0129] The coupling agent may be a silane-based coupling agent. Examples of such silane-based coupling agents include trimethoxysilylbenzoic acid, γ-methacrylateoxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ-isocyanatetopropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, and β-(epoxycyclohexyl)ethyltrimethoxysilane. These can be used individually or in combination of two or more.

[0130] Specifically, the silane coupling agent can be used in an amount of 0.01 parts by weight or more and 1 part by weight or less per 100 parts by weight of the photosensitive resin composition.

[0131] Furthermore, the photosensitive resin composition for color filters may further contain a surfactant, such as a fluorinated surfactant, as needed.

[0132] Examples of fluorinated surfactants include, but are not limited to, DIC's F-482, F-484, and F-478.

[0133] The surfactant is preferably present in an amount of 0.01% to 5% by weight relative to the total amount of the photosensitive resin composition, and more preferably in an amount of 0.01% to 2% by weight. If it falls outside this range, it is undesirable because it may cause problems such as the formation of foreign matter after development.

[0134] Furthermore, the photosensitive resin composition may contain a certain amount of other additives, such as antioxidants and stabilizers, as long as they do not impair its physical properties.

[0135] [Photosensitive resin film, color filter, and display device] According to another embodiment, a photosensitive resin film manufactured using the photosensitive resin composition according to one embodiment is provided.

[0136] The photosensitive resin film of one embodiment can be broadly classified into positive photoresist compositions and negative photoresist compositions. The photosensitive resin film of one embodiment may also be a negative photoresist. This has the advantage that no coloration occurs due to the photoresist and that it is relatively more photosensitive than a positive photoresist.

[0137] In yet another embodiment, a color filter manufactured using the above-described photosensitive resin composition is provided.

[0138] A method for manufacturing a color filter according to one embodiment is as follows.

[0139] A photosensitive resin composition layer is formed on a glass substrate by applying the above-mentioned photosensitive resin composition to a thickness of, for example, 0.5 μm to 10 μm using an appropriate method such as spin coating, roller coating, or spray coating.

[0140] Next, the substrate on which the photosensitive resin composition layer is formed is irradiated with light to form the pattern required for the color filter. UV, electron beams, or X-rays can be used as the light source for irradiation; for example, UV in the 190nm to 450nm range, specifically in the 200nm to 400nm range, can be used. The irradiation process can also be carried out using a photoresist mask. After performing this irradiation process, the photosensitive resin composition layer that has been irradiated with the light source is treated with a developer solution. At this time, the photosensitive resin composition layer in the unexposed areas is dissolved, forming the pattern required for the color filter. By repeating this process for the required number of colors, a color filter with the desired pattern can be obtained. Furthermore, if the image pattern obtained by development in the above process is cured again by heating or chemical irradiation, crack resistance, solvent resistance, etc., can be improved.

[0141] In yet another embodiment, an image sensor and display device including the color filter described above are provided.

[0142] The image sensor may be a CMOS image sensor or the like.

[0143] The display device may be a liquid crystal display device or the like. [Examples]

[0144] The present invention will be described in more detail below through examples. However, the following examples are merely preferred embodiments of the present invention, and the present invention is not limited to these examples.

[0145] (Example of combination) Synthesis Example 1: Compound represented by chemical formula 1-1 (1) Production of intermediate 1-1 [ka]

[0146] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were placed in a 250 ml flask and stirred while cooling to 0°C. 3.61 g of diethylamine was then added to the flask and stirred while raising the temperature to 45°C. After the reaction was complete, the reactants were cooled and added to 1000 ml of diethyl ether to form a precipitate. The resulting precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 1-1.

[0147] (2) Production of intermediates 1-2 [ka]

[0148] 5.0 g of intermediate 1-1, 1.33 g of o-toluidine, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The resulting precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 1-2.

[0149] (3) Preparation of the compound represented by chemical formula 1-1 (compound 1) [ka]

[0150] 3.0 g of intermediates 1-2, 2.71 g of epichlorohydrin, 2.02 g of potassium carbonate, 64 g of potassium hydroxide, 0.88 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain compound 1. [ka] ...[Chemical formula 1-1] Maldi-TOF MS: 569 m / z

[0151] Synthesis Example 2: Compound represented by chemical formulas 1-2 (1) Production of intermediate 2-1 [ka]

[0152] 5.0 g of intermediate 1-1, 1.51 g of 2,6-dimethylaniline, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 2-1.

[0153] (2) Preparation of the compound represented by chemical formula 1-2 (compound 2) [ka]

[0154] 3.0 g of intermediate 2-1, 2.64 g of epichlorohydrin, 1.97 g of potassium carbonate, 1.60 g of potassium hydroxide, 0.85 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain compound 2. [ka] ...[Chemical formula 1-2] Maldi-TOF MS: 583 m / z

[0155] Synthesis Example 3: Compounds represented by chemical formulas 1-3 (1) Production of intermediate 3-1 [ka]

[0156] 5.0 g of intermediate 1-1, 1.51 g of 2,4-dimethylaniline, 1.75 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 3-1.

[0157] (2) Preparation of the compound represented by chemical formulas 1-3 (compound 3) [ka]

[0158] In a 100 ml flask, 3.0 g of intermediate 3-1, 2.64 g of epichlorohydrin, 1.97 g of potassium carbonate, 1.60 g of potassium hydroxide, 0.85 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added, and the mixture was heated and stirred at 60°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain compound 3. [ka] ...[Chemical formula 1-3] Maldi-TOF MS: 583 m / z

[0159] Synthesis Example 4: Compounds represented by chemical formulas 1-4 (1) Production of intermediate 4-1 [ka]

[0160] 5.0 g of intermediate 1-1, 1.68 g of 2,4,6-trimethylaniline, 1.75 g of N,N-diisopropyl-ethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 4-1.

[0161] (2) Preparation of the compound represented by chemical formulas 1-4 (compound 4) [ka]

[0162] 3.0 g of intermediate 4-1, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain compound 4. [ka] ...[Chemical formula 1-4] Maldi-TOF MS: 597 m / z

[0163] Synthesis Example 5: Compounds represented by chemical formulas 1-5 (1) Production of intermediate 5-1 [ka]

[0164] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were placed in a 250 ml flask and stirred while cooling to 0°C. 4.40 g of 2-(ethylamino)ethanol was then added to the flask and stirred while raising the temperature to 45°C. After the reaction was complete, the reaction mixture was cooled and added to 1000 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 5-1.

[0165] (2) Production of intermediate 5-2 [ka]

[0166] 5.0 g of intermediate 5-1, 1.46 g of N-ethylaniline, 1.69 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 5-2.

[0167] (3) Preparation of compounds represented by chemical formulas 1-5 (compound 5) [ka]

[0168] 3.0 g of intermediate 5-2, 2.56 g of epichlorohydrin, 1.91 g of potassium carbonate, 1.55 g of potassium hydroxide, 0.83 g of sodium iodide and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and then stirred while heating at 60 °C. After completion of the reaction, extraction was performed with dichloromethane. After extraction, it was concentrated and purified by column chromatography. After purification, it was dried under vacuum to obtain Compound 5. [[ID=‎1]] [[ID=‎2]] [[ID=‎3]]

Chemical formula

[0169] [[ID=‎12]] [[ID=‎13]]Synthesis Example 6: Compound represented by Chemical formula 1-6[[ID=‎14]] [[ID=‎15]](1) Production of intermediate 6-1[[ID=‎16]] [[ID=‎17]] [[ID=‎18]]

Chemical formula

[0170] [[ID=‎24]] [[ID=‎25]]10 g of Compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were added to a 250 ml flask, and then stirred while cooling to 0 °C. After adding 5.19 g of diethanolamine to the above flask, the temperature was raised to 45 °C and stirred. After completion of the reaction, the reaction product was cooled and added to 1000 mL of diethyl ether to form a precipitate. The obtained precipitate was suction filtered and additionally washed with diethyl ether. The filtrate was dried to obtain intermediate 6-1. [[ID=‎26]] [[ID=‎27]]

[0171] [[ID=‎28]] [[ID=‎29]](2) Production of intermediate 6-2[[ID=‎30]] [[ID=‎31]] [[ID=‎32]]

Chemical formula

[0172] 5.0 g of intermediate 6-1, 1.41 g of N-ethylaniline, 1.64 g of N,N-diisopropylethylamine and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and then stirred while heating at 125 °C. After completion of the reaction, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The obtained precipitate was suction filtered and additionally washed with diethyl ether. The filtrate was dried to obtain intermediate 6-2.

[0173] (3) Production of the compound represented by Chemical Formula 1-6 (Compound 6)

Chemical formula

[0174] 3.0 g of intermediate 6-2, 4.97 g of epichlorohydrin, 3.71 g of potassium carbonate, 3.01 g of potassium hydroxide, 1.61 g of sodium iodide and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and then stirred while heating at 60 °C. After completion of the reaction, it was extracted with dichloromethane. After extraction, it was concentrated and purified by column chromatography. After purification, it was dried under vacuum to obtain Compound 6.

Chemical formula

[0175] Synthesis Example 7: Compound Represented by Chemical Formula 1-7 (1) Production of intermediate 7-1 [ka]

[0176] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were placed in a 250 ml flask and stirred while cooling to 0°C. 4.30 g of 3-pyrrolidinol was then added to the flask and stirred while raising the temperature to 45°C. After the reaction was complete, the reactants were cooled and added to 1000 ml of diethyl ether to form a precipitate. The precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain intermediate 7-1.

[0177] (2) Production of intermediate 7-2 [ka]

[0178] 5.0 g of intermediate 7-1, 1.46 g of N-ethylaniline, 1.70 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with 1-methyl-2-pyrrolidone. The filtrate was dried to obtain intermediate 7-2.

[0179] (3) Preparation of the compound represented by chemical formulas 1-7 (compound 7) [ka]

[0180] 3.0 g of intermediate 7-2, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and then stirred while heating at 60 °C. After completion of the reaction, extraction was carried out with dichloromethane. After extraction, it was concentrated and purified by column chromatography. After purification, it was dried under vacuum to obtain compound 7.

Chemical formula

[0181] Synthesis Example 8: Compound represented by Chemical formula 1-8 (1) Production of intermediate 8-1

Chemical formula

[0182] 5.0 g of intermediate 5-1, 1.43 g of indoline, 1.69 g of N,N-diisopropyl-ethylamine and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and then stirred while heating at 125 °C. After completion of the reaction, the reaction product was cooled and added to 500 mL of diethyl ether to form a precipitate. The obtained precipitate was suction filtered and further washed with diethyl ether. The filtrate was dried to obtain intermediate 8-2.

[0183] (2) Production of the compound (Compound 8) represented by Chemical formula 1-8 [ka]

[0184] 3.0 g of intermediate 8-2, 2.57 g of epichlorohydrin, 1.92 g of potassium carbonate, 1.56 g of potassium hydroxide, 0.83 g of sodium iodide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain compound 8. [ka] ...[Chemical formula 1-8] Maldi-TOF MS: 597 m / z

[0185] Comparative Synthesis Example 1 (1) Preparation of comparative intermediate 1 [ka]

[0186] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were placed in a 250 ml flask and stirred while cooling to 0°C. 6.08 g of 4-amino-m-cresol was then added to the flask and stirred while raising the temperature to 45°C. After the reaction was complete, the reactants were cooled and added to 1000 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain comparative intermediate 1.

[0187] (2) Preparation of comparative intermediate 2 [ka]

[0188] 5.0 g of comparative intermediate 1, 2.23 g of diethylamine, 3.94 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After 1 hour, the temperature was raised to 125°C and the mixture was stirred. After the reaction was complete, the reactants were cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain comparative intermediate 2.

[0189] (3) Preparation of the compound represented by chemical formula C-1 (comparative compound 1) [ka]

[0190] 3.0 g of comparative intermediate 2, 2.63 g of epichlorohydrin, 1.59 g of potassium hydroxide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 50°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the mixture was concentrated and purified by column chromatography. After purification, the mixture was vacuum-dried to obtain comparative compound 1. [ka] ...[Chemical formula C-1] Maldi-to-Focus MS: 585 m / z

[0191] Comparative Synthesis Example 2 Preparation of the compound represented by chemical formula C-2 (comparative compound 2) [ka]

[0192] 5.0 g of intermediate 1-1, 1.86 g of N-ethyl-2,6-dimethylbenzenamine, 1.75 g of N,N-diisopropyl-ethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 125°C. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. After redissolution with dichloromethane, the precipitate was concentrated and purified by column chromatography. After purification, the compound represented by the following chemical formula C-2 (comparative compound 2) was prepared by vacuum drying. [ka] ...[Chemical formula C-2] Maldi-to-Focus MS: 555 m / z

[0193] Comparative Synthesis Example 3 (1) Preparation of comparative intermediate 3-1 [ka]

[0194] 10 g of compound A (CAS No. 77545-45-0) and 100 g of isopropyl alcohol were placed in a 250 ml flask and stirred while cooling to 0°C. 6.77 g of 4-(ethylamino)phenol was then added to the flask and stirred while raising the temperature to 45°C. After the reaction was complete, the reaction mixture was cooled and added to 1000 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain comparative intermediate 3-1.

[0195] (2) Preparation of comparative intermediate 3-2 [ka]

[0196] 5.0 g of comparative intermediate 3-1, 1.32 g of N-ethylaniline, 1.53 g of N,N-diisopropylethylamine, and 40 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 60°C. After 1 hour, the temperature was raised to 125°C and the mixture was stirred. After the reaction was complete, the reaction mixture was cooled and added to 500 ml of diethyl ether to form a precipitate. The obtained precipitate was filtered by suction and washed again with diethyl ether. The filtrate was dried to obtain comparative intermediate 3-2.

[0197] (3) Preparation of compound 3 represented by chemical formula C-3 (comparative compound) [ka]

[0198] 3.0 g of comparative intermediate 3-2, 2.35 g of epichlorohydrin, 1.59 g of potassium hydroxide, and 30 g of 1-methyl-2-pyrrolidone were added to a 100 ml flask, and the mixture was stirred while heating at 50°C. After the reaction was complete, the mixture was extracted with dichloromethane. After extraction, the solution was concentrated and purified by column chromatography. After purification, the solution was vacuum-dried to produce the compound represented by the following chemical formula C-3 (comparative compound 3). [ka] ...[Chemical formula C-3] Maldi-TOF MS: 647 m / z

[0199] Production of yellow pigment dispersion A yellow pigment dispersion was obtained by mixing 12.0 parts by weight of yellow pigment (CIPIGMENT Yellow 138), 3.0 parts by weight of dispersant (BYK-LPN6919, manufacturer: BYK), and 85.0 parts by weight of solvent (propylene glycol monomethyl ether acetate, PGMEA). 300 parts of zirconia beads (diameter: 0.4 μm) were added to 100 parts by weight of this mixture, and the mixture was shaken for 3 hours using a paint shaker to disperse the particles. The zirconia beads were then removed by filtration.

[0200] Manufacturing of photosensitive resin compositions (Example 1) The photosensitive resin composition of Example 1 was prepared by mixing the components shown in Table 1 below. Specifically, the photopolymerization initiator was dissolved in a solvent and stirred at room temperature for 2 hours. Then, an acrylic binder resin and a photopolymerizable compound were added and stirred at room temperature for 2 hours. Next, the resulting reaction product was mixed with a compound represented by chemical formula 1-1 (dye) and a pigment (in the form of a pigment dispersion) as colorants and stirred at room temperature for 1 hour. Finally, the product was filtered three times to remove impurities, thereby preparing the photosensitive resin composition.

[0201] [Table 1]

[0202] (Example 2) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 2 (represented by chemical formula 1-2) was used instead of compound 1 (represented by chemical formula 1-1).

[0203] (Example 3) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 3 (represented by chemical formula 1-3) was used instead of compound 1 (represented by chemical formula 1-1).

[0204] (Example 4) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 4 (represented by chemical formula 1-4) was used instead of compound 1 (represented by chemical formula 1-1).

[0205] (Example 5) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 5 (represented by chemical formula 1-5) was used instead of compound 1 (represented by chemical formula 1-1).

[0206] (Example 6) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 6 (represented by chemical formula 1-6) was used instead of compound 1 (represented by chemical formula 1-1).

[0207] (Example 7) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 7 (represented by chemical formula 1-7) was used instead of compound 1 (represented by chemical formula 1-1).

[0208] (Example 8) A photosensitive resin composition was prepared in the same manner as in Example 1, except that compound 8 (represented by chemical formula 1-8) was used instead of compound 1 (represented by chemical formula 1-1).

[0209] (Comparative Example 1) A photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 1 (a compound represented by chemical formula C-1) was used instead of compound 1 (a compound represented by chemical formula 1-1).

[0210] (Comparative Example 2) A photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 2 (a compound represented by chemical formula C-2) was used instead of compound 1 (a compound represented by chemical formula 1-1).

[0211] (Comparative Example 3) A photosensitive resin composition was prepared in the same manner as in Example 1, except that comparative compound 3 (a compound represented by chemical formula C-3) was used instead of compound 1 (a compound represented by chemical formula 1-1).

[0212] Evaluation Example 1: Reliability Color filter test pieces were prepared using the photosensitive resin compositions produced in Examples 1 to 8 and Comparative Examples 1 to 3.

[0213] Specifically, each photosensitive resin composition was applied to a degreased and cleaned 1 mm thick glass substrate to a thickness of 1 to 3 μm, and the coating was dried on a hot plate at 90°C for 2 minutes to obtain the coating film.

[0214] The durability (reliability) of each color filter test specimen was evaluated from two aspects: chemical resistance and light resistance.

[0215] (1) Chemical resistance: The absorbance intensity at the maximum absorption wavelength (λmax) was measured for each color filter test specimen. Specifically, the maximum absorption wavelength (λmax) of each color filter test specimen was confirmed using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer, and the absorbance intensity at that wavelength was measured at the same time.

[0216] Furthermore, each color filter test specimen was immersed in NMP (N-Methyl-2-pyrrolidone) solvent at 50°C for 10 minutes, then removed, washed with ultrapure water for 30 seconds, and dried by blowing with compressed air. Subsequently, the absorbance intensity at the maximum absorption wavelength (λmax) was measured using the same method as described above.

[0217] The chemical resistance of each color filter test piece was quantified by substituting the absorbance intensity before and after solvent exposure into Equation 1 below, and the results are shown in Table 2 below. [Formula 1] Chemical resistance = {1 - (absorbance intensity after NMP immersion) / (absorbance intensity before NMP immersion)} × 100%

[0218] (2) Lightfastness: The absorbance intensity at the maximum absorption wavelength (λmax) was measured for each color filter test specimen. Specifically, the maximum absorption wavelength (λmax) of each color filter test specimen was confirmed using a Shimadzu UV-3600 Plus UV-Vis-NIR spectrometer, and the absorbance intensity at that wavelength was measured at the same time.

[0219] Furthermore, each color filter test piece was exposed to 50 mJ / cm² using an exposure device. 2 After full-surface exposure under the specified conditions, the absorbance intensity at the maximum absorption wavelength (λmax) was measured using the same method as described above.

[0220] The absorbance of each color filter test piece before and after exposure was substituted into Equation 2 below to quantify its lightfastness, and the results are shown in Table 2 below. [Formula 2] Lightfastness = {1 - (Absorbance after light exposure) / (Absorbance before light exposure)} × 100%

[0221] [Table 2]

[0222] From Table 2 above, it can be seen that the photosensitive resin compositions of Examples 1 to 8, which contain the compound according to one embodiment as a dye, have superior chemical resistance and light resistance compared to the photosensitive resin compositions of Comparative Examples 1 to 3.

[0223] Evaluation Example 2: Brightness Color filter test pieces were manufactured using the photosensitive resin compositions produced in Examples 1 to 8 and Comparative Examples 1 to 3, in the same manner as in Evaluation Example 1.

[0224] Specifically, each photosensitive resin composition was applied to a degreased and cleaned 1 mm thick glass substrate to a thickness of 1 μm to 3 μm, and the coating was dried on a hot plate at 90°C for 2 minutes to obtain the coating film.

[0225] Each coating was exposed using a high-pressure mercury lamp with a dominant wavelength of 365 nm, and then dried for 5 minutes in a hot air circulating drying oven at 200°C. The brightness of the pixel layer was measured using a spectrophotometer (MCPD3000, Otsuka Electronics Co., Ltd.), and the results are shown in Table 3 below.

[0226] [Table 3]

[0227] From Table 3 above, it can be confirmed that the photosensitive resin compositions of Examples 1 to 8, which contain the compound according to one embodiment as a dye, have superior brightness compared to the photosensitive resin compositions of Comparative Examples 1 to 3.

[0228] When a compound represented by chemical formula 1 is included as a dye, a photosensitive resin composition with excellent lightfastness, chemical resistance, and brightness can be realized simultaneously.

[0229] Examples 1 to 8 are presented here as representative examples, but it would be possible to adjust within the scope of one embodiment to control light resistance, chemical resistance, brightness, etc., to the desired level.

[0230] Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and can be implemented in various ways within the scope of the claims, detailed description of the invention, and accompanying drawings, and these also naturally fall within the scope of the present invention.

Claims

1. (A) Coloring agents; (B) photopolymerizable compound; (C) Photopolymerization initiator; (D) Binder resin; and (E) containing a solvent, The coloring agent is a photosensitive resin composition comprising a compound represented by the following chemical formula 1A or chemical formula 1B. 【Chemistry 1】 ...[Chemical formula 1A] 【Chemistry 2】 ...[Chemical formula 1B] (In the above chemical formulas 1A and 1B, L １ and L ２ Each of these is independently a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms, or a combination thereof, L １ and L ２ However, it is not a single bond at the same time. R １ ~R ３ Each of these is independently a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or a combination thereof. L １ and R １ They either condense with each other to form a condensed ring, or they do not condense with each other. R ２ and R ３ either condense with each other to form a condensed ring or do not condense with each other.

2. The substituted or unsubstituted oxyalkylene group having 1 to 20 carbon atoms is represented by the following chemical formula 2 in the photosensitive resin composition according to claim 1: 【Transformation 3】 ...[Chemical formula 2] (In the above chemical formula 2, L ３ This is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms. n is an integer between 1 and 10.

3. The photosensitive resin composition according to claim 1, wherein the compound represented by chemical formula 1A or chemical formula 1B is a dye.

4. The photosensitive resin composition according to claim 1, wherein the compound represented by chemical formula 1A or chemical formula 1B is represented by any one of the following chemical formulas 1-1 to 1-8. 【Chemistry 4】 ...[Chemical formula 1-1] 【Transformation 5】 ...[Chemical formula 1-2] 【Transformation 6】 ...[Chemical formula 1-3] 【Transformation 7】 ...[Chemical formula 1-4] 【Transformation 8】 ...[Chemical formula 1-5] 【Chemistry 9】 ...[Chemical formula 1-6] 【Chemistry 10】 ...[Chemical formula 1-7] 【Chemistry 11】 ...[Chemical formula 1-8]

5. The photosensitive resin composition according to claim 1, wherein the compound represented by chemical formula 1A or chemical formula 1B is contained in an amount of 1% by weight or more and 10% by weight or less based on the total amount of the photosensitive resin composition.

6. The photosensitive resin composition according to claim 1, wherein the coloring agent further comprises a pigment.

7. The photosensitive resin composition according to claim 1, wherein the pigment comprises a red pigment, a yellow pigment, or a combination thereof.

8. The photosensitive resin composition is, in relation to the total amount of the photosensitive resin composition, The aforementioned (A) coloring agent: 10% by weight or more and 30% by weight or less; The above (B) photopolymerizable compound: 0.1% by weight or more and 10% by weight or less; The above (C) photopolymerization initiator in an amount of 0.1% to 5% by weight; The above (D) binder resin 0.5% by weight or more and 10% by weight or less; and The photosensitive resin composition according to claim 1, comprising the amount of the solvent residue (E) mentioned above.

9. A photosensitive resin film manufactured using the photosensitive resin composition described in any one of claims 1 to 8.

10. The photosensitive resin film according to claim 1, wherein the photosensitive resin film is a negative photoresist.

11. A color filter comprising the photosensitive resin film described in claim 10.

Images